United States Court of Appeals
         FOR THE DISTRICT OF COLUMBIA CIRCUIT



Argued December 15, 2017               Decided July 31, 2018

                        No. 17-3006

                UNITED STATES OF AMERICA,
                        APPELLEE

                              v.

MARQUETE MURRAY, ALSO KNOWN AS TWIN, ALSO KNOWN AS
                     QUETE,
                   APPELLANT


        Appeal from the United States District Court
                for the District of Columbia
                   (No. 1:16-cr-00121-8)


    Gregory Stuart Smith, appointed by the court, argued the
cause and filed the briefs for appellant.

     Eric S. Nguyen, Assistant U.S. Attorney, argued the cause
for appellee. With him on the brief was Elizabeth Trosman,
Assistant U.S. Attorney.

   Before: GARLAND, Chief Judge, and SRINIVASAN and
MILLETT, Circuit Judges.

    Opinion for the Court filed by Chief Judge GARLAND.
                                2

     GARLAND, Chief Judge: Appellant Marquete Murray
challenges the sentence that the district court imposed following
his guilty plea. Murray’s appeal presents two questions:
whether the government’s actions following entry of the plea
breached its plea agreement with Murray, and whether Murray’s
counsel provided constitutionally ineffective assistance in
relation to that claimed breach.

     We reject the government’s contention that it did not breach
its plea agreement with Murray. Nevertheless, because
Murray’s counsel failed to object, we can grant Murray relief on
this ground only if the government’s breach was plain -- that is,
clear or obvious -- which it was not. That, however, does not
end this matter. Because we also reject the government’s
contention that Murray has no colorable claim of ineffective
assistance of counsel, we remand the case to the district court for
further proceedings.

                                 I

     The root problem in this case is that Murray was sentenced
based on a U.S. Sentencing Guidelines range that deviated from
the estimated range set out in his plea agreement -- despite the
fact that nothing unanticipated by the agreement transpired
between the plea and sentencing. This is how that came to pass.

     On July 14, 2016, a federal grand jury indicted Murray on
a narcotics conspiracy charge, as well as on a second charge of
unlawfully using a communication facility to facilitate drug
crimes. On October 16, with advice of counsel, Murray entered
into a plea agreement with the Office of the U.S. Attorney for
the District of Columbia, pursuant to which he would plead
guilty in federal court to the conspiracy count, and would also
plead guilty to two other charges in two unrelated cases in the
Superior Court of the District of Columbia: misdemeanor
                                  3

assault and carrying a pistol without a license.1 In exchange, the
government agreed, among other things, to dismiss the
remaining count in the federal indictment, the remaining count
in the misdemeanor assault case, and a third D.C. Superior Court
case in its entirety.

     The plea agreement included an agreed-upon “Estimated
Guidelines Range,” meant “to assist the Court in determining the
appropriate sentence.” Plea Agreement ¶ 4 (J.A. 24). The
parties calculated Murray’s initial base offense level as 20
because the conspiracy offense involved approximately 30
grams of heroin and 45 grams of PCP. See U.S.S.G.
§ 2D1.1(c)(10) & cmt. 8(B). The parties then applied a three-
level reduction that lowered Murray’s offense level to 17 based
on his acceptance of responsibility. See id. § 3E1.1. The plea
agreement also stated the parties’ agreement that Murray’s
estimated criminal history category was Category I:

          Based upon the information now available to [the U.S.
          Attorney’s] Office, your client [Murray] has no
          criminal convictions.

          Accordingly, your client is estimated to have 0
          criminal history points and your client’s Criminal
          History Category is estimated to be I. Your client
          acknowledges that if additional convictions are
          discovered during the pre-sentence investigation by the
          United States Probation Office, your client’s criminal
          history points may increase.



     1
       The U.S. Attorney for the District of Columbia acts as chief
prosecutor in both the U.S. District Court for the District of Columbia
and in the Superior Court of the District of Columbia. See United
States v. Weathers, 186 F.3d 948, 949 n.1 (D.C. Cir. 1999).
                                  4

Plea Agreement ¶ 4.B (J.A. 26). Based on the estimated offense
level and criminal history category, the parties agreed that
Murray’s Estimated Guidelines Range was 24 to 30 months’
incarceration. Id. ¶ 4.C (J.A. 26).

     The agreement further stated that Murray understood the
Estimated Guidelines Range was not binding on the United
States Probation Office or the sentencing court. And it warned
that any post-agreement misconduct that Murray committed
could increase his base offense level or justify an upward
departure. Id. (J.A. 27).

     Finally, although the parties agreed that a sentence within
the Estimated Guidelines Range “would constitute a reasonable
sentence in light of all of the factors set forth in 18 U.S.C.
§ 3553(a),” both parties “reserve[d] the right to seek a sentence”
outside “the Estimated Guidelines Range based on § 3553(a)
factors.” Id. ¶ 5 (J.A. 27).2


     2
      After calculating the applicable Guidelines range, “the court
must then consider the arguments of the parties and the seven
sentencing factors set forth in 18 U.S.C. § 3553(a) to determine the
appropriate sentence, including whether a variance from the advisory
Guidelines range is warranted.” United States v. Williams, 773 F.3d
98, 108 (D.C. Cir. 2014). The § 3553(a) factors include the (now
advisory) range established by the Guidelines. See 18 U.S.C.
§ 3553(a)(4). They also include such factors as “the nature and
circumstances of the offense and the history and characteristics of the
defendant,” id. § 3553(a)(1); the need for the sentence to “reflect the
seriousness of the offense,” to “promote respect for the law,” to
“provide just punishment,” to “afford adequate deterrence,” to “protect
the public,” and to “provide the defendant with needed educational or
vocational training,” id. § 3553(a)(2); and the need to “avoid
unwarranted sentence disparities” among similarly situated
defendants, id. § 3553(a)(6). See United States v. Simpson, 430 F.3d
1177, 1186 (D.C. Cir. 2005).
                                  5

     On October 25, 2016, Murray pled guilty in federal court
pursuant to the plea agreement. Three weeks later, on
November 17, he entered the two Superior Court pleas required
by the plea agreement.

