United States v. Staveley ( 2022 )

United States Court of Appeals
For the First Circuit
No. 21-1842
UNITED STATES OF AMERICA,
Appellee,
v.
DAVID STAVELEY, a/k/a Kurt D. Sanborn, a/k/a David Sanborn,
a/k/a Kurt Sanborn, a/k/a David Adler Staveley,
Defendant, Appellant.
APPEAL FROM THE UNITED STATES DISTRICT COURT
FOR THE DISTRICT OF RHODE ISLAND
[Hon. Mary S. McElroy, U.S. District Judge]
Before
Thompson, Selya, and Gelpí,
Circuit Judges.
Kara Hoopis Manosh for appellant.
Lauren S. Zurier, Assistant United States Attorney, with whom
Zachary A. Cunha, United States Attorney, was on brief, for
appellee.
August 2, 2022
SELYA, Circuit Judge. In United States v. Teeter, 257
F.3d 14 (1st Cir. 2001), and its progeny, this court has upheld
the general validity of appeal waivers in criminal cases. See id.
at 23; see also United States v. O'farrill-López, 991 F.3d 45, 48
(1st Cir. 2021); United States v. Almonte-Nuñez, 771 F.3d 84, 88
(1st Cir. 2014); United States v. Nguyen, 618 F.3d 72, 74 (1st
Cir. 2010). Those decisions paint the backdrop for this appeal,
in which defendant-appellant David Staveley asks us to override an
appeal waiver and allow him to proceed with an appeal based on
what he alleges to be the ineffective assistance of his counsel
below. This entreaty runs headlong into the well-established Mala
rule, which instructs that a "fact-specific claim[] of ineffective
assistance [of counsel] cannot make [its] debut on direct review"
when the record is insufficiently "developed to allow reasoned
consideration of the claim." United States v. Mala, 7 F.3d 1058,
1063 (1st Cir. 1993).
In our view, the Mala rule must prevail. Thus, we hold
that ineffective assistance of counsel claims, not raised in the
district court and not within an exception to Mala, are inadequate
to overcome an appeal waiver. Consequently, we dismiss the appeal.
I
We briefly rehearse the background and travel of the
case. Because this appeal follows a guilty plea, we take the facts
from the change-of-plea colloquy, the unchallenged portions of the
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presentence investigation report (PSI Report), and the transcript
of the disposition hearing. See United States v. Lessard, 35 F.4th
37, 40 (1st Cir. 2022).
When the COVID-19 pandemic ravaged the nation, Congress
created emergency financial assistance programs to ameliorate the
economic consequences wrought by the crisis. See Coronavirus Aid,
Relief, and Economic Security Act, Pub. L. No. 116-136, 134 Stat.
281 (2020). One of these programs — the Paycheck Protection
Program (PPP) — provided small businesses with funds necessary to
meet their employees' salaries and other operating expenses. See
id. § 1102, 134 Stat. at 286-94.
In April of 2020, the defendant — along with a
co-conspirator — submitted several false and fraudulent loan
applications seeking PPP funds. Those applications were
ostensibly made on behalf of various entities, claiming that the
entities had several employees and large payrolls. In reality,
those entities — at the time the applications were made — either
had no employees at all or paid out no wages in the relevant time
frame.
After these machinations came to light, the defendant
was charged by criminal complaint in the District of Rhode Island.
The affidavit accompanying the complaint alleged in substance that
the defendant had committed bank fraud, see 18 U.S.C. § 1344, had
conspired to commit bank fraud, see id. §§ 1344, 1349, and had
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perpetrated other federal crimes, see 15 U.S.C. § 645(a) & 18
U.S.C. § 371 (conspiracy to make false statements to influence the
Small Business Administration); 18 U.S.C. § 1028A (aggravated
identity theft). While awaiting trial, the defendant was released
on personal recognizance and was later required to stay in home
confinement.
In disregard of the conditions of his release, the
defendant fled from the state. To avoid apprehension, he staged
a fake suicide and — while on the lam — used false identities and
stolen license plates. Those events led to an additional federal
charge for failing to appear in court. See id. § 3146(a)(1).
Approximately one year later, the defendant — who by
then had been charged by a grand jury — agreed to plead guilty to
conspiracy to commit bank fraud, see id. §§ 1344, 1349, and to
failure to appear in court, see id. § 3146(a)(1). His plea
agreement contained a waiver-of-appeal provision, which stated
that the defendant agreed to forgo his right to appeal the
convictions and sentences imposed so long as the sentences imposed
were within or below the guideline sentencing range (as determined
by the sentencing court). At the change-of-plea hearing, the
district court specifically addressed the waiver-of-appeal
provision and confirmed that the defendant understood its
significance.
