Thompson v. United States

United States Court of Appeals
For the First Circuit

No. 20-1267

TREZJUAN THOMPSON,

Petitioner, Appellant,

v.

UNITED STATES,

Respondent, Appellee.

APPEAL FROM THE UNITED STATES DISTRICT COURT
FOR THE DISTRICT OF MAINE

[Hon. D. Brock Hornby, U.S. District Judge]

Before

Kayatta, Lynch, and Howard,
Circuit Judges.

Seth Kretzer, with whom Law Offices of Seth Kretzer was on
brief, for appellant.
Lindsay B. Feinberg, Assistant United States Attorney, with
whom Darcie N. McElwee, United States Attorney, was on brief, for
appellee.

April 11, 2023
 LYNCH, Circuit Judge. In 2011, Trezjuan Thompson

pleaded guilty in the U.S. District Court for the District of Maine

to two counts of conspiracy to distribute a substance containing

cocaine base and one count of malicious damage or destruction of

property by fire. During sentencing in that case in 2013, the

court determined that Thompson was a "career offender" within the

meaning of the U.S. Sentencing Guidelines ("Guidelines"), a

designation which increased his advisory Guidelines Sentencing

Range ("GSR"). See U.S. Sent'g Guidelines Manual § 4B1.1 (U.S.

Sent'g Comm'n 2010) [hereinafter U.S.S.G.]. The court's

conclusion that this enhancement applied rested in part on its

determination that Thompson's 2007 Maine state court conviction

for unlawful trafficking in scheduled drugs qualified as a

"controlled substance offense" under the Guidelines -- a

determination to which Thompson's counsel did not object. See id.

§§ 4B1.1-.2.

In this collateral challenge to his sentence under 28

U.S.C. § 2255, Thompson contends that he received constitutionally

ineffective assistance of counsel at his 2013 sentencing based on

his counsel's failure to object to the use of the Maine drug

conviction as a predicate offense for the career offender

enhancement. The district court denied Thompson's § 2255 motion.

United States v. Thompson, No. 10-cr-200, 2020 WL 86446, at *2 (D.

Me. Jan. 7, 2020). We hold that Thompson has not met his burden

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of showing that his counsel's performance was deficient, and

affirm.

I.

A.

In December 2010, a federal grand jury sitting in the

District of Maine returned a six-count indictment charging

Thompson with, inter alia, two counts of conspiracy to distribute

and possess with intent to distribute a substance containing five

grams or more of cocaine base, see 21 U.S.C. §§ 841(a)(1), 846,

and one count of malicious damage or destruction of property by

fire (i.e., arson), see 18 U.S.C. § 844(i).1

In May 2011, Thompson, represented by counsel, pleaded

guilty to the two drug conspiracy counts and the arson charge.2

During his plea colloquy, Thompson affirmed that the prosecution

version of the facts was accurate. The prosecution version

specified that each of the drug conspiracies involved twenty-eight

1 The indictment also charged Thompson with two counts of
using a communication facility to commit a drug felony, see 21
U.S.C. § 843(b), and one count of possession of an unregistered
firearm, see 26 U.S.C. § 5861(d).

2 Although the plea was not pursuant to a formal plea
agreement, Thompson's counsel represented in a later hearing
before a magistrate judge that the government had "offered" to
dismiss the remaining counts, as well as a felon-in-possession-
of-a-firearm charge against Thompson under a separate indictment,
if Thompson were to plead guilty to these three counts. Consistent
with this representation, the government moved to dismiss the
remaining counts and the separate indictment after the district
court sentenced Thompson. The court granted the motion.

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grams or more of cocaine base -- more than the five grams charged

in the indictment. It also stated that the property targeted by

Thompson in the arson offense was an apartment that Thompson's

former live-in girlfriend, who had obtained a state court

protection from abuse order against Thompson, shared with her two

minor children.

The initial presentence report produced following

Thompson's guilty plea concluded that Thompson was subject to the

career offender enhancement set forth in Guidelines section 4B1.1.

