Deangelo Whiteside v. United States

PUBLISHED

UNITED STATES COURT OF APPEALS
FOR THE FOURTH CIRCUIT

No. 13-7152

DEANGELO MARQUIS WHITESIDE,

Petitioner - Appellant,

v.

UNITED STATES OF AMERICA,

Respondent - Appellee.

Appeal from the United States District Court for the Western
District of North Carolina, at Asheville. Martin K. Reidinger,
District Judge. (1:09-cr-00069-MR-1; 1:12-cv-00118-MR)

Argued: January 29, 2014 Decided: April 8, 2014

Before WILKINSON and GREGORY, Circuit Judges, and DAVIS, Senior
Circuit Judge.

Vacated and remanded for resentencing by published opinion.
Judge Gregory wrote the majority opinion, in which Senior Judge
Davis joined. Senior Judge Davis wrote a separate concurring
opinion, and Judge Wilkinson wrote a dissenting opinion.

ARGUED: Ann Loraine Hester, FEDERAL DEFENDERS OF WESTERN NORTH
CAROLINA, INC., Charlotte, North Carolina, for Appellant. Amy
Elizabeth Ray, OFFICE OF THE UNITED STATES ATTORNEY, Asheville,
North Carolina, for Appellee. ON BRIEF: Henderson Hill,
Executive Director, FEDERAL DEFENDERS OF WESTERN NORTH CAROLINA,
INC., Charlotte, North Carolina, for Appellant. Anne M.
Tompkins, United States Attorney, OFFICE OF THE UNITED STATES
ATTORNEY, Charlotte, North Carolina, for Appellee.
GREGORY, Circuit Judge:

This case presents the question of whether a federal inmate

may use a 28 U.S.C. § 2255 motion to challenge a sentence that

was based on the career offender enhancement under the United

States Sentencing Guidelines when subsequent case law reveals

the enhancement to be inapplicable to him. We find that he may,

and in doing so hold that the mistake results in a fundamental

miscarriage of justice that is cognizable on collateral review.

For the reasons stated below, we grant a certificate of

appealability, vacate the petitioner’s sentence, and remand the

case for resentencing.

I.

The facts relevant to this appeal are brief and largely

undisputed. In July 2009, the petitioner-appellant, Deangelo

Whiteside, was indicted on charges of possession with intent to

distribute at least 50 grams of crack cocaine, in violation of

21 U.S.C. § 841(a)(1). Shortly thereafter, the government filed

an Information pursuant to 21 U.S.C. § 851 notifying Whiteside

that it intended to seek an enhanced penalty based on a 2002

North Carolina felony drug conviction.

Whiteside then entered into a plea agreement with the

government. The agreement acknowledged the possibility that

Whiteside might be designated a career offender under U.S.S.G.
2
§ 4B1.1. It also contained several waivers of Whiteside’s

rights to challenge his conviction and sentence in an appeal or

collateral proceeding. As discussed in more detail below, the

parties dispute whether these provisions bar Whiteside’s current

claim.

Whiteside pled guilty to the offense in October 2009 and

the probation office began preparing a presentence report. The

probation officer concluded that Whiteside was responsible for

1,951.9 grams of powder cocaine and 468.3 grams of crack

cocaine, generating a base offense level of 32. 1 The probation

officer also determined that a 1999 North Carolina conviction

for felony possession with intent to sell and deliver cocaine,

along with the 2002 drug conviction, qualified Whiteside for the

career offender enhancement under § 4B1.1. 2 The enhancement

1
The probation officer disagreed with the government’s
stipulation in the plea agreement that Whiteside would be held
responsible for more than 50 and less than 150 grams of crack
cocaine.
2
The career offender enhancement defines a “career
offender,” and provides that a defendant is such an offender if

(1) [he] was at least eighteen years old at the time
[he] committed the instant offense of conviction;
(2) the instant offense of conviction is a felony that
is either a crime of violence or a controlled
substance offense; and (3) [he] has at least two prior
felony convictions of either a crime of violence or a
controlled substance offense.

U.S.S.G. § 4B1.1(a). For purposes of the enhancement, a “prior
felony conviction” includes “a prior . . . state conviction for
(Continued)
3
raised Whiteside’s base offense level to 37 and his criminal

history category from V to VI. After a three-level reduction

for acceptance of responsibility, Whiteside’s Sentencing

Guidelines range was 262 to 327 months in prison. In light of

the government’s § 851 Information, the prior felony drug

convictions also subjected Whiteside to a mandatory minimum term

of imprisonment of twenty years.

Prior to Whiteside’s sentencing hearing, the government

filed a § 5K1.1 motion seeking a downward departure based on the

petitioner’s substantial assistance. The government recommended

that Whiteside receive a sentence based on a total offense level

of 32 and a criminal history category VI, which yielded a 210 to

262 month Guidelines range. The district court granted the

government’s motion and, on July 9, 2010, sentenced Whiteside to

210 months’ imprisonment, a sentence below both his Guidelines

range and the twenty-year mandatory minimum.

On August 17, 2011, this Court issued its en banc decision

in United States v. Simmons, 649 F.3d 237 (4th Cir. 2011). In

Simmons, we overruled circuit precedent and held that a North

Carolina conviction is a crime punishable by a term of

an offense punishable by . . . imprisonment for a term exceeding
one year, regardless of whether such offense is specifically
designated as a felony.” Id. § 4B1.2 cmt. n.1.

4
imprisonment exceeding one year only when the defendant’s

particular criminal history and the nature of his offense so

warrant. See id. at 247 & n.9. It is undisputed that under

Simmons, Whiteside’s predicate convictions were not punishable

by more than a year in prison, and were he sentenced today he

would not be subject to either the career offender enhancement

or the twenty-year statutory minimum penalty.

Whiteside argues that without those enhancements he would

have faced a Guidelines range of 140 to 175 months and a

statutory term of ten years to life. Assuming the same downward

departure based on substantial assistance – eighty percent of

the low end of the Guidelines – Whiteside contends that his

sentence would have been 112 months, roughly eight years shorter

than the sentence he received.

On May 18, 2012, Whiteside filed a 28 U.S.C. § 2255 motion

to vacate his sentence. He argued that, in light of Simmons, he

did not qualify as a career offender and that he should be

resentenced without the enhancement. 3 The district court

dismissed Whiteside’s motion to vacate, concluding that it was

untimely, that Whiteside waived his right to collaterally attack

3
Whiteside subsequently filed a supplement to his motion to
vacate, making the same arguments, but seeking, in the
alternative, relief under 28 U.S.C. § 2241, a writ of coram
nobis, and a writ of audita querela.

5
his sentence in his plea agreement, and that he was not eligible

for post-conviction relief because he received a sentence

beneath the statutory maximum. The district court also declined

to issue a certificate of appealability. This appeal followed.

II.

A.

We must first address whether Whiteside’s motion to vacate

is procedurally barred. The first question on this point is

whether Whiteside in his plea agreement waived his right to

collaterally attack his sentence. We review this issue de novo.

See United States v. Copeland, 707 F.3d 522, 528 (4th Cir.

2013).

The relevant portions of Whiteside’s plea agreement are as

follows:

20. Defendant, in exchange for the concessions made
by the United States in this plea agreement,
waives all such rights to contest the conviction
except for: (1) claims of ineffective assistance
of counsel or (2) prosecutorial misconduct.
Defendant also . . . knowingly and expressly
waives all rights conferred by 18 U.S.C. § 3742
or otherwise to appeal whatever sentence is
imposed with the two exceptions set forth above.
Defendant also reserves right to appeal ruling as
to career offender pursuant to USSG § 4Bl.l.

21. Also, in exchange for the concessions made by the
United States, defendant agrees that the United
States preserves all its rights and duties with
respect to appeal as set forth in 18 U.S.C.
§ 3742(b), while the defendant waives all rights

6
 to appeal or collaterally attack the sentence of
conviction with the two exceptions set forth
above.

The government contends that under these terms, Whiteside

waived his right to collaterally attack his sentence on all

grounds except that of ineffective assistance of counsel or

prosecutorial misconduct. We disagree, finding that the

language of the plea agreement is ambiguous and does not clearly

specify which rights were waived.

In short, the paragraphs quoted above contradict one

another. Paragraph 20 states that the defendant may challenge

his conviction only on the two grounds just mentioned. It goes

on to state that the defendant retains his right to appeal his

sentence with respect to the career offender enhancement.

However, paragraph 21 then states that he may only challenge his

sentence (through either a direct appeal or § 2255 motion) on

ineffective assistance or prosecutorial misconduct grounds.

This simply does not make sense. Either the parties intended to

limit the defendant’s right to challenge his sentence to two

grounds, a result which would render the career offender

reference at the end of paragraph 20 superfluous, or the

statement in paragraph 21 limiting Whiteside’s rights to

challenge his sentence to two grounds was a mistake and should

instead have cited three possible bases for a challenge. Either

reading is problematic, leaving it impossible to say exactly

7
which rights Whiteside waived. When a plea agreement is

unclear, it must be construed against the government. See

United States v. Jordan, 509 F.3d 191, 199-200 (4th Cir. 2007).

As such, we hold that Whiteside did not waive his right to

challenge the career offender enhancement in a collateral

proceeding.

B.

We next consider whether Whiteside’s motion to vacate was

timely. A § 2255 petitioner ordinarily has one year from the

date on which his conviction becomes final in order to file a

motion to vacate. 28 U.S.C. § 2255(f(1). Whiteside’s

conviction became final on August 17, 2010, but he did not file

his motion until May 18, 2012, well beyond the one-year period.

However, the statute of limitations in § 2255(f)(1) may be

equitably tolled in certain circumstances. Specifically,

equitable tolling applies if the petitioner can show “‘(1) that

he has been pursuing his rights diligently, and (2) that some

extraordinary circumstance stood in his way’ and prevented

timely filing.” Holland v. Florida, 560 U.S. 631, 649 (2010)

(quoting Pace v. DiGuglielmo, 544 U.S. 408, 418 (2005)). Relief

is limited to cases “where – due to circumstances external to

the party’s own conduct – it would be unconscionable to enforce

the limitation period against the party and gross injustice

8
would result.” United States v. Sosa, 364 F.3d 507, 512 (4th

Cir. 2004).

As explained below, we find that the erroneous application

of the career offender enhancement worked a gross miscarriage of

justice. We also hold that Whiteside pursued his rights

diligently by filing his motion within a year of our decision in

Simmons and that extraordinary circumstances prevented him from

filing the motion earlier. Our decision is based on the simple

fact that our case law prior to Simmons absolutely foreclosed

Whiteside’s current argument. In United States v. Jones, 195

F.3d 205 (4th Cir. 1999), and then again in United States v.