     On December 1, 2016, the Probation Office released a
Presentence Investigation Report (PSR) regarding Murray.3 The
PSR concluded, as had the plea agreement, that Murray’s
offense level was 17. PSR ¶¶ 65, 103. But in calculating
Murray’s criminal history category, it did not conclude -- as the
agreement did -- that Murray’s criminal history score was 0.
Instead, it gave Murray a score of 2 because “the defendant pled
guilty to two District of Columbia Superior Court cases
following his guilty plea” in federal court. PSR ¶ 109.

     The two Superior Court pleas were the same pleas that
Murray’s plea agreement had required. With some exceptions
not relevant here, when a defendant has previously pled guilty
but not yet been sentenced, one point is added to his criminal
history for each such plea. See U.S.S.G. §§ 4A1.1(c),
4A1.2(a)(4). The Probation Office therefore concluded that
Murray’s criminal history score was in fact 2 -- not 0 as in the
plea agreement -- which placed him in Criminal History
Category II, rather than in Category I as contemplated by the
agreement. As a result, the Probation Office calculated a final
sentencing range of 27 to 33 months’ incarceration, PSR ¶ 103,
rather than the agreement’s Estimated Guidelines Range of 24
to 30 months. See U.S.S.G. ch. 5, pt. A (sentencing table). Both



     3
       The PSR was filed under seal. “Insofar as we refer to
information derived from the PSR, it is unsealed to the limited extent
referenced in this opinion, although the full document shall remain
physically withheld from public review.” United States v. Reeves, 586
F.3d 20, 22 n.1 (D.C. Cir. 2009).
                                6

government and defense counsel reviewed the PSR; neither
noted any material inaccuracies. See PSR addendum.

    The PSR also identified “the defendant’s youth” -- he was
24 years old at the time of sentencing -- as a “factor that may
warrant a [downward] variance from the applicable guideline[s]
range.” PSR ¶ 130. Subsequently, the Probation Office
recommended a 21-month sentence to the court. See Sentencing
Hearing Tr. 10 (J.A. 80).

     Following the Probation Office’s report, each party
submitted a sentencing memorandum to the court. The
government affirmed the PSR’s Sentencing Guidelines range of
27 to 33 months. It did not mention the plea agreement’s
estimated range of 24 to 30 months, nor did it call to the court’s
attention the fact that the difference in ranges was due to
counting, for criminal history purposes, the Superior Court
convictions resulting from the plea agreement. Finally, based on
the § 3553(a) factors, the government asked the court to
sentence Murray to the top of the (new) range: 33 months. See
Government’s Mem. in Aid of Sentencing 8-13 (J.A. 42-47).

     Murray’s counsel submitted a short sentencing
memorandum as well. Like the government’s memorandum,
Murray’s did not call the court’s attention to the difference
between the plea agreement’s Estimated Guidelines Range and
the PSR calculation. Instead, defense counsel merely cited
Murray’s youth and need for further education and vocational
training as support for a variance below the sentencing range --
specifically, a sentence of 24 months. Def. Murray’s Sentencing
Mem. 1-2 (J.A. 48-49).

    The sentencing hearing took place on January 6, 2017. The
court began by explaining its Sentencing Guidelines
calculations. It noted that, at the time of the plea, Murray had no
                              7

previous criminal convictions but had since pled guilty in two
D.C. Superior Court cases. Sentencing Hearing Tr. 6 (J.A. 76).
Based on those two pleas, the court calculated that Murray had
two criminal history points, which put him in Criminal History
Category II. Id. With an offense level of 17 and a Category II
criminal history, the court (like the PSR) calculated the
Sentencing Guidelines range as 27 to 33 months. Id. When
asked whether that range was correct, both the government and
Murray’s attorney agreed that it was. Id. at 6-7 (J.A. 76-77).

    After noting the Probation Office’s recommendation of 21
months’ imprisonment, the court invited the government to
speak. Following an extended allocution, the government
repeated the 33-month recommendation it had presented in its
sentencing memorandum.

     Murray’s counsel then addressed the court. He did not note
that the new sentencing range exceeded the plea agreement’s
Estimated Guidelines Range, nor did he object to the
government’s recommendation on the ground that it was above
that range. Instead, counsel rested on his previously filed
memorandum requesting a downward variance of 24 months’
incarceration. Sentencing Hearing Tr. 32 (J.A. 102). Having
heard from both parties, the court accepted the government’s
recommendation and sentenced Murray to 33 months in prison.

     Following the sentencing, Murray’s lawyer moved to
withdraw. The lawyer explained that, in a post-sentencing
meeting, Murray “became upset at Counsel’s low-key approach
at the Sentencing Hearing, and expressed his displeasure.” Mot.
for Withdrawal of Counsel 2 (J.A. 67). Appellate counsel was
                                   8

contacted on January 25, 2017, and Murray filed this appeal the
same day.4

     Murray raises two contentions on appeal. First, he asserts
that the government breached the plea agreement between the
parties, and that he is therefore entitled to resentencing. Second,
he argues that his trial counsel provided constitutionally
ineffective assistance in relation to that breach.

