United States v. Keniel Thomas

United States Court of Appeals
FOR THE DISTRICT OF COLUMBIA CIRCUIT

Argued November 19, 2020 Decided June 11, 2021

No. 19-3015

UNITED STATES OF AMERICA,
APPELLEE

v.

KENIEL AEON THOMAS, ALSO KNOWN AS DAVID MORGAN,
APPELLANT

Appeal from the United States District Court
for the District of Columbia
(No. 1:18-cr-00310-1)

Rosanna M. Taormina, Assistant Federal Public Defender,
argued the cause for appellant. With her on the briefs was A.J.
Kramer, Federal Public Defender. Tony Axam Jr., Assistant
Federal Public Defender, entered an appearance.

Nicholas P. Coleman, Assistant U.S. Attorney, argued the
cause for appellee. With him on the brief were Elizabeth
Trosman and Kathryn L. Rakoczy, Assistant U.S. Attorneys.
 2
Before: HENDERSON and GARLAND, * Circuit Judges, and
GINSBURG, Senior Circuit Judge.

Opinion for the Court filed by Senior Circuit Judge
GINSBURG.

Concurring opinion filed by Circuit Judge HENDERSON

GINSBURG, Senior Circuit Judge: Keniel Thomas, a
resident of Jamaica, pleaded guilty to one count of interstate
communication with intent to extort, in violation of 18 U.S.C.
§ 875(b), after botching a lottery scam. 1 In the plea agreement,
Thomas waived most of his rights to appeal. He retained only
the rights to claim he received ineffective assistance of counsel
and to appeal any upward departure from the sentencing
guidelines range calculated by the district court. At sentencing,
the district court did depart upward and sentenced Thomas to
nearly six years’ imprisonment.

Thomas mounts several challenges to his sentence. First,
he argues the Government plainly breached the plea agreement
at sentencing. We disagree. Second, he claims his waiver of
rights to appeal is unenforceable and then raises four issues
within the scope of the waiver. We assume without deciding
the waiver was ineffective and reject these challenges on their
merits. Third, Thomas argues the district court abused its

*
Then-Judge Garland was a member of the panel at the time this case
was submitted but did not participate in the final disposition of the
case.
1
In a lottery scam, “scammers lead victims to believe they have won
a drawing or lottery, but the cash or prizes will not be released
without upfront payment of fees or taxes. Scammers frequently
target the elderly.” U.S. Embassy in Jamaica, Lottery Scams,
https://jm.usembassy.gov/u-s-citizen-services/victims-of-
crime/scams (last visited May 14, 2021).
 3
discretion by departing upward from the guidelines range. We
find no abuse of discretion. Finally, Thomas claims his
attorney made mistakes at sentencing and during the plea
bargaining process that deprived him of his right to the
effective assistance of counsel under the Sixth Amendment to
the Constitution of the United States. We remand some of
Thomas’s ineffective assistance claims to the district court for
further fact-finding and deny the rest.

I. Background

We first discuss the plea agreement and the stipulated
facts. After that, we summarize additional evidence the
Government presented with its sentencing memorandum and
the proceedings at the sentencing hearing.

A. The plea agreement

As part of his plea agreement, Thomas stipulated to a
statement of offense that established the following facts.

***

In June 2014, Thomas made a call to William Webster,
whom Thomas knew to be an elderly former judge. Thomas
identified himself as the head of the Mega Millions lottery and
told the Judge he was the winner of an eight-figure prize. To
collect it, Webster needed only to make an advance payment of
$50,000 to cover taxes. If Thomas thought Judge Webster
would be easily fooled due to his advanced age, then he was
seriously mistaken. Perhaps unbeknownst to Thomas, he was
trying to scam a man who once headed the Federal Bureau of
Investigation. After hanging up with Thomas, Judge Webster
phoned the Bureau.
 4
The next day, Judge Webster called Thomas back, this
time recording their conversation for the FBI. Thomas restated
many of his falsehoods from the day before, except this time
the fake prize amount quadrupled and the fake tax payment
dropped to $20,000. Judge Webster humored Thomas, but did
not agree to anything. Undeterred, Thomas made several more
calls to Judge Webster over the following month.

Eventually Thomas became frustrated and resorted to
threats instead of false promises. On July 17, he called Judge
Webster’s home phone and reached his wife, Lynda Webster.
Thomas demanded the Websters pay him $6,000. If they did
not pay him, then he would have both of them killed by a sniper
and set fire to their home. To make his threats more plausible,
Thomas recounted personal identifying information about the
Judge, including his previous employment. He further told
Mrs. Webster he had been surveilling her home. He correctly
described the house and correctly stated no one had been home
the previous evening.

Thomas made more threats in additional conversations
with Mrs. Webster over the following days. On July 21, in an
especially shocking outburst, Thomas told her, “it is so easy
killing you, you just a take a shot and put it in your sniper, aim,
and the back of the head … all you see is blood and marrow
flying out.” He urged the Websters to pay him $6,000 in order
to avoid this fate.

Having no success in securing the $6,000, Thomas
apparently gave up on the Websters. Three years later, federal
agents arrested him entering the United States at a New York
airport.

***
 5
In a deal with the Department of Justice, Thomas admitted
to the facts above and pleaded guilty to one count of interstate
communication with intent to extort, 18 U.S.C. § 875(b). In
exchange, the Department agreed not to bring any additional
charges.

In the plea agreement, the parties estimated his offense
level under the Sentencing Guidelines at 20, comprising a base
offense level of 18, U.S.S.G. § 2B3.2; a two-level increase
because his extortionate conduct included death threats,
U.S.S.G. § 2B3.2(b)(1); a one-level increase because he tried
to extort more than $20,000, U.S.S.G. § 2B3.2(b)(2); a two-
level increase for conduct aimed a vulnerable victim, U.S.S.G.
§ 3A1.1; and a three-level decrease for acceptance of
responsibility, U.S.S.G. § 3E1.1. Thomas had no prior
criminal convictions, so this offense level resulted in an
estimated guidelines range of 33 to 41 months in prison. See
U.S.S.G. § 5A. In the agreement, Thomas waived his right to
appeal “except to the extent” the court sentenced him “above
the statutory maximum or the guidelines range determined by
the Court” but he reserved the right to claim he received
ineffective assistance of counsel.

