In the
United States Court of Appeals
For the Seventh Circuit
____________________
No. 17-2618
MICHAEL DANIELS,
Petitioner-Appellant,
v.
UNITED STATES OF AMERICA,
Respondent-Appellee.
____________________
Appeal from the United States District Court
for the Eastern District of Wisconsin.
No. 15-CV-1440 — J.P. Stadtmueller, Judge.
____________________
ARGUED FEBRUARY 21, 2019 — DECIDED OCTOBER 4, 2019
____________________
Before EASTERBROOK, SYKES, and BARRETT, Circuit Judges.
SYKES, Circuit Judge. In 1991 Michael Daniels was sen-
tenced to 35 years in prison for drug-trafficking crimes he
committed while leading the violent Brothers of the Struggle
street gang in Milwaukee in the 1980s. Based on two of his
many prior crimes, he was sentenced as a career offender
under the then-mandatory Sentencing Guidelines. But the
designation did not affect his sentencing range, which was
360 months to life with or without it.
2 No. 17-2618
More than two decades later, Daniels moved to vacate his
sentence under 28 U.S.C. § 2255 on the authority of Johnson v.
United States, 135 S. Ct. 2551 (2015), which invalidated the
“residual clause” in the Armed Career Criminal Act as
unconstitutionally vague. Daniels argued that the identically
phrased residual clause in the career-offender guideline is
likewise unconstitutionally vague. Because one of the predi-
cate convictions for his career-offender status qualified only
under the residual clause, Daniels maintained that he was
entitled to resentencing. The district judge disagreed, relying
on Beckles v. United States, 137 S. Ct. 886 (2017), which fore-
closes vagueness challenges to the post-Booker advisory
Sentencing Guidelines. The judge certified his decision for
appeal based on uncertainty about the status of circuit
precedent regarding vagueness challenges to the pre-Booker
mandatory Guidelines.
The parties addressed that question in their initial briefs.
In the meantime, a panel of this court issued a definitive
answer, ruling that defendants who were sentenced under
the mandatory Guidelines may bring Johnson-based vague-
ness challenges to the career-offender guideline. Cross v.
United States, 892 F.3d 288, 304–06 (7th Cir. 2018). Applying
Johnson, the panel in Cross invalidated the residual clause of
the “crime of violence” definition in the career-offender
guideline and applied that ruling retroactively, authorizing
relief under § 2255. Id. at 299–304.
We directed the parties to file new briefs addressing the
effect of Cross on this case. We now affirm. Under Johnson
and Cross, Daniels was wrongly designated a career offend-
er. But the error was harmless because it did not affect his
sentence.
No. 17-2618 3
I. Background
On direct appeal 26 years ago, we described Daniels’s ex-
tensive involvement with a violent drug-trafficking organi-
zation in Milwaukee in the 1980s. See United States v. Goines,
988 F.2d 750, 756–57, 778–79 (7th Cir. 1993). To briefly recap,
Daniels helped the Brothers of the Struggle gain a foothold
in the city, ran one of the gang’s drug houses, recruited
others to join the conspiracy, and generally “ruled with the
proverbial iron fist through intimidation.” Id. at 779.
Daniels and 14 coconspirators were arrested in 1990 and
charged in a 36-count indictment with conspiracy and
related drug-trafficking and firearms offenses. After a seven-
week trial, a jury found him guilty of three crimes: (1) con-
spiracy to possess cocaine with intent to distribute, 21 U.S.C.
§§ 841(a)(1), 846; (2) using a communication facility to
further the distribution of cocaine, id. § 843(b); and (3) using
a firearm in relation to a drug-trafficking crime, 18 U.S.C.
§ 924(c). He was sentenced in 1991 under the then-
mandatory Sentencing Guidelines. His lengthy criminal
record placed him in criminal-history category V, and his
offense level was 38. Two of his prior convictions—a 1982
conviction for “rape and indecent liberties to a child” and a
1988 conviction for possession of a controlled substance with
intent to distribute—qualified as a “crime of violence” and a
“controlled substance offense,” respectively, and thus count-
ed as the two predicates necessary to trigger application of
the career-offender guideline. U.S.S.G. § 4B1.1–.2.
Accordingly, Daniels was designated a career offender
based on these two convictions, which raised his criminal-
history category to VI. But the designation had no effect on
the sentencing range. With an offense level of 38 and a
4 No. 17-2618
criminal-history category of either V or VI, the range was the
same: 360 months to life. The judge imposed concurrent
sentences of 420 months for the two drug crimes and a
consecutive sentence of 60 months for the firearm offense.
