# United States Court of Appeals

FOR THE DISTRICT OF COLUMBIA CIRCUIT

Argued November 19, 2020 Decided June 11, 2021

No. 19

- 3015

U

NITED S TATES OF A MERICA
, A PPELLEE

v.

K ENIEL A EON T HOMAS
, ALSO KNOWN AS D AVID M ORGAN
, A PPELLANT

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. T ony 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: H ENDERSON and G ARLAND
, * Circuit Judges , and

G INSBURG
, Senior Circuit Judge

.

Opinion for the Court filed by Senior Circuit Judge

G INSBURG

.

Concurring opinion filed by Circuit Judge H ENDERSON

G INSBURG
, 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 right s to appeal . He retained only the right s to claim he received ineffective assistance of counsel
and to appeal an y upward departure from the sentencing guidelines range calculated by the district court

. At s entencing,

t he district court did depart upward and sentenced Thomas to nearly six years’ imprisonment

.

Thomas mount s 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 in eff ective 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 Scam s , 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 claim s his
attorney made mistakes at sentenc ing and during the plea bargaining process that deprived hi m of hi s 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 c ourt 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 t he 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 J udge 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

wo uld be easily fooled due to his advanced age

, then he was seriously mis taken

. Perhaps unbeknownst to Thomas, h e was trying to scam a man who once h ead ed 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
d rop ped 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 threat s more plausible,
Thomas recounted personal identifying information abo u t the

J udge, 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 c onversations
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 plead ed guilty to one count of interstate
communication with intent to extor t , 1 8 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. Thom as 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 “abo ve the statutory maximum or the guidelines range determined by
the C ourt” 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 conspir acy. 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 man6

identified in the record as “P.W.” Judge Webster immediately
contacted the FBI

.

At the Bureau’s reque st , 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 a s a “money mul e” for
Thomas and his associates. The FBI identified dozens of other victims in the United States, m any of them elderly

. Agents
were able to trace over $300,000 of payments flowing to Thomas and his associates, but estimated the t otal loss was much highe r. 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 p aragraph of the PSR). The court accepted the unrebutted evidence presented in the sentencing exhibits and the agent’s testimony as its findings of fact

.

T he district court went on to impose a sentence longer than
the Government had requested

. T he 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

T he 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

I n 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 the8

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 t he prosecutor stood his ground : “Our posi tion 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 read ing
of case s from the Third and Seventh Circuits

, which held i t is
“irrel evant” 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 ap plies.” 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 wa s no breach here. The Government promised to argue for the stipulated g uidelines 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 C ourt 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 t he 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 pr esumab ly
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 i s 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 m ight 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 C ourt sentence[d]10

[him] above the statuto ry maximum or g uidelines 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 simi lar waiver). Thomas
raises several issues that fall within the scope of th e 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 sentence d
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 provid e 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 can not 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 jud ge
to “ inform the defendant of, and determine that t he defendant understands, ” certain important terms and consequences of the plea agreement . The purpose of th e Rule, generally, is “to

ensure that [the defendant] understands

... his rights a s a criminal de fendant” 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. 201 8)

.

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, w e did not “pause to parse the precise legal meaning of ‘reasonableness.’”12

Id. at 396. I nstead, we refused to enforce the waiver based upon “the common meaning” of the district court’s
pronouncement. Id.

S crupulous 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 agre ement 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: P rovide enough expl anation 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 amend s the written agreement.

During the Rule 11 colloquy in this case , the c ourt 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

c ourt 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 a n “arguable13

divergence ” between the court’s explanation and the agreement
as written , and so the c ourt’s explanation should control

.

We agree the two arguably diverge insofar as “ u nless” 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

. T he natural understanding

, however, is that the right retained is the right mentioned

– that is, the right to appeal the upward departure. As t he

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. Th at 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.,

Conc urring 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 se ntencing.”
892 F.3d at 395.14

1. Stipulated guidelines enhancemen ts

Thomas fault s 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 argu es 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 forfeit ed an issue through a failure to object, we will not review at all when a defend ant 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 th e distinction between forfeiture and waiver). For instance, when a defendant makes a “tac tical 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 “strateg y or tactic ”). This rule discourages sandbagging, that is,

purpose ful ly induc ing the district court to commit a n error that
can form the b asis for an appeal in the event of a n unfavorable result at trial or sentencing. Harrison , 103 F.3d at 992.