B. Sentencing

After Thomas pleaded guilty, the Government submitted a
sentencing memorandum accompanied by 38 exhibits, which
gave a fuller picture of the FBI’s investigation than had the
statement of offense. The evidence suggested a long-running
and intricate conspiracy. According to the sentencing
memorandum, it was not Thomas but his associate “Stone”
who first contacted Judge Webster. In March 2014, Stone
called Judge Webster, informed him he had won the lottery,
and instructed him to send $1,000 to a California man
 6
identified in the record as “P.W.” Judge Webster immediately
contacted the FBI.

At the Bureau’s request, Judge Webster stayed in phone
and email contact with Stone, and his associates “Dudley,”
“Reinhardt,” “Davis,” and “Winslow” over the next few
months. The FBI’s investigation revealed P.W. was a victim
who had been tricked into serving as a “money mule” for
Thomas and his associates. The FBI identified dozens of other
victims in the United States, many of them elderly. Agents
were able to trace over $300,000 of payments flowing to
Thomas and his associates, but estimated the total loss was
much higher. For instance, one eighty-two year old victim
claimed to have lost over $600,000, although the FBI was able
to trace less than one-third of his loss.

Thomas did not dispute any of these facts in his sentencing
memorandum. At the sentencing hearing, however, Thomas’s
attorney objected to a paragraph in the presentence
investigation report (PSR) prepared by the Probation Office
that mentioned there were victims besides the Websters. The
district judge overruled the objection after an FBI agent
testified to the findings of the investigation. The agent’s
testimony corroborated the evidence in the Government’s
sentencing memorandum (and thus the disputed paragraph of
the PSR). The court accepted the unrebutted evidence
presented in the sentencing exhibits and the agent’s testimony
as its findings of fact.

The district court went on to impose a sentence longer than
the Government had requested. The court applied an offense-
level enhancement not mentioned in the plea agreement
because it found Thomas “demonstrated the ability to carry
out” his threats. See U.S.S.G. § 2B3.2(b)(3)(B)(ii). This
brought the sentencing guidelines range up to 46-57 months.
 7
The court then applied two upward departures suggested in the
Extortion Guideline: one for extortion that “involved organized
criminal activity” and one for “a threat to a family member of
the victim.” U.S.S.G. § 2B3.2 cmt. n.8. As a result, the court
sentenced Thomas to 71 months in prison, 30 months more
than the maximum estimated in the agreement.

II. Analysis

We begin our analysis with the alleged breach of the plea
agreement. Second, we analyze the waiver of appellate rights
in the plea agreement and the issues that it arguably bars.
Third, we review the district court’s decision to depart from the
guidelines range. In the final section, we address Thomas’s
ineffective assistance of counsel claims.

A. Breach of plea agreement

In the plea agreement, the Government promised it would
not “seek any offense-level calculation different” from the
calculation in the agreement. ECF No. 20, at 4. On appeal,
Thomas argues the Government breached the plea agreement
by seeking a sentencing enhancement for a demonstrated
ability to carry out an extortionate threat.

Because Thomas did not object at sentencing, our review
is for plain error. Puckett v. United States, 556 U.S. 129, 133-
34 (2009). We may reverse only if any breach (1) was “clear
or obvious, rather than subject to reasonable dispute,”
(2) prejudiced the defendant, and (3) resulted in a miscarriage
of justice. Id. at 135. We find no breach here regardless of the
standard of review.

The Government did not mention the demonstrated-ability
enhancement in its sentencing memorandum. At the
 8
sentencing hearing, the judge on her own initiative asked the
prosecutor about it. The prosecutor, noting he was in an
“unfortunate and somewhat difficult position,” stated it “was
our interpretation and our understanding of the facts that we
have before us that this offense did not involve the ability of
the defendant to carry out this threat given what we knew at the
time.” The judge pushed back, asking “in this case don’t we
have the defendant talking to Lynda Webster and … trying to
demonstrate with pretty concrete evidence his ability to carry
out his threat?” But the prosecutor stood his ground: “Our
position is that he was not able to otherwise demonstrate the
ability to carry that out through those threats.” The judge asked
whether the Government’s position was contrary to her reading
of cases from the Third and Seventh Circuits, which held it is
“irrelevant” whether the defendant “actually had the ability to
carry it out.” The prosecutor said, no, “we’re basing it in large
part on the facts … in our case.” The court asked whether
actual ability was irrelevant “as a legal matter” – trying to
understand whether the Government took that position
“because he was in Jamaica, we didn’t think he had the ability
to carry it out; you don’t think it applies.” The prosecutor said
no, “as a legal matter, we are not saying that.” After taking a
moment to confer with a colleague, he concluded: “We are not
arguing that legally that it doesn’t apply. We are not asking
that it apply in this case.”

There was no breach here. The Government promised to
argue for the stipulated guidelines range (which it did), but it
never promised to convince the judge this range was correctly
calculated. See Plea Agreement, ECF 20, at 5 (“[Thomas]
acknowledges that the Court is not obligated to follow any
recommendation of the Government at the time of
sentencing”).
 9
Thomas interprets the double negative in the prosecutor’s
penultimate sentence, “We are not arguing that legally that it
doesn’t apply,” as “effectively agree[ing]” the court should
apply the demonstrated-ability enhancement, and argues this
constitutes a breach. We read the transcript differently. The
prosecutor resisted the court’s characterization of the
Government’s position, namely, that the enhancement is
appropriate only where the defendant had the power to carry
out his threats, so Thomas’s being in Jamaica (and presumably
unable to harm the Websters) was dispositive. Rather, the
prosecutor seemed to agree with the court’s view of the law but
maintain that the totality of the facts did not support the
enhancement.

This is how the Government reads the transcript as well.
As it points out, nothing in the plea agreement required the
prosecutor to argue for a bright-line rule that a defendant’s
inability to make good on his threats is dispositive; to the
contrary, he had an ethical duty to answer the court’s questions
honestly.

