Thompson v. United States ( 2023 )

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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