Application of the enhancement increased Thompson's criminal

history category and the base offense level for the drug conspiracy

counts and lengthened his advisory GSR. See U.S.S.G. § 4B1.1; id.

ch. 5, pt. A (setting GSRs based on criminal history categories

and offense levels). As explained in more detail below, the

enhancement requires that "the defendant ha[ve] at least two prior

felony convictions of either a crime of violence or a controlled

substance offense." Id. § 4B1.1. The presentence report concluded

that this condition was satisfied by two of Thompson's prior state

court convictions: a 2006 Massachusetts conviction for assault and

battery with a dangerous weapon ("ABDW") and a 2007 Maine

conviction for unlawful trafficking in scheduled drugs.

Thompson's counsel objected that the Massachusetts ABDW

conviction did not qualify as "a crime of violence" as defined in

the Guidelines, relying on then-recent First Circuit case law

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interpreting a similar provision in the Armed Career Criminal Act

("ACCA"), 18 U.S.C. § 924(e). See United States v. Dancy, 640

F.3d 455 (1st Cir. 2011); United States v. Holloway, 630 F.3d 252

(1st Cir. 2011).3 During a presentence conference in September

2011, Thompson's counsel informed the district court that an ACCA

case involving "the exact same issue" raised in this objection was

then pending before this court.4 See United States v. Hart, 674

F.3d 33 (1st Cir. 2012).5 On Thompson's counsel's motion, the

court continued sentencing pending this court's decision in Hart.

Thompson's counsel did not challenge the use of the Maine

drug conviction as a predicate offense. At the same presentence

conference, Thompson's counsel represented to the court that he

had "t[aken] a look at the law on this and . . . th[ought he] ha[d]

a feel for it," and that Thompson "ha[d]n't admitted to the

information yet for [the] prior conviction, [but] he intend[ed]

3 Dancy and Holloway both involved the ACCA's "residual
clause," which the Supreme Court has since held unconstitutional
on vagueness grounds. Johnson v. United States, 576 U.S. 591, 606
(2015); see Dancy, 640 F.3d at 467-70; Holloway, 630 F.3d at 260-
62.

4 Thompson's counsel also represented to the court that
"Thompson's family ha[d] been in touch" with a Massachusetts lawyer
to assess whether there was a state law basis for challenging
Thompson's Massachusetts conviction.

5 Like Dancy and Holloway, Hart involved the ACCA's
"residual clause," since held unconstitutionally vague by the
Supreme Court. Johnson, 576 U.S. at 591; see Hart, 674 F.3d at
40-44.

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to." Thompson's counsel added: "I don't think that's in dispute."

While Hart was pending, Thompson's first attorney withdrew as

counsel. The court appointed a new attorney to serve as defense

counsel.

In March 2012, this court issued its opinion in Hart,

holding, unfavorably to Thompson's position, that a Massachusetts

ABDW conviction qualified as a predicate offense for ACCA purposes.

See 674 F.3d at 44. Shortly thereafter, Thompson's second attorney

withdrew as counsel. The court appointed a third attorney to serve

as Thompson's counsel.

Represented by this third attorney, Thompson moved to

withdraw his guilty plea. The district court denied the motion in

April 2013.

Thompson's third attorney advanced several arguments on

Thompson's behalf during sentencing in 2013. The third attorney

preserved Thompson's objection to the use of the Massachusetts

ABDW conviction as a predicate offense, although he acknowledged

that "the Hart decision was on point" and success on this score

would require that that decision be overruled. The district court

ruled that the career offender enhancement applied based on both

the Massachusetts ABDW conviction and the Maine drug conviction.

Defense counsel also argued that Thompson's offense

level and, as a result, his GSR should be reduced to reflect his

acceptance of responsibility through his guilty plea. See U.S.S.G.

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§ 3E1.1. The final presentence report took the position that

Thompson was not entitled to an acceptance-of-responsibility

adjustment because he "ha[d] failed to withdraw from criminal

conduct and ha[d] new criminal charges since his incarceration."

See id. § 3E1.1 cmt. n.1(B). Thompson's counsel argued that the

government had failed to substantiate the allegations of new

criminal conduct and that Thompson should receive the adjustment,

and cross-examined the witnesses offered by the government during

the sentencing hearing to prove the alleged criminal conduct. The

court found that the government had sufficiently supported the

allegations of new criminal conduct and that an adjustment for

acceptance of responsibility was unwarranted.

