United States of America v. Wayne Holroyd

United States Court of Appeals
FOR THE DISTRICT OF COLUMBIA CIRCUIT
Argued October 14, 2022 Decided April 19, 2024
No. 20-3083
UNITED S TATES OF A MERICA,
APPELLEE
v.
WAYNE HOLROYD ,
APPELLANT
Appeal from the United States District Court
for the District of Columbia
(No. 1:17-cr-00234-2)
Robin M. Earnest, appointed by the court, argued the cause
and filed the briefs for appellant.
Kevin Birney, Assistant U.S. Attorney, argued the cause
for appellee. With him on the brief were Chrisellen R. Kolb
and Elizabeth H. Danello, Assistant U.S. Attorneys.
Before: HENDERSON and P ILLARD, Circuit Judges, and
EDWARDS , Senior Circuit Judge.
Opinion for the Court filed by Circuit Judge HENDERSON.

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KAREN LEC RAFT HENDERSON, Circuit Judge: Wayne
Holroyd pleaded guilty to conspiracy to distribute and to
possess with intent to distribute more than 280 grams of a
mixture and substance containing a detectable amount of crack
cocaine. See 21 U.S.C. §§ 846, 841(a)(1) and (b)(1)(A). After
his plea but before he was sentenced, the Congress amended
the “safety valve” provision of the statute used to compute
Holroyd’s sentence, expanding the eligibility of a drug
offender to be sentenced without regard to the statutory
mandatory minimum. First Step Act of 2018, Pub. L. No. 115-
391, § 402, 132 Stat. 5194, 5221. The district court
subsequently sentenced Holroyd to the statutory minimum of
120 months’ imprisonment dictated by 21 U.S.C.
§ 841(b)(1)(A). Holroyd contends that his counsel should have
argued that he was eligible for sentencing without regard to the
statutory minimum under the recently revised safety valve
provision. See 18 U.S.C. § 3553(f). Because the United States
Supreme Court recently rejected Holroyd’s construction of one
of the safety valve provision requirements, 18 U.S.C.
§ 3553(f)(1), we affirm the district court’s sentence. Pulsifer v.
United States, 144 S. Ct. 718, 725 (2024).1
I.
Holroyd was arrested in December 2017 and charged in a
superseding indictment with one count of conspiracy and five
related counts involving the unlawful possession and
distribution of a controlled substance. In October 2018 Holroyd
pleaded guilty to one count of conspiracy to distribute and to
possess with intent to distribute more than 280 grams of crack
1 We heard oral argument in this appeal in October 2022,
shortly before the Supreme Court granted review in Pulsifer. See
Pulsifer v. United States, 143 S. Ct. 978 (2023) (granting certiorari).
By order dated January 23, 2023, we held Holroyd’s appeal in
abeyance pending Pulsifer’s resolution. Order, ECF Doc. # 1982528.

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cocaine in exchange for the government’s agreement to drop
the other counts. Holroyd attested in the agreement and at
sentencing that he had reviewed and understood the terms of
his plea agreement.
Two provisions of Holroyd’s plea agreement are relevant.
First, the plea agreement specified that, regardless of the
sentencing guidelines range otherwise calculated, Holroyd’s
conviction carried a mandatory minimum sentence of 120
months. The agreement did not stipulate Holroyd’s appropriate
criminal history category or sentencing guideline range. The
government contended that the district court should classify
Holroyd as a “career offender,” see U.S.S.G. § 4B1.1, due to
his two past convictions for controlled substance offenses, and
thus increase his potential sentence from 87–108 months to
262–327 months. The plea agreement specifically stated that
both parties retained the option to argue about the appropriate
sentencing guideline range based on Holroyd’s criminal history
at the sentencing hearing. Second, Holroyd waived his right to
appeal his sentence except as to a sentence above the statutory
maximum or applicable guidelines range or an ineffective
assistance of counsel claim.
One month after his plea hearing, Holroyd’s counsel
moved to withdraw from the case and Holroyd personally
wrote the district court to withdraw his plea. The district court
appointed new counsel to represent Holroyd and, after
consulting with that counsel, Holroyd abandoned his motion to
withdraw his guilty plea.
At Holroyd’s sentencing hearing in May 2019, the
government no longer sought to treat Holroyd as a career
offender, notwithstanding the Probation Office’s
recommendation to do so, and requested the court to sentence
him to the mandatory minimum of 120 months’ imprisonment.