Harp, 406 F.3d 242 (4th Cir. 2005), we rejected the arguments

that we later accepted in Simmons. Had Whiteside filed a habeas

petition prior to Simmons it would have been summarily denied on

the basis of these decisions, as was the case for numerous other

petitioners. See, e.g., Robinson v. United States, No. 5:07-cv-

140, 2011 WL 676184 (E.D.N.C. Feb. 18, 2011); Jordan v. United

States, No. 1:09-cv-816, 2010 WL 2347076 (M.D.N.C. June 3,

2010). We think this condition – the complete lack of any

chance at success – constitutes an “extraordinary circumstance”

that warrants equitable considerations. The obstacle was

clearly external to Whiteside – indeed, it was our incorrect

interpretation of which North Carolina convictions support the

career offender enhancement that prevented him from seeking

9
relief. Once this was corrected and Whiteside had an

opportunity for meaningful review, he filed his motion in a

timely manner. This is not a case of a petitioner who has slept

on his rights and later seeks relief from his indolence;

instead, once Whiteside’s right to review obtained any real

significance, he acted.

The government nevertheless contends that Whiteside should

have filed his petition prior to Simmons in spite of its sure

defeat. In addition to simply having an air of absurdity about

it, this argument would lead to the perverse result of reading

the AEDPA’s time limitations to encourage inmates to flood the

courts with baseless petitions on the off chance that the law

might one day change. Further, if Whiteside had filed his

petition prior to Simmons and it had been denied, his current

claim would possibly be barred as a successive petition. See

§ 2255(h). 4 Given the timing of Whiteside’s conviction and our

decision in Simmons, the result of the government’s position is

that at no point would Whiteside have been entitled to relief

4
We expressly do not decide whether the savings clause in
§ 2255(e) might justify relief from a Simmons sentencing error
through the filing of a § 2241 petition. While we have not
previously “extended the reach of the savings clause to those
petitioners challenging only their sentence,” United States v.
Poole, 531 F.3d 263, 267 n.7, 274 (4th Cir. 2008), we note that
the Eleventh Circuit recently permitted a federal inmate to use
§ 2255(e) to bring a § 2241 petition challenging the legality of
his sentence. Bryant v. Warden, 738 F.3d 1253 (11th Cir. 2013).

10
from an error that we consider to be a fundamental miscarriage

of justice. We cannot accept such an outcome.

Nor are we bound to. We recognize that we previously held

that the futility of a petitioner’s claim does not constitute a

circumstance external to his control. Minter v. Beck, 230 F.3d

663, 666 (4th Cir. 2000). However, our decision in Minter

preceded the recent Supreme Court decision in Holland, which

adopted an expansive reading of the role of equity in habeas

cases. In Holland, the Supreme Court reviewed an Eleventh

Circuit rule holding that attorney negligence in failing to meet

a filing deadline may never serve as a basis for equitable

tolling absent a showing of bad faith or dishonesty on the part

of the attorney. 560 U.S. at 644. The Court rejected this rule

as overly rigid. Noting equity’s longstanding role in habeas

relief, the Court stated that principles of equitable tolling

are consistent with the “AEDPA’s basic purpose of eliminating

delays . . . without undermining basic habeas corpus principles

and by harmonizing the statute with prior law, under which a

petition’s timeliness was always determined under equitable

principles.” Id. at 648. In light of this, the Court held that

the AEDPA’s statutes of limitations “do[] not set forth ‘an

inflexible rule requiring dismissal whenever’ its ‘clock has

run.’” Id. at 645 (quoting Day v. McDonough, 547 U.S. 198, 205

(2010)). The Court further explained that, while courts of

11
equity are of course governed by “rules and precedents,” equity

also requires “flexibility” and the avoidance of “mechanical

rules.” Id. at 649-50 (internal quotation marks and citations

omitted); see also id. at 650 (courts must “exercise judgment in

light of prior precedent, but with awareness of the fact that

specific circumstances, often hard to predict in advance, could

warrant special treatment in an appropriate case”).

Although Holland dealt with attorney misconduct, an issue

not before this Court, the decision’s broader point was that the

“exercise of a court’s equity powers . . . must be made on a

case-by-case basis . . . .” Id. at 649-50; see also Jones v.

United States, 689 F.3d 621, 626-28 (6th Cir. 2012) (citing

Holland and applying equitable tolling where inmate filed

petition within three months of Supreme Court’s decision in

Begay v. United States, 553 U.S. 137 (2008), entitling him to

relief). To the extent Minter created a bright-line rule that

futility may not constitute an extraordinary circumstance,

Holland requires that we at least apply such a rule on a case-

by-case basis. 5

5
Moreover, the factual differences in the cases aside, our
outcome is entirely consistent with Holland. Indeed, the
circumstances here are arguably more compelling, given that
attorney errors are generally attributable to clients, see
Holland, 560 U.S. at 656 (Alito, J., concurring) (citation
omitted), while this case deals with our own error in
(Continued)
12
 When examining the particular circumstances of Whiteside’s

case, we find that he satisfies the requirements necessary for

equitable tolling. He has successfully demonstrated that his

sentence amounted to a fundamental miscarriage of justice.

Correcting unjust incarcerations is the whole purpose of § 2255.

As the Supreme Court explained in Holland, the AEDPA’s time

limitations do not foreclose this relief to all those who are

unable to meet the statute’s deadlines. Had Whiteside filed

within the one-year statute of limitations, he likely would have

been forced to suffer the injustice with no future chance at

relief. The timing of our decisions should not be the sole

determinant of a petitioner’s access to justice. Whiteside’s

inability to obtain meaningful relief prior to our decision in

Simmons is an extraordinary circumstance that warrants some

flexibility on our behalf in order “to accord all the relief

necessary to correct . . . particular injustices.” Id. at 650

(quoting Hazel-Atlas Glass Co. v. Hartford-Empire Co., 322 U.S.

238, 248 (1944)). 6 Accordingly, we equitably toll the

limitations period and review Whiteside’s claim.

interpreting prior case law. There is no similar justification
for punishing a petitioner for our mistake.
6
Indeed, even the government recognizes that on a case-by-
case basis, Simmons relief should be afforded to some
(Continued)
13
 III.

Turning to the merits of the case, we are asked to decide

whether a petitioner may challenge his sentence on collateral

review based on an incorrect application of the career offender

enhancement. Because it is the only response that is both

consistent with the realities of federal sentencing and just, we

answer yes.

Section 2255 allows federal prisoners to move to set aside

sentences that are imposed “in violation of the Constitution or

laws of the United States.” Thus, § 2255 relief is not limited

to constitutional errors. See Davis v. United States, 417 U.S.

333, 345-56 (1974). However, a non-constitutional error may

only serve as a basis for collateral attack when it involves “a

fundamental defect which inherently results in a complete

petitioners notwithstanding limitations or appeal waivers. See
Mungro v. United States, Nos. 5:11-cv-141-RLV & 5:04-cr-18-RLV-
CH-1, 2013 WL 6800822, at *6-*7 & n.3 (W.D.N.C. Dec. 23, 2013)
(granting § 2255 motion to vacate the prisoner's mandatory life
sentence on Simmons grounds, and noting that the government had
waived “reliance on the statute-of-limitations defense”);
Sturvidant v. United States, Nos. 3:12-CV-66-FDW & 3:09-cr-39-
FDW-6, 2013 WL 6669025, at *1, *3 (W.D.N.C. Dec. 18, 2013)
(granting Simmons relief after government “declined to enforce”
the defendant’s plea-agreement waiver of the right to
collaterally attack his sentence). As the government apparently
concluded in Mungro, we conclude that in this case “it would be
unconscionable to enforce the limitation period against the
[petitioner] and gross injustice would result” were we to do so.
Minter, 230 F.3d at 667 (quoting Harris v. Hutchinson, 209 F.3d
325, 330 (4th Cir. 2000) (§ 2254 case)).

14
miscarriage of justice.” United States v. Addonizio, 442 U.S.

178, 185 (1979) (internal quotation marks omitted). The Supreme

Court has provided only the general contours of what constitutes

a complete miscarriage of justice. For example, in Hill v.

United States, 368 U.S. 424, 429 (1962), the Court reviewed a

sentencing judge’s failure to inform a defendant that he had the

right to speak at his sentencing hearing. The Court

characterized this mistake as a mere failure to follow the

formal requirements of a rule, and held that it did not

constitute a basis for habeas relief. Id.; see also Peguero v.

United States, 526 U.S. 23 (1999) (failure to inform defendant

of the right to appeal where defendant knew of the right);

United States v. Timmreck, 441 U.S. 780 (1979) (failure to

mention a special parole term at Rule 11 hearing). In contrast,

in Davis the Court held that a post-conviction change in the law

that rendered the defendant’s conduct no longer criminal is

correctable on collateral review because “[t]here can be no

doubt that such a circumstance inherently results in a complete

miscarriage of justice . . . .” 417 U.S. at 346 (internal

quotation marks omitted).

Like a number of our sister circuits, we have held that

“ordinary misapplication of the guidelines does not amount to a

miscarriage of justice.” United States v. Mikalajunas, 186 F.3d

490, 496 (4th Cir. 1999) (collecting cases); see also United

15
States v. Pregent, 190 F.3d 279, 283-84 (4th Cir. 1999).

However, we have not offered a considered explanation of what

constitutes an “ordinary” Guidelines error as opposed to

something more fundamental. In Mikalajunas, we held that an

improper two-level enhancement for restraint of the victim did

not amount to a complete miscarriage of justice. 186 F.3d at

496. In Pregent, we considered whether a defendant whose

criminal history had been wrongly calculated resulting in a

sentence four months too long was entitled to seek relief from

the supervised release portion of his sentence. 190 F.3d at 283

& n.4. Although we assumed that the error was cognizable on

collateral review, we dismissed the defendant’s claim as

untimely. We have not had occasion to address the specific

issue presented in this case: whether the career offender

enhancement is so significant that its improper application

amounts to a fundamental miscarriage of justice. 7

7
Our friend in dissent accuses us of running “roughshod”
over circuit precedent. This is demonstrably not the case.
Aside from the fact, explained below, that the career offender
enhancement is plainly not a run-of-the-mill guideline, the
dissent ignores the particulars of our prior cases. In United
States v. Pettiford, 612 F.3d 270, 275 (4th Cir. 2010), the
petitioner filed a motion to vacate his Armed Career Criminal
Act enhanced sentence following a state court vacatur of two of
his predicate offenses. We denied the motion because it was
undisputed that, following the vacatur, the petitioner still had
three remaining ACCA qualifying convictions in his record. Id.
at 276-77. Thus, our statement regarding the availability of
collateral review to correct Guidelines errors was pure dicta.
(Continued)
16
 Three courts of appeals have, however, confronted this

precise question, albeit with differing results. In Sun Bear v.