Even if we understood the double negative as a feeble
admission the enhancement might apply, we would still hold
the prosecution did not breach the agreement. The fact is that,
as agreed, the Government did not at any point “seek” the
enhancement. The district court raised it without any
prompting – explicit or implicit – from the Government and
applied it over the Government’s repeated objection.

B. Waiver of rights to appeal

In exchange for “concessions made by the Government”
in the plea agreement, Thomas waived his right to “appeal the
sentence in this case … and the manner in which the sentence
was determined, except to the extent the Court sentence[d]
 10
[him] above the statutory maximum or guidelines range
determined by the court.” A waiver of the right to appeal is
“generally enforceable,” so long as it is “knowing, intelligent,
and voluntary.” United States v. Guillen, 561 F.3d 527, 528-
29 (D.C. Cir. 2009) (analyzing a similar waiver). Thomas
raises several issues that fall within the scope of the waiver. 2
He attempts to bypass the waiver in two ways.

First, Thomas argues that because the district court
departed upward from the guidelines range he is free to
challenge his sentence upon any ground whatsoever. This is
belied by the text of the agreement, which barred an appeal
“except to the extent” the court sentenced him above the
guidelines range. See United States v. Hunt, 843 F.3d 1022,
1027 (D.C. Cir. 2016) (“Like statutory construction,
interpretation of a plea agreement begins with plain language”
(citations omitted)). The extent to which the court sentenced
Thomas above the guidelines range is the portion of the
sentence attributable to the upward departure. Cf. Cohen v. de
la Cruz, 523 U.S. 213, 218 (1998) (interpreting “to the extent
obtained by” fraud to mean “the share … that is obtained by
fraud”). To challenge the underlying guidelines calculation or
other aspects of the sentencing would be to go beyond the
extent of the upward departure.

Second, Thomas argues the district court’s explanation of
the waiver of rights to appeal at his plea hearing effectively

2
Specifically, he asserts the district court abused its discretion and/or
clearly erred by (1) finding an incorrect “amount demanded” under
the Extortion Guideline, (2) applying the “vulnerable victim”
enhancement under U.S.S.G. § 3A1.1(b)(1), (3) applying the
demonstrated-ability enhancement, (4) describing the lottery scam as
an “extortion scheme” rather than a scheme to defraud, and (5)
failing to provide a reasonable basis for rejecting a downward
variance based upon his status as a deportable alien.
 11
altered the terms of the waiver to allow appeal on any issue in
the event of an upward departure. This contention cannot be
rejected as easily as the previous one.

Before a district court may accept a guilty plea, Rule 11(b)
of the Federal Rules of Criminal Procedure requires the judge
to “inform the defendant of, and determine that the defendant
understands,” certain important terms and consequences of the
plea agreement. The purpose of the Rule, generally, is “to
ensure that [the defendant] understands … his rights as a
criminal defendant” before entering a guilty plea. United
States v. Vonn, 535 U.S. 55, 62 (2002). A waiver of rights to
appeal is a consequential term in a plea agreement, so the Rule
specifically requires the judge to explain its terms to the
defendant and to confirm the waiver is entered knowingly,
intelligently, and voluntarily. Fed. R. Crim. P. 11(b)(1)(N); see
also United States v. Lee, 888 F.3d 503, 506 (D.C. Cir. 2018).

Due to the vital constitutional interests Rule 11 safeguards,
we have insisted that district courts “scrupulously adhere” to
its requirements. United States v. Brown, 892 F.3d 385, 395
(D.C. Cir. 2018) (quoting United States v. Shemirani, 802 F.3d
1, 3 (D.C. Cir. 2015)). If “the district court mischaracterize[s]
the meaning of the waiver in a fundamental way” at the plea
hearing, then “the district court’s oral pronouncement controls,
and the appeal is not barred.” Brown, 892 F.3d at 395 (quoting
United States v. Godoy, 706 F.3d 493, 495-96 (D.C. Cir. 2013),
cleaned up); see also, e.g., Hunt, 843 F.3d at 1028-29; United
States v. Kaufman, 791 F.3d 86, 88 (D.C. Cir. 2016). A
representative case is Brown, where the district court
summarized a waiver provision nearly identical to the one here
as follows: “[W]ith regard to certain circumstances, you may
even have … the right to appeal the sentence … on the grounds
of reasonableness.” 892 F.3d at 395. On appeal, we did not
“pause to parse the precise legal meaning of ‘reasonableness.’”
 12
Id. at 396. Instead, we refused to enforce the waiver based
upon “the common meaning” of the district court’s
pronouncement. Id.

Scrupulous implementation of Rule 11 does not require “a
litany or other ritual which can be carried out only by word-
for-word adherence to a set ‘script.’” Fed. R. Crim. P. 11(h),
Advisory Committee’s Notes to 1983 Amendment. To the
contrary, a lifeless recitation of the plea agreement is
disfavored; “a more meaningful explanation” in the judge’s
own words is preferred. Id. (quoting United States v. Saft, 558
F.2d 1073, 1079 (2d Cir. 1977)). It is, admittedly, a delicate
balance the district court must strike: Provide enough
explanation to dispel any misunderstanding without simply
reading the agreement aloud, but in doing so, take care not to
create a new or different misconception that effectively amends
the written agreement.

During the Rule 11 colloquy in this case, the court
explained the waiver as follows:

THE COURT: Do you understand that by pleading guilty
you are giving up all of your rights … to appeal your
sentence, unless you are sentenced to a period of
imprisonment longer than the statutory maximum or the
court departs upward from the applicable recommended
sentencing guideline range, which is all set out in your plea
letter at page 7, paragraph 10? Do you understand that?

THE DEFENDANT: Yes, Your Honor.

The key difference between the written agreement and the
court’s explanation is that the court paraphrased “except to the
extent” as “unless.” Thomas says there is an “arguable
 13
divergence” between the court’s explanation and the agreement
as written, and so the court’s explanation should control.

