Court Opinion

ID: 4304878
Source: CourtListenerOpinion
Date Created: 2018-08-17 15:00:44.2109+00
Date Added: 2024-06-11T14:34:55.982583
License: Public Domain

United States Court of Appeals
          FOR THE DISTRICT OF COLUMBIA CIRCUIT

Argued October 6, 2017               Decided August 17, 2018

                         No. 16-3005

                     IN RE: SEALED CASE
                            ______

               Consolidated with No. 16-3024
                          ______

         Appeal from the United States District Court
                 for the District of Columbia
                    (No. 1:10-cr-00172-1)
                            ______

   Before: SRINIVASAN and WILKINS, Circuit Judges, and
SENTELLE, Senior Circuit Judge.

    Opinion for the Court filed by Circuit Judge SRINIVASAN.

     SRINIVASAN, Circuit Judge: Often, when a criminal
defendant agrees to plead guilty, he also agrees to waive his
right to take an appeal or seek collateral review after he is
sentenced. The appeal waiver generally precludes him from
bringing an appeal on any as-yet-unknown claim that might
arise in his upcoming sentencing proceedings. So, for instance,
if the defendant comes to believe that the trial court committed
an error in determining his sentence, his appeal waiver
generally would bar him from appealing on that ground.

    But what if the claim the defendant wishes to raise on
appeal concerns, not an alleged error committed by the trial
                                2
court at sentencing, but instead the performance of the
defendant’s own attorney at sentencing?         Suppose the
attorney’s performance in the sentencing proceeding is so poor
that it violates the defendant’s Sixth Amendment right to
counsel. Does a defendant’s generic appeal waiver encompass
a claim that he received ineffective assistance of counsel in
connection with his sentencing?

     We conclude that a generic appeal waiver does not affect
a defendant’s ability to appeal his sentence on yet-to-arise
ineffective-assistance-of-counsel grounds. The appellant in
this case executed a generic appeal waiver, with no explicit
waiver of his right to appeal on ineffective-assistance-of-
counsel grounds. The appeal waiver thus does not prevent him
from appealing on the basis that he received ineffective
assistance of counsel in his sentencing proceeding. As to the
ultimate merits of appellant’s ineffective-assistance claims, we
cannot conclusively resolve them on the record before us. In
those circumstances, we ordinarily remand the claims to the
district court for further proceedings, and we do so here.

                                I.

     Appellant pleaded guilty to one count of conspiracy to
distribute five kilograms or more of cocaine on board an
aircraft registered in the United States and one count of
conspiracy to distribute and possess with intent to distribute
1,000 kilograms or more of marijuana. As part of the plea
agreement, appellant “waive[d] any and all appeals and
collateral attacks in this case and agree[d] that this case [would]
become final once he ha[d] been sentenced.” Plea Agreement
¶ 24.

    At the sentencing hearing, the district court first sought to
determine the appropriate sentencing-guidelines range. The
                                3
Presentence Report recommended a three-level increase in
appellant’s base offense level based on his major role in a drug
trafficking conspiracy. See U.S.S.G. § 3B1.1(b) (2009).
Appellant’s counsel argued against the adjustment, contending
that appellant was not a manager or supervisor of the
conspiracy. The district court declined to adjust appellant’s
base offense level based on his role in the conspiracy. The
court determined that the appropriate guidelines range was 135
to 168 months of imprisonment.

    The district court then set out various considerations
guiding its determination of appellant’s sentence. One
consideration was that the court considered appellant neither a
major participant nor a minor participant in the conspiracy.
The court ultimately decided to sentence appellant to 120
months of imprisonment on each of the two counts of
conviction, with the sentences to run concurrently.

                               II.

     Appellant seeks to appeal his sentence on the ground that
he received ineffective assistance of counsel at sentencing in
various respects. Among appellant’s ineffective-assistance
arguments, he contends that his counsel should have argued for
a downward adjustment based on his minor role in the
drug-trafficking conspiracy.