Thompson's third attorney further argued that, under the

Supreme Court's then-recent decision in Alleyne v. United States,

570 U.S. 99 (2013), and its earlier decision in Apprendi v. New

Jersey, 530 U.S. 466 (2000), Thompson's GSR and statutory minimum

sentence for the drug conspiracy counts had to be based on the

five grams of cocaine base charged in the indictment, rather than

the higher quantity of twenty-eight grams admitted by Thompson

during his plea colloquy and used in the presentence report's

calculations. The district court ultimately declined to resolve

this issue, making alternative findings as to the appropriate GSR

and stating that it would impose the same sentence under either

GSR.

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 Finally, defense counsel made several arguments in favor

of a downward variant sentence. Counsel observed that the Maine

drug conviction had triggered multiple enhancements under the

Guidelines, and that the court should consider this "double

counting" when determining Thompson's sentence. Counsel also

emphasized to the court various mitigating factors from Thompson's

background, including his father's history of incarceration;

Thompson's educational, mental health, and substance abuse

problems; and Thompson's efforts to take advantage of educational

and treatment opportunities while incarcerated pending sentencing.

The court noted, when pronouncing Thompson's sentence, that it had

"take[n] . . . into account" as "ameliorating things" Thompson's

"difficult childhood" and "mental and emotional issues."

The district court imposed a sentence of 327 months'

imprisonment on the conspiracy charges (below the GSR recommended

in the presentence report) and 240 months' imprisonment on the

arson charge, to be served concurrently. It reasoned that this

sentence was within the GSR if Thompson's Alleyne argument was

correct, and was an appropriate downward variance, based on

mitigating factors concerning "the defendant's upbringing and

childhood" and other statutory sentencing factors, if the

defense's interpretation of Alleyne was incorrect.

On direct appeal, this court affirmed Thompson's

conviction and sentence. United States v. Thompson, 851 F.3d 129,

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132 (1st Cir. 2017) (per curiam). The panel rejected arguments

advanced by Thompson's appellate counsel regarding the

voluntariness of Thompson's plea and the use of his Massachusetts

ABDW conviction as a career offender predicate offense. See id.

at 130-31. Those points are not at issue in this collateral

proceeding. Thompson also submitted a supplemental pro se brief

raising various additional arguments, which the panel "decline[d]

to address . . . specifically," id. at 130 n.2, because they

"lack[ed] arguable merit," id. (quoting United States v. Rose, 802

F.3d 114, 117 (1st Cir. 2015)).6

B.

In spring 2018, Thompson filed a timely pro se motion

under 28 U.S.C. § 2255 to vacate, set aside, or correct his

sentence.7 The motion challenged Thompson's guilty plea and

sentence on an array of grounds. The motion argued, in part, that

Thompson had received ineffective assistance of counsel during the

6 Thompson's pro se brief at times referenced the career
offender enhancement and, arguably, his Maine drug conviction. We
do not read the brief, however, as challenging the use of the Maine
drug conviction as a career offender predicate offense or as
alleging ineffective assistance of counsel based on failure to
make that argument in the district court. Nor does the government
develop any argument that this court's decision on Thompson's
direct appeal resolved either issue in a way that affects this
appeal.

7 Thompson filed an unsigned motion in March 2018. The
district court ordered him to file a signed motion, which he did
in April 2018.

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2013 sentencing because "any competent effective counsel" would

have challenged the use of his Maine drug conviction as a predicate

offense for the career offender enhancement. In support of this

assertion, Thompson cited this court's decision in United States

v. Mulkern, 854 F.3d 87 (1st Cir. 2017), decided nearly four years

after his sentencing. The government opposed the motion.

A magistrate judge recommended that the district court

deny the motion. Thompson v. United States, No. 10-cr-00200, 2019

WL 2453643, at *6 (D. Me. June 12, 2019). The magistrate judge

reasoned that the ineffective assistance claim failed "because an

attorney's failure to anticipate a change in the law does not

constitute deficient performance or cause prejudice." Id. at *5

n.9. Thompson filed an objection to this recommendation that

renewed his ineffectiveness argument, and the government filed a

response.

The district court adopted the magistrate judge's

recommendation and denied Thompson's motion.8 Thompson, 2020 WL

86446, at *2. The court declined to issue a certificate of

appealability because it concluded that Thompson had not made a

8 The district court denied the motion without holding an
evidentiary hearing. Thompson, 2020 WL 86446, at *2. The
magistrate judge had concluded that such a hearing was unwarranted.
Thompson, 2019 WL 2453643, at *6. Thompson did not challenge the
decision not to hold an evidentiary hearing in his request for a
certificate of appealability, and he does not mention the issue in
his brief, so we do not consider the matter.