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The district court convened the disposition hearing on
October 7, 2021. At that hearing, the sentencing court determined
the defendant's total offense level and criminal history category.
Based on those determinations, the court found that the defendant's
guideline range suggested an aggregate sentence between fifty-one
and sixty-three months of incarceration.
The government argued for consecutive sentences
aggregating a within-Guidelines sentence of fifty-six months.
During the course of its argument, the government disputed the
defendant's claim that his post-traumatic stress disorder (PTSD)
stemmed from an alleged sexual assault while he had been in federal
custody for an earlier offense. It noted that the PSI Report
sketched an unclear picture of the factual basis for those
allegations.
Defense counsel rejoined that the appropriate sentences
would be time served with supervised release. He argued — among
other things — that the defendant's sentences should be mitigated
because the defendant had been diagnosed with PTSD. Although
acknowledging that the government had called into question the
underlying cause of that PTSD, he countered that he had provided
the district court with medical records substantiating the PTSD
diagnosis.
When mulling the sentencing factors, the district court
commented that "[t]he fact that serving time in prison for [the
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defendant] is more difficult because of the PTSD and the things
that [the defendant had] been through . . . is something that is
awful." Nevertheless, the court concluded that it was "also a
risk that [the defendant] knew [he] w[as] taking at the time that
[he] w[as] engaging in th[e] behavior." The court then imposed a
sentence of forty-four months for the conspiracy charge and a
sentence of twelve months for the failure-to-appear charge, to be
served consecutively. That aggregate sentence added up to a
within-Guidelines sentence. Finally, the court — pursuant to the
plea agreement — dismissed the other charges against the defendant.
Shortly after the disposition hearing, the defendant
sought and received court-appointed counsel pursuant to the
Criminal Justice Act. See id. § 3006A. The defendant's new
counsel then brought this timely appeal.
II
The defendant asserts — for the first time on appeal —
that his guilty plea (and, thus, his convictions and his aggregate
sentence) should be vacated because his then-counsel afforded him
ineffective assistance in derogation of his Sixth Amendment rights
both at the time he entered his plea and at sentencing. See U.S.
Const. amend. VI; see also Strickland v. Washington, 466 U.S. 668,
687-88 (1984); Hill v. Lockhart, 474 U.S. 52, 58 (1985) (applying
Strickland to claims of ineffective assistance in guilty-plea
context). As we explain below, this assertion blinks reality.
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Although "[t]he Sixth Amendment guarantees criminal
defendants the right to effective assistance of counsel," there is
no guarantee that a defendant can assert a violation of that right
for the first time on direct appeal of a conviction or sentence.
United States v. Chambers, 710 F.3d 23, 31 (1st Cir. 2013)
(alteration in original) (quoting Scarpa v. Dubois, 38 F.3d 1, 8
(1st Cir. 1994)). That admonition is doubly relevant where, as
here, a valid waiver-of-appeal provision may operate to preclude
the defendant's claims. Our inquiry begins with the threshold
issue: whether the waiver-of-appeal provision in the defendant's
plea agreement requires dismissal of the defendant's appeal.
A
We begin with first principles. In Teeter, we held that
a presentence waiver of appellate rights in a criminal case is
presumptively enforceable when it is made knowingly and
voluntarily. See Teeter, 257 F.3d at 25. At the same time, we
rejected the notion that such waivers are invalid simply because
they are made before a defendant has any real "clue as to the
nature and magnitude of the sentencing errors" that may occur.
Id. at 21. Recognizing the "obvious dangers attendant to the
practice," though, we held that such waivers must "meet stringent
criteria" to ensure that they have been entered into knowingly and
voluntarily. Id. at 23.
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We also held that "limits must be set on the effect that
can be given to [such waivers]." Id. at 24. Although a knowing
and voluntary waiver of appellate rights is presumptively
enforceable, "no appeal waiver serves as an absolute bar to all
appellate claims." Garza v. Idaho, 139 S. Ct. 738, 744 (2019).
For instance, a waiver does not apply unless a "claim of error
falls within the scope of the waiver." O'farrill-López, 991 F.3d
at 48 (citing Teeter, 257 F.3d at 24); see Almonte-Nuñez, 771 F.3d
at 88. And because presentence appeal waivers are "made before
any manifestation of sentencing error emerges, appellate courts
must remain free to grant relief from them in egregious cases."