We agree the two arguably diverge insofar as “unless” is
less precise and broader than “except to the extent.” The
written terms of the agreement, as explained above, were
specific. 3 The district court’s paraphrase, taken literally, tells
the defendant he is not giving up all his rights to appeal if the
district court departs upward, but does not specify which rights
would be retained if that happened. The natural understanding,
however, is that the right retained is the right mentioned – that
is, the right to appeal the upward departure. As the
Government put the point at oral argument, “There’s no reason
why the decision to … go above the guidelines range should
then make everything else appealable. That isn’t … a
reasonable interpretation of the provision.”

In light of these conflicting considerations, I think that
whether the district court fundamentally mischaracterized the
waiver provision is a close question. But see Henderson, J.,
Concurring Op., post. We need not answer it, however, because
Thomas’s challenges to the arguably waived issues lack merit.
See United States v. Fry, 851 F.3d 1329, 1331-32 (D.C. Cir.
2017) (“Because the waiver question does not go to our court’s
jurisdiction, we can forgo deciding it if we reject [defendant’s]
sentencing challenges on the merits”).

3
This is not to say the written waiver was beyond improvement. The
written waiver in Brown, for example, was even more specific; it
stated the defendant could appeal an above-guidelines sentence but
could not “raise on appeal other issues regarding the sentencing.”
892 F.3d at 395.
 14
1. Stipulated guidelines enhancements

Thomas faults the district court for applying two offense
level enhancements recommended in the plea agreement, to
wit, the vulnerable victim enhancement, U.S.S.G.
§ 3A1.1(b)(1), and the enhancement for extortion where the
amount demanded exceeded $20,000, U.S.S.G. § 2B3.2(b)(2).
The Government argues he waived his right to challenge this
aspect of the guidelines calculation, quite apart from the
explicit waiver of his right to appeal, by negotiating and
accepting a plea deal that stipulated the enhancements apply.
Therefore, the Government argues, we should not review this
aspect of the guidelines calculation even for plain error.

The Government is correct. While we review for plain
error when a defendant has forfeited an issue through a failure
to object, we will not review at all when a defendant acts
intentionally to waive an issue. United States v. Laslie, 716
F.3d 612, 614 (D.C. Cir. 2013) (citing United States v. Olano,
507 U.S. 725, 733 (1993) for the distinction between forfeiture
and waiver). For instance, when a defendant makes a “tactical
decision” to request a certain jury instruction, he is barred from
complaining about the instruction on appeal; any error was
“invited” by the defendant. United States v. Harrison, 103 F.3d
986, 992 (D.C. Cir. 1997); Brown, 892 F.3d at 392-93; cf.
United States v. Long, ___ F.3d ___, No. 20-3064, 2021 WL
1972245, at *6-7 (D.C. Cir. May 18, 2021) (no waiver where
counsel made a “mistake” rather than employing a “strategy or
tactic”). This rule discourages sandbagging, that is,
purposefully inducing the district court to commit an error that
can form the basis for an appeal in the event of an unfavorable
result at trial or sentencing. Harrison, 103 F.3d at 992.

Negotiating a plea agreement, like requesting a jury
instruction, requires counsel to think strategically. See Guillen,
 15
561 F.3d at 530. In both situations counsel must evaluate the
various options and advise the defendant of their respective
risks and benefits. And in both situations there is a potential
for sandbagging. Therefore, we have held a defendant waives
his right to contest a guidelines adjustment to which he has
stipulated in his plea agreement: “This court does not allow
parties to reopen issues waived by stipulation at trial.” Laslie,
716 F.3d at 615.

We have no doubt that Thomas intentionally waived the
issues he now seeks to raise; there was no mere forfeiture or
mistake. Thomas’s plea agreement provided for an offense
level increase because the “amount demanded” exceeded
$20,000, U.S.S.G. § 2B3.2(b)(2), and another increase because
“a victim of the offense was a vulnerable victim,” U.S.S.G.
§ 3A1.1(b)(1). At the Rule 11 hearing, the judge asked Thomas
whether he understood the estimate in the plea agreement that
his offense level would be increased “by one offense level
because you demanded over $20,000[] and by two offense
levels because the two victims were vulnerable victims.”
Thomas confirmed that he understood. When the Probation
Office produced the PSR, it confirmed the parties’ guidelines
calculation. In his sentencing memorandum Thomas adverted
to this portion of the PSR but did not object to it. Finally, when
at the sentencing hearing the court accepted the
recommendation to apply these two enhancements, Thomas,
through counsel, again stated he did not object.

Despite all this, Thomas argues there was no waiver
because the district court stated it had an “independent
obligation” to calculate the guidelines range rather than relying
solely upon the calculation estimated by the parties. Therefore,
he says, his stipulation did not induce the district court’s
decision and we should review for plain error after all. The
point is not well taken; the district court has an “independent
 16
obligation” to calculate the guidelines range in every case.
Freeman v. United States, 564 U.S. 522, 529 (2011). If that
undercut the defendant’s waiver here, it would do so
everywhere. Therefore, we hold Thomas waived his challenge
to the two disputed enhancements.

2. Demonstrated ability

The Extortion by … Threat of Injury Guideline provides
for an enhancement of three offense levels if “the offense
involved preparation to carry out” or the defendant “otherwise
demonstrated the ability to carry out” a threat of death, serious
injury, or kidnapping. U.S.S.G. § 2B3.2(b)(3)(B). Application
Note 6 explains the enhancement would be appropriate if, for
example, “an extortionate demand containing … a threat to
kidnap a person [were] accompanied by information showing
study of that person’s routine.” The district court applied this
enhancement over the objection of both Thomas and the
Government.