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Holroyd’s counsel argued that he was not a career offender and
should receive only the statutory minimum sentence in light of
his age, the long time period between his past and current
convictions and his intervening good behavior. Counsel agreed
that Holroyd faced the mandatory minimum but requested that
the Court sentence him to no more than 120 months’
imprisonment.
At some point, Holroyd asked his counsel to argue that he
was eligible to avoid the statutory minimum based on the
recently amended safety valve provision, 18 U.S.C. § 3553(f).
See First Step Act § 402. Instead, his counsel informed the
district court that, although Holroyd believed that he was
eligible to avoid the mandatory minimum sentence, counsel
disagreed. Counsel further informed the district court that he
had “promised” Holroyd that he would “review it after the
sentencing and file a motion for reconsideration if there is an
argument to pursue on that basis.” App. 104–05. The district
court then sentenced Holroyd to the 120-month mandatory
minimum. Holroyd’s counsel did not move for reconsideration.
II.
In 1994 the Congress added a safety valve provision to the
sentencing guidelines to prevent a less culpable drug
trafficking offender from receiving the same sentence as a
more culpable offender due to the mandatory minimum
sentences associated with their crimes. Mandatory Minimum
Sentencing Reform Act of 1994, Pub. L. No. 103-322, § 80001,
108 Stat. 1796, 1985–86 (codified as amended at 18 U.S.C.
§ 3553(f)); see In re Sealed Case, 105 F.3d 1460, 1461 (D.C.
Cir. 1997) (citing H.R. R EP . NO. 103-460, at 4 (1994)); see also
Dorsey v. United States, 567 U.S. 260, 285 (2012) (Congress
enacted section 3553(f) to allow drug offender with minimal
criminal history to avoid a mandatory minimum sentence).

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Fourteen years later, the Congress amended the safety valve to
relax the criminal-history disqualifications under 18 U.S.C.
§ 3553(f)(1) and to expand a minor drug offender’s eligibility.
First Step Act § 402.
The amended safety valve provision requires the court to
sentence a defendant “without regard to any statutory minimum
sentence” if it finds:
(1) the defendant does not have—
(A) more than 4 criminal history
points, excluding any criminal history
points resulting from a 1-point offense, as
determined under the sentencing
guidelines;
(B) a prior 3-point offense, as
determined under the sentencing
guidelines; and
(C) a prior 2-point violent offense, as
determined under the sentencing
guidelines;
(2) the defendant did not use violence or
credible threats of violence or possess a firearm
or other dangerous weapon (or induce another
participant to do so) in connection with the
offense;
(3) the offense did not result in death or
serious bodily injury to any person;
(4) the defendant was not an organizer,
leader, manager, or supervisor of others in the

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offense, as determined under the sentencing
guidelines and was not engaged in a continuing
criminal enterprise, as defined in section 408 of
the Controlled Substances Act; and
(5) not later than the time of the sentencing
hearing, the defendant has truthfully provided to
the Government all information and evidence
the defendant has concerning the offense or
offenses that were part of the same course of
conduct or of a common scheme or plan, but the
fact that the defendant has no relevant or useful
other information to provide or that the
Government is already aware of the information
shall not preclude a determination by the court
that the defendant has complied with this
requirement.
18 U.S.C. § 3553(f)(1)–(5).
Holroyd contends his counsel was constitutionally
ineffective in representing him at sentencing because counsel
failed to give the correct interpretation to 18 U.S.C.
§ 3553(f)(1). He argues that his two past convictions did not
exclude him from the safety valve under section 3553(f)(1)
because the word “and” between subparagraphs (B) and (C)
must be read conjunctively so that only a defendant who has
convictions satisfying (A), (B) and (C) cumulatively is
ineligible. Holroyd insists that, had his counsel argued that he
satisfied 18 U.S.C. § 3553(f)(1) because his past convictions
did not trigger subparagraphs (A), (B) and (C), the district court
could have sentenced him below 21 U.S.C. § 841(b)’s
mandatory minimum sentence. The district court instead
sentenced him to the mandatory minimum of 120 months’
imprisonment.

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III.
A defendant who first raises an ineffective assistance
argument on appeal must provide “factual allegations that, if
true, would establish a violation of his Sixth Amendment right
to counsel.” United States v. Mohammed, 693 F.3d 192, 202
(D.C. Cir. 2012) (alterations accepted) (quoting United States
v. Poston, 902 F.2d 90, 99 n.9 (D.C. Cir. 1990)). The
allegations must establish that his counsel’s performance “fell
below an objective standard of reasonableness,” Strickland v.
Washington, 466 U.S. 668, 688 (1984), and that “there is a
reasonable probability that, but for counsel’s unprofessional
errors, the result of the proceeding would have been different,”
id. at 694.
We ordinarily remand an ineffective assistance of counsel
claim first raised on appeal for an evidentiary hearing in district
court unless it is “clear from the record that counsel was or was
not ineffective, or that the supposed defect in representation
amounted to a strategic choice by defense counsel.” United
States v. Weaver, 281 F.3d 228, 233–34 (D.C. Cir. 2002). In
addition, we do not remand an ineffective assistance claim if
the record manifests the defendant was not prejudiced. See,
e.g., United States v. Udo, 795 F.3d 24, 30 (D.C. Cir. 2015)
(“Here, remand is not needed because the record makes clear
that [the defendant] is not entitled to relief.”). Finally, we have
foregone remand if the defendant alleges his counsel was
ineffective by failing to raise an “obvious” legal argument;
instead, we have exercised de novo review of the purely legal
question. United States v. Winstead, 890 F.3d 1082, 1090 (D.C.
Cir. 2018) (“[W]e would normally remand serious claims of
ineffective assistance to the district judge to determine whether
effective counsel could have changed the result . . . . But this is