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"substantial showing of the denial of a constitutional right."

Id. (citing 28 U.S.C. § 2253(c)(2)).

Thompson then requested that this court grant a

certificate of appealability. This court granted that request

with respect to a single issue: "[W]hether counsel provided

constitutionally ineffective assistance by failing to argue that

Thompson's [Maine drug conviction] did not qualify as a 'controlled

substance offense' for purposes of U.S.S.G. § 4B1.2(b)." This

court also granted Thompson's request for the appointment of

counsel to represent him in this appeal.

II.

In reviewing the denial of a § 2255 motion alleging

ineffective assistance of counsel, we assess the district court's

legal conclusions de novo and its factual findings for clear error.

Fernandez-Garay v. United States, 996 F.3d 57, 61 (1st Cir. 2021).

We first lay out relevant law regarding the career

offender enhancement and the Maine statute underlying Thompson's

prior drug conviction. We then analyze Thompson's ineffective

assistance claim.

A.

The career offender enhancement, which imposes increased

criminal history categories and base offense levels on qualifying

defendants, appears in section 4B1.1 of the Guidelines:

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 A defendant is a career offender if (1) the
defendant was at least eighteen years old at
the time the defendant 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) the defendant 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); see id. § 4B1.1(b) (listing effects of

enhancement). The first two conditions, as well as the status of

Thompson's Massachusetts ABDW conviction as a predicate "crime of

violence," are not at issue in this appeal, which concerns only

the purported ineffectiveness of Thompson's counsel in failing to

argue that Thompson's Maine drug conviction did not qualify as a

predicate "controlled substance offense."

"[C]ontrolled substance offense" is defined in

Guidelines section 4B1.2:

The term "controlled substance offense" means
an offense under federal or state law,
punishable by imprisonment for a term
exceeding one year, that prohibits the
manufacture, import, export, distribution, or
dispensing of a controlled substance (or a
counterfeit substance) or the possession of a
controlled substance (or a counterfeit
substance) with intent to manufacture, import,
export, distribute, or dispense.

Id. § 4B1.2(b); see id. § 4B1.1 cmt. n.1 (cross-referencing this

definition); see also United States v. Bryant, 571 F.3d 147, 157

(1st Cir. 2009) (explaining that this definition "requires that

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the statute under which the defendant was charged involves an

intent to distribute or other indicia of trafficking").

To assess whether a state conviction qualifies as a

"controlled substance offense" under this definition, a "court

should use a categorical or modified categorical approach." United

States v. Mohamed, 920 F.3d 94, 101 (1st Cir. 2019); see, e.g.,

Bryant, 571 F.3d at 156-59, 157 n.7 (applying categorical approach

to career offender enhancement). In applying the categorical

approach, rather than looking at the actual facts of the

defendant's prior offense, the court "must presume that the

conviction 'rested upon [nothing] more than the least of th[e]

acts' criminalized [by the statute of conviction], and then

determine whether" those acts satisfy the sentencing enhancement's

requirements. Moncrieffe v. Holder, 569 U.S. 184, 190-91 (2013)

(first and second alterations in original) (quoting Johnson v.

United States, 559 U.S. 133, 137 (2010)).

When the statute of conviction "contains statutory

phrases that cover several different generic crimes, some of which

[would categorically trigger the sentencing enhancement] and some

of which [would] not," courts may apply the "modified categorical

approach" and "determine which statutory phrase was the basis for

the conviction by consulting the trial record -- including charging

documents, plea agreements, transcripts of plea colloquies,

findings of fact and conclusions of law from a bench trial, and

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jury instructions and verdict forms." Johnson, 559 U.S. at 144.

Such documents are referred to as Shepard documents, after the

Supreme Court's decision in Shepard v. United States, 544 U.S. 13

(2005). See, e.g., Hart, 674 F.3d at 41. If the Shepard documents

"do not identify the offense of conviction, . . . the conviction

may only serve as a predicate offense if each of the possible

offenses of conviction would qualify as a [predicate offense]."

Holloway, 630 F.3d at 257 (citing Shepard, 544 U.S. at 26).