The district court did not abuse its discretion by applying
the enhancement on these facts, which closely track the
example from Note 6. Indeed, the Seventh Circuit upheld
application of the enhancement to similar facts in United States
v. Hacha, 727 F.3d 815 (2013). There the extortionist, who
threatened to harm the victim’s parents, demonstrated his
ability to carry out the threat by telling the victim (1) his
parents’ names, (2) their address in Mexico City, and (3) the
color of their house. Id. at 817. Here, Thomas showed the
Websters he knew their names, home address, and house color,
and went farther still. To corroborate his claim the house was
under surveillance, he correctly told Mrs. Webster she was not
home the night before.
 17
Thomas argues he did not demonstrate an ability to carry
out his threats because he did not actually have the ability to
carry them out; he was, after all, in Jamaica at the time. But
the defendant being out of the country is not dispositive
because having and demonstrating an ability are not the same
thing. See United State v. White, 654 F. App’x 956, 969-70
(11th Cir. 2016) (holding the defendant, who was in Mexico at
the time, demonstrated the ability to carry out threats against
Florida officials when he revealed he knew their names,
addresses, and grandchildren’s names).

3. “Extortion scheme” or “scheme to defraud”

Thomas claims the court erred by referring several times
at sentencing to an “extortion scheme.” According to Thomas,
the scheme is more accurately characterized as a “scheme to
defraud” because most calls to victims did not include
extortionate threats. Thomas never objected to the court’s
characterization at sentencing, so our review is for plain error.
Even granting that the court’s use of the phrase was inaccurate,
the challenge fails because Thomas does not explain how it
affected his substantial rights.

4. Smith variance

As a deportable alien, Thomas is not eligible for “the
benefits of 18 U.S.C. § 3624(c), which directs the Bureau of
Prisons, to the extent practicable, to assure that prisoners spend
part of … their sentences … under conditions — possibly
including home confinement — that will ‘afford the prisoner a
reasonable opportunity to adjust to and prepare for his re-entry
into the community.’” United States v. Smith, 27 F.3d 649, 651
(D.C. Cir. 1994). In his PSR, the Probation Office raised the
possibility of a downward departure to compensate for the
increased severity of Thomas’s punishment due to his
 18
ineligibility for this and other Bureau of Prisons programs (a
Smith departure). See id. at 655. At the sentencing hearing,
defense counsel declined to argue in support of this departure
because he was bound by the plea agreement not to argue for
any departures, but he said he intended to argue later for a
downward variance on those same grounds (a Smith variance).
At the appropriate time, however, defense counsel did not raise
Smith or otherwise make the case for a variance. Later in the
hearing, the district judge independently considered granting a
variance or departure under Smith. She concluded neither was
warranted: “[G]iven the fact that you committed your current
offense while you were in Jamaica, it appears to me that being
abroad doesn’t impede your criminal conduct here; I’d only
delay bringing you to justice here.”

Thomas argues the district court did not articulate a
reasoned basis for declining to impose a departure or a variance
under Smith. See Rita v. United States, 551 U.S. 338, 356
(2007) (“The sentencing judge should set forth enough to
satisfy the appellate court that he has considered the parties'
arguments and has a reasoned basis for exercising his own legal
decisionmaking authority”). Because Thomas did not object to
the district court’s statement of reasons at sentencing, our
review would be for plain error if we were to reach this
argument. United States v. Locke, 664 F.3d 353, 357 (D.C. Cir.
2011). For reasons stated later in this opinion, however, we
hold Thomas’s attorney was ineffective as a matter of law in
failing to argue for and present evidence supporting a Smith
variance and in failing to object to the district court’s stated
reason for denying one. This ineffective assistance of counsel
claim will be remanded to the district court so it can determine
whether counsel’s errors were prejudicial. On remand, the
district court will need to consider arguments for the variance
and will have to provide a reasoned basis for accepting or
rejecting them. Consequently, we need not decide whether the
 19
district court plainly erred. Cf. United States v. Soto, 132 F.3d
56, 59 (D.C. Cir. 1997) (“In view of our conclusion that
counsel was ineffective, we need not reach [the defendant’s]
alternative argument that the district court committed plain
error”).

C. Upward departures

In Application Note 8 to the Extortion Guideline, the
Sentencing Commission advises that “[i]f the offense involved
organized criminal activity, or a threat to a family member of
the victim, an upward departure may be warranted.” U.S.S.G.
§ 2B3.2 cmt. n.8. The district court found Thomas’s offense
involved both organized criminal activity and a threat to a
family member and departed upward upon both grounds.

Thomas attacks the rationales for both departures. He first
argues the district court erred by treating Application Note 8 as
a “directive” rather than a suggestion. As the transcript shows,
however, the district court well understood the departures to be
permissive: “So I am going to address the two departures …
that are expressly recommended for consideration where the
facts warrant.”

The district court was clearly correct the conduct involved
threats to a family member. Thomas told Mrs. Webster several
times he would murder her husband if he was not paid. These
threats were recorded and Thomas admits to making them.

Thomas insists “a threat to a family member of the victim”
means a threat communicated to that family member. Under
this interpretation, the departure would be justified only in rare
circumstances, if ever, because the person with whom the
extortionist speaks will usually be “the victim” of the extortion,
not a relative of the victim. Thomas’s reading of the Guideline
 20
is strained and unnatural: If a victim said an extortionist called
and threatened to kill his toddler, one would not understand the
victim to have put the child on the phone. The better
interpretation is that the departure is permitted where the
defendant threatens the victim with harm to a member of the
victim’s family.

Regarding the organized crime departure, Thomas asks us
to view the phone calls to Mrs. Webster in isolation. Because
none of Thomas’s associates joined him on the calls, he reasons
the offense did not involve organized crime. The district court
was not required to take such a narrow view. The extortionate
threats were made as the culmination of a plot that involved
Thomas and other members of his criminal organization.
Thomas’s associates also contacted the Websters, and Thomas
directed the Websters to send money to his mules as part of a
complex, orchestrated scheme. Even looking only to the
recording of the July 21 phone call, there is evidence of
organized crime. Thomas spoke in the first-person plural (e.g.,
“We know where your home is. We have your address. We
have everything about you. So easy that we go set your home
ablaze.”) and directed Mrs. Webster to send money to his
“good friend” in New York.