A few years later, the Supreme Court’s decision in Bailey
v. United States, 516 U.S. 137 (1995), cast doubt on the § 924(c)
conviction, and Daniels filed a § 2255 motion to vacate his
sentence. The judge granted the motion, vacated the firearm
conviction, and resentenced him on the two remaining
counts. His offense level increased to 40 because he became
eligible for a firearm-related enhancement that was previ-
ously precluded by the separate § 924(c) conviction. His
criminal-history category remained the same. As before, the
career-offender designation had no effect: The sentencing
range was 360 months to life with or without it. The judge
reimposed the same 420-month sentence for the two remain-
ing convictions, explaining that he saw no reason to revisit
the original sentence.
Daniels unsuccessfully appealed the judge’s resentencing
decision and thereafter filed a flurry of motions challenging
other aspects of his sentence. One such motion attacked the
career-offender designation. While that motion was pending,
Daniels wrote to the U.S. Probation Office asking it to review
his career-offender label. On review the Probation Office
determined that Daniels was not in fact a career offender
because the 1988 drug conviction was for simple felony drug
possession, not possession with intent to distribute, 1 and
1 The original charge was for possession of controlled substances with
intent to distribute.
No. 17-2618 5
none of his other convictions qualified as career-offender
predicates.
On February 9, 2009, the Probation Office sent a letter to
the Bureau of Prisons removing the career-offender designa-
tion to ensure that the original misdesignation would not
affect Daniels’s security classification. The letter also ex-
plained that eliminating the career-offender label did not
change Daniels’s Guidelines sentencing range, which re-
mained 360 months to life. The judge reviewed the letter and
acknowledged that “one of [Daniels’s] prior felony convic-
tions was erroneously found to be a ‘controlled substance
offense’ as defined in § 4B1.2, when it in fact did not meet
the definition.” Because the Guidelines range did not
change, the judge took no further action.
In 2015 Daniels moved to reduce his sentence under
18 U.S.C. § 3582(c)(2) based on a retroactive amendment to
the Sentencing Guidelines for certain drug offenses. He
reminded the court that he was no longer a career offender.
The Probation Office reduced Daniels’s offense level in light
of the amendment but advised the judge that the change did
not affect the Guidelines range and therefore no adjustment
in the sentence was warranted. The judge agreed and denied
the motion.
Later in 2015 Daniels filed the present § 2255 motion. He
again challenged his career-offender designation, only this
time he invoked the Supreme Court’s decision in Johnson,
which invalidated the residual clause in the Armed Career
Criminal Act on vagueness grounds. 135 S. Ct. at 2563.
Daniels argued that the identically worded residual clause in
the career-offender guideline is likewise unconstitutionally
vague. His 1982 conviction for sexual abuse of a minor had
6 No. 17-2618
been counted as a crime of violence only under the residual
clause, so in light of Johnson, Daniels had yet another reason
to attack the career-offender designation. 2
The district court stayed the motion to await further legal
developments—notably, the Supreme Court’s decision in
Beckles, which rejected a Johnson-based vagueness challenge
to the residual clause of the career-offender guideline in the
post-Booker advisory Guidelines. Beckles, 137 S. Ct. at 895.
Beckles did not, however, address whether offenders who
were sentenced under the mandatory Guidelines may raise
vagueness challenges. Id. at 892.
After Beckles, the judge lifted the stay and surveyed our
pre-Beckles circuit precedent on vagueness challenges to the
Sentencing Guidelines, including United States v. Hurlburt,
835 F.3d 715 (7th Cir. 2016) (en banc); United States v. Tichen-
or, 683 F.3d 358 (7th Cir. 2012); and United States v. Brierton,
165 F.3d 1133 (7th Cir. 1999). Briefly stated, in Brierton we
ruled that the mandatory Guidelines cannot be challenged
on vagueness grounds, 165 F.3d at 1139, and Tichenor ex-
tended that holding to the post-Booker advisory Guidelines,
2 As we’ve noted, over the years Daniels filed multiple requests for relief
from his sentence. Other than the Bailey challenge to the § 924(c) convic-
tion, none were captioned as a § 2255 motion. Under Magwood v.
Patterson, 705 U.S. 320 (2010), and Suggs v. United States, 705 F.3d 279, 282
(7th Cir. 2013), the sentence imposed after Daniels successfully chal-
lenged his § 924(c) conviction is deemed a new judgment for § 2255
purposes. Based on his many other requests for relief, however, the
present § 2255 motion might constitute a successive petition requiring
authorization. See 28 U.S.C. § 2255(h). Based on the “convoluted proce-
dural history” of the case and the substantive changes in the law, the
government agrees that it should not be so construed. We accept that
concession.