    The government argues that, by executing a general appeal
waiver, appellant relinquished his right to appeal his sentence
on grounds of ineffective assistance of counsel. We disagree.
We conclude that appellant’s generic appeal waiver did not
encompass a claim that his attorney provided him
constitutionally ineffective assistance at sentencing. While
appellant thus can raise his ineffective-assistance claims in this
appeal, we cannot definitively resolve the claims on the
                                4
existing record. We therefore remand the claims to the district
court in accordance with our customary practice.

                               A.

     We first consider the implications of appellant’s generic
appeal waiver for his ability to appeal on the ground that he
received ineffective assistance of counsel at sentencing. In
addressing that issue, we begin with an overview of the
principles governing the enforceability of appeal waivers and
then apply those principles to the specific context of
ineffective-assistance-of-counsel claims.

                               1.

     In United States v. Guillen, this court held that a defendant
can validly waive her right to appeal a sentence that has not yet
been imposed, as long as her decision is “knowing, intelligent,
and voluntary.” 561 F.3d 527, 529-30 (D.C. Cir. 2009). We
acknowledged that such a waiver presents distinct
considerations because it is an “anticipatory waiver—that is,
one made before the defendant knows what the sentence will
be.” Id. at 529. But an “anticipatory waiver” nonetheless
meets the condition that it be “a knowing waiver if the
defendant is aware of and understands the risks involved in his
decision.” Id. Therefore, we explained, if “the record shows
that the defendant knows what he is doing and his choice is
made with eyes open, then the Court will enforce an
anticipatory waiver” of the right to appeal a sentence. Id. at
529-30 (formatting modified and citation omitted).

    As a general matter, “an allegation that the sentencing
judge misapplied the Sentencing Guidelines or abused his or
her discretion is not subject to appeal in the face of a valid
appeal waiver.” United States v. Adams, 780 F.3d 1182, 1184
                                5
(D.C. Cir. 2015) (quoting United States v. Andis, 333 F.3d 886,
892 (8th Cir. 2003) (en banc)). Consistent with that
understanding, we have held that an appeal waiver barred a
defendant from appealing her sentence on the grounds that the
district court: imposed a substantively unreasonable sentence,
id. at 1183; erred in declining to permit the defendant to
introduce certain evidence at sentencing or in limiting cross-
examination of the government’s sentencing witnesses, id. at
1183-84; or abused its discretion in denying a downward
variance from the sentencing guidelines range, United States v.
Ortega-Hernandez, 804 F.3d 447, 451 (D.C. Cir. 2015).

     Enforcing an appeal waiver in such circumstances “serves
the important function of resolving a criminal case swiftly and
finally.” United States v. Hunt, 843 F.3d 1022, 1027 (D.C. Cir.
2016). And allowing a defendant to waive his right to appeal
his yet-to-be-imposed sentence also “improves the defendant’s
bargaining position and increases the probability he will reach
a satisfactory plea agreement with the Government.” Guillen,
561 F.3d at 530.

     But while an appeal waiver is generally enforceable if the
defendant has the requisite awareness and understanding of
“the risks involved in his decision,” id. at 529, a generic appeal
waiver does not establish a defendant’s acceptance of every
“defect or error that may be thrust upon him by either an
ineffective attorney or an errant sentencing court,” id. at 530.
“Most obvious,” we have explained, “a waiver should not be
enforced insofar as the defendant makes a colorable claim he
received ineffective assistance of counsel in agreeing to the
waiver” in the first place. Id. If the claim has merit, the
defendant would not have “understood the consequences of his
waiver.” Id. “Nor should a waiver be enforced if the
sentencing court’s failure in some material way to follow a
prescribed sentencing procedure results in a miscarriage of
                                6
justice.” Id. at 531. That would be the case if, for example, the
sentence “is unlawful because it exceeds the statutory
maximum” or because it is “colorably alleged to rest upon a
constitutionally impermissible factor, such as the defendant’s
race or religion.” Id.