Finally, Thomas attacks the extent of the organized-crime
departure. He argues the district court abused its discretion by
adding one offense level to account for the scope of the
organization’s crimes because, in doing so, the court
analogized to the loss table in the Robbery Guideline, U.S.S.G.
§ 2B3.1(b)(7). He says the court should have looked instead to
the Fraud Guideline, U.S.S.G. § 2B1.1. But the loss table in
the Fraud Guideline escalates much more quickly: it prescribes
an increase of eight levels if the loss exceeded $95,000 and an
increase of 12 levels if the loss exceeded $250,000. Therefore,
 21
Thomas benefitted from the analogy and has neither standing
nor reason to complain about it.

D. Ineffective assistance

Thomas claims his defense attorney made several errors
during plea negotiations and at sentencing that deprived him of
his Sixth Amendment right to counsel. To prevail on these
claims, Thomas must show (1) his attorney made errors so
serious he was not functioning as “counsel,” and (2) the errors
were prejudicial. United States v. Rashad, 331 F.3d 908, 909
(D.C. Cir. 2003). When a defendant asserts ineffective
assistance claims for the first time on direct appeal, we
“remand the claim for an evidentiary hearing unless the trial
record alone conclusively shows that the defendant either is or
is not entitled to relief.” Id. at 909-10 (cleaned up).

The Government agrees that several of the ineffective
assistance claims should be remanded to the district court for
fact-finding. 4 It argues, however, that four of the claims should
be dismissed in this appeal, viz., that defense counsel: (1) failed
to argue for or present facts supporting a Smith variance, and
failed to object to the district court’s reason for rejecting one; 5
(2) “affirmatively agreed” to “incorrect” offense-level
enhancements; (3) failed to argue persuasively against the
“demonstrated ability” enhancement; (4) did not object to the

4
The Government does not object to remanding the ineffective
assistance claims based upon defense counsel’s failure: (1) to present
“documentation” supporting a Smith variance, (2) raise mitigating
facts contained in the Government’s sentencing exhibits, (3) review
the exhibits with Thomas, and (4) submit character letters Thomas’s
family and friends had written. We remand these claims to the
district court for further proceedings.
5
The Government agrees this claim must be remanded in part. See
supra, n.4. As discussed below, we remand it in full.
 22
Government’s breach of the plea agreement; and (5) presented
no argument against the “organized criminal activity” and
“threat to family member” departures. We will address these
individually.

1. Smith variance

The record conclusively shows Thomas’s counsel made
unprofessional errors in failing to seek a downward variance
due to Thomas’s status as a deportable alien. Even before the
Supreme Court’s decision in United States v. Booker allowed
judges to vary from the Sentencing Guidelines, 543 U.S. 220
(2005), this Circuit recognized “a downward departure may be
appropriate where the defendant’s status as a deportable alien
is likely to cause a fortuitous increase in the severity of his
sentence.” Smith, 27 F.3d at 655. In Thomas’s PSR, the
Probation Office noted his “status as a deportable alien may
warrant a downward departure.”

Defense counsel did not zealously or diligently pursue a
Smith variance. 6 In Thomas’s sentencing memorandum,
counsel did not even echo the Probation Office’s call for a
sentencing reduction or otherwise bring up Smith. Defense
counsel later submitted a supplemental sentencing
memorandum requesting a downward variance based upon
Thomas’s susceptibility to “physical beating” in jail, which
Thomas attributed to his nationality. The supplemental
memorandum again failed to mention Smith or the Probation
Office’s suggestion. Then, at sentencing, the court asked the

6
The plea agreement prohibited defense counsel from seeking a
downward departure, so counsel would have needed to request a
Smith variance rather than a Smith departure. This difference is
immaterial here because, as defense counsel recognized, the
considerations animating Smith apply equally to a variance and a
departure.
 23
parties to comment on the possibility of a Smith departure.
Defense counsel, being unable to seek a downward departure,
could not opine but stated he would raise Smith again when the
court considered variances. When the time came, however,
defense counsel did not raise Smith, choosing instead to rest on
the arguments in his original sentencing memorandum. 7

The court returned to the issue on its own later in the
hearing, stating:

I have also considered whether or not there should be a
downward variance or departure due to your deportation
after this sentence and the fact that there might be an
increase in the severity of your sentence because of your
inability to serve the last part of your sentence in a
community-based confinement or in some kind of reentry
program. But given the fact that you committed your
current offense while you were in Jamaica, it appears to
me that being abroad doesn't impede your criminal
conduct here; I'd only delay bringing you to justice here.

Defense counsel did not object to this explanation.

It is clear from the record that defense counsel acted
unprofessionally in failing to seek a Smith variance after the
issue was flagged in the PSR. Cf. Soto, 132 F.3d at 58-59
(holding counsel was clearly ineffective where he failed to
raise a “potentially helpful” provision of the Guidelines). The

7
Specifically, when the time came to discuss variances, the judge
listed the five variances defense counsel requested in the sentencing
memorandum (which did not include a variance under Smith), and
asked him “Is that basically it?” Counsel responded, “Yes, Your
Honor, that is effectively it.” The judge asked whether counsel had
anything to add to his variance arguments, but counsel stated: “There
is nothing more to amplify.”
 24
record shows this was not a strategic choice; counsel stated his
intent to raise the issue, but then failed to do so. This was an
error serious enough, if it affected the outcome, to deprive
Thomas of his constitutional right to counsel.

What is less clear is whether Thomas suffered any
prejudice. Despite counsel’s failure to request the variance, the
district court considered whether to grant it. The district court
may or may not have been persuaded had counsel offered a
cogent argument. We remand this claim to the district court to
allow Thomas to present arguments and evidence supporting a
Smith variance.

2. Stipulated guidelines enhancements

In his plea agreement, Thomas stipulated to two
enhancements of his offense level that he now argues were
inappropriate: (1) a one-level increase because “the amount
demanded … exceeded $20,000,” U.S.S.G. § 2B3.2(b)(2), and
(2) a two-level increase because Thomas “knew or should have
known that a victim of the offense was a vulnerable victim,”
U.S.S.G. § 3A1.1(b)(1).