                                   II

      “In interpreting the terms of a plea agreement, we look to
principles of contract law. In evaluating whether a plea
agreement has been breached, we look to the reasonable
understanding of the parties and construe any ambiguities in the
agreement against the government.” United States v. Henry, 758
F.3d 427, 431 (D.C. Cir. 2014) (citations omitted). But because
Murray raises his claim of breach for the first time on appeal, we
can review it only for plain error. See Puckett v. United States,
556 U.S. 129, 134 (2009); United States v. King-Gore, 875 F.3d
1141, 1144 (D.C. Cir. 2017). Meeting that standard requires
satisfying four prongs: “First, there must be an error or defect
. . . . Second, the legal error must be clear or obvious, rather
than subject to reasonable dispute. Third, the error must have
affected the appellant’s substantial rights, which in the ordinary
case means he must demonstrate that it affected the outcome of
the district court proceedings. Fourth and finally, . . . the error
[must] seriously affect[] the fairness, integrity or public
reputation of judicial proceedings.” Puckett, 556 U.S. at 135
(citations and internal quotation marks omitted).




     4
      In its brief, the government challenged Murray’s appeal as
untimely, but it has since waived that challenge by letter to the court.
                                9

     Murray contends that the government breached the plea
agreement in two ways. First, he says that the parties
understood that the Estimated Guidelines Range would be the
actual Guidelines range at sentencing, unless he committed
further criminal conduct or unless the government discovered
prior convictions that it did not know about. Because the
conduct underlying the Superior Court pleas occurred prior to
the agreement and was known to the government, Murray
maintains that both parties understood those pleas would not
count towards his criminal history category. As a consequence,
he concludes, the government breached the agreement by failing
to schedule the pleas to take place after his federal sentencing so
as not to affect his Guidelines range at the time of that
sentencing. Second, Murray contends that, after the government
failed to make that scheduling arrangement, it breached the
agreement again by arguing for a 33-month sentence, which
exceeded the agreed-upon Estimated Guidelines Range of 24 to
30 months.

     On each point, we hold that Murray’s is the best reading of
the agreement but that his reading is not so clear or obvious as
to prevail under the plain error standard.

                                A

    We begin with Murray’s contention that the government
breached the agreement by failing to schedule his Superior
Court pleas to follow his federal sentencing.

    1. Looking to the reasonable understanding of the parties
and construing any ambiguities against the government, we
conclude that Murray is correct: the best reading of the
agreement is that the parties understood the Estimated
Guidelines Range would be the final Guidelines range at
sentencing, absent any material changes in the known
                                10

circumstances. Consequently, it was also reasonably understood
that the Superior Court pleas would not count towards Murray’s
criminal history category.

     There is no dispute that, at the time of the agreement,
Murray had no criminal convictions. Nor is there any dispute
that, when the two pleas were counted, they increased Murray’s
criminal history score and category, and thus his Guidelines
range, above the numbers “estimated” in the plea agreement.
His score increased from 0 to 2, and his criminal history
category from I to II. Instead of a Guidelines range of 24 to 30
months, this made his range 27 to 33 months.

     It is true, as the government says, that the “agreement
repeatedly made clear that the projected guidelines range was
only an estimate and could change before sentencing.” U.S. Br.
14. But it is also true that both parties knew Murray would soon
plead to the Superior Court charges as required by the plea
agreement. Thus, if those Superior Court pleas had been
expected to increase the Guidelines calculations, there would
have been no reason to include in the plea agreement three
“estimates” that the parties knew would be wrong by the time of
sentencing.

     Indeed, the purpose of including an estimated Guidelines
range in a plea agreement is to predict, for the benefit of both the
defendant and the government, the range that will be used at
sentencing. See United States v. Habbas, 527 F.3d 266, 270 (2d
Cir. 2008) (noting that estimated Guidelines ranges “ensure that
guilty pleas indeed represent intelligent choices by defendants”
(citation omitted)). And, as Murray’s plea agreement says, its
“Sentencing Guidelines Analysis” was intended “to assist the
Court in determining the appropriate sentence.” Plea Agreement
¶ 4 (J.A. 24). If the parties had known from the get-go that the
Estimated Guidelines Range would be wrong at the time of the
                                11

sentencing, it would not have been of much assistance to the
court -- or to the parties in deciding whether to enter into the
plea agreement.

     Other language in the plea agreement confirms this reading.
The agreement states that, “[b]ased upon the information now
available to this Office, your client has no criminal convictions,”
and that, as a consequence, “your client is estimated to have 0
criminal history points.” Plea Agreement ¶ 4.B (J.A. 26)
(emphasis added). It then goes on to say that “if additional
convictions are discovered during the pre-sentence
investigation” by the Probation Office, “your client’s criminal
history points may increase.” Id. (emphasis added).

     The “information now available” to the U.S. Attorney’s
Office included the fact that Murray would soon have two
Superior Court convictions. Likewise, there was nothing to
“discover” about those two convictions; the government knew
full well that they were coming. See MERRIAM-WEBSTER’S
COLLEGIATE DICTIONARY 357 (11th ed. 2009) (defining to
“discover” as “to make known or visible”; “to obtain sight or
knowledge of for the first time”; “find out”). Thus, it would be
surprising if the plea agreement’s reference to “information now
available” excluded the upcoming convictions, and equally
surprising if those convictions were included within the category
of convictions that might be “discovered.”