     In addition, “we will not bar the door to a criminal
defendant’s appeal if his waiver only arguably or ambiguously
forecloses his claims.” Hunt, 843 F.3d at 1027. Applying that
understanding, we declined to construe a defendant’s general
waiver of the right to appeal a sentence to preclude him from
appealing on a claim that the district court erred in imposing a
particular condition of supervised release—viz., a condition
that he stay away from a housing project where he had
distributed drugs. Id. at 1027-29. While the defendant had
agreed “to waive the right to appeal the sentence in [the] case,
including any . . . term of supervised release,” id. at 1027, the
reference to a “term” of supervised release, we reasoned, was
sufficiently ambiguous that he “did not necessarily give up the
right to appeal a condition of such release,” id. at 1028.

     The upshot of our decisions is that a general appeal waiver
will be understood to preclude appealing a sentence on a host
of grounds. But a generic waiver of appeal rights will not bar
every appeal concerning a defendant’s sentence. The central
question in that regard is whether the defendant is “aware of
and understands the risks involved in his decision,” Guillen,
561 F.3d at 529, with any ambiguity about the scope of his
waiver construed in his favor, Hunt, 843 F.3d at 1027.

                                2.

     Appellant generally “waive[d] any and all appeals and
collateral attacks in this case and agree[d] that this case [would]
become final once he ha[d] been sentenced.” Plea Agreement
                                7
¶ 24. He received no specific information about whether that
waiver pertains to claims of ineffective assistance of counsel.

     The plea agreement itself does not expressly address the
issue. Nor did the district court do so in its plea colloquy with
appellant. The district judge asked if appellant understood that
he was “giving up certain of [his] rights to challenge the
sentence,” and then quoted the language of the appeal waiver.
Plea Tr. 23. The judge (understandably) did not advise
appellant that, by generically giving up his right to appeal, he
was forgoing any appeal on the ground that his attorney later
performed so poorly at sentencing that he “was not functioning
as the ‘counsel’ guaranteed by the Sixth Amendment.”
Strickland v. Washington, 466 U.S. 668, 687 (1984). As for
whether appellant’s counsel shed any light on the matter,
appellant contends that his attorney did not advise him that the
appeal waiver encompassed ineffective-assistance-of-counsel
claims.

     The question, then, is whether the generic language of the
appeal waiver, standing alone, gave appellant the requisite
awareness and understanding of “the risks involved,” Guillen,
561 F.3d at 529 —i.e., that if he were to receive constitutionally
ineffective assistance of counsel at sentencing, he would be
unable to appeal or seek collateral review on that ground. The
government submits that Guillen itself settles that a generic
waiver encompasses claims of ineffective assistance of counsel
at sentencing. The government points to our observation that a
waiver will not preclude a “colorable claim” that the defendant
“received ineffective assistance of counsel in agreeing to the
waiver.” Guillen, 561 F.3d at 530. But that statement, contrary
to the government’s assumption, did not suggest that the waiver
reaches all ineffective-assistance claims beyond those
concerning the waiver itself. Rather, we merely “mention[ed]
some circumstances” in which there would be no waiver,
                                8
identifying the referenced one as the “[m]ost obvious”
example. Id. (emphasis added). We did not speak to the status
of other types of ineffective-assistance claims under a generic
appeal waiver, including claims of ineffective assistance at
sentencing.

     Addressing the matter here, we note at the outset that our
general duty to construe ambiguities in an appeal waiver in the
defendant’s favor is especially salient in the context of claims
alleging ineffective assistance of counsel. Because “[t]he right
to the effective assistance of counsel at trial is a bedrock
principle in our justice system,” a person’s “inability to present
a claim of trial error is of particular concern when the claim is
one of ineffective assistance of counsel.” Martinez v. Ryan,
566 U.S. 1, 12 (2012); see also United States v. Taylor, 139
F.3d 924, 931 (D.C. Cir. 1998) (“The court . . . must ‘indulge
every reasonable presumption against the waiver of the
unimpaired assistance of counsel.’” (quoting Campbell v.
United States, 352 F.2d 359, 361 (D.C. Cir. 1965))). That
understanding about “the effective assistance of counsel at
trial” is equally true about ineffective assistance at sentencing.