To determine whether these enhancements apply, a court
may consider only the “relevant conduct” as defined in the
Guidelines, which includes acts and omissions “that occurred
during the commission of the offense of conviction, in
preparation for that offense, or in the course of attempting to
avoid detection or responsibility for that offense.” U.S.S.G.
§ 1B1.3(a). Whether the two enhancements were appropriate
would depend in large part upon whether the relevant conduct
included the calls to Mrs. Webster only or included also the
calls to Judge Webster: Thomas demanded $50,000 during his
attempt to defraud Judge Webster, but demanded only $6,000
from Mrs. Webster; Judge Webster was arguably a vulnerable
 25
victim because he was over 90 years old at the time of the
offense, but there is no suggestion Mrs. Webster was unusually
vulnerable. The Government asserted in the district court that
the relevant conduct included the calls to both Websters, but it
does not defend that position on appeal; nor does it otherwise
argue the enhancements were correctly applied.

Even if the enhancements were erroneous, however,
Thomas’s objections fail because he cannot make a plausible
showing of prejudice. Thomas principally argues that, if his
counsel had informed him that the relevant conduct did not
support some of the enhancements recommended in the
agreement, then he would have negotiated a more lenient
agreement. To prevail on this claim, Thomas would have to
“show a reasonable probability that the end result of the
criminal process would have been more favorable by reason of
a plea to a lesser charge or a sentence of less prison time.”
Brock-Miller v. United States, 887 F.3d 298, 312 (7th Cir.
2018) (quoting Missouri v. Frye, 566 U.S. 134, 147 (2012))
(applying this standard of prejudice to a claim that but-for
counsel’s errors, the defendant would have “negotiated a more
favorable plea agreement”).

Thomas cannot make that showing. Given the uncharged
conduct in the stipulated facts and the extra-plea evidence, it is
completely unreasonable to believe the Government would
have offered Thomas a more lenient deal if counsel had
objected to the enhancements. Even if he convinced
prosecutors they had erred, they surely would have added
counts sufficient to maintain at least the same recommended
guidelines range. Indeed, the prosecution stressed to the
district court that the sentence should reflect the “harm the
defendant inflicted on numerous vulnerable victims,” including
losses of “at least $300,000” and “likely much higher.” ECF
No. 28 at 10, 13.
 26

Alternatively, Thomas argues “it is not unlikely that he
would have chosen either to enter an open plea or to proceed to
trial, but for counsel’s errors.” For the open plea claim, he must
show he would have obtained a more favorable sentence but
for counsel’s errors. See Garcia v. United States, 679 F.3d
1013, 1015 (8th Cir. 2012); United States v. Booth, 432 F.3d
542, 546-47 (3d Cir. 2005). The claim he would have
proceeded to trial is governed by the standard announced in Lee
v. United States, 137 S. Ct. 1958, 1965 (2017) (“[W]hen a
defendant claims that his counsel’s deficient performance
deprived him of a trial by causing him to accept a plea, the
defendant can show prejudice by demonstrating a reasonable
probability that, but for counsel’s errors, he would not have
pleaded guilty and would have insisted on going to trial.”
(cleaned up)).

Thomas cannot satisfy either standard. Again, the
Government had evidence of uncharged conduct that would
have supported numerous fraud counts on top of the lone
extortion count in the information. It is highly improbable that
Thomas would choose to proceed without a plea deal simply
because defense counsel pointed out some logical
inconsistencies in the Government’s offer.

Because Thomas cannot show prejudice on these claims,
we shall not remand them to the district court.

3. Demonstrated ability

Thomas’s next ineffective assistance claim is that defense
counsel “failed to effectively argue” that the court should not
apply the demonstrated-ability enhancement of U.S.S.G.
§ 2B3.2(b)(3)(B)(ii). This claim must fail because the district
court was bound to apply the enhancement for reasons already
 27
stated. Cf. United States v. Winstead, 890 F.3d 1082, 1090
(D.C. Cir. 2018) (examining whether the argument counsel
failed to raise was a “winning argument” in order to determine
whether raising it would have changed the result).

4. Breach of plea agreement

Thomas claims defense counsel’s performance was
constitutionally deficient because he failed to object to the
Government’s breach of the plea agreement. As already
discussed, however, the Government did not breach the plea
agreement. We reject this claim because “failure to raise a
meritless objection is not deficient performance.” United
States v. Islam, 932 F.3d 957, 964 (D.C. Cir. 2019).

5. Upward departures

Finally, Thomas claims defense counsel “presented no
substantive argument against” the two upward departures. This
is true. Nevertheless, as we explained, the departures were
justified. There is no reason to believe an argument against
them could have affected the outcome. We shall not remand
this claim.
 28
III. Conclusion

We reject all of Thomas’s substantive challenges to his
sentence. We remand the case to the district court so it may
consider his claims that he received ineffective assistance of
counsel due to counsel’s failure to (1) argue for or present facts
supporting a Smith variance, or object to the district court’s
reasons for rejecting one, (2) raise mitigating facts contained in
the Government’s sentencing exhibits, (3) review the
sentencing exhibits with Thomas, and (4) submit character
letters Thomas’s family and friends had written.

So ordered.
 KAREN LECRAFT HENDERSON, Circuit Judge, concurring:
I write separately to record my view that the district court
“scrupulously adhere[d] to the obligations of Rule 11,” United
States v. Shemirani, 802 F.3d 1, 3 (D.C. Cir. 2015), including
the requirement to “inform the defendant of, and determine that
the defendant understands, . . . the terms of any plea-agreement
provision waiving the right to appeal or to collaterally attack
the sentence,” Fed. R. Crim. P. 11(b)(1)(N). Accordingly,
although I join the rest of my colleague’s opinion for the Court,
I depart from his conclusion that “whether the district court
fundamentally mischaracterized the waiver provision is a close
call.” Op. at 13.