United States, 644 F.3d 700 (8th Cir. 2011) (en banc), the

Eighth Circuit considered the question following the Supreme

Court’s decision in Begay, which limited the category of

defendants eligible for career offender status by narrowing the

definition of a crime of violence. See 553 U.S. at 148. 8 Sun

Bear held that career offender status is an “ordinary question[]

of [G]uideline interpretation,” and that misapplication of this

status is not an error that results “in a complete miscarriage

of justice.” 644 F.3d at 704 (citation omitted). 9

The Seventh Circuit initially reached a different

conclusion. In Narvaez, the court held that because of changes

Likewise, as explained above, in Pregent we assumed that the
petitioner had stated a cognizable claim before dismissing his
petition as untimely. 190 F.3d at 284. Moreover, the
petitioner in Pregent was arguing for the termination of the
supervised release portion of his sentence, a far cry from the
situation confronting Whiteside. Id. at 283.
8
The court first acknowledged that Begay set forth a
substantive rule that could be applied retroactively on
collateral appeal. We need not consider this preliminary issue
with respect to Simmons, since we have previously determined
that Simmons announced a substantive rule that may be raised in
a habeas proceeding. See Miller v. United States, 735 F.3d 141,
147 (4th Cir. 2013).
9
It is worth noting that the sentence imposed in Sun Bear
was within the Guidelines range applicable even in the absence
of the career offender enhancement. Id. at 705.

17
to the law under Begay and Chambers v. United States, 555 U.S.

122 (2009), the defendant “never should have been classified as

a career offender and never should have been subjected to the

enhanced punishment reserved for such repetitive and violent

offenders.” Narvaez, 674 F.3d at 627 (emphasis omitted). The

court deemed the resulting career offender sentence a

miscarriage of justice even though it fell beneath the

applicable statutory maximum. Id. at 629. The court explained:

The imposition of the career offender status branded
Mr. Narvaez as a malefactor deserving of far greater
punishment than that usually meted out for an
otherwise similarly situated individual who had
committed the same offense. It created a legal
presumption that he was to be treated differently from
other offenders because he belonged in a special
category reserved for the violent and incorrigible.
No amount of evidence in mitigation or extenuation
could erase that branding or its effect on his
sentence. His designation as a career offender simply
took as unchallenged a premise that was not true and
gave him no way of avoiding the consequences of that
designation.

Id.

Narvaez, however, dealt with a sentence issued prior to

United States v. Booker, 543 U.S. 220 (2005), when the

Guidelines remained mandatory. Shortly after the Narvaez

decision, the Seventh Circuit limited its holding to sentences

issued under the mandatory Guidelines. See Hawkins v. United

States, 706 F.3d 820, 824 (7th Cir. 2013) supplemented on denial

of reh’g, 724 F.3d 915 (7th Cir. 2013), cert. denied, 134 S. Ct.

18
1280 (Feb. 24, 2014). In Hawkins, the court held that post-

Booker, Guidelines errors were “less serious,” and that as long

as the sentence imposed was beneath the statutory maximum it was

not subject to correction on collateral review.

The Eleventh Circuit then reached the opposite conclusion

of both the Eighth and Seventh Circuits. In a case that was

recently vacated pending rehearing en banc, Spencer v. United

States, 727 F.3d 1076, 1087 (11th Cir. 2013), vacated pending

reh’g en banc, (11th Cir. Mar. 7, 2014), the court stated that

an erroneous career offender enhancement amounts to a

fundamental miscarriage of justice because “categorization as a

career offender is not merely a formal requirement of a criminal

procedural rule.” This was true because, even post-Booker, “the

Guidelines are the heart of the substantive law of federal

sentencing.” Id. at 1087. Central to the panel’s reasoning was

the Supreme Court’s recent decision in Peugh v. United States,

___ U.S. ___, 133 S. Ct. 2072 (2013).

In Peugh, the Court held that retroactive application of a

Guideline that increases a defendant’s applicable Guidelines

range violates the Ex Post Facto Clause of the Constitution.

Id. at 2084. In the process, the Court reaffirmed the important

role that the Guidelines play in sentences issued post-Booker.

The Court stated that the Guidelines remain “the lodestone of

sentencing,” id., and that “[t]he post-Booker federal sentencing

19
scheme aims to achieve uniformity by ensuring that sentencing

decisions are anchored by the Guidelines . . . .” Id. at 2083

(emphasis added). The Court also noted the requirement that

“‘district courts must begin their analysis with the Guidelines

and remain cognizant of them throughout the sentencing

process.’” Id. (quoting Gall v. United States, 552 U.S. 38, 50

n.6 (2007)). The Court explained that this and other hurdles

“make the imposition of a non-Guidelines sentence less likely,”

id. at 2083-84, and that an increase in the Guidelines range

still creates a “significant risk of a higher sentence.” Id. at

2088. In support, the Court cited Sentencing Commission data

showing that, absent a government motion for a variance, roughly

eighty percent of defendants since 2007 have received within-

Guidelines sentences. Id. at 2084.

Relying on the Supreme Court’s recent pronouncements and

citing additional statistical data concerning the career

offender enhancement, the Spencer panel held, “[w]e cannot

pretend that, because of Booker, career offender status no

longer matters to sentence length.” 727 F.3d at 1088. Instead,

“an erroneous career offender Guideline calculation, even though

20
advisory, . . . can amount to a fundamental defect in the

sentencing analysis.” Id. at 1088-89. 10

We agree with the Spencer panel’s reasoning and hold that

an erroneous application of the career offender enhancement

amounts to a fundamental miscarriage of justice that is

cognizable on collateral review. By no rubric can the impact of

the career offender enhancement be considered “ordinary.” The

Supreme Court has recognized that career offender status creates

“a category of offender subject to particularly severe

punishment.” Buford v. United States, 532 U.S. 59, 60 (2001).

And as cited in Spencer, Sentencing Commission data show the

continued impact of the enhancement on sentences administered

post-Booker. For example, in 2012, the mean sentence for

criminal history category VI non-career offenders was 84 months

and the median was 60 months. For career offenders, those

figures increased to a mean of 163 months and a median of 151

months. For drug trafficking offenses, criminal history

category VI non-career offenders received a mean sentence of 115

10
After Peugh, the panel in Hawkins released supplemental
opinions discussing Peugh’s impact on its case. See 724 F.3d
915 (7th Cir. 2013). Disagreeing with the Eleventh Circuit, the
court upheld its earlier decision that the advisory nature of
the Guidelines prevented the petitioner from obtaining relief.
Id. at 916-17.

21
months and a median of 96 months; those figures jumped to 154

months and 144 months respectively for career offenders.

Whiteside’s case is representative of the enhancement’s

dramatic impact. Absent the enhancement, he would have faced a

Guidelines range of 140 to 175 months; after it was applied, his

range skyrocketed to 262 to 327 months. 11 The district court

eventually departed downward from this range to a period of 210

months; but that is exactly the point: the court departed

downward from what was believed to be the applicable Guidelines

range in fashioning the ultimate sentence. The Guidelines

range, although advisory, retained its anchoring effect

throughout Whiteside’s sentencing. It is just that the anchor

was dropped in the wrong place. The Supreme Court has

recognized this effect, stating that “[e]ven if the sentencing

judge sees a reason to vary from the Guidelines, ‘if the judge

uses the sentencing range as the beginning point to explain the

decision to deviate from it, then the Guidelines are in a real

sense the basis for the sentence.’” Peugh, 133 S. Ct. at 2083

(quoting Freeman v. United States, 564 U.S. ___, ___, 131 S. Ct.

2685, 2692 (2011) (plurality opinion)) (emphasis in original).

11
These figures put aside consideration of the statutory
minimum penalty, which, of course, we also know was improperly
applied in light of Simmons.

22
 In Whiteside’s case, had the district court begun with the

correct range, it almost certainly would have imposed a

different sentence. Consider that if the court had employed the

same twenty percent downward departure based on substantial

assistance, Whiteside would have received a sentence of 112

months as compared to 210 months. And in the abstract, it is

highly unlikely that any defendant with a Guidelines range of

140 to 175 months who has been granted a § 5K1.1 motion for a

downward departure would receive a sentence 35 months in excess

of the high-end of that range. At the very least, the § 3553

factors supporting such an increase would be subject to rigorous

review under Gall on direct appeal.

It is not by accident that the career offender enhancement

so significantly impacts defendants’ sentences. Unlike most of

the Guidelines, which are based on the policy calculations of

the Sentencing Commission, the career offender enhancement

derives from a congressional requirement. A statute provides

that “[t]he Commission shall assure that the [G]uidelines

specify a sentence to a term of imprisonment at or near the

maximum term authorized” for those who qualify for the

enhancement. 28 U.S.C. § 994(h). Heeding this charge, the

Commission fashioned strict penalties for career offenders:

their criminal history categories are automatically boosted to

VI, the highest possible rung, and their offense levels become

23
tied to the statutory maximum penalty as opposed to the actual

conduct of conviction. See U.S.S.G. § 4B1.1(b). Both factors

contributed to the significant increase in Whiteside’s

Guidelines range.

Clearly then, the impact of the career offender enhancement

is far from ordinary. It is certainly nothing like the two-

level enhancement for restraint of the victim which we rejected

as a source of habeas relief in Mikalajunas. That case presents

a far better example of a garden variety Guidelines adjustment

that, while possibly having an impact on the defendant’s

sentence, cannot be said to constitute a fundamental miscarriage

of justice. In contrast, an enhancement that casts the

defendant as a hopeless recidivist worthy of the strictest

possible punishment, and that has the effect of robbing a

defendant of his freedom for some eight years, is fundamentally

different. 12

The government is certainly correct in remarking that this

case does not present exactly the kind of error recognized by

12
The dissent faults us for failing to provide a “non-
arbitrary” line delimiting the types of sentencing errors that
constitute “extraordinary circumstances.” Post at 47. Given
the inherent folly of attempting to forecast the contours of
“extraordinary” events, our review is quite properly limited to
the case before us, and we decide only that when subsequent case
law makes manifestly clear that a petitioner was wrongly
designated a career offender he may challenge his sentence
through a § 2255 motion.

24
the Supreme Court in Davis. The petitioner in Davis was

convicted for actions later deemed not criminal. 417 U.S. at

346. The Court remarked that “[t]here can be no room for doubt

that such a circumstance inherently results in a complete

miscarriage of justice . . . .” Id. (internal quotation marks

and citation omitted). We reached a similar result in applying

Simmons to vacate a felon-in-possession conviction in Miller.

Here, the instant conviction for which Whiteside was sentenced

remains valid. Regardless, though, Whiteside is almost

certainly serving time he would not be absent the enhancement.