     We cannot conclude that a defendant who executes a
generic appeal waiver “is aware of and understands the risk[]”
that, by doing so, she waives any ability to appeal if her counsel
later provides constitutionally ineffective assistance at
sentencing.     Guillen, 561 F.3d at 529.           The key to
understanding why lies in recognizing that (i) the defendant
retains her Sixth Amendment right to counsel in the upcoming
sentencing proceeding, and (ii) unlike other rights, her right to
counsel can practically be vindicated only through an appeal or
collateral proceeding.

    First, a defendant who generically waives a right to appeal
of course retains a Sixth Amendment right to counsel at
                                 9
sentencing. The government has not suggested that appellant
in this case, or defendants in appellant’s circumstances
generally, somehow give up the right to counsel by generically
waiving the right to appeal. And a defendant’s right to
counsel’s assistance at sentencing necessarily means the right
to effective counsel. After all, ineffective counsel is no counsel
at all, as far as the Sixth Amendment is concerned. See
Strickland, 466 U.S. at 687.

     Second, a defendant can practically vindicate the right to
the effective assistance of counsel at sentencing only through
an appeal or collateral proceeding. Ineffective-assistance
claims differ from other sorts of claims in that respect. With
other claims that may arise at sentencing, the defendant’s
counsel can often present the issue in the sentencing court
itself. The defendant thus would retain some ability to air the
issue even if she waives her ability to take an appeal or seek
collateral review.

     That is not the case with an ineffective-assistance claim
that arises at sentencing. Counsel cannot be expected to raise
such an ineffective-assistance claim in the sentencing court
itself: an attorney, to say the least, will be “unlikely to raise an
ineffective-assistance claim against himself.” Massaro v.
United States, 538 U.S. 500, 502-03 (2003).

     Nor is the defendant herself well positioned to identify her
counsel’s deficient performance and bring it to the sentencing
court’s attention. We have recognized that counsel fulfills an
essential function at sentencing by navigating the sentencing
guidelines and presenting the various considerations that may
drive the court’s sentencing determination. See United States
v. Soto, 132 F.3d 56, 59 (D.C. Cir. 1997). Any expectation that
a defendant would understand and identify her counsel’s
inadequacies would be tantamount to assigning her principal
                                10
responsibility to carry out the representation herself, in the face
of “the dangers and disadvantages of self-representation.”
Faretta v. California, 422 U.S. 806, 835 (1975).

     Additionally, “[i]neffective assistance claims often depend
on evidence outside the trial record.” Martinez, 566 U.S. at 13.
Claims of ineffective assistance thus frequently require the
development of a record on collateral review (or on remand
from an appeal). Those considerations underlay the Supreme
Court’s decision in Massaro v. United States. 538 U.S. 500.
There, the Court held that ineffective-assistance claims may be
brought for the first time on collateral review. It grounded that
conclusion in its recognition that the trial “record in many cases
will not disclose the facts necessary to decide either prong of
the Strickland analysis” governing ineffective-assistance
claims. Id. at 505. That is all the more reason defendants
cannot be expected to catch such claims and bring them
initially in the district court.

     For those reasons, the ability to bring an ineffective-
assistance claim on collateral review or on appeal (with the
possibility of a remand for factual development) is essential to
vindicating a defendant’s right to counsel at sentencing. It
follows that a waiver of the right to appeal and collateral
review, if construed to encompass ineffective-assistance-of-
counsel claims, acts essentially as a waiver of the right to
counsel at sentencing.