N egotiating a plea agreement , like requesting a jury instruction, requires counsel to think strategic ally

. See Guillen

,15

561 F.3d at 530. In both situations counsel must evaluate the various options and advise the defendant of the ir 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 adjust ment to which he has stipulate d 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
lev el increase because the “ amount demanded” exceed ed $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 th e 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 understo od

. When t h e 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 accepte d the recommendation to apply these two enhancements, Thomas, through counsel, again stated he did not object.

Despite all this, Thomas argues there wa s no waiver because the district court stated it had an “independent obligation” to calculate the gu idelines 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 dis trict court has an “independent16

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

every where

. Therefore, we hold Thomas waived his challenge
to the two disputed enhancements

.

2. Demonstrated ability

The E xtortion by

... Threat of Injury G uideline 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 contain ing

... 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 discretio n 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 a n 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

. S ee 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 vic tims did not include
extortionate threat s. 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, t he P robation Office raised the possibility of a downward departure to compensate for the increased severity of Thomas’s punishment due to his18

ineligibility for this and other Bureau of Prisons programs (a
Smith departure). See id. at 655. At the sentencing h earing, 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 bri nging 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 co urt’s statement of reasons at sentencing, our review would be for plain error i f 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 r easoned basis for accepting or rejecting them. Consequently

, w e need not decide whether the19

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 re ach [ the defendant’s] alternative argument that the district court committed plain error”).

C. Upward departures

In Application Note 8 to the E xtortion G uideline, 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 dep arted 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 t he transcript shows, however, the district court well understood the departures to be permissiv e: “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 th at family member. U nder
this interpretation

, the departure would be justified only in rare circumstances, if ever, because t he 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 Guideline20

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 th e 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. Webst er 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 o f 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 s poke 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 di rect ed 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 c ourt 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 los s 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 fu nctioning 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 defens e 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 Gove rnment’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
i ndividually

.

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), th is C ircuit recognized “a downward departur e 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

wa rrant 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 supplement al 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 o pine but stated he would raise Smith again when the

court considered variances. When the time came, however,
d efense counsel did not raise Smith , choosing instead to rest on the arguments in his original sentencing memorandum

. 7

The court returned to t he 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 par t 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 cou nsel 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 var iance 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 consid ered 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. Stipulat ed g uidelines enhancements

In his plea agreement, Thomas stipulated to two
enhancements of his offense level that he now argues were
in appropriate : (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 appl y , a court

ma y 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 up on whether the relevant conduct
included t he 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 vulnerable25

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 Webster s , 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 princi pally 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

“ sho w 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 State s, 887 F.3d 298, 312 (7th Cir. 2018) (quoting Miss ouri 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 convinc ed prosecutors they had erred, they s urely would have added

counts sufficient to maintain at least the same recommended guidelines range

. Indeed, t he prosecution s tressed 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 th e open plea claim

, he must
show he would have obtained a more favorable sentence but
for counsel’s errors

. S ee 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)

. T he 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 pl ea, 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 cou nsel 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 fai l because the district
court was bou nd to apply the enhancement for reasons already27

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 hav e 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

agree ment. 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. U pward departures

Finally, Thomas claim s defense counsel “presented no substantive argument against” the tw o 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
support ing 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 famil y and friends had written.

So ordered.K AREN L E C RAFT H ENDERSON

, 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 d efendant 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 depar t from his conclusion that “whether the district court fundamentally mischaracterized the waiver provision is a close
call.” Op. at 13

.

A n a ppeal waiver is generally enforceable. See United
States v. Guillen , 561 F.3d 527, 529 (D.C. Cir. 2009). But i f a judge mischaracterize s 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.
Buchan an , 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 misch aracterization, the doctrine fulfills a primary purpose of Rule 11

— namely , ensur ing 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 re ading 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

. I n 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.

T he district judge struck that balance appropriately here

. Under the plea agreement, Thomas waived his right to appeal
his sentence “ e xcept 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 yo u 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 t o 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 mis characterizati on, let alone a fundamental
mis characterization.3

F aulty

- colloquy cases are repeat offenders in our Court so

we have a good basis to mak e comparisons

. W e have issued at least five published opinion s holding that the district court’s oral pronouncement cont radicted 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 th at 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

. B ut see id. at 410 (Kavanaugh, J., dissenting in part) ( dis trict 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 , 70 6 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 written4

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, w ere we inclined to fault the district court for omitting detail, that would not automatically merit reversal. I f a judge’ s complete failure to discuss the appeal waiver does not necessarily constitute reversible error

, s ee 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 evide nce 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. a t
1079

— even though Rule 11 ’s purpose would be frustrated

— thus a “lifeless recitation ” is what we may come to expect

.