The mere fact that he was properly convicted does not somehow

excuse an obviously legally erroneous sentence. 13

13
The dissent refuses to acknowledge the basic truth
underlying our decision: that Whiteside is not, and was not,
properly designated a career offender. Our sentencing regime
prior to Simmons was overinclusive; it swept up defendants whose
criminal histories, when viewed individually – a general bugaboo
of the dissent – did not expose them to the enhancement.
Simmons corrected this mistake by directing district courts to
examine the specifics of the defendant’s predicate convictions.
Under this approach, there is no question Whiteside should not
have received the enhancement. Simply because a criminal
defendant was at one point classified a career offender does not
mean that classification was ever correct. Neither the Eighth
nor Seventh circuits had any trouble recognizing that by
narrowing the definition of the terms “crime of violence” and
“violent felony,” Begay and Chambers exposed “errors” in how the
Guidelines had been applied. See Sun Bear, 644 F.3d at 704;
Hawkins, 706 F.3d at 823. The effect of Simmons on Whiteside’s
case is no different. This point is underscored by our decision
in Miller finding Simmons to have announced a new substantive
rule retroactive on collateral review. 735 F.3d at 147. In
Miller, we recognized that by “alter[ing] ‘the class of persons
(Continued)
25
 Nor does the fact that Whiteside was sentenced beneath the

applicable statutory maximum mitigate the mistake. Contrary to

the government’s contention, this fact alone does not make a

sentence “lawful,” for several reasons. First, such a

conclusion is contrary to our well-established principles of

appellate review. While sentencing review is highly

deferential, that “does not mean there is no review at all.”

United States v. Abu Ali, 528 F.3d 210, 268-69 (4th Cir. 2008).

“If Gall had intended to dispense with any semblance of

meaningful review, there would have been no need for the

decision . . . to direct district courts to ‘correctly

calculat[e] the applicable Guidelines range.’” Id. at 265-66

(quoting Gall, 552 U.S. at 49). And when sentencing courts vary

from the Guidelines, they must “consider the extent of the

deviation and ensure that the justification is sufficiently

that the law punishes,’” Simmons had a dramatic impact on the
substantive rights of criminal defendants. Id. at 146 (quoting
Schriro v. Summerlin, 542 U.S. 348, 353 (2004)). The Miller
court had no hesitation in overturning the petitioner’s
conviction – and his accompanying sentence of 72 months,
potentially less time than Whiteside is wrongly serving - even
though the conviction was originally consistent with controlling
precedent. Id. at 143, 147. Given the continued importance of
the Guidelines generally post-Booker, and the impact of the
career offender enhancement in particular, there is no reason,
in theory or in practice, to reach a different result here. At
the very least, there can be no honest question that Whiteside’s
designation as a career offender was in fact “erroneous.”

26
compelling to support the degree of the variance.” Gall, 552

U.S. at 50. We have demonstrated our willingness to vacate non-

Guidelines sentences that are unreasonable in light of the

district court’s explanations. See, e.g., United States v.

Engle, 592 F.3d 495, 505 (4th Cir. 2010); Abu Ali, 528 F.3d at

268-69.

Of course, these standards are utilized only on direct

appeal. But they highlight the rigor with which we view our

role in ensuring that each and every defendant sentenced in

federal court receives a fair and reasonable sentence, to say

nothing of a lawful one.

The animating principles of fundamental justice are no

different here. First, through no fault of his own, Whiteside’s

opportunity for such review did not arise until after the period

in which to file a direct appeal had lapsed. Had Whiteside

challenged his career offender status on direct appeal, his

argument would have been rejected by our pre-Simmons line of

cases. See United States v. Harp, 406 F.3d 242 (4th Cir. 2005);

United States v. Jones, 195 F.3d 205 (4th Cir. 1999). He should

not be punished – and we mean literally punished, as in

additional time spent in federal prison, time which the law does

not countenance – for this fact. Acknowledging that a defendant

would likely be entitled to a vacated sentence on direct appeal

but not on a timely filed habeas motion simply due to the timing

27
of one of our decisions contributes to the conclusion that

denial of review operates a complete miscarriage of justice.

Second, the Supreme Court just last year told us that the

advisory nature of the Guidelines does not cure the harm that

results from utilizing an incorrect Guidelines range as a

starting point. See Peugh, 133 S. Ct. at 2086; see also

Spencer, 727 F.3d at 1087 (“The Seventh Circuit [in Hawkins] may

think that mistakenly categorizing a defendant as a career

offender became not very serious once Booker made the Guidelines

advisory, but the Supreme Court told us in June . . . that the

Guidelines are still ‘the lodestone of sentencing.’” (quoting

Peugh, 133 S. Ct. 2084)) (citation omitted). In Peugh, the

Court ruled that retroactive application of a Guideline violates

the Constitution even when the vacated sentence is beneath the

statutory maximum. The Court stated, “that a district court may

ultimately sentence a given defendant outside the Guidelines

range does not deprive the Guidelines of force as the framework

for sentencing.” Peugh, 133 S. Ct. 2076. And though Peugh

concerned a direct appeal, it found error of constitutional

magnitude, indicating that the mistake also would have been

correctable on collateral review.

In addition to the continued vitality of the Guidelines in

an advisory system, Peugh also drew on the principles of

fairness and justice that animate the Ex Post Facto Clause. Id.

28
at 2085 (“[T]he Clause also safeguards a fundamental fairness

interest . . . in having the government abide by the rules of

law it establishes to govern the circumstances under which it

can deprive a person of his or her liberty or life.” (internal

quotation marks and citation omitted) (ellipsis in original));

id. (“[The Clause] does not merely protect reliance interests.

It also reflects principles of fundamental justice.”). We find

that these principles map easily onto our analysis of whether

Whiteside was subject to a fundamental miscarriage of justice.

Because of the career offender enhancement, Whiteside’s sentence

is plainly at odds with what he would receive were he sentenced

today. He is not a career offender, and he should not serve a

sentence that was based on his classification as one. The mere

fact that his sentence was beneath the statutory maximum does

not somehow assuage this fundamental unfairness.

In the face of this clear injustice, the government pleads

that we respect - with something approaching sanctity - the

finality of sentencing decisions. We agree that finality is an

important consideration. It encourages defendants to accept

their punishments and move forward with their lives; as well, it

minimizes the misuse of judicial resources. Perhaps most

importantly, in cases involving victims, finality offers these

individuals some degree of peace of mind and a sense that their

suffering has not been forgotten. But we do not agree that

29
these considerations, to the extent that they apply here, can or

should outweigh the plain injustice that would result from

denying the petitioner what he seeks, which is only a chance to

be sentenced according to the factors that everyone agrees

should apply. Were we to conclude otherwise, we would be

putting “bureaucratic achievement” ahead of our task of ensuring

that all those who come before us receive meaningful review of

their claims. Gilbert v. United States, 641 F.3d 1293, 1337

(11th Cir. 2011) (Hill, J., dissenting). We are more than mere

gatekeepers. Congress has given us the authority on collateral

review to relieve errors that amount to fundamental defects in

process or justice. Erroneous application of the career

offender enhancement works such an injustice, and we will not

turn a blind eye to so obvious an error simply for the sake of

finality. 14

14
Unfortunately, our dissenting colleague sounds the alarm
that after today’s decision no criminal sentence is safe from
collateral attack. The dissent’s attempts to expand our holding
on our behalf could only result from its larger, misguided goal
of convincing the reader that habeas relief is somehow harmed by
its utilization. Somewhat amazingly, the dissent is explicit on
this point. Post at 68. With due respect to our colleague’s
views, habeas review is not merely a deterrent that fulfills its
purpose by its threatened use; criminal defendants are aided
only when it is employed. The dissent would have its own
exaltation of the history of the Great Writ and § 2255 relief
contribute to the mechanism’s futility. Accusing us of Whig
history, the dissent’s approach is rank with the fearful
mistrust of individualized decision-making inherent to
traditional conservatism. The suggestion that district courts
(Continued)
30
 Because we find that Whiteside suffered a fundamental

miscarriage of justice, we need not address his additional claim

that the error violated his constitutional rights to due

process. We have, however, considered the constitutional

question to the extent necessary to grant a certificate of

appealability, which has yet to issue in this case. See 28

U.S.C. § 2255(c) (permitting issuance of a certificate of

appealability only where petitioner “has made a substantial

showing of the denial of a constitutional right”) (emphasis

added). A certificate of appealability may issue on a

constitutional question that is “debatable.” Miller-El v.

Cockrell, 537 U.S. 322, 337, 338 (2003). We are satisfied that,

for the same reasons discussed above with regard to the

fundamental defect/miscarriage of justice claim, it is at least

debatable that erroneous application of the career offender

enhancement deprived Whiteside of his liberty in violation of

and future panels of this court cannot discern actual injustices
from less serious errors casts too critical an eye on the judges
throughout our circuit. In short, we simply do not share the
view that the criminal justice system is somehow harmed when
defendants are sentenced according to a proper understanding and
application of the law.

31
his due process rights. We therefore grant a certificate of

appealability. 15

IV.

For the reasons stated above, we hold that equitable

tolling applies to Whiteside’s claim. We also hold that

erroneous application of the career offender enhancement amounts

to a fundamental miscarriage of justice that can be corrected on

collateral review. We grant a certificate of appealability,

vacate Whiteside’s sentence, and remand the case for

resentencing.

VACATED AND REMANDED FOR RESENTENCING

15
Although Whiteside fashioned his due process claim on the
Supreme Court’s decision in Hicks v. Oklahoma, 447 U.S. 343
(1980), we think any such claim more aptly derives from Simmons
itself. For this reason, we need not address the government’s
position that the claim is barred by the non-retroactivity
doctrine of Teague v. Lane, 489 U.S. 288 (1989) (holding that
new rules of criminal procedure may not be raised in post-
conviction proceedings), since we have already held that Simmons
announced a substantive rule that is applicable on collateral
review. See Miller, 735 F.3d at 147.

32
DAVIS, Senior Circuit Judge, concurring:

I am pleased to join Judge Gregory’s extraordinarily

compelling opinion, which fully responds to the dissent’s

overwrought and formalistic protestations that our judgment here

presages an end to law as we know it. (Evidently, it is not

enough simply for the dissent to say that there is no

miscarriage of justice shown on this record.)

The dissenting opinion is hopelessly pleased with itself.

This is not surprising, as it prostrates itself at the altar of

finality, draped in the sacred shroud of judicial restraint.

There is much that could be said about the dissenting opinion’s

paean to finality, but one can hardly say it more poignantly or

more persuasively than has Judge Rovner. See Hawkins v. United

States, 724 F.3d 915, 919-25 (7th Cir. 2013) (Rovner, J.,

dissenting from the denial of rehearing), en banc reh’g denied,

725 F.3d 680 (7th Cir. 2013) (Rovner, J., joined by Wood,

Williams, and Hamilton, JJ., dissenting from denial of rehearing

en banc).

In any event, what’s remarkable is that, as viewed through

the lens of our good friend’s dissenting opinion, it is

perfectly fine for the United States Department of Justice,

which is to say the Executive Branch, to bypass supposed

reverence for finality on a case-by-case basis, through waivers

of limitations and other devices, see ante, Maj. op., n.6, but

33
the Third Branch is duty-bound never to acknowledge instances in

which law’s interest in finality must give way to competing

values rooted in our shared abhorrence of manifest injustice. To

devolve to the Executive Branch sole authority to identify a

cognizable miscarriage of justice amounts to judicial

abdication, not judicial restraint. Such an approach enjoys no

legitimate place in our scheme of institutional checks and

balances. The Third Branch’s transcendent role, in our enviable

but imperfect system of criminal justice, is to afford

protection from the loss of individual liberty resulting from

profoundly erroneous decision-making, and not least of all,

erroneous decision-making by the Third Branch itself, as in this

very case.