At the 2013 sentencing, the government offered as proof

of Thompson's Maine drug conviction a copy of a judgment dated

March 13, 2007, from a Maine superior court, which specified that

Thompson pleaded guilty to one count of "Unlawful Trafficking of

Scheduled Drugs, Class B" under Maine Revised Statutes Annotated

title 17-A, section 1103, with a "[d]ate of [v]iolation(s)" of

June 5, 2006. A class B crime in Maine carries a sentence of up

to ten years' imprisonment, greater than the more-than-one-year

sentence required to qualify as a controlled substance offense.

See Me. Rev. Stat. Ann. tit. 17-A, § 1604(1)(B) (West Supp. 2022);9

U.S.S.G. § 4B1.2(b).

9 At the time of Thompson's offense and conviction, the
ten-year maximum penalty for Class B crimes was codified in a
different section but was substantively the same. See Me. Rev.
Stat. Ann. tit. 17-A, § 1252(2)(B) (West 2006), repealed by 2019
Me. Laws ch. 113, § A-1.

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 The relevant portion of the statute of conviction,

section 1103, describes multiple "Class B crime[s]":

[A] person is guilty of unlawful trafficking
in a scheduled drug if the person
intentionally or knowingly trafficks in what
the person knows or believes to be a scheduled
drug, which is in fact a scheduled drug, and
the drug is:

A. A schedule W drug. Violation of this
paragraph is a Class B crime; . . .

C. Marijuana in a quantity of 20 pounds or
more. Violation of this paragraph is a
Class B crime;

D. Marijuana and the person grows or
cultivates 500 or more plants. Violation
of this paragraph is a Class B
crime . . . .

Me. Rev. Stat. Ann. tit. 17-A, § 1103(1-A) (West 2006). Schedule

W includes a number of drugs, including cocaine and heroin. See

id. § 1102(1).

At the time of Thompson's drug offense and conviction,

Maine law defined "Traffick" to mean:

A. To make, create, manufacture;

B. To grow or cultivate, except for
marijuana;

C. To sell, barter, trade, exchange or
otherwise furnish for consideration;

D. To possess with the intent to do any act
mentioned in paragraph C; or

E. To possess 2 grams or more of heroin or
90 or more individual bags, folds,

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 packages, envelopes or containers of any
kind containing heroin.

Id. § 1101(17), amended by 2021 Me. Laws ch. 396, § 1.10

In 2017, roughly four years after Thompson's 2013

sentencing, this court decided Mulkern. See 854 F.3d 87. Applying

the modified categorical approach, this court held that a

conviction for "trafficking" heroin under section 1103 did not

qualify as a "serious drug offense" under the ACCA -- that is, as

relevant here, an offense that "involv[es] manufacturing,

distributing, or possessing with intent to manufacture or

distribute, a controlled substance." 18 U.S.C.

§ 924(e)(2)(A)(ii); see Mulkern, 854 F.3d at 95-97. This was

because the statutory definition of "traffick[ing]" in heroin

included simple possession of two grams or more without any intent

to manufacture or distribute. See Mulkern, 854 F.3d at 94-97; Me.

Rev. Stat. Ann. tit. 17-A, § 1101(17)(E). The government does not

appear to dispute that, after Mulkern, a conviction under section

1103 for trafficking heroin during the time period of Thompson's

Maine drug conviction would not qualify as a controlled substance

offense. See U.S.S.G. § 4B1.2(b) (restricting controlled

substance offenses to offenses that "prohibit[] the manufacture,

import, export, distribution, or dispensing of a controlled

10 The statute has since been amended to eliminate
subsection (E). See 2021 Me. Laws ch. 396, § 1.

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substance . . . or the possession of a controlled substance . . .

with intent to manufacture, import, export, distribute, or

dispense"); see also Bryant, 571 F.3d at 157 (explaining that "the

definition of 'controlled substance offense' requires that the

statute under which the defendant was charged involves an intent

to distribute or other indicia of trafficking").

Two years later, in Mohamed, this court held that a

conviction under section 1103 for trafficking cocaine did qualify

as a controlled substance offense under the Guidelines. See 920

F.3d at 99-105. The upshot is that "a conviction under [section

1103] for trafficking heroin [at the time of Thompson's offense

and conviction] . . . does not categorically qualify" as a

controlled substance offense because a defendant could have been

convicted for simple possession without intent to distribute.