     Moreover, such exclusion and inclusion could be viewed
as misleading to Murray and hence in violation of the
prosecutor’s “implied obligation of good faith and fair dealing”
in connection with plea agreements. United States v. Ahn, 231
F.3d 26, 35-36 (D.C. Cir. 2000) (quoting United States v. Jones,
58 F.3d 688, 692 (D.C. Cir. 1995)); accord Henry, 758 F.3d at
431. This is yet another reason to read the agreement as
                                 12

including an understanding that those convictions would not
affect Murray’s Sentencing Guidelines range.5

     2. The conclusion we have just reached leads to the further
inference that the agreement contemplated that Murray would
enter his Superior Court pleas after being sentenced in federal
court. This follows because the Sentencing Guidelines provide
that a defendant is assigned one criminal history point for each
prior offense to which the defendant has pled guilty but not yet
been sentenced. See U.S.S.G. §§ 4A1.1(c), 4A1.2(a)(4).

     That is what happened to Murray: at his federal sentencing,
the court correctly gave him 2 criminal history points for his two
Superior Court pleas, notwithstanding that he had not yet been
sentenced on those pleas. Thus, if the understanding that those
pleas would not count toward his Sentencing Guidelines range
was to be honored, there also had to be an understanding that he
would not enter his Superior Court pleas until after the federal
sentencing was completed. The government breached this
understanding by scheduling Murray’s D.C. Superior Court
pleas before his federal sentencing.



     5
       Further support for our reading comes from the warning at the
end of the section of the agreement entitled “Estimated Applicable
Guidelines Range.” That section opens by stating that, “[b]ased upon
the agreed total offense level and the estimated criminal history
category set forth above” -- the latter being Category I, based on 0
criminal history points -- “your client’s estimated Sentencing
Guidelines range is 24 months to 30 months.” Plea Agreement ¶ 4.C
(J.A. 26). The end of the section warns, however, that “the terms of
this section apply only to conduct that occurred before the execution
of this Agreement.” Id. (J.A. 27) (emphasis added). The conduct
underlying the two Superior Court convictions did in fact occur before
the plea agreement was signed -- 8 months and 16 months before that
date. See PSR ¶¶ 67-68.
                                 13

     The government rejects this conclusion on the ground that
“[p]leading guilty to the other crimes was a condition of
[Murray’s] getting the benefits of the agreement.” U.S. Br. 17.
It reads the “Breach of Agreement” section, Plea Agreement
¶ 11 (J.A. 31-32), to suggest the parties intended that Murray
perform all of his promises first. The government posits that
this section gave it recourse at Murray’s federal sentencing for
any failure by Murray to fulfill his obligations, and therefore
contemplated that he would complete all his obligations by that
time. Recording of Oral Arg. 27:40.

      The government’s reading finds no support in the
agreement’s text. Murray certainly agreed to plead guilty to the
Superior Court charges as part of the overall plea agreement.
But although the agreement addressed the timing of the
government’s obligation to dismiss the remaining counts in each
court vis-à-vis Murray’s obligation to plead guilty in that court,6
it said nothing about the sequencing of activity between the two
courts. And we will not read into the agreement’s silence on the
issue of timing an implied condition favoring the government.
See Bank of N.Y. Mellon Tr. Co. v. Morgan Stanley Mortg.
Capital, Inc., 821 F.3d 297, 305 (2d Cir. 2016) (“Conditions
precedent are not readily assumed. While specific, talismanic
words are not required, the law nevertheless demands that
conditions precedent be expressed in unmistakable language.”
 (internal quotation marks omitted)); 15 SAMUEL WILLISTON &
RICHARD A. LORD, WILLISTON ON CONTRACTS § 44:47 (4th ed.
1990). If anything, the plea agreement suggested the opposite
by addressing the federal plea and sentencing first and the


    6
       See Plea Agreement ¶ 3 (J.A. 24) (providing that, in
consideration for the federal plea, the remaining federal count would
be dismissed at the federal sentencing; and that after the Superior
Court pleas, the government would move for dismissal of the
remaining Superior Court counts at the Superior Court sentencing).
                                 14

Superior Court pleas and sentencing second.                See Plea
Agreement ¶¶ 1, 3 (J.A. 23-24).

     Despite this lack of textual support, the government insists
that it “was entitled to know” that Murray would “h[o]ld up his
end of the bargain before making its sentencing
recommendation.” U.S. Br. 17-18. That may be true, but
Murray was equally entitled to know that the government would
dismiss his remaining federal count in exchange for his pleading
to the Superior Court counts. And Murray could not be assured
of that dismissal until his federal sentencing. See supra note 6.

     The government further argues that, if Murray had been
permitted to wait until after the federal sentencing to plead to the
Superior Court charges, and thereafter refused to plead, the
government would have been without recourse. But the
agreement contained many incentives for Murray to comply --
and many negative consequences if he did not. If Murray
refused to plead to the two Superior Court charges, he could be
tried on those charges, on the remaining Superior Court charges,
possibly on the dismissed federal charge (depending on double
jeopardy considerations), and possibly on other federal charges
as well.7 In addition, the government would be “free to use
against” him all statements he had made to the government and
to the court, including at his plea colloquy. Plea Agreement ¶ 11
(J.A. 31).