The dissenting opinion favors what’s “finished” over what’s

“right” and thereby blinks at a profound miscarriage of justice.

It is wrong to do so.

34
WILKINSON, Circuit Judge, dissenting:

Deangelo Whiteside was properly designated a career

offender in the course of his federal sentencing proceedings.

Now, years later, the majority vacates that sentence. In

invalidating Whiteside’s sentence, the majority creates a

circuit split over whether career-offender designations are

cognizable on collateral review, and ignores settled law as to

whether changes in circuit precedent can reset the statute of

limitations for post-conviction review of federal criminal

proceedings.

The majority opinion represents a dramatic expansion of

federal collateral review that is unsupported by law or

precedent. It makes a shambles of the retroactivity doctrines

that have long safeguarded the basic finality of criminal

convictions. It disrupts the orderly administration of our

criminal-justice system.

If it were purely a matter of orderly administration, that

might be an arid basis on which to deny relief. But there was

no injustice done here. Whiteside pled guilty to possession

with intent to distribute at least 50 grams of crack cocaine in

violation of 21 U.S.C. § 841(a)(1), and his two predicate felony

drug offenses plainly qualified him for career-offender status

under U.S.S.G. § 4B1.1, a status to which Whiteside did not

object.

35
 None of these convictions has ever been invalidated. No

procedural or substantive irregularity ever marked the plea or

sentencing proceedings. In short, Whiteside was sentenced

according to the law as it existed at that time. Absent a

constitutional violation or miscarriage of justice, neither of

which is remotely present here, that is all a criminal defendant

can ask or expect. Moreover, the defendant must raise the

petition in a timely manner, which Whiteside has failed to do.

My colleagues attempt a basic restructuring of the purposes

of collateral review in not one, but two, respects. It is bad

enough that the majority envisions collateral proceedings as a

form of error correction intended, not so subtly, to supplant

direct review. The comparative question the majority poses is

even worse. It inquires whether yesterday’s result was the same

that would or should obtain today. To the contrary, collateral

review is what its name implies: whether the proceedings under

review conformed to law as it instructed at the time. If they

did, the rule of law was honored and upheld, and further inquiry

is impermissible.

Because any other disposition of this case would open

concededly lawful proceedings to endless and untimely collateral

attack, I would affirm the district court’s dismissal of the

petition. For the reasons set forth below, I respectfully

dissent.

36
 I.

The majority opinion creates a square circuit conflict over

whether allegedly erroneous career-offender designations in

particular, and what Sentencing Guidelines errors in general,

are cognizable on a 28 U.S.C. § 2255 petition for collateral

review. On one side are the opinions of the Seventh and Eighth

Circuits holding challenges to career-offender designations not

cognizable. See Hawkins v. United States, 706 F.3d 820, 823

(7th Cir. 2013), supplemented on denial of reh’g, 724 F.3d 915

(7th Cir. 2013), cert. denied, 82 U.S.L.W. 3308 (U.S. Feb. 24,

2014) (No. 13-538); Sun Bear v. United States, 644 F.3d 700,

705-06 (8th Cir. 2011) (en banc). On the other side are my

colleagues in the majority and, until recently, an opinion in

the Eleventh Circuit, see Spencer v. United States, 727 F.3d

1076, 1088-89 (11th Cir. 2013), vacated pending reh’g en banc,

(11th Cir. Mar. 7, 2014) (No. 10-10676). As I see this dispute

as both a primary and threshold issue, I shall address it first.

Like traditional habeas corpus, § 2255 “does not encompass

all claimed errors in conviction and sentencing.” United States

v. Addonizio, 442 U.S. 178, 185 (1979). A trial error that is

neither constitutional nor jurisdictional is cognizable under

§ 2255 only if it constitutes “a fundamental defect which

inherently results in a complete miscarriage of justice, [or] an

omission inconsistent with the rudimentary demands of fair

37
procedure.” Hill v. United States, 368 U.S. 424, 428 (1962).

Courts have consistently reaffirmed this principle since Hill.

See, e.g., Brecht v. Abrahamson, 507 U.S. 619, 634 n.8 (1993);

United States v. Timmreck, 441 U.S. 780, 783-84 (1979); United

States v. Mikalajunas, 186 F.3d 490, 495-96 (4th Cir. 1999).

As neither Whiteside nor the majority claims that the

district court lacked jurisdiction when it sentenced him as a

career offender, Whiteside’s claim is only cognizable if it

alleges a constitutional error or a fundamental defect resulting

in a miscarriage of justice. Whiteside can satisfy neither of

these requirements.

A.

The heart of collateral review is the correction of

constitutional error. In fact, a certificate of appealability,

which is necessary to appeal from a district court’s final order

in a § 2255 proceeding, requires the petitioner to make “a

substantial showing of the denial of a constitutional right.”

28 U.S.C. § 2253(c)(2). Whiteside has made no “substantial

showing” of the denial of a “constitutional right.” And even if

he had made such a showing, he could not possibly prevail on the

merits of his claim.

The only colorable constitutional claim even plausibly

available to Whiteside is that he was denied due process in

violation of the Fifth Amendment. But there was no denial of

38
due process here. There is no claim of procedural irregularity

occurring at any point in these proceedings. While the

sentencing regime in force at the time of Whiteside’s sentencing

was later overturned in United States v. Simmons, 649 F.3d 237,

241 (4th Cir. 2011) (en banc), nothing in that case suggests

that Whiteside’s sentence failed to comply with the law in force

at the time the sentence was imposed. The method for analyzing

predicate state-court convictions applied in Whitside’s case had

been affirmed by numerous panels of this court. See, e.g.,

United States v. Harp, 406 F.3d 242, 246 (4th Cir. 2005); United

States v. Jones, 195 F.3d 205, 207 (4th Cir. 1999). Indeed, the

case that overturned the rule in force at the time of

Whiteside’s sentencing did not occur until August 2011, well

after Whiteside’s own case was finalized in August 2010.

I thus cannot embrace the paradox that a manifestly lawful

criminal proceeding amounts to an unlawful deprivation of due

process. Lawful one day, unlawful the next -– it makes no

sense. The doctrinal hook for Whiteside’s due process

challenge, the Supreme Court’s decision in Hicks v. Oklahoma,

447 U.S. 343 (1980), provides no support for his claim. In

Hicks, the jury imposed a mandatory-minimum 40-year sentence

after being instructed that it was required to do so in light of

the petitioner’s two prior state convictions. Later, the

Oklahoma Court of Criminal Appeals declared the mandatory-

39
minimum law unconstitutional but refused to vacate the

petitioner’s sentence. The Supreme Court reversed, finding that

the petitioner’s due process rights were violated when the

jury’s discretion to sentence below the mandatory-minimum 40-

year term was improperly limited, even though the sentence

imposed was beneath the statutory maximum. See Hicks, 447 U.S.

at 344-46.

Hicks differs markedly from this case: the Hicks jury was

barred from exercising its full sentencing discretion, whereas

the district court here not only recognized that it had

discretion to depart from the Guidelines range, but in fact did

so when it sentenced Whiteside to a below-Guidelines sentence.

This distinction makes all the difference. Whiteside was

entitled to a sentence somewhere between the statutory minimum

and maximum, imposed after the Guidelines range was properly

calculated in accordance with the law that existed at the time.

This he received, and thus there is no violation of any sort

anywhere to be found.

But even if Hicks could be bent and stretched to support

Whiteside’s due process claim, it would still be procedurally

unavailable to him. Under Teague v. Lane, 489 U.S. 288 (1989),

a court may not apply a new rule of constitutional criminal

procedure on habeas except in two narrow and infrequent

instances: where the rule places conduct outside the scope of

40
criminal sanction, see Saffle v. Parks, 494 U.S. 484, 494

(1990), or constitutes a “‘watershed rule[] of criminal

procedure’ implicating the fundamental fairness and accuracy of

the criminal proceeding,” id. at 495 (quoting Teague, 489 U.S.

at 311 (plurality opinion)); see also United States v. Martinez,

139 F.3d 412, 416 (4th Cir. 1998) (holding that Teague applies

to § 2255 petitions).

Teague insisted, then, that retroactivity doctrine not

succumb to a severe case of presentism, where a decision later

in time not only becomes the law, but seeks to discredit all

that went before. Thus, a rule is new for Teague purposes if it

was not “dictated by precedent existing at the time the

defendant’s conviction became final.” Graham v. Collins, 506

U.S. 461, 467 (1993) (quoting Teague, 489 U.S. at 301) (emphasis

and internal quotation marks omitted). A novel “application of

an old rule in a manner that was not dictated by precedent”

counts as a new rule for Teague purposes. Stringer v. Black,

503 U.S. 222, 228 (1992).

Because Hicks does not apply at all to Whiteside’s

situation, let alone squarely address it, Whiteside’s attempt to

extend Hicks would require us to announce and retroactively

apply a new rule of constitutional criminal procedure on

collateral review: namely that a criminal defendant has a

constitutional right to an amended sentence based on later

41
decisional law that calls into question an advisory Guidelines

calculation manifestly correct at the time it was imposed. This

case is thus very different from Miller v. United States, in

which we held that, under the retroactivity principles announced

in Schriro v. Summerlin, 542 U.S. 348 (2004), Simmons was a

substantive rule and thus applied retroactively where the

petitioner’s § 2255 petition alleged actual innocence of a

conviction for firearm possession by a felon. 735 F.3d 141,

145-47 (4th Cir. 2013). Here, by contrast, Whiteside asks us to

announce a novel due process rule that is completely distinct

from Simmons itself.

Furthermore, Whiteside’s proposed new rule would not fit in

either of the Teague exceptions. It does not place any conduct

outside the reach of the criminal law. Nor does it present the

exceedingly rare case of a “watershed rule of criminal

procedure,” since the procedural rule that Whiteside wants us to

announce is not “implicit in the concept of ordered liberty.”

Teague, 489 U.S. at 311 (quoting Mackey v. United States, 401

U.S. 667, 693 (1971) (Harlan, J., concurring in the judgments in

part and dissenting in part)) (internal quotation marks

omitted). Thus, Teague forbids the constitutional relief that

Whiteside seeks.

Seeking to avoid Teague’s restrictions, the majority tries

to hang its constitutional case on Simmons itself and issue the

42
certificate of appealability on that basis. See Maj. Op. at 31

& n.15. But Simmons, even if declared retroactive by Miller, is

a case about statutory interpretation -- namely the

interpretation of federal sentencing law -- not the

Constitution. Given that Hicks is far afield and that any rule

derived obliquely from it cannot possibly be made retroactive

under Teague, Whiteside has no constitutional claim and no

entitlement to a certificate of appealability.

B.