     In that light, the question is whether a defendant who
retains a right to counsel at sentencing would nevertheless
understand that, by generically waiving her right to appeal, she
would essentially give up her ability to preserve her right to
counsel. We do not think so. Indeed, the defendant might
agree to an appeal waiver in significant measure precisely
because of her right to counsel’s assistance at sentencing: even
                               11
if she relinquishes her ability to raise a sentencing error on
appeal, she at least will have her attorney’s assistance in
identifying any sentencing error to the sentencing court itself,
in the hope that the sentencing court will correct the error and
obviate any need for an appeal. The government’s own
attorney appeared to assume as much in appellant’s sentencing
hearing, stating: “the defendant agreed to waive his right to
appeal, I think except for ineffective assistance of counsel.”
Sentencing Tr. 34-35.

     In short, construing a generic appeal waiver to extend to
ineffective-assistance-of-counsel claims would be inconsistent
with our understanding that a defendant must be “aware of and
understand[] the risks involved in his decision.” Guillen, 561
F.3d at 529. A contrary conclusion would mean that the
defendant retained her right to counsel at sentencing while
nonetheless giving up her ability to preserve that right. We do
not believe that a generic appeal waiver brings about that result,
much less that it unambiguously does so. See Hunt, 843 F.3d
at 1027.

     We note a final consideration pointing in the same
direction. If a generic appeal waiver did encompass a claim of
ineffective assistance of counsel at sentencing, the waiver then
would give rise to a conflict of interest for counsel: an attorney
generally cannot advise a client about whether to waive a
pending claim against the attorney herself, see John Wesley
Hall, Jr., Professional Responsibility in Criminal Defense
Practice § 10:27 (3d ed. 2017), and the same is necessarily true
of advice about whether to waive a future claim against the
attorney. A number of state bar associations thus have
determined that agreements to waive claims against an attorney
violate state ethics rules as conflicts of interest. Id. What is
more, if counsel operates under a conflict of interest when
giving advice about an appeal waiver, the waiver would be
                               12
unenforceable “insofar as” there is then “a colorable claim”
that the defendant “received ineffective assistance of counsel
in agreeing to the waiver.” Guillen, 561 F.3d at 530. The better
resolution, and the one we adopt here, is to conclude that a
generic appeal waiver does not reach claims of ineffective
assistance of counsel at sentencing.

     We recognize that other courts of appeals have determined
otherwise. Several of our sister circuits have held that a general
waiver of appeal rights bars a defendant from appealing on the
ground that counsel provided ineffective assistance at
sentencing. See Williams v. United States, 396 F.3d 1340,
1341-42 (11th Cir. 2005); United States v. White, 307 F.3d 336,
338, 343-44 (5th Cir. 2002); United States v. Cockerham, 237
F.3d 1179, 1180, 1185-86 (10th Cir. 2001). But see United
States v. Johnson, 410 F.3d 137, 151 (4th Cir. 2005). But for
the reasons set out in this opinion, we respectfully reach a
different conclusion, guided by our own court’s precedents
governing the enforceability of appeals waivers. See Guillen,
561 F.3d at 529-31; Hunt, 843 F.3d at 1026-29.

     It bears noting, finally, that the views of those courts (and
ours) might be of limited practical significance on a
prospective basis. After the plea agreement in this case was
executed, the Department of Justice issued a memorandum to
all federal prosecutors directing that they “no longer seek in
plea agreements to have a defendant waive claims of
ineffective assistance of counsel whether those claims are made
on collateral attack or, when permitted by circuit law, made on
direct appeal.” U.S. Dep’t of Justice, Department Policy on
Waivers of Claims of Ineffective Assistance of Counsel (Oct.
14, 2014). Although the government conceivably could
rescind that directive at some point, as things now stand, the
question of whether an appeal waiver reaches ineffective-
assistance claims is unlikely to arise in future cases.
                               13
                               B.