Teeter, 257 F.3d at 25. "[I]f denying a right of appeal would
work a miscarriage of justice, the appellate court, in its sound
discretion, may refuse to honor the waiver." Id.With this foundation in place, we turn to the case at
hand. As an initial matter, the defendant appears to concede that
his appeal falls within the literal scope of the waiver-of-appeal
provision. He nonetheless argues, in broad strokes, that the
waiver of appeal is nugatory because he did not enter into his
guilty plea knowingly and voluntarily. As a fallback, he submits
that enforcement of the waiver would result in a miscarriage of
justice.
The common thread that runs through the defendant's
arguments is his allegation of ineffective assistance of counsel.
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The attorney who represented him below was — he says — asleep at
the wheel. But that allegation is not properly before us based on
our well-established Mala rule and, therefore, does not denature
the operation of the defendant's waiver.
To reach this conclusion, our starting point is whether
the waiver appears presumptively enforceable. Answering that
query will dictate how we evaluate the defendant's asseverational
array.
B
Under Teeter, we determine whether a presentence waiver
of appellate rights was entered into knowingly and voluntarily by
looking to the "text of the plea agreement and the content of the
change-of-plea colloquy" — the "critically important" sources for
a "determination of knowledge and volition." Teeter, 257 F.3d at
24; see Nguyen, 618 F.3d at 74. The waiver's scope must be clear
and definite. See Teeter, 257 F.3d at 24; Nguyen, 618 F.3d at 74.
The district court also must "question the defendant specifically
about [his] understanding of the waiver provision and adequately
inform [him] of its ramifications." Teeter, 257 F.3d at 24; see
Nguyen, 618 F.3d at 74. "If this appraisal shows that the waiver
was made knowingly and voluntarily," it is "presumptively
enforceable." Nguyen, 618 F.3d at 74.
Here, the plea agreement and the transcript of the
change-of-plea colloquy make manifest that the defendant's waiver
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of appellate rights is presumptively valid. The plea agreement
"contains a clear statement elucidating the waiver and delineating
its scope." Teeter, 257 F.3d at 24. Indeed, the defendant does
not argue to the contrary.
The change-of-plea colloquy reflects that the district
court's questioning anent the waiver was unimpugnable. The
adequacy of such an inquiry "depends on the specifics of the case,
including questions asked or statements made by the judge,
characteristics of the defendant, and evidence that the defendant
understood that he was waiving his right to appeal." United States
v. Morillo, 910 F.3d 1, 3 (1st Cir. 2018).
The court below twice inquired whether the defendant
understood that — by entering into the plea agreement — he would
be relinquishing the right to appeal the sentences to be imposed.
Though the district court did not refer specifically to his waived
right to appeal the convictions, it confirmed generally that
counsel had read and discussed the plea agreement with the
defendant and that the defendant understood the agreement's terms.
That line of questioning — in the circumstances of this case — was
satisfactory to "confirm the defendant's understanding of the
waiver and [his] acquiescence in the relinquishment of rights that
it betokens." Teeter, 257 F.3d at 24 n.7; see United States v.
Rodriguez-Monserrate, 22 F.4th 35, 43 (1st Cir. 2021).
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In an effort to blunt the force of this reasoning, the
defendant suggests that the court failed to comply with Federal
Rule of Criminal Procedure 11(b)(1)(N). That rule requires that
when a defendant seeks to waive his right to appeal a sentence
while pleading guilty, the district court "must inform the
defendant of, and determine that the defendant
understands, . . . the terms of any plea-agreement provision
waiving the right to appeal or to collaterally attack the
sentence." Fed. R. Crim. P. 11(b)(1)(N).
We have held that when a defendant challenges the
enforceability of an appeal waiver based on an unpreserved claim
of a Rule 11(b)(1)(N) violation, review is only for plain error.
See Rodriguez-Monserrate, 22 F.4th at 42; Morillo, 910 F.3d at 3.
And in this instance, the record is devoid of any semblance of a
Rule 11(b)(1)(N) error, plain or otherwise.
The alleged Rule 11(b)(1)(N) error is based on the
brevity of the court's questioning. The defendant insists that
the court should have asked more than once about his waiver. More
thorough inquiry was required, the defendant argues, because he
was not adequately prepared by counsel and was unaware that he was
giving up the right to direct appeal of any ineffective assistance
claim.