United States v. Mulkern, 49 F.4th 623, 633 (1st Cir. 2022)

(summarizing these decisions in ACCA context). But "in the case

of cocaine (and most other controlled substances), Maine's

statutory regime does require the jury to find distributive

intent," and so a trafficking conviction involving those drugs

does "categorically qualif[y]" as a controlled substance offense.

Id. This case law concerning Maine's trafficking statute did not,

however, exist at the time of Thompson's sentencing in 2013.

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 B.

We turn to the merits of Thompson's appeal. To succeed

in his claim of ineffective assistance of counsel, Thompson "must

show both deficient performance by counsel and resulting

prejudice." Tevlin v. Spencer, 621 F.3d 59, 66 (1st Cir. 2010)

(citing Strickland v. Washington, 466 U.S. 668, 687 (1984)). Our

analysis begins and ends with the deficiency prong.

Demonstrating deficient performance requires Thompson to

establish that his "counsel's representation 'fell below an

objective standard of reasonableness.'" Id. (quoting Strickland,

466 U.S. at 688). "Review of counsel's performance must be

deferential, and reasonableness must be considered in light of

'prevailing professional norms.'" Id. (quoting Strickland, 466

U.S. at 688). "There are countless ways to provide effective

assistance in any given case," Strickland, 466 U.S. at 689, and

there is a "strong presumption that counsel's conduct falls within

the wide range of reasonable professional assistance," Tevlin, 621

F.3d at 66 (quoting Strickland, 466 U.S. at 689); see also id.

("[A party claiming ineffective assistance of counsel] must

overcome the presumption that . . . the challenged action might be

considered sound trial strategy." (internal quotation marks

omitted) (omission in original) (quoting Strickland, 466 U.S. at

689)). As a result, "[a]n attorney's performance is

deficient . . . 'only where, given the facts known at the time,

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counsel's choice was so patently unreasonable that no competent

attorney would have made it.'" Vargas-De Jesús v. United States,

813 F.3d 414, 417-18 (1st Cir. 2016) (quoting Knight v. Spencer,

447 F.3d 6, 15 (1st Cir. 2006)).

Thompson contends that his counsel performed deficiently

at his 2013 sentencing under this standard by failing to object to

the use of the Maine drug conviction as a career offender predicate

offense. He argues that, under Mulkern's reasoning, not every

Maine trafficking conviction qualifies as a controlled substance

offense, and asserts that any "reasonable defense lawyer" would

have objected under the circumstances of Thompson's sentencing,

since the state court judgment offered by the government to prove

the Maine drug offense did not specify "the quantity or type of

drug that Thompson trafficked in." We note that, had the state

court judgment specified the type of drugs trafficked, the Mulkern

argument now made would fail if that drug were not heroin.

Although Thompson acknowledges that Mulkern was not decided until

2017, nearly four years after his 2013 sentencing, he asserts that

earlier precedent applying the categorical approach, such as the

Supreme Court's decision in Shepard, sufficed to put defense

counsel on notice of the principles underlying the decision. We

reject Thompson's argument for several reasons.

First, the line of cases beginning with Mulkern on which

Thompson relies did not exist at the time of his sentencing in

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2013. "Absent 'unusual circumstances,' 'the case law is clear

that an attorney's assistance is not rendered ineffective because

he failed to anticipate a new rule of law.'" United States v.

Castillo-Martinez, 16 F.4th 906, 918 (1st Cir. 2021) (quoting

Powell v. United States, 430 F.3d 490, 491 (1st Cir. 2005) (per

curiam)); see also Strickland, 466 U.S. at 689 ("A fair assessment

of attorney performance requires that every effort be made to

eliminate the distorting effects of hindsight . . . and to evaluate

the conduct from counsel's perspective at the time."). Based on

the law as it existed at the time of Thompson's sentencing, we

cannot say that the failure to anticipate Mulkern's holding and

challenge the use of the Maine drug conviction as a predicate

offense on that basis was "so patently unreasonable that no

competent attorney would have" acted similarly. Vargas-De Jesús,

813 F.3d at 418 (quoting Knight, 447 F.3d at 15).

It is true, as Thompson points out, that the Supreme

Court had introduced the categorical and modified categorical

approaches prior to Thompson's sentencing. See, e.g., Shepard,

544 U.S. at 16-23. But the existence of this high-level framework

does not make Mulkern a straightforward application of existing

law that any competent counsel would have anticipated. Thompson

does not argue that any binding precedent existed that applied the

categorical or modified categorical approach to the Maine

trafficking statute or to a similar statute in the context of the

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career offender enhancement and concluded that the statute, or any

of its subdivisions, categorically did not satisfy the

enhancement, such as would have previewed Mulkern's reasoning.