No. 17-2618 7
683 F.3d at 364–65. But we overruled Tichenor in Hurlburt
based on the Supreme Court’s intervening decision in Peugh
v. United States, 569 U.S. 530 (2013). Hurlburt, 835 F.3d at 722–
25. Beckles clearly displaced Hurlburt, but the status of earlier
circuit caselaw remained unclear. The judge denied the
§ 2255 motion but granted a certificate of appealability,
noting the “analytical minefield” in our caselaw after Beckles.
This appeal followed. While briefing was underway,
Daniels submitted additional pro se filings to the district
court concerning his career-offender status. On Novem-
ber 14, 2018, the Probation Office again wrote to the Bureau
of Prisons noting the mistaken career-offender designation
and explaining that the misdesignation did not affect Dan-
iels’s Guidelines range and “will not impact the terms or
conditions of his supervised release.” The Probation Office
also explained that if Daniels ever faces a future revocation
proceeding, a criminal-history category V will be used “in
any [Guidelines] calculations.”
After the parties filed their initial briefs but before oral
argument, another panel of this court addressed the “analyt-
ical minefield” that troubled the district judge, ruling that
the Supreme Court’s holding in Beckles is limited to the
advisory Guidelines. Cross, 892 F.3d at 304–07. The mandato-
ry Guidelines, Cross explained, are meaningfully different
and may be challenged on vagueness grounds. Id. Applying
the logic of Johnson, the Cross panel invalidated the residual
clause in the career-offender guideline and applied that
ruling retroactively to authorize § 2255 relief for two defend-
ants who were sentenced as career offenders under the
mandatory Guidelines. Id. at 307.
8 No. 17-2618
In light of Cross, we struck the parties’ briefs and in-
structed them to file new briefs addressing its effect on this
case.
II. Discussion
This § 2255 appeal presents only legal issues, so our re-
view is de novo. Hrobowski v. United States, 904 F.3d 566, 569
(7th Cir. 2018). As we’ve explained, Daniels was sentenced as
a career offender based on a 1988 drug conviction and a 1982
conviction for sexual abuse of a minor. The former was
counted as a “controlled substance offense” for career-
offender purposes. U.S.S.G. § 4B1.2(b). The latter was con-
sidered a career-offender predicate under the residual clause
of the definition of “crime of violence.” Id. § 4B1.2(a)(2). For
years Daniels has argued that neither conviction actually
qualifies, making the career-offender label erroneous.
We begin with the obvious: The Probation Office uncov-
ered and corrected the career-offender misdesignation long
ago. In 2009 the Probation Office determined that the 1988
drug conviction was for simple felony possession of con-
trolled substances, which doesn’t qualify as a predicate
controlled-substance offense. That knocked out one of the
two necessary predicates for the career-offender designation,
and although the error had no effect on Daniels’s sentencing
range, the Probation Office took steps to correct the misdes-
ignation with the Bureau of Prisons.
After Cross, it’s now clear that the 1982 conviction also
should not have been counted. The government has not
raised a timeliness objection to this new claim: Daniels filed
his § 2255 motion within one year of the Supreme Court’s
decision in Johnson, as required by 28 U.S.C. § 2255(f)(3).
No. 17-2618 9
And the claim is clearly cognizable under Cross. The 1982
conviction for sexual abuse of a minor was included as a
career-offender predicate only under the residual clause of
the “crime of violence” definition in the Guidelines. U.S.S.G.
§ 4B1.2(a)(2). Cross invalidated the residual clause as uncon-
stitutionally vague in light of Johnson and applied that ruling
retroactively, authorizing relief under § 2255. 892 F.3d at
299–307. Beckles wasn’t an obstacle in Cross because it only
addressed the post-Booker advisory Guidelines. See id. at 304.
Other circuits disagree, but Cross controls and Beckles is not
an obstacle here either. See D’Antoni v. United States, 916 F.3d
658, 664 n.4 (7th Cir. 2019) (collecting cases from other
circuits).
All this is undisputed. Everyone agrees that Daniels was
mistakenly designated a career offender based on two
nonqualifying predicates. “Since the parties do not dispute
the error, we [need] only address whether the error [is]
harmless.” United States v. Lomax, 816 F.3d 468, 478 (7th Cir.
2016).
The parties debate whether the Chapman or Brecht stand-
ard governs the harmless-error analysis. The former applies
to constitutional errors identified and reviewed on direct
appeal and requires the government to demonstrate that the
error “was harmless beyond a reasonable doubt.” Chapman
v. California, 386 U.S. 18, 24 (1967). The latter applies to
constitutional errors identified on collateral review under
28 U.S.C. § 2254. Under Brecht v. Abrahamson, a state prisoner
must show that the error “had [a] substantial and injurious
effect or influence in determining the jury’s verdict.”