The defendant's arguments are groundless. When the goal
is to achieve a clear understanding, brevity can be a plus rather
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than a minus. Here, moreover, the district court's inquiry was
thorough, and the key question was twice repeated. And, finally,
the change-of-plea hearing was not the defendant's first rodeo —
he had previously pleaded guilty to federal fraud violations on
two unrelated occasions.
We add that nothing contained in the defendant's
briefing suggests that the "waiver deserved enhanced scrutiny."
Morillo, 910 F.3d at 3. The defendant does not, for example, claim
that he was an inexperienced youth, that he did not understand the
English language, or that the district court's statements were
contradictory. Instead, the defendant's arguments hint that the
court should have remediated the supposed ineffectiveness of his
own counsel or drilled down to lay bare what kinds of claims would
be barred by his waiver. No circumstances in the record suggest
the necessity for such granular detail. The district court was
entitled to rely on the defendant's representations that he was
satisfied with his counsel's handiwork, that he had reviewed the
terms of the plea agreement with his counsel, and that he
understood all of those terms. See Nguyen, 618 F.3d at 75.
The short of it is that the court's questioning was
adequate and certainly clearer than questioning that we have
approved in other cases. See, e.g., United States v. De-La-Cruz
Castro, 299 F.3d 5, 12 (1st Cir. 2002) (upholding waiver
notwithstanding district court's somewhat confusing qualification
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that defendant could appeal "in some circumstances" (quotations
omitted)). No more was exigible.
C
This brings us to the defendant's principal reasons as
to why the waiver-of-appeal provision should not be enforced.
Those reasons are premised on his claims of ineffective assistance
of counsel concerning both his guilty plea and his aggregate
sentence.
But "[w]e have held with a regularity bordering on the
monotonous that fact-specific claims of ineffective assistance
cannot make their debut on direct review of criminal convictions."
Mala, 7 F.3d at 1063; see United States v. Padilla-Galarza, 990
F.3d 60, 93 (1st Cir. 2021); United States v. Tkhilaishvili, 926
F.3d 1, 20 (1st Cir. 2019); United States v. Santana-Dones, 920
F.3d 70, 82 (1st Cir. 2019). This so-called Mala rule is a
"prudential precept" based on practical realities. Padilla-
Galarza, 990 F.3d at 93; see Mala, 7 F.3d at 1063. Defendants
bringing ineffective-assistance claims "must show, first, that
counsel's performance was constitutionally deficient and, second,
that the deficient performance prejudiced the defense." Mala, 7
F.3d at 1063 (citing Strickland, 466 U.S. at 687). Those showings
"typically require the resolution of factual issues that cannot
efficaciously be addressed in the first instance by an appellate
tribunal." Id. After all, it is the trial court that "has a
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superior vantage from which to 'assess both the quality of the
legal representation afforded to the defendant in the district
court and the impact of any shortfall in that representation.'"
Padilla-Galarza, 990 F.3d at 93-94 (quoting Mala, 7 F.3d at 1063).
To be sure, not all ineffective-assistance claims come
within the reach of the Mala rule. We may consider such claims,
first brought on direct appeal, in those rare instances when "the
critical facts are not genuinely in dispute and the record is
sufficiently developed to allow reasoned consideration." United
States v. Miller, 911 F.3d 638, 642 (1st Cir. 2018) (quoting United
States v. Natanel, 938 F.2d 302, 309 (1st Cir. 1991)).
The defendant in this case seeks to avail himself of
this so-called Natanel exception. But this exception "is narrow,
and its applicability depends on the particular circumstances of
a given case." Padilla-Galarza, 990 F.3d at 94. Contrary to the
defendant's importunings, his claims do not fit within the isthmian
confines of the Natanel exception. We explain briefly.
1
The defendant asserts — in spite of copious evidence
that he fully understood his plea agreement and was satisfied with
his representation — that he received ineffective assistance of
counsel in advance of the change-of-plea hearing, rendering his
guilty plea unknowing and involuntary. He avers that — through
fault of his counsel — he was unable to access the discovery
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materials while in pretrial custody before the hearing and was
generally unaware of the evidence supporting the prosecution.
Because he was not apprised of the evidence before agreeing to
plead guilty, his thesis runs, he could not have entered into the
waiver of appeal knowingly and voluntarily.
This claim is fact-specific and, thus, within the
heartland of the Mala rule. Consequently, it would be improvident
to address the defendant's one-sided version of the facts on direct
appeal.