Case law from other circuits involving arguably similar state

statutes was mixed. Cf. Vargas-De Jesús, 813 F.3d at 418 (finding

counsel was not deficient in not raising a potential claim in part

because case law, including "out-of-circuit precedent," was

"hardly favorable" toward that claim at the time). Compare United

States v. Madera-Madera, 333 F.3d 1228, 1230-34 (11th Cir. 2003)

(concluding that conviction under state statute that classified

possession of specified quantity of heroin as "trafficking"

satisfied Guidelines provision similar to definition of controlled

substance offense), and United States v. James, 430 F.3d 1150,

1153-56 (11th Cir. 2005) (reasoning similarly in ACCA context),

aff'd on other grounds, 550 U.S. 192 (2007), and overruled on other

grounds by Johnson v. United States, 576 U.S. 591 (2015), with,

e.g., United States v. Brandon, 247 F.3d 186, 191-97 (4th Cir.

2001) (declining to infer intent to distribute, for purposes of

sentencing enhancement, from state "trafficking" statute that

criminalized simple possession of a small quantity of cocaine),

and United States v. Lopez-Salas, 513 F.3d 174, 179-81 (5th Cir.

2008) (similar). Mulkern itself reversed a district court decision

that reached the opposite result in applying the modified

categorical approach to the Maine statute. See 854 F.3d at 89.

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Nor has Thompson provided any other evidence or argument that, at

the time of his 2013 sentencing, challenging the Maine drug

conviction's predicate status in hopes of obtaining a ruling like

Mulkern would have been standard practice among defense counsel.

Cf. Strickland, 466 U.S. at 688 (discussing use of "American Bar

Association standards and the like" as tools for measuring

deficiency).

And, to the extent counsel could have anticipated that

a ruling like Mulkern may have been possible, a speculative

challenge to the use of the Maine drug conviction as a predicate

offense would have presented strategic risks. Cf. Vargas-De Jesús,

813 F.3d at 418-19 (describing strategic reasons for counsel's

declining to raise speculative legal argument). Drawing the

sentencing court's attention to, and potentially prompting the

government to offer more documentation of the specific drugs

involved in, Thompson's Maine drug offense would risk counsel's

efforts to focus the court on mitigating factors. Cf., e.g., Old

Chief v. United States, 519 U.S. 172, 185-86 (1997) (explaining

strategic reasons why defendant at trial may prefer to stipulate

to past conviction that is element of charged offense, rather than

have government present evidence of past conduct to jury).

Further, since "the Strickland standard . . . 'reflects

the reality that lawyers do not enjoy the benefit of endless time,

energy[,] or financial resources,'" "competent defense counsel is

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'entitled . . . to balance limited resources in accord with

effective . . . strategies,'" Bucci v. United States, 662 F.3d 18,

31 (1st Cir. 2011) (first quoting Rogers v. Zant, 13 F.3d 384, 387

(11th Cir. 1994); and then quoting Harrington v. Richter, 562 U.S.

86, 107 (2011)), and is not required to "raise every

conceivable . . . claim," id. (quoting Engle v. Isaac, 456 U.S.

107, 134 (1982)); see also Peralta v. United States, 597 F.3d 74,

82 (1st Cir. 2010) (per curiam) (reasoning that "counsel inevitably

must decide where to focus his or her efforts" and concluding that

counsel's reasonable decision about how to allocate resources did

not constitute deficient performance). Defense counsel could

reasonably have concluded that time and resources were better spent

developing the other arguments made at sentencing, and that

Thompson's interests were best served by keeping the court's

attention on those potentially stronger arguments.11

Second, in any event, Thompson has not established that

his counsel performed deficiently even under Mulkern and

11 This reasoning does not rest on the logic, derided by
Thompson in his reply brief, that "very good work by a defense
lawyer in one part of a case 'covers-up' or 'fills-in' or 'papers-
over' deficient performance demonstrated in some other aspect of
representation." Instead, we conclude, on the facts of this case,
that a competent defense attorney seeking to secure the best
possible outcome for Thompson at sentencing could reasonably have
concluded that Thompson's interests were best served by forgoing
a speculative challenge to the use of his Maine drug conviction as
a predicate offense in favor of other tactics. See Vargas-De
Jesús, 813 F.3d at 418-19.