     But the dispositive question is not whether the government
could get all that it wanted in the event of a breach by Murray;
the question is what the agreement provided. “[L]ook[ing] to


     7
      E.g., Plea Agreement ¶ 11 (J.A. 31) (providing that in the event
of a breach of the agreement, Murray would “be fully subject to
criminal prosecution for any other crimes, including perjury and
obstruction of justice”).
                               15

the reasonable understanding of the parties and constru[ing] any
ambiguities in the agreement against the government,” Henry,
758 F.3d at 431, we conclude that Murray’s plea agreement
evidenced the understanding that his upcoming Superior Court
pleas would not count towards his Sentencing Guidelines range
at his federal sentencing, and hence that the two Superior Court
pleas would be entered after that sentencing. By scheduling
those pleas before his federal sentencing, the government
breached that understanding.

     3. Nevertheless, we cannot provide Murray with relief
unless the breach constituted plain error because he did not
object in the district court. See Puckett, 556 U.S. at 134;
King-Gore, 875 F.3d at 1144. And to find plain error, it is not
enough to base our reading on the parties’ “reasonable
understanding” and on “constru[ing] any ambiguities” against
the government. Henry, 758 F.3d at 431. Rather, we must find
that the breach was “clear or obvious.” Puckett, 556 U.S. at 135.
We cannot so find here.

     Murray’s assertion that the government breached the plea
agreement by failing to effectuate the parties’ understanding that
his final criminal history category would not include the
Superior Court pleas requires resolving two ambiguities (or,
really, two silences): (1) the agreement does not expressly
address whether the not-yet-entered pleas would affect his final
criminal history category and Guidelines range, and (2) the
agreement does not expressly address the expected timing of
those pleas.

    Although the first ambiguity alone might not be enough to
render the agreement’s expectations unclear, we cannot say the
same for the second. Scheduling the pleas after the federal
sentencing appears to have been the only way the Estimated
Guidelines Range would have been a useful prediction. But that
                                16

timing was unmentioned in the agreement, and relies on an
analysis of Guidelines provisions that are also unmentioned in
the agreement. See U.S.S.G. §§ 4A1.1(c), 4A1.2(a)(4). It is not
at all obvious that the parties understood those provisions.

     Yes, counsel for both parties should have been schooled in
the relevant Guidelines. See United States v. Soto, 132 F.3d 56,
59 (D.C. Cir. 1997); U.S. DEP’T OF JUSTICE, UNITED STATES
ATTORNEYS’ MANUAL § 9-27.710 cmt. (rev. 2018). And
defense counsel’s failure to understand them may be part of the
ineffective assistance claim we address below. But the question
before us is what the parties clearly agreed to, not what they
should have agreed to in order to effectuate their unspoken
understanding. And -- notwithstanding our conclusion above
that Murray’s is the best reading of the agreement -- we cannot
say that his position is so obvious as to grant him relief.

     There is also another, factual issue that makes the error less
than obvious. It is one that we passed over in our prior
discussion, but that we cannot simply assume in evaluating the
plain error question. That is: who actually scheduled the
Superior Court pleas and federal sentencing hearing, and who
had the power to change their timing? The record does not
reflect whether the government scheduled the proceedings on its
own, whether the prosecutor and defense counsel found
mutually agreeable dates, whether the designated courts set the
dates based on their own calendars, or whether either court
would have been amenable to a scheduling change if asked. The
absence of a factual record that resolves at least some of these
matters is yet another factor leaving Murray’s claim of a
government breach less than plain.
                                 17

                                 B

     We next address Murray’s argument that the government
further breached the plea agreement by recommending that the
court sentence him to 33 months’ incarceration.

    1. Murray argues that, even if the government could not
have avoided scheduling the Superior Court pleas before the
federal sentencing, or inadvertently did so, it still could have
avoided breaching the agreement by recommending a sentence
of no more than 30 months. That sentence would have fallen
within the final 27-to-33-month range but also would have been
consistent with the 24-to-30-month range contemplated by the
plea agreement. We agree that, under the best reading of the
agreement, the government’s 33-month recommendation
constituted a breach.

     The government maintains that, “[e]ven if the parties did
not realize that the two separate guilty pleas . . . would increase
the applicable guidelines range, . . . the agreement expressly
[reserved the government’s right] to seek a sentence above the
estimated range.” U.S. Br. 8. It is true that, under the plea
agreement, Murray “reserve[d] the right to seek a sentence
below the Estimated Guidelines Range . . . and the Government
reserve[d] the right to seek a sentence above the Estimated
Guidelines Range[,] based on § 3553(a) factors.” Plea
Agreement ¶ 5 (J.A. 27). But that reservation was more
qualified than the government acknowledges.

    The below- or above-Guidelines sentence referenced in the
plea agreement is known as a “variance.”8 “[T]o sustain an


    8
       A “variance” refers to a non-Guidelines sentence imposed
“outside the guidelines framework” based on the applicable factors in
18 U.S.C. § 3553(a) taken as a whole. U.S.S.G. § 1B1.1 cmt.
                                  18

upward variance, the district court . . . ‘must state the specific
reason why the defendant’s conduct was more harmful or
egregious than the typical case represented by th[e] [relevant
Sentencing Guidelines] range.’” United States v. Brown, 892
F.3d 385, 404 (D.C. Cir. 2018) (quoting United States v. Brown,
808 F.3d 865, 867 (D.C. Cir. 2015)); see United States v. Brown,
857 F.3d 403, 405 (D.C. Cir. 2017) (“A judge imposing an
above-Guidelines sentence must offer in court, and in writing,
a specific reason why the defendant’s case calls for a more
severe sentence than other cases falling within the same
Guidelines categories.” (internal quotation marks omitted)).