507 U.S. 619, 623, 633–34 (1993) (quotation marks omitted).
10 No. 17-2618
The Supreme Court has not addressed which standard
applies in § 2255 cases, but some of our sister circuits have
adopted Brecht in this context. 3 We haven’t taken a firm
position, and our caselaw gestures in conflicting directions.
Compare Lanier v. United States, 220 F.3d 833, 839 (7th Cir.
2000) (applying a harmless-error test resembling the
Chapman formulation), with Sorich v. United States, 709 F.3d
670, 674 (7th Cir. 2013) (using the Brecht standard to evaluate
constitutional error in jury instructions).
We don’t need to resolve that tension. The error here is
harmless under any standard. We have long held that
Guidelines-calculation errors that don’t affect a defendant’s
sentencing range are harmless as a matter of law. See, e.g.,
United States v. Harmon, 721 F.3d 877, 892 (7th Cir. 2013)
(concluding that any error in calculating a defendant’s
criminal-history category “was harmless” because “his
guidelines range was the same—360 months to life—
whether he was in criminal history category I or II”). It’s
undisputed that the career-offender misdesignation did not
affect the Guidelines range: with or without it, Daniels faced
360 months to life in prison. Accordingly, no record-sensitive
evaluation of the type described in either Chapman or Brecht
is needed.
Daniels identifies several cases where we examined the
judge’s sentencing remarks to determine harmlessness even
though the Guidelines range was the same with or without
3 See United States v. Smith, 723 F.3d 510, 517 (4th Cir. 2013); United States
v. Dago, 441 F.3d 1238, 1246 (10th Cir. 2006); United States v. Montalvo,
331 F.3d 1052, 1058 (9th Cir. 2003) (per curiam); Ross v. United States,
289 F.3d 677, 682 (11th Cir. 2002); Murr v. United States, 200 F.3d 895, 906
(6th Cir. 2000).
No. 17-2618 11
the error. See Lomax, 816 F.3d at 479; United States v. Ander-
son, 517 F.3d 953, 966 (7th Cir. 2008). For example, he points
to language from Lomax stressing that “had the district court
relied on [the] career offender status when choosing the
appropriate sentence, the error would not have been harm-
less even though the guideline range would have been the
same.” 816 F.3d at 479. We note for starters that this was
unexplained dicta. Even so, it merely suggests that if the
judge had explicitly tied the sentence to the career-offender
misdesignation, the error would have been harmful. Here
the judge never mentioned the career-offender designation
in announcing his sentencing decision. No further inquiry is
required.
Nor does Narvaez v. United States help Daniels’s position.
There the § 2255 petitioner pleaded guilty to bank robbery
and was sentenced as a career offender based on two prior
Wisconsin convictions for failing to return to confinement.
The career-offender designation “increased the then-
mandatory sentencing range … from 100–125 months to
151–188 months,” and the judge imposed a prison term at
the midpoint of the enhanced Guidelines range. Narvaez v.
United States, 674 F.3d 621, 624 (7th Cir. 2011). After the
Supreme Court cast doubt on whether his prior convictions
qualified as “crimes of violence,” the petitioner moved to
vacate his sentence under § 2255. We reversed the district
court’s denial of relief, holding that the petitioner “never
should have been classified as a career offender and never
should have been subjected to the enhanced punishment.”
Id. at 627. Daniels compares his circumstances to Narvaez but
overlooks a crucial distinction: In that case the career-
offender misdesignation increased the Guidelines range. Not
so here.
12 No. 17-2618
Finally, Daniels argues that the career-offender misdes-
ignation carries prejudicial collateral consequences. He lists
three: The Bureau of Prison’s security-classification rules
account for an inmate’s criminal-history category, the Guide-
lines rules on supervised release similarly consider a de-
fendant’s criminal-history category, and future changes in
the law that might otherwise benefit him may not apply to
career offenders.
But the Probation Office addressed any possible collateral
effects of the misdesignation in two separate letters to the
Bureau of Prisons. Its 2009 letter explained that Daniels is
not in fact a career offender, ensuring that the initial misdes-
ignation will not affect his security classification. In the 2018
letter, the Probation Office explained that the initial misdes-
ignation “will not impact the terms of conditions of his
supervised release” and that the correct criminal-history
category will be used in any Guidelines calculations “if
Mr. Daniels face[s] future revocation proceedings.”
In short, although Daniels was wrongly designated a ca-
reer offender, the error was harmless because it did not
affect the Guidelines range. The district judge properly
denied the § 2255 motion.
AFFIRMED