Given that Whiteside has no available constitutional claim,

the majority must show that, in light of Simmons, his sentence

is marred by a fundamental defect that resulted in a miscarriage

of justice. This it cannot do. Although some questions of

federal law are cognizable on § 2255, advisory Guidelines

determinations are not except in the most extraordinary of

circumstances. This is not such a case, and underlying the

majority’s attempt to find Whiteside’s claim cognizable are

three serious and pervasive errors.

First, the majority refuses to recognize that, after United

States v. Booker, 543 U.S. 220 (2005), errors in calculating

Guidelines ranges are “less serious” than they were previously

because the ranges are no longer binding on sentencing judges.

Hawkins, 706 F.3d at 824. The situation might be different if

the Guidelines were still mandatory. But those who fought for

43
so long to escape the binding strictures of Guidelines sentences

cannot now complain that just because they influence sentencing

behavior they must be treated as binding law. Far from binding,

they may not even be presumed reasonable. See Gall v. United

States, 552 U.S. 38, 50 (2007). The majority today refuses to

respect the major tradeoff of the post-Booker regime: now that

the Guidelines are merely advisory, they lack the force of

binding law at the sentencing phase and thus the ability to

activate collateral review. As Justice Sutherland observed, if

laws are not “upheld when they pinch as well as when they

comfort, they may as well be abandoned.” Home Bldg. & Loan

Ass’n v. Blaisdell, 290 U.S. 398, 483 (1934) (Sutherland, J.,

dissenting). The majority disregards this honored maxim and

seeks to have it both ways.

That the Guidelines are advisory is no mere theoretical

point; on remand, the district court will be perfectly free to

impose the exact same sentence on Whiteside. It is notable that

the district court granted Whiteside only a limited downward

departure for substantial assistance, a departure that was

itself broadly discretionary. See United States v. Pearce, 191

F.3d 488, 492 (4th Cir. 1999). From a recommended Guidelines

range of 262 to 327 months, the district court departed by less

than 20 percent from the bottom of the Guidelines range. The

district court could have departed downward significantly more

44
but did not, strongly suggesting that it viewed Whiteside’s

criminal record as serious and the Guidelines range as generally

appropriate.

The scenarios spun by the majority on what might or might

not happen on resentencing are nothing more than rank

speculation. The majority suggests that the district court

would likely be unable to satisfy 18 U.S.C. § 3553’s sentencing

factors and “rigorous review under Gall on direct appeal” if it

departed by 20 percent above the top of the newly calculated

Guidelines range of 140 to 175 months and imposed an identical

sentence of 210 months. Maj. Op. at 23. Quite apart from this

bald attempt to put the hammer to the district court, such

speculation ignores the “broad sentencing discretion” afforded

trial judges, Alleyne v. United States, 133 S. Ct. 2151, 2163

(2013), and the lengthy criminal record described in Whiteside’s

presentencing report that will be available for consideration on

resentencing. Whiteside’s record includes, but is not limited

to, 10 controlled-substances offenses, 7 counts of assault with

a deadly weapon on a government officer, and additional counts

of assault, hit and run, and resisting a public officer --

convictions that Simmons does nothing to undermine. This

lengthy record is impossible to minimize, since, quite

independently of the career-offender designation, Whiteside’s

extensive criminal history caused the presentencing report to

45
recommend a criminal-history category of V. Thus, the

assumption underlying the majority’s ruling -- that but for the

career-offender enhancement Whiteside could have shaved years

and years off his sentence -- is highly questionable.

Second, the majority argues that, because the Guidelines

still exert a substantial influence on sentencing, career-

offender designations are serious enough to be cognizable on

collateral review. No one could deny that the Guidelines are

still influential even after Booker. Mere influence on the

ultimate sentence, however, is insufficient to warrant

correction under § 2255. See, e.g., Daniels v. United States,

532 U.S. 374, 376 (2001) (holding that § 2255 cannot generally

be used to challenge predicate convictions under the Armed

Career Criminal Act of 1984); Addonizio, 442 U.S. at 190

(holding that § 2255 is unavailable to prisoner seeking

resentencing when post-sentencing changes in parole release-date

calculations allegedly increased effective sentence beyond that

which original sentencing judge intended); Mikalajunas, 186 F.3d

at 496 (holding that erroneous sentencing enhancement for

restraint of victim was “ordinary misapplication of the

[Guidelines] that does not amount to a miscarriage of justice”).

The majority never explains how the reality of error

correction customarily reserved for direct appeal is to be

reconciled with the broad scope it now proposes for § 2255

46
review. Nor can it, since there is no clear line to

differentiate why this Guidelines calculation is open to

collateral attack and others are not. The majority apparently

believes that career-offender designations are “far from

ordinary” and should be subject to challenge, Maj. Op. at 24,

but why stop there? I cannot fathom. The majority offers no

basis in law for its ruling, and the main reason given is that a

career-offender designation results in a substantially larger

prison term and “casts the defendant as a hopeless recidivist

worthy of the strictest possible punishment.” Id. It is left

to the reader to divine why the application of such a penalty

constitutes “extraordinary circumstances” justifying collateral

review. United States v. Pregent, 190 F.3d 279, 283 (4th Cir.

1999). Every Guidelines calculation may affect the sentencing

range to a greater or lesser degree, and the majority does not

even hint at a non-arbitrary dividing line. Instead of a legal

principle, all we get is the majority’s pronunciamento along

with the irrelevant observation that Congress, as it had every

right to do, outlined the contours of the career-offender

enhancement for those whose extensive history of law-breaking

posed a continuing social threat. See Maj. Op. at 23.

Finally, the majority confuses a change in law favorable to

a defendant with a fundamental breakdown in procedure or

justice. As explained above, Whiteside’s sentence was imposed

47
properly, with no procedural irregularities or substantive

errors. Thus, to hold that Whiteside’s situation warrants

§ 2255 relief implies that every change in law creates a

manifest injustice no matter how lawful the prior proceeding.

But “[p]recedential decisions come pouring out of the federal

courts of appeals and the Supreme Court.” Hawkins, 706 F.3d at

824. This ebb and flow of decisional law seldom implicates the

fundamental canons of justice. See Teague, 489 U.S. at 313

(noting that, because procedures falling under Teague’s second

exception are “so central to an accurate determination of

innocence or guilt, we believe it unlikely that many such

components of basic due process have yet to emerge”).

Rather than fundamental recastings of the foundations of

justice, most changes in law represent close and contestable

questions on which capable jurists can reasonably disagree.

Simmons is a case in point. The Simmons panel, which

incidentally included a former Supreme Court Justice, held that

Carachuri-Rosendo v. Holder, 560 U.S. 563 (2010), the basis for

the en banc majority’s decision, did not “compel[] a different

result” from the Harp regime for analyzing predicate state-court

convictions. United States v. Simmons, 635 F.3d 140, 142 (4th

Cir. 2011), rev’d en banc, 649 F.3d 237 (4th Cir. 2011). The en

banc decision featured opposing views, ably and earnestly

advanced. Compare Simmons, 649 F.3d at 239 (Motz, J.), with id.

48
at 250 (Duncan, J., dissenting), and id. (Agee, J., dissenting).

To say now that those on the losing side of the debate were

party to some “miscarriage of justice” requiring collateral

relief, Hill, 368 U.S. at 428, disserves those whom I know my

friends in the majority hold in the highest esteem.

To further say that a criminal defendant lawfully sentenced

prior to Simmons was the victim of some manifest injustice is to

adopt a naively Whig history of law as an unbroken march toward

progress and enlightenment, when in truth it is more often a

matter of fits and starts, of limitless gray areas, all bereft

of the guarantee that later attempts to reconcile public safety

with human liberty will necessarily be better than earlier ones.

The majority’s approach to retroactivity also ignores the

analogous reality that plea bargains are contracts under which,

in exchange for avoiding the uncertainties of trial, the

defendant “assumes the risk of future changes in circumstances

in light of which [his] bargain may prove to have been a bad

one.” United States v. Bownes, 405 F.3d 634, 636 (7th Cir.

2005). This assumed risk includes the forfeiture of later

advantageous legal developments. To say that a later change in

law should automatically make a plea agreement or, as here, a

lawful prior proceeding invalid is to render law provisional and

judgment advisory, good only until the inevitable next round.

49
 Once we recognize that a favorable change in law does not

automatically render prior lawfully imposed sentences unjust, it

becomes clear why collateral review is a poor forum for

correcting sentencing errors. Unlike with ineffective-

assistance-of-counsel claims, sentencing issues can usually,

even if not always, be effectively fixed on direct appeal. The

majority’s invocation of the “rigor” with which appellate courts

review sentences on direct appeal only supports this point.

Maj. Op. at 27; see also id. at 23. It does nothing to

undermine a “basic distinction between direct review and

collateral review”: that “an error that may justify reversal on

direct appeal will not necessarily support a collateral attack

on a final judgment.” Addonizio, 442 U.S. at 184.

C.

In addition to being conceptually unsound, the majority’s

holding that Whiteside’s claim is cognizable under § 2255 leads

it to misread Supreme Court precedent and run roughshod over our

own.

The Supreme Court cases upon which the majority and

Whiteside rely are in another room. In Peugh v. United States,

the Court held that the Ex Post Facto Clause forbids a district

court from using Sentencing Guidelines promulgated after the

original offense to sentence a defendant if the later Guidelines

increase the recommended sentencing range. 133 S. Ct. 2072,

50
2084 (2013). But Peugh is readily distinguishable. First, it

deals with constitutional error. Second, it deals with direct

appeal. The standard for ex post facto challenges articulated

in a case like Peugh –- that the change in law create merely “a

‘significant risk’ of a higher sentence,” Peugh, 133 S. Ct. at

2088 -- is substantially less demanding than the requirement of

a fundamental defect leading to a miscarriage of justice for

collateral attack on non-constitutional errors. And third,

there is no indication that the Supreme Court intended Peugh’s

holding to apply retroactively to already-final sentences such

as Whiteside’s. See Hawkins, 724 F.3d at 916-18.

Johnson v. United States, 544 U.S. 295 (2005), similarly

fails to support Whiteside’s position. Johnson dealt with

§ 2255’s one-year statute of limitations. There, the Supreme

Court stated that it shared the petitioner’s “preliminary

assumption that if he filed his § 2255 motion in time, he is

entitled to federal resentencing now that the State has vacated

one of the judgments supporting his enhanced sentence.” Id. at

302-03. This assumption was irrelevant to the disposition of

the case, however, since the Court held that the § 2255 petition

at issue was time-barred. Id. at 311. Furthermore, the

assumption was made in the context of the vacatur of predicate

state convictions; here, there is no question that Whiteside’s

51
state convictions are still valid and that the district court

could, would, and should consider them on resentencing.

Finally Davis v. United States, 417 U.S. 333 (1974), is

inapposite to this case. In Davis, the Supreme Court held that

§ 2255 could be used to challenge a conviction when an

intervening change in law rendered the act upon which the

conviction was based one “that the law does not make criminal.”

417 U.S. at 346. Davis held: “There can be no room for doubt

that such a circumstance ‘inherently results in a complete

miscarriage of justice’ and ‘present[s] exceptional

circumstances’ that justify collateral relief under § 2255.”