An appeal waiver is generally enforceable. See United
States v. Guillen, 561 F.3d 527, 529 (D.C. Cir. 2009). But if a
judge mischaracterizes the waiver “in a fundamental way”—at
least in a way that benefits the defendant—“‘the district court’s
oral pronouncement controls.’” United States v. Godoy, 706
F.3d 493, 495–96 (D.C. Cir. 2013) (quoting United States v.
Buchanan, 59 F.3d 914, 918 (9th Cir. 1995)). This doctrine
naturally follows from the premise that criminal defendants
“need to be able to trust the oral pronouncements of district
court judges.” Buchanan, 59 F.3d at 918. If applicable only to
a genuine mischaracterization, the doctrine fulfills a primary
purpose of Rule 11—namely, ensuring that the defendant’s
waiver is knowing and voluntary. See Shemirani, 802 F.3d at
2 (citing United States v. Vonn, 535 U.S. 55, 62 (2002)). An
appellate court, however, should not use a magnifying glass to
scrutinize a minor change in phraseology that nonetheless jibes
with the written document, whether or not it benefits the
defendant.

Rule 11, after all, “does not say that compliance can be
achieved only by reading the specified items in haec verba.”
United States v. Saft, 558 F.2d 1073, 1079 (2d Cir. 1977)
(Friendly, J.). “To the contrary, a lifeless recitation of the plea
agreement is disfavored.” Op. at 12. In an ideal plea colloquy,
 2
the judge explains, rather than recites, the waiver provision. As
my colleague notes, this requires striking a “delicate balance.”
Id. The judge should “[p]rovide enough explanation to dispel
any misunderstanding without simply reading the agreement
aloud, but in doing so, take care not to create a new or different
misconception that effectively amends the written agreement.”
Id.

The district judge struck that balance appropriately here.
Under the plea agreement, Thomas waived his right to appeal
his sentence “except to the extent the Court sentence[d] [him]
above the statutory maximum or guidelines range determined
by the Court.” Summarizing this language during the plea
colloquy, the district judge told Thomas that he was waiving
his right to appeal “unless you are sentenced to a period of
imprisonment longer than the statutory maximum or the Court
departs upward from the applicable recommended sentencing
guideline range[,] which is all set out in your plea letter at page
7, paragraph 10.”

Granted, “unless” and “except to the extent” do not have
identical meanings. Unless denotes an exception; except to the
extent also denotes an exception but introduces detail about the
scope of the exception. In other words, unless is “less precise
and broader than” except to the extent. Op. at 13.
Notwithstanding the district court’s summary informed
Thomas that he would regain certain appeal rights should he
receive an above-Guidelines sentence, it failed to identify
which appeal rights would be restored. Certainly the court
could have—and perhaps should have—explained that an
above-Guidelines sentence would not vitiate the appeal waiver
in toto. But, in my view, its failure to do so falls far short of a
mischaracterization, let alone a fundamental
mischaracterization.
 3
Faulty-colloquy cases are repeat offenders in our Court so
we have a good basis to make comparisons. We have issued at
least five published opinions holding that the district court’s
oral pronouncement contradicted the terms of a written appeal
waiver. See, e.g., Godoy, 706 F.3d at 495; United States v.
Fareri, 712 F.3d 593, 594 (D.C. Cir. 2013); United States v.
Kaufman, 791 F.3d 86, 88 (D.C. Cir. 2015); United States v.
Hunt, 843 F.3d 1022, 1028 (D.C. Cir. 2016); United States v.
Brown, 892 F.3d 385, 395–96 (D.C. Cir. 2018) (per curiam).
All but one—Fareri is the exception—address waiver terms
that are similar or identical to the language in Thomas’s plea
agreement.

In Godoy, the judge told the defendant that he could appeal
his sentence if “the Court has done something illegal, such as
imposing a period of imprisonment longer than the statutory
maximum.” 706 F.3d at 495 (emphasis omitted). Although the
government argued that a reasonable person would interpret
“such as” to mean “limited to,” we rejected the argument. See
id. In Kaufman, the judge told the defendant that he could
appeal “if [he] believe[d] the sentence is illegal” or if he did
not “like” the sentence. 791 F.3d at 88 (alterations in original).
Hunt was similar. 843 F.3d at 1025. And in Brown, the judge
told the defendant that he could appeal “on the grounds of
reasonableness.” 892 F.3d at 395. But see id. at 410
(Kavanaugh, J., dissenting in part) (district judge noted appeal
would apply only “with regard to certain circumstances”).
Each of these statements, “[t]aken for [their] plain meaning—
which is how criminal defendants should be entitled to take the
statements of district court judges,” Godoy, 706 F.3d at 495—
arguably led the defendant to think that he had a broader right
to appeal than the plea agreement promised.

Nothing of that sort happened here. Although the district
court’s pronouncement was less detailed than the written
 4
agreement, it did not mischaracterize that agreement.
Moreover, the district judge’s words had other virtues.
“Unless” is a crisp and simple word. Its use made plain what
might be obscured by the more complex “except to the extent”
formulation: the precise condition that would resurrect
Thomas’s appeal rights.

Moreover, were we inclined to fault the district court for
omitting detail, that would not automatically merit reversal. If
a judge’s complete failure to discuss the appeal waiver does not
necessarily constitute reversible error, see United States v. Lee,
888 F.3d 503, 506 (D.C. Cir. 2018), neither does a single
change in phraseology. What matters is whether Thomas
understood what he was giving up. I agree that “[t]he natural
understanding” of the district court’s pronouncement “is that
the right retained is the right mentioned—that is, the right to
appeal the upward departure.” Op. at 13. A “natural
understanding” is the best evidence of what Thomas “might
reasonably have understood the court to mean,” Hunt, 843 F.3d
at 1028, even if an alternative meaning—no matter how
implausible—might literally be consistent with the court’s
words.

Labeling the district judge’s words a “close call” may also
have an unintended effect on judges who, notwithstanding our
admonition to the contrary, may decide that the safest course is
to recite appeal waivers verbatim. This, too, would hurt
criminal defendants, most of whom are not lawyers and may
struggle to comprehend “the dark emptiness of legal jargon.”
Fisher v. United States, 328 U.S. 463, 487 (1946) (Frankfurter,
J., dissenting). But a judge who simply reads the text of the
appeal waiver is unlikely to be reversed, Saft, 558 F.2d. at
1079—even though Rule 11’s purpose would be frustrated—
thus a “lifeless recitation” is what we may come to expect.