     In recommending a 33-month sentence, the government did
not say that it was seeking a variance. Nor did it provide the
court with reasons that would support the imposition of a
variance. See Government’s Mem. in Aid of Sentencing 8-13
(J.A. 42-47); Sentencing Hearing Tr. 13-29 (J.A. 83-99). It did
not once attempt “to distinguish [Murray’s] case from others
falling into the same Guidelines categories.” Brown, 857 F.3d
at 405. It did not tell the court why “the Guidelines ‘do not
fully’ capture the egregiousness of th[e] defendant’s conduct.”
Id. at 406 (quoting United States v. Ransom, 756 F.3d 770, 775
(D.C. Cir. 2014)). It did not make that argument about the
Estimated Guidelines Range, as to which it reserved the right to


background (emphasis added) (citing Irizarry v. United States, 553
U.S. 708, 709-16 (2008)). A “departure” refers to a “non-Guidelines
sentence[] imposed under the framework set out in the Guidelines. . . .
based on the sentencing guidelines, policy statements, and official
commentary of the Sentencing Commission.” Irizarry, 553 U.S. at
714 (emphasis added) (internal quotation marks omitted); see U.S.S.G.
§ 1B1.1(b) & cmt. 1(E). Because the plea agreement stipulated that
neither party would seek a “departure,” Plea Agreement ¶ 4.C (J.A.
26-27), the reservation of the right to seek a below- or above-
Guidelines range in Paragraph 5 of the agreement constituted the right
to seek a variance.
                                  19

seek a variance. It did not even make that argument about the
final Guidelines range calculated by the district court.

     Instead, the government simply gave the court a variety of
reasons for sentencing Murray at the top of the final sentencing
range. See, e.g., Sentencing Hearing Tr. 14-15 (J.A. 84-85)
(positing that the 30 grams of heroin “could have potentially
reached, if it was sold not to informants, many, many
individuals on the street”); id. at 16 (J.A. 86) (calculating that
the 45 grams of PCP could have yielded “$1,600 in profit”); id.
at 17 (J.A. 87) (citing Murray’s “very keen knowledge of how
illegal narcotics are sold”).9 Although those reasons track
§ 3553(a) factors, see supra note 2 (describing the factors), that
alone did not indicate that the government was seeking a
variance. The courts use the same factors to determine the
appropriate sentence within a Guidelines range and to determine
whether an above-Guidelines sentence is appropriate. See
Brown, 857 F.3d at 406; United States v. Williams, 773 F.3d 98,
108 (D.C. Cir. 2014).

     As we have explained, the 33-month sentence that the
government recommended was within the range only because
the Superior Court pleas had been included in the final
Guidelines calculation -- contrary to the understanding reflected
in the plea agreement. But asking for a sentence that the
government claimed was within the range was not the same as
asking for a variance. In so doing, the government did not


     9
       See also Sentencing Hearing Tr. 17 (J.A. 87) (saying, “we’re
very concerned” because “[w]e don’t know if [Murray] realizes how
serious his involvement is”); id. at 17-18 (J.A. 87-88) (arguing that
Murray was “infecting our community with illegal drugs that can . . .
dramatically change individuals’ lives”); id. at 22 (J.A. 92) (agreeing
with Murray’s grandmother that he “needs to stop hanging around the
streets, and he needs to . . . get away from that bad crowd”).
                                20

exercise its reservation but rather breached its agreement. See
United States v. Palladino, 347 F.3d 29, 34 (2d Cir. 2003)
(concluding that, in light of an estimated Guidelines range
accompanied by similar “based upon information now known to
the Office” language in the plea agreement, the “defendant had
a reasonable expectation that the Government would not press
the Court for an enhanced offense level in the absence of new
information”); see also United States v. Canada, 960 F.2d 263,
269 (1st Cir. 1992) (stating that Supreme Court precedent
“prohibits not only explicit repudiation of the government’s
assurances, but must in the interests of fairness be read to forbid
end-runs around them” (internal quotation marks omitted)).

    2. Notwithstanding this conclusion, we cannot say that our
reading of the plea agreement is sufficiently clear or obvious so
as to qualify Murray for relief. The agreement does not
expressly say that the government must seek a “variance,” nor
does it explain the kind of reasons the government would need
to assert to obtain a variance. It merely says that “the
Government reserves the right to seek a sentence above the
Estimated Guidelines Range based on § 3553(a) factors.” Plea
Agreement ¶ 5 (J.A. 27). And that is literally what the
government did, basing its request for an above-Guidelines
sentence on reasons that tracked § 3553(a) factors. See supra
Part II.B.1 (noting that the § 3553(a) factors are relevant to
recommendations for sentences both inside and outside the
calculated Guidelines range).

    Given that the sentencing court correctly calculated a 27-to-
33-month final range, the government’s 33-month
recommendation was within the Sentencing Guidelines range,
and did not technically require a variance. And even if it did, it
is only when the government’s reservation is placed in the
context of the legal requirements for a variance that we find it
more reasonable to read the reservation as restricted to seeking
                               21

an above-Guidelines sentence on the ground that “the
defendant’s case calls for a more severe sentence than other
cases falling within the same Guidelines categories” -- i.e., on
the ground that a variance is warranted. Brown, 857 F.3d at 405.
Therefore, it is not clear or obvious that the agreement limited
the government to showing a variance was warranted in order to
request an above-the-range sentence.