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an unusual case. The textual issue is a purely legal question.”).2
Because Holroyd’s ineffective assistance claim turns on the
resolution of a purely legal question, we conclude that remand
is unnecessary.
Holroyd alleges his counsel at sentencing was ineffective
because he failed to read 18 U.S.C. § 3553(f)(1) so as to make
Holroyd eligible for the safety valve. The sentencing hearing
transcript shows that, despite Holroyd’s request, defense
counsel declined to argue that Holroyd was eligible to avoid
the mandatory minimum sentence. Instead, counsel conceded
that the statutory minimum, 21 U.S.C. § 841(b)(1)(A), applied
to Holroyd. If counsel had made Holroyd’s requested argument
and the district court had adopted it, Holroyd could have been
sentenced to between 87–108 months’ imprisonment instead of
120 months’.
For Holroyd’s ineffective assistance argument to succeed,
he must demonstrate both that: (1) counsel’s decision not to
argue at sentencing or to move for reconsideration on the basis
of Holroyd’s eligibility for the safety valve was objectively
deficient representation; and (2) his counsel’s decision
prejudiced him at sentencing—i.e., there was a reasonable
probability that, but for counsel’s decision, he would have
received a different sentence. Strickland, 466 U.S. at 687. Both
2 In United States v. Winstead, we held that defense counsel’s
failure to raise a textual argument at sentencing—“the only serious
argument the defendant had in the entire case”—was deficient. 890
F.3d at 1090. We concluded that a remand was unnecessary,
however, because “[t]he textual issue is a purely legal question” and
“[i]f accepted, [ ] would make an enormous difference to Appellant’s
sentence.” Id. We chose to review the defendant’s argument de novo
or “as if it had been raised below.” Id.

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prongs turn on the purely legal question whether Holroyd’s
proposed interpretation of section 3553(f)(1) was correct.
The Supreme Court recently adopted a different
construction of the safety valve provision. See Pulsifer, 144 S.
Ct. at 725. The Court held that a defendant satisfies the
criminal-history requirement only when he “does not have”
more than 4 criminal-history points, excluding 1-point
offenses; “does not have” a prior 3-point offense; and “does
not have” a prior 2-point violent offense. Id. at 725. If he meets
any of Paragraph (f)(1)’s disqualifying criteria, he is ineligible
for the safety valve. Id. Thus, Paragraph (f)(1) “creates an
eligibility checklist.” Id. at 731.
The Supreme Court first addressed Paragraph (f)(1)’s
grammatical structure, concluding it supports two possible
constructions: Pulsifer’s interpretation that only a defendant
with the full package—4 criminal-history points, a prior 3-
point offense, and a prior 2-point violent offense—is ineligible
for the safety valve; and the government’s interpretation that a
defendant with any of the Paragraph (f)(1) criteria is ineligible.
Id. at 726.
Because the text on its own could support either
construction, the Supreme Court turned to Paragraph (f)(1)’s
context. Pulsifer’s (and Holroyd’s) interpretation would render
subparagraph (f)(1)(A) superfluous because subparagraphs (B)
and (C) already add up to 5 criminal-history points. Id. at 731–
33. That reading would also deny the provision’s role as a
“gatekeeper” by extending leniency to a defendant with more
serious offenses. Id. at 733–34. For example, Pulsifer’s reading
would give safety valve eligibility to a serial offender with 15
criminal-history points computed from five 3-point offenses
but offer no relief to an offender with a single 3-point offense
and a single 2-point violent offense. Id. at 734. Instead, under

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the High Court’s interpretation, a defendant cannot have any of
Paragraph (f)(1)’s criteria to qualify for the safety valve. Id. at
737.
Holroyd concedes that he has a 6-point criminal history
based on two previous 3-point offenses. He therefore does not
satisfy subparagraphs (f)(1)(A) or (B). See Pulsifer, 144 S. Ct.
at 737 (finding Pulsifer ineligible because he had “two prior
three-point offenses totaling six points”). Because Holroyd is
ineligible for the safety valve, his counsel’s decision not to
argue Holroyd’s eligibility was not deficient and did not
prejudice Holroyd. See Udo, 795 F.3d at 33 (holding defendant
was not prejudiced because there was “no reasonable
probability that the outcome of the trial would have been
different had [defendant]’s counsel done all that [the
defendant] now argues he should have”).
For the foregoing reasons, we affirm the judgment of the
district court.
So ordered.

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