Id. at 346-47 (alteration in original). But nothing in Davis

suggests that its holding should extend to cases where, as here,

the intervening change in law did not undermine the underlying

convictions. The difference is one of night and day. To say as

the majority does that “this case does not present exactly the

kind of error” at issue in Davis is an understatement, to put it

mildly. Maj. Op. at 24.

If the majority opinion distorts Supreme Court precedent,

it tramples our own. Whiteside states that “[d]eciding this

case requires the Court to break new ground in this Circuit,” a

euphemistic way of inviting us to disregard our prior precedent.

Appellant’s Reply Br. at 27.

52
 Sadly, the invitation has been accepted. We held in United

States v. Pregent, “[b]arring extraordinary circumstances

. . . , an error in the application of the Sentencing Guidelines

cannot be raised in a § 2255 proceeding.” 190 F.3d at 283-84;

see also United States v. Goines, 357 F.3d 469, 477 (4th Cir.

2004) (“[Guidelines] claims ordinarily are not cognizable in

§ 2255 proceedings.”); Mikalajunas, 186 F.3d at 496 (“[A]

misapplication of the [Sentencing Guidelines] typically does not

constitute a miscarriage of justice.”). These cases all came

from the era in which the Sentencing Guidelines were virtually

mandatory. Their teachings are all the more compelling in the

present advisory Guidelines period. For if Guidelines

calculations were not cognizable on collateral review in their

all-but-mandatory form prior to Booker, they certainly cannot be

cognizable in their new advisory status.

Moreover, the holdings in the above cases stem from the

fact that § 2255 is designed for “cases in which ‘the sentence

was in excess of the maximum authorized by law.’” Pregent, 190

F.3d at 284 (quoting 28 U.S.C. § 2255(a)). Here, however,

Whiteside’s career-offender designation did not increase his

statutory maximum. As Judge King recognized in United States v.

Powell, because career-offender designations do not lead to

“sentences exceeding the applicable statutory maximum,” they are

thus not challengeable under § 2255. 691 F.3d 554, 563 n.2 (4th

53
Cir. 2012) (King, J., dissenting in part and concurring in the

judgment in part).

Similarly, in United States v. Pettiford, 612 F.3d 270 (4th

Cir. 2010), we ruled that there was no miscarriage of justice,

and thus no remedy available under § 2255, for a prisoner

challenging his career-offender sentence when two of the

underlying predicate convictions had been vacated but the

career-offender designation was still supported by the remaining

convictions. In that case, as here, the district court could

have imposed an identical sentence following vacatur. Thus,

there was “no evidence that [the petitioner’s] sentencing was

constitutionally defective or flawed in a fundamental way.”

Pettiford, 612 F.3d at 278.

II.

In addition to being non-cognizable, Whiteside’s claim for

relief is time-barred. 28 U.S.C. § 2255(f) provides for a one-

year statute of limitations that is triggered by one of four

conditions, whichever occurs latest:

(1) the date on which the judgment of conviction
becomes final;

(2) the date on which the impediment to making a
motion created by governmental action in violation of
the Constitution or laws of the United States is
removed, if the movant was prevented from making a
motion by such governmental action;

(3) the date on which the right asserted was initially
recognized by the Supreme Court, if that right has

54
 been newly recognized by the Supreme Court and made
retroactively applicable to cases on collateral
review; or

(4) the date on which the facts supporting the claim
or claims presented could have been discovered through
the exercise of due diligence.

28 U.S.C. § 2255(f)(1)-(4).

A.

Whiteside contends that his claim fits under (f)(4), and

that United States v. Simmons, 649 F.3d 237 (4th Cir. 2011) (en

banc), qualified as a new “fact” for purposes of that provision.

Whiteside’s suit is timely under this theory, since he filed

less than a year after Simmons was handed down. Although the

majority does not adopt Whiteside’s statutory argument, an

explanation of the statutory scheme is still necessary to

illustrate the many ways in which the majority’s equitable

holding negates it.

Whiteside grounds his argument on the Supreme Court’s

decision in Johnson v. United States, 544 U.S. 295 (2005). In

Johnson, the defendant’s sentence in the original proceeding was

enhanced on the basis of a state conviction which was later

vacated. Following vacatur, Johnson sought federal post-

conviction relief, contending that his enhanced sentence was no

longer valid. Johnson’s conviction had become final more than a

year before his § 2255 petition was filed, but the Court

concluded that the vacatur qualified as a new fact for purposes

55
of (f)(4). See Johnson, 544 U.S. at 300-02. As the Court

noted:

We commonly speak of the “fact of a prior conviction,”
and an order vacating a predicate conviction is spoken
of as a fact just as sensibly as the order entering
it. In either case, a claim of such a fact is subject
to proof or disproof like any other factual issue.

Id. at 306-07 (citation omitted).

Johnson does not govern Whiteside’s claim. Simmons

represented a change of law, not fact. The circuits to have

considered this type of issue have uniformly reached the same

conclusion. See, e.g., Phillips v. United States, 734 F.3d 573,

580 (6th Cir. 2013); Sanchez v. United States, 318 F. App’x 801,

804 & n.6 (11th Cir. 2009) (unpublished per curiam); Lo v.

Endicott, 506 F.3d 572, 575 (7th Cir. 2007); E.J.R.E. v. United

States, 453 F.3d 1094, 1098 (8th Cir. 2006); Shannon v. Newland,

410 F.3d 1083, 1088-89 (9th Cir. 2005); see also Minter v. Beck,

230 F.3d 663, 666 (4th Cir. 2000) (rejecting, in a similar

context, defendant’s attempt to invoke a change in law outside

(f)(3)).

Contrary to the vacatur at issue in Johnson, Simmons did

not directly alter Whiteside’s legal status as a prior state

offender. See Lo, 506 F.3d at 575. A conviction is a fact for

sentencing purposes, but a relevant legal rule is not. Simmons,

“unlike a predicate conviction, is a ruling exclusively within

the domain of the courts and is incapable of being proved or

56
disproved.” E.J.R.E., 453 F.3d at 1098. This point is

illustrated by the simple observation that “[w]e would never

. . . ask a jury to decide whether a judicial decision had

indeed changed [the] law in the relevant way, nor would the

parties introduce evidence on the question.” Shannon, 410 F.3d

at 1089. Indeed, if this change in law is a “fact,” then what

would not be?

Instead of altering the factual landscape, Simmons merely

announced a generally applicable legal rule. But a decision

“establishing an abstract proposition of law arguably helpful to

the petitioner’s claim does not constitute the ‘factual

predicate’ for that claim.” Id. Decisions that update the

legal significance of certain facts without modifying them do

not qualify under (f)(4). Simmons did precisely this: unlike a

vacatur decision, it altered the legal significance of

Whiteside’s prior convictions without amending the convictions

themselves. See Owens v. Boyd, 235 F.3d 356, 359 (7th Cir.

2000) (“Time begins when the prisoner knows (or through

diligence could discover) the important facts, not when the

prisoner recognizes their legal significance.”); see also United

States v. Pollard, 416 F.3d 48, 55 (D.C. Cir. 2005).

Whiteside’s (f)(4) argument fails for the additional reason

that it would effectively nullify (f)(3), which provides for

tolling in instances where the defendant’s claim is founded on a

57
right “newly recognized by the Supreme Court and made

retroactively applicable to cases on collateral review.” 28

U.S.C. § 2255(f)(3). As the Eighth Circuit has reasoned:

[The specific criteria enumerated in (f)(3) for
tolling the limitations period] impliedly reject[] the
notion that the creation of a new right by the Supreme
Court that is not made retroactive to cases on
collateral review, other rulings of law by the Supreme
Court, and decisions taken from the courts of appeal
in all instances, could trigger any of the limitations
periods enumerated under § 2255.

E.J.R.E., 453 F.3d at 1098.

If changes in law are cognizable under (f)(4), then (f)(3)

becomes superfluous because any claim brought under (f)(3) could

also be brought under (f)(4). See Lo, 506 F.3d at 575. “To

suggest, as [the petitioner] does, that any decision by any

court on any issue could constitute a ‘factual predicate’ would

swallow up the specifically delineated limitations in” (f)(3).

Id. at 576. These considerations indicate that “subsequent

interpretations of the law can be the basis of delay in filing a

§ 2255 motion only in accordance with” (f)(3) -- not (f)(4).

Sun Bear v. United States, 644 F.3d 700, 702 n.5 (8th Cir. 2011)

(en banc) (internal quotation marks omitted). Notably,

Whiteside does not even attempt to argue that his claim

satisfies the requirements specified in (f)(3).

58
 B.

Recognizing the speciousness of his statutory argument,

Whiteside asserts in the alternative -- in an argument embraced

by the majority -- that the statute of limitations should be

equitably tolled. Equitable tolling of petitions for collateral

review is available only when a defendant demonstrates “(1) that

he has been pursuing his rights diligently, and (2) that some

extraordinary circumstance stood in his way and prevented timely

filing.” Holland v. Florida, 560 U.S. 631, 649 (2010) (internal

quotation marks omitted). Under this court’s precedent,

equitable tolling is appropriate in those “rare instances where

-- due to circumstances external to the party’s own conduct --

it would be unconscionable to enforce the limitation period

against the party and gross injustice would result.” Rouse v.

Lee, 339 F.3d 238, 246 (4th Cir. 2003) (quoting Harris v.

Hutchinson, 209 F.3d 325, 330 (4th Cir. 2000)) (internal

quotation marks omitted); see also United States v. Sosa, 364

F.3d 507, 512 (4th Cir. 2004).

Whiteside claims that he was prevented from timely filing

by the unfavorable precedent that would have governed his claim

had he sued prior to Simmons. The standard announced in

Holland, however, focuses not on whether unfavorable precedent

would have rendered a timely claim futile, but on whether a

factor beyond the defendant’s control prevented him from filing

59
within the limitations period at all. See Shannon, 410 F.3d at

1090. Although Simmons plainly made a collateral attack on

Whiteside’s sentence more plausible, nothing prevented Whiteside

from filing his petition within the one-year statute of

limitations. See E.J.R.E., 453 F.3d at 1098.

This court’s decision in Minter v. Beck confirms this line

of reasoning. In that case, as here, the defendant’s claim

originally seemed foreclosed by extant precedent. After the

issuance of a favorable decision, however, he sought to

collaterally attack his sentence, invoking a provision

equivalent to (f)(2). Minter contended that the newly issued

decision, by nullifying the unfavorable precedent that had

previously barred his claim, served to remove an “impediment” to

filing. After rejecting this argument, the court held that

equitable tolling was inappropriate. Minter, 230 F.3d at 666-

67. The court reasoned that unfavorable precedent may have

rendered a timely claim unsuccessful, but did not actually bar

Minter from making the attempt. As the court observed,

“futility . . . is not a valid justification for filing an

untimely” petition. Id. at 666. Nothing in Holland undermines

this central holding. The majority’s Orwellian declaration that

Minter establishes a “bright-line rule” that must be applied on

a “case-by-case basis” is contradictory at best, and scornful of

precedent at worst. Maj. Op. at 12.