                                C

    In sum, we conclude that the government breached its plea
agreement with appellant Murray. But Murray did not object to
the breaches in the district court, and we therefore cannot
provide him with relief because the breaches were not plain.
Although Murray’s interpretation of the agreement’s ambiguous
language is the best one, we cannot say that the breaches should
“have been obvious to the trial court.” King-Gore, 875 F.3d at
1145; see Puckett, 556 U.S. at 135.

                               III

     Murray also contends that his district court counsel was
constitutionally ineffective. In order to succeed on this claim,
Murray must show: (1) “that counsel’s performance was
deficient,” and (2) “that the deficient performance prejudiced the
defense.” Strickland v. Washington, 466 U.S. 668, 687 (1984).
In United States v. Rashad, 331 F.3d 908 (D.C. Cir. 2003), we
explained this circuit’s approach to ineffective assistance claims
that are first raised on appeal:

         Due to the fact-intensive nature of the Strickland
         inquiry and the likelihood, when a defendant asserts his
         sixth amendment claim for the first time on direct
         appeal, that the relevant facts will not be part of the
         trial record, this court’s general practice is to remand
                               22

         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 (citation and internal quotation marks omitted). In
short, all that is required for a remand is “a colorable and
previously unexplored claim of ineffective assistance.” Id. at
908; see, e.g., United States v. Gray-Burriss, 791 F.3d 50, 64
(D.C. Cir. 2015).

     The government insists that Murray has failed to establish
a colorable claim of ineffective assistance of counsel, and hence
that a remand is unwarranted. We disagree. We address the two
prongs of the Strickland test below.

                               A

    The first, “deficiency” prong of Strickland requires a
showing that the lawyer’s performance “fell below an objective
standard of reasonableness.” 466 U.S. at 688. Murray has a
colorable claim that his counsel’s representation fell below that
standard.

     As discussed above, our best reading of the plea agreement
is that the parties expected that, absent a change in material
facts, the Estimated Guidelines Range would be the final
Guidelines range that Murray would face at sentencing --
notwithstanding his required Superior Court pleas -- and hence
that his attorney should have delayed his Superior Court pleas
(if that were possible) until after his federal plea. Murray
claims, moreover, that his attorney made no “attempts at all to
delay [his] D.C. Superior Court pleas.” Murray Br. 4.

    That constitutes a colorable claim of deficient performance.
This circuit has held that a failure by defense counsel to seek a
                               23

delay in sentencing can be objectively unreasonable, and
therefore constitutionally deficient, in light of the reasonably
likely benefits of doing so. United States v. Abney, 812 F.3d
1079, 1088 (D.C. Cir. 2016). But the facts relevant to this claim
-- including what counsel told Murray about the nature of the
plea agreement -- are not part of the trial record. See Rashad,
331 F.3d at 911. To put them on record, Murray likely will have
to testify, question his former counsel, and possibly question the
prosecutor as well. Accordingly, if there is also a colorable
claim of prejudice -- a question we address below -- a remand to
resolve this issue is required.

     Murray also claims that his counsel was deficient because
he failed to object when the prosecutor recommended a sentence
(33 months) that was above the 30-month ceiling of the
Estimated Guidelines Range. Even if counsel could not have
engineered a change in the sequencing of the pleas and the
sentencing, Murray argues that he should have objected to the
33-month sentence and alerted the district court that the
recommendation breached the plea agreement.

     This, too, is a colorable claim of deficient performance.
Under our best reading of the plea agreement, counsel had an
obligation to object when the prosecutor breached that
agreement by making a recommendation above the Estimated
Guidelines Range without seeking a variance. He certainly had
time to do so. The government submitted its memorandum
more than a month before sentencing. Counsel could have
raised the issue in his own memorandum or at sentencing.
Instead, counsel’s sentencing argument was, as his own motion
for withdrawal characterized it, “low-key.”          Counsel’s
memorandum was bare bones, referring in cursory fashion to
Murray’s youth and need for further education. At the
sentencing hearing, counsel then rested on that memorandum,
making no mention of the sentencing range to which the parties
                                   24

had agreed. Indeed, when the court asked Murray’s counsel if
he wanted to provide any explanation for the conduct underlying
the Superior Court pleas, counsel declined. Sentencing Hearing
Tr. 32-34 (J.A. 102-04).

     Once again, however, this deficiency claim rests on facts --
including the nature of counsel’s advice during plea bargaining
-- that are not part of the trial record. And so, once again, a
remand will be required if Murray also has a colorable claim of
prejudice.

                                    B

     To satisfy the second Strickland prong, Murray must show
“that the deficient performance prejudiced” him. 466 U.S. at
687. The prejudice that Murray alleges is an inappropriately
high sentence. See Murray Br. 18.10 To establish prejudice in
the sentencing context, a defendant need only show a
“reasonable probability that, but for counsel’s unprofessional
errors, the result of [sentencing] would have been different.”
See United States v. Eli, 379 F.3d 1016, 1019 (D.C. Cir. 2004)
(citation omitted); accord Campbell v. Smith, 770 F.3d 540, 549
(D.C. Cir. 2014) (applying this standard to claim that counsel
provided ineffective assistance of counsel by failing to object to
the government’s breach at sentencing). “The question isn’t
whether [Murray’s] prison term would have been drastically
shorter -- just whether it was reasonably likely that the prison
term would not have been as long . . . .” In re Sealed Case, 573
F.3d 844, 852 (D.C. Cir. 2009).