     Because the appeal waiver does not preclude appellant
from appealing on the ground that he received ineffective
assistance of counsel at sentencing, we turn to the merits of his
ineffective-assistance claims. When a defendant asserts a
colorable ineffective-assistance claim on appeal, this court’s
practice is to remand to the district court “unless the record
alone conclusively shows that the defendant either is or is not
entitled to relief.” United States v. Bell, 708 F.3d 223, 225
(D.C. Cir. 2013) (internal quotation marks omitted).

     To raise a colorable claim for ineffective assistance of
counsel, a defendant must allege sufficient facts to “show two
things: (1) that counsel’s performance was deficient, and (2)
that the deficient performance prejudiced the defense.” United
States v. Anderson, 632 F.3d 1264, 1268 (D.C. Cir. 2011)
(internal quotation marks omitted); see also Strickland, 466
U.S. at 687. Appellant raises at least one colorable claim that
he received ineffective assistance of counsel at sentencing in
violation of his Sixth Amendment rights. In particular,
appellant plausibly alleges that his counsel failed to argue for a
downward adjustment to his sentence based on his minor role
in the offense, that a constitutionally effective attorney would
have made that argument, and that counsel’s failure to do so
prejudiced appellant.

    Section 3B1.2 of the Sentencing Guidelines allows for a
two-level reduction in offense level if the defendant “was a
minor participant in any criminal activity.”          U.S.S.G.
§ 3B1.2(b). That adjustment applies to defendants who were
“substantially less culpable than the average participant.” Id.
cmt. 3(A). Whether the adjustment applies is a fact-specific
determination. Id. cmt. 3(C).
                              14
     Appellant’s attorney made no argument in his sentencing
memoranda or in the sentencing hearing that appellant should
receive a downward adjustment under section 3B1.2(b) for
minor role. That adjustment arguably applied to appellant’s
circumstances. Counsel’s failure to “specifically request” a
potentially applicable downward adjustment might have
amounted to deficient performance. See Soto, 132 F.3d at 58-
59. And if the district court had decided to apply a minor-role
adjustment, appellant’s offense level would have been reduced
by at least two levels under section 3B1.2 of the Sentencing
Guidelines and up to four additional levels under a relevant
corresponding guideline provision, section 2D1.1(a)(5).
Together, the application of those provisions would have
lowered appellant’s guidelines range from 135-168 months of
imprisonment to 70-87 months. U.S.S.G. § 5A. The possibility
that appellant would have received a lower sentence is
sufficient evidence of prejudice to warrant a remand. See
United States v. Rashad, 331 F.3d 908, 911-12 (D.C. Cir.
2003).

     The government’s responses do not persuade us otherwise.
The government argues that appellant’s attorney did in fact
argue for a minor role adjustment when objecting to the
presentence report. But those brief objections had been offered
by appellant’s previous attorney over a year before sentencing;
they were not reiterated by appellant’s new counsel during the
sentencing proceedings. The government additionally argues
that any deficiency in counsel’s performance did not prejudice
appellant because the district court affirmatively rejected the
minor role adjustment during the sentencing hearing. But
while the court, at various points in the sentencing hearing,
offered its view that the minor role adjustment did not apply,
the court did so without having been presented with any
argument on the matter from appellant’s counsel in his
sentencing memoranda or during the hearing. It is possible
                              15
that, had the court heard an argument specifically raising the
applicable guidelines provision, explaining the factors that go
into the determination, and showing that the facts of this case
fit those factors, the court would have made a different choice.
That kind of fact-specific prejudice inquiry is best conducted
by the district court on remand. See Bell, 708 F.3d at 225.

     Because appellant raises at least one colorable claim of
ineffective assistance of counsel that cannot be conclusively
accepted or rejected on the record before us in this appeal, we
remand the matter to the district court. On remand, the court
can fully consider the claim along with the other ineffective-
assistance claims raised by appellant.

                      *   *    *   *    *

     For the foregoing reasons, we remand the case to the
district court for further proceedings.

                                                    So ordered.