60
 Tellingly, Whiteside makes no allegation that he was unable

to file in a timely fashion -- only that doing so would probably

have been unsuccessful in light of extant case law. Indeed, any

such allegation would be frivolous given the many defendants who

filed suits prior to Simmons asserting the exact same

substantive claim that Whiteside now raises, including of course

Simmons himself. See, e.g., United States v. Brandon, 376 F.

App’x 343 (4th Cir. 2010) (unpublished per curiam); United

States v. Summers, 361 F. App’x 539 (4th Cir. 2010) (unpublished

per curiam); United States v. Simmons, 340 F. App’x 141 (4th

Cir. 2009) (unpublished per curiam), vacated, 130 S. Ct. 3455

(2010). These claims were not entirely meritless even under

then-existing precedent: the Supreme Court’s decision in

Carachuri-Rosendo v. Holder, 560 U.S. 563 (2010), and the Sixth

Circuit’s opinion in United States v. Pruitt, 545 F.3d 416 (6th

Cir. 2008), both strongly foreshadowed Simmons. Equitable

tolling should not be applied where, as here, the only

impediment to timely filing was the discouragement felt by the

petitioner on calculating his odds of success.

Furthermore, Whiteside has failed to demonstrate that

“gross injustice” would result should this court deny his

request for equitable tolling and find his claim time-barred.

See Green v. Johnson, 515 F.3d 290, 304 (4th Cir. 2008)

(internal quotation marks omitted). As explained above and

61
contrary to the majority’s assertion, see Maj. Op. at 21,

Whiteside’s petition for collateral relief fails on the merits

for the simple reason that the claimed sentencing error involved

nothing more than a miscalculation of the advisory Guidelines

range. Despite Whiteside’s contentions to the contrary, this

type of error does not represent “a fundamental defect which

inherently results in a complete miscarriage of justice.” Hill

v. United States, 368 U.S. 424, 428 (1962). For similar

reasons, a dismissal of Whiteside’s claims on procedural grounds

also falls short of constituting a “gross injustice.”

Finally, as several circuits have noted, it is quite

improper to use the doctrine of equitable tolling to circumvent

the express limitations contained in § 2255. See, e.g., Lo, 506

F.3d at 576. Equitable tolling is instead intended to address

obstacles to filing not otherwise governed by the statutory

provisions. Owens, 235 F.3d at 360. In this case, Whiteside’s

statutory and equitable arguments both stem from the change in

law precipitated by Simmons. Changes in law are governed by

(f)(3), which lays out a set of requirements that Whiteside

fails to satisfy. To permit Whiteside to “succeed on this

recharacterized argument” would thus “usurp the congressionally

mandated limits on habeas petitions.” Lo, 506 F.3d at 576.

In this case, Simmons came down roughly a year after

Whiteside’s conviction became final. That may seem a short time

62
to the majority, but its equitable reasoning applies equally to

a long history of three, five, or even ten years, or whenever a

change in circuit decisional law or Guidelines interpretation

may appear. This sort of reasoning makes a mockery of

Congress’s desire to have post-conviction petitions filed when

the evidence is not stale or missing altogether.

III.

It has often been noted that one of the casualties of

expanded collateral review is the finality of criminal

convictions. The majority pays the kind of lip service to this

value that is typical when a principle is about to be

disregarded. See Maj. Op. at 29. In the majority’s eyes,

finality is an empty and hollow concept with no meaning

comparable to a defendant’s rights to relitigation. But the

evisceration of the finality principles imposes costs, and many

of these costs are born by the judicial system. See McCleskey

v. Zant, 499 U.S. 467, 491 (1991); United States v. Addonizio,

442 U.S. 178, 184 n.11 (1979); Henry J. Friendly, Is Innocence

Irrelevant? Collateral Attack on Criminal Judgments, 38 U. Chi.

L. Rev. 142, 148-49 (1970).

As the Seventh Circuit emphasized in Hawkins, collateral

review of years-old proceedings ties up prosecutorial resources

that could otherwise be used to promptly resolve new criminal

cases. See Hawkins v. United States, 706 F.3d 820, 824 (7th

63
Cir. 2013), supplemented on denial of reh’g, 724 F.3d 915 (7th

Cir. 2013), cert. denied, 82 U.S.L.W. 3308 (U.S. Feb. 24, 2014)

(No. 13-538). Furthermore, post-conviction petitioners occupy

the time of defense counsel who might otherwise turn their

valuable but finite energies to a defense when it matters most:

at trial. And the ultimate victims of this burdened system are

other litigants, civil and criminal, who find the courthouse

door clogged by the ever-rising number of post-conviction

petitions.

By undermining finality, expansive collateral review also

harms our criminal-justice system more broadly. Because endless

collateral review keeps convictions and sentences in legal limbo

and makes it more doubtful that announced punishment will

actually be imposed, it eviscerates the deterrent effect of

criminal law. See Teague v. Lane, 489 U.S. 288, 309 (1989)

(plurality opinion). For similar reasons, it reduces public

confidence in our criminal-justice system, see Addonizio, 442

U.S. at 184 n.11. And it threatens to diminish the quality of

judging in the first instance, since, as Professor Bator

recognized long ago, there is “nothing more subversive of a

judge’s sense of responsibility, of the inner subjective

conscientiousness which is so essential a part of the difficult

and subtle art of judging well, than an indiscriminate

acceptance of the notion that all the shots will always be

64
called by someone else.” Paul M. Bator, Finality in Criminal

Law and Federal Habeas Corpus for State Prisoners, 76 Harv. L.

Rev. 441, 451 (1963).

Ultimately, repetitious litigation under the guise of

collateral error correction “disparages the entire criminal

justice system,” McCleksey, 499 U.S. at 492, by undermining a

key justification for the existence of final judgments: to give

all interested parties –- defendants, victims, and society alike

-- closure and a chance to move on and look forward rather than

back. As Justice Harlan put it:

At some point, the criminal process, if it is to
function at all, must turn its attention from whether
a man ought properly to be incarcerated to how he is
to be treated once convicted. If law, criminal or
otherwise, is worth having and enforcing, it must at
some time provide a definitive answer to the question
litigants present or else it never provides an answer
at all. Surely it is an unpleasant task to strip a
man of his freedom and subject him to institutional
restraints. But this does not mean that in so doing,
we should always be halting or tentative. No one, not
criminal defendants, not the judicial system, not
society as a whole is benefited by a judgment
providing a man shall tentatively go to jail today,
but tomorrow and every day thereafter his continued
incarceration shall be subject to fresh litigation on
issues already resolved.

Mackey v. United States, 401 U.S. 667, 690-91 (1971) (Harlan,

J., concurring in the judgments in part and dissenting in part).

At the time Justice Jackson lamented the flood of post-

conviction petitions in Brown v. Allen, the federal courts heard

approximately 500 state-prisoner habeas petitions a year. 344

65
U.S. 443, 536 n.8 (1953) (Jackson, J., concurring in the

result). In recent years, they have heard close to 20,000

annually, of which fewer than one-half of one percent have

succeeded. Joseph L. Hoffmann & Nancy J. King, Justice, Too

Much and Too Expensive, N.Y. Times, Apr. 16, 2011, at WK8.

Ultimately, “no one in a position to observe the functioning of

our byzantine federal-habeas system can believe it an efficient

device for separating the truly deserving from the multitude of

prisoners pressing false claims.” McQuiggin v. Perkins, 133 S.

Ct. 1924, 1942-43 (2013) (Scalia, J., dissenting).

Reasonable people may disagree over the proper tradeoff

between finality and error correction, but it is not up to

judges to supplant Congress’s judgment on this point with their

own. Above some constitutional crossbar, which most would agree

is easily cleared by our current system, Congress alone

possesses the power and responsibility to define the contours of

federal collateral review. And by Congress’s own terms, the

proper focus of such review is on whether, in the direct

proceedings, there was a “violation of the Constitution or laws

of the United States.” 28 U.S.C. § 2255(a). Because

Whiteside’s sentence was properly imposed according to the

undisputed law in force at the time, there was no such

violation.

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 When the majority expands the scope of § 2255 in excess of

what Congress intended, or excuses Whiteside’s untimely petition

in clear violation of statutory requirements, it augments its

own power at Congress’s expense. As is often the case in

federal post-conviction review, dissatisfaction with the

underlying provisions of the criminal law fuels expansion of

what should be a selectively utilized device for collateral

attack. Whatever problems may exist in our substantive criminal

and sentencing regimes, reform is properly committed to Congress

via its constitutional authority, not to judges through the

backdoor of collateral review.

Seldom has a court broken more china en route to a result.

Certificates of appealability, doctrines of retroactivity,

statutes of limitation, pertinent precedents are all

disregarded. Law is relegated to the margins. All that need be

staked is one’s own claim to sole possession of the “truth” and

“right.” Instead of respecting the limitations that Congress,

the Supreme Court, and our precedent have imposed on § 2255, the

majority conflates claims that are cognizable only on direct

appeal with the sort of fundamental defects that represent the

proper focus of § 2255. The Supreme Court has warned against an

approach under which

the writ would become a delayed motion for a new
trial, renewed from time to time as the legal climate
changed. . . . Wise judicial administration of the

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 federal courts counsels against such [a] course, at
least where the error does not trench on any
constitutional rights of defendants nor involve the
jurisdiction of the trial court.

Sunal v. Large, 332 U.S. 174, 182 (1947).

The majority’s approach devalues collateral review by

transforming its nature. The Great Writ, upon which § 2255 was

modeled, has earned its name not only because of its power, but

because, when used properly, it is used sparingly and to correct

certain fundamental infractions. Today, the majority renders

post-conviction review unrecognizable as compared to its

intended role at the Founding: to challenge sentences in

violation of a court’s “jurisdiction or detention by the

Executive without proper legal process.” McCleskey, 499 U.S. at

478 (internal citation omitted); see also Swain v. Pressley, 430

U.S. 372, 385-86 (1977) (Burger, C.J., concurring in part and

concurring in the judgment).

The Great Writ stands for the fundamental proposition that

government too is subject to the given law. Here the government

observed the law; it is, sadly, a court that accords no meaning

to that fact. How is it that requiring someone to serve a

sentence lawfully imposed and constitutionally rendered becomes

a “plain injustice” and a “fundamental unfairness”? Maj. Op. at

29. This path vindicates no fundamental liberty. It only

transforms collateral review into a double of direct review, a

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redundant mechanism for routine error correction, deployed to

unsettle sentences that were imposed years earlier under

governing law, in accordance with unexceptionable procedure, and

by a sovereign acting in accordance with its sovereign duty to

protect citizens from those who repeatedly violate its criminal

laws.

For the aforementioned reasons, and because I view this

decision as wholly wrong and deeply damaging to our criminal-

justice system, I respectfully dissent.

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