     10
         At oral argument, Murray’s appellate counsel advised, for the
first time, that he “reserve[d] the right” to argue for vacatur of the plea
agreement on remand. Recording of Oral Arg. 8:40. We leave that
issue for the district court to address.
                               25

     The government insists that, even if Murray’s counsel
performed deficiently, he cannot show his mistakes made any
difference to the outcome of the case. As the government
accurately recounts, the district court correctly determined that
Murray faced a Guidelines range of 27 to 33 months (as a
consequence of the two Superior Court pleas), understood that
Murray had a “relatively minimal criminal history,” Sentencing
Hearing Tr. 37 (J.A. 107), and found Murray’s to be a
“particularly difficult sentencing because Mr. Murray is such a
young man,” id. at 35 (J.A. 105). “But notwithstanding [his]
young age,” the court told Murray:

         I’ve concluded that the appropriate sentence in this
         case is at the high end of the sentencing guidelines
         range of 33 months. And I’ve done that both because
         of the concern about safety of the community . . . . But
         also because it’s my sincere, sincere hope that coming
         down on that side here with you now . . . will send you
         the message that you need for your life. Because I can
         tell you that I agree with [the government] that if this
         doesn’t do it . . . . I really have grave doubts about the
         rest of your life.

Id. at 37-38 (J.A. 107-08); see also id. at 35 (J.A. 105)
(admonishing Murray that “heroin and PCP are both particularly
dangerous and destructive drugs”). Against that background, the
government contends that no “additional arguments about the
guidelines or appellant’s guilty pleas would have persuaded the
court to impose a lower sentence.” U.S. Br. 24. Again, we
disagree.

     First, we must back up to Murray’s first colorable claim of
deficient performance: counsel’s failure to insist that the
Superior Court pleas be scheduled after the federal sentencing.
Had those pleas not yet taken place at the time of the sentencing,
                               26

the 27-to-33-month range would not have been correct. Instead,
the Estimated Guidelines Range of 24 to 30 months would have
been correct, and a 33-month sentence would have required a
variance -- a disposition that the government did not request and
that the court did not indicate it would accept. See Sentencing
Hearing Tr. 39 (J.A. 109) (statement by the district court judge
that “I’m not going to vary or depart upward . . . I will stay
within the sentencing guidelines”). Because “in most cases the
Guidelines range will affect the sentence,” Molina-Martinez v.
United States, 136 S. Ct. 1338, 1349 (2016), the prospect that
effective performance would have put Murray’s 33-month
sentence above the Guidelines range is sufficient to establish a
reasonable probability of prejudice. Cf. id. (holding that “a
defendant sentenced under an incorrect Guidelines range should
be able to rely on that fact to show a reasonable probability that
the district court would have imposed a different sentence under
the correct range”).

     Murray’s second colorable claim of deficient performance
likewise yields a colorable claim of prejudice. Even if the final
sentencing range ended up at 27 to 33 months, there is at least
a “reasonable likelihood,” United States v. Mohammed, 693 F.3d
193, 204 (D.C. Cir. 2012), that a timely objection to the
prosecutor’s 33-month recommendation would have yielded a
lower prison term. It is true, as the government says, that the
district court fully and adequately explained the 33-month
sentence at which it arrived. But it did so on the basis of a
recommendation by the prosecutor that it deemed “helpful.”
Sentencing Hearing Tr. 32 (J.A. 102). The court was not
advised that, in reaching their plea agreement, the parties
assumed that 30 months was the top of the range that Murray
would face, even with the Superior Court pleas. Nor was the
court advised that the prosecutor was breaching that agreement
by recommending 33 months.
                               27

     Had the court known these things, it might well have
considered a lower sentence. Even if the final sentencing range
had been 27 to 33 months (because of the two Superior Court
pleas), the court could still have effectuated the parties’
understanding by sentencing Murray to between 27 and 30
months, which would have fallen within both the Estimated
Guidelines Range and the final range. It might have done so by
recognizing, as Murray urges, that his final sentencing range had
increased beyond what the plea agreement contemplated
“simply because he had done what it required, apparently based
solely on the serendipity of his D.C. Superior Court plea dates.”
Murray Br. 17. This possibility is particularly reasonable given
the Probation Office’s recommendation that Murray be
sentenced to only 21 months, Sentencing Hearing Tr. 10 (J.A.
80), and the court’s acknowledgment that this was “a
particularly difficult sentencing,” id. at 35 (J.A. 105).

     In any event, all that is required to satisfy the second
Strickland prong is a “reasonable likelihood” that the court
would impose a sentence lower than 33 months, and all that is
required for a Rashad remand is that this possibility be
“colorable.” Mohammed, 693 F.3d at 204. “At this stage,
[Murray] need not prove actual prejudice, but merely show that
the record does not ‘conclusively establish[] that he could not do
so if given the chance.’” Id. (quoting Rashad, 331 F.3d at 912).
He has done so.
                             28

                             IV

    For the foregoing reasons, although we conclude that the
government breached its plea agreement with the appellant, we
cannot vacate his sentence because the error was not plain. We
can and do, however, remand Murray’s ineffective assistance
claim for further proceedings in the district court because
Murray has raised a colorable claim of ineffective assistance.

                                                  So ordered.