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subsequent cases. Thompson does not dispute that, had his counsel

objected during sentencing, the government would have had the

opportunity to submit additional Shepard documents showing that

his Maine drug conviction was under a subdivision of the Maine

trafficking statute that does qualify as a controlled substance

offense, if such documents were available. He also does not

develop any argument that, at the time of his state offense and

conviction, the Maine trafficking statute criminalized any conduct

that would not qualify as a controlled substance offense other

than heroin-possession offenses of the type identified in

Mulkern.12 As a result, even if his counsel could have anticipated

Mulkern at the time of his sentencing in 2013, challenging the use

of the Maine drug conviction as a predicate offense would have

made sense only if his attorney believed that the conviction had

been for simple heroin possession -- or, at least, that the

government could not produce Shepard documents proving otherwise.

Thompson surely knows what drugs he trafficked in Maine,

but he has offered no evidence or even argument that his conviction

was for simple heroin possession, or that there is any reason to

12 Thompson's brief asserts that Maine law also defined
"Traffick" to include simple possession of two grams or more of
fentanyl. This provision was not added until 2015, see 2015 Me.
Laws ch. 346, § 1, and so could not have been the basis of
Thompson's 2007 conviction. Maine's legislature eliminated the
fentanyl- and heroin-specific portions of the definition of
"Traffick" in 2021. See 2021 Me. Laws ch. 396, § 1.

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believe the government would have been unable to produce Shepard

documents showing otherwise. Nor does he provide any reason to

believe that his counsel was unaware of the drugs underlying his

Maine conviction. Nothing in his argument addresses the

possibility that, based on communications with Thompson or other

investigation, Thompson's counsel reasonably concluded both that

the Maine drug conviction was not of the heroin-possession variety

and that the government would be able to prove as much in response

to any objection. Given that possibility, Thompson has not

rebutted our "strong presumption that [his] counsel's conduct

f[ell] within the wide range of reasonable professional

assistance."13 Tevlin, 621 F.3d at 66 (quoting Strickland, 466

U.S. at 689).

It is also significant that three different attorneys

who independently represented Thompson during the sentencing phase

did not raise any objection to the use of the Maine drug conviction

13 Thompson's counsel asserted at oral argument that we
should excuse the lack of support on this point by construing
Thompson's pro se district court filings liberally. But there is
simply nothing in Thompson's filings, however liberally construed,
that fills this gap in his deficiency claim. Although "courts
have historically loosened the reins for pro se parties, the right
of self-representation is not a license not to comply with relevant
rules of procedural and substantive law." Tang v. Citizens Bank,
N.A., 821 F.3d 206, 220 n.13 (1st Cir. 2016) (internal quotation
marks omitted) (quoting Eagle Eye Fishing Corp. v. U.S. Dep't of
Com., 20 F.3d 503, 506 (1st Cir. 1994)); see also, e.g., Voravongsa
v. Wall, 349 F.3d 1, 8 (1st Cir. 2003) (declining to excuse
untimeliness of habeas petition based on petitioner's pro se
status).

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as a predicate offense. Cf. White v. Fla., Dep't of Corr., 939

F.2d 912, 914 (11th Cir. 1991) (concluding that counsel was not

deficient in failing to recognize an error in a hearing transcript

because "[t]he error . . . went undiscovered by several attorneys

and judges for approximately five years . . . [and] was not

obvious"). While it is of course possible for multiple attorneys

to perform deficiently, Thompson's counsels' unanimity on this

point buttresses our conclusion that, "given the facts known at

the time, counsel[s'] choice was [not] so patently unreasonable

that no competent attorney would have made it." Vargas-De Jesús,

813 F.3d at 418 (quoting Knight, 447 F.3d at 15).

Thompson has not shown that his counsel performed

deficiently. Because Thompson "has the burden of showing both

deficient performance and prejudice," his failure to establish the

former means we need not address the latter. United States v.

Rodriguez, 675 F.3d 48, 58 (1st Cir. 2012) (citing Strickland, 466

U.S. at 687). The ineffective assistance claim fails, and we

affirm.

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