The defendant acknowledges as much by conceding that the
record does not illuminate any issues regarding access to discovery
materials. Though he submits extra-record documents on appeal
purporting to show that he could not access the evidence while in
custody, those submissions are insufficient to ground his claim.
Crucially, the record is tenebrous as to whether
counsel's performance was constitutionally deficient. The
defendant admitted the government's factual proffer under oath.
What is more, he declared that he was satisfied with his attorney's
representation. To square these admissions against his nascent
claim that he was not seasonably provided with the evidence raises
factual questions not only as to the truth of the defendant's
claims but also as to whether counsel furnished him with other
information, guidance, or advice sufficient to remediate any
alleged inability to review the evidence in his case ahead of his
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plea. Given the limitations of the record on appeal, there is no
principled way that we can answer those questions with "only [the
defendant's] word as to what occurred." United States v. Torres-
Rosario, 447 F.3d 61, 65 (1st Cir. 2006).
We think it follows that we cannot review these
allegations of ineffective assistance in a manner sufficient to
assess the enforceability of the defendant's waiver. See United
States v. Chandler, 534 F.3d 45, 51 (1st Cir. 2008); see also
United States v. Edgar, 348 F.3d 867, 869 (10th Cir. 2003)
(declining to address ineffective-assistance claim related to
enforceability of waiver despite well-established rule that court
"will not enforce a waiver that is the product of ineffective
assistance of counsel"). Simply put, the connective tissue
necessary to make out the defendant's ineffective assistance of
counsel claim concerning his plea lies well outside the record on
appeal. That means, of course, that we cannot proceed to find the
waiver of appeal unenforceable on this ground.
2
The defendant's fallback position is that the
waiver-of-appeal provision should not be enforced by reason of the
miscarriage of justice exception to the appeal-waiver framework.
See Teeter, 257 F.3d at 25. He complains that counsel should have
taken further measures to substantiate his claim that he was
assaulted while in federal custody to mitigate his sentence. In
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the defendant's view, enforcing the waiver to preclude this claim
would amount to a miscarriage of justice because the alleged error
is of constitutional dimension and occurred after he entered his
plea.
Once again, these allegations of ineffective assistance
are prematurely before us on direct review. They therefore afford
no foothold for refusing to enforce the waiver. On this record,
addressing the defendant's allegations of ineffective assistance
at sentencing would require us to "play[] blindman's buff." Mala,
7 F.3d at 1063.
For one thing, the record is not transparent on the
critical facts as to counsel's performance — the first element of
the Strickland test. The record reflects that defense counsel
made the district court aware of the PTSD diagnosis stemming from
the alleged assault. That counsel did not further substantiate
the assault allegations may well have been an informed choice.
There is little in the record to explain "why counsel acted as he
did." Torres-Rosario, 447 F.3d at 64 (emphasis in original). That
sort of "information [is] rarely developed in the existing
[appellate] record." Id. And absent such information, "it is
virtually impossible to assess what reasoning, if any, guided
counsel's actions." Tkhilaishvili, 926 F.3d at 20; see Massaro v.
United States, 538 U.S. 500, 505 (2003) (explaining that "appellate
court[s] may have no way of knowing whether a seemingly unusual or
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misguided action by counsel had a sound strategic motive or was
taken because the counsel's alternatives were even worse").
For another thing, we are confident that the district
court would be in a better position to assess the second element
of the Strickland test: whether the defendant has shown "that
there is a reasonable probability that, but for counsel's
unprofessional errors, the result of the proceeding would have
been different." Strickland, 466 U.S. at 694. At the disposition
hearing, the district court acknowledged the defendant's PTSD "and
the things that [the defendant had] been through," which strongly
indicates that the court gave at least some credit to the
defendant's allegations of assault. In these circumstances, it
would be imprudent for us to guess whether additional
substantiation regarding the assault would or would not have
altered the court's decisionmaking calculus. Cf. United States v.
Ladd, 885 F.2d 954, 961 (1st Cir. 1989) ("[R]obes and gavels are
the tools of a jurist's trade — not tea leaves or crystal balls.").
We are especially reluctant to step into the district judge's shoes
when — as in this case — the arguments at issue were designed to
influence her discretionary weighing of the sentencing factors.
It would be both more efficient and more desirable for the district
judge, in the first instance, to say whether a different balance
would have been struck.
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Because the defendant's allegations of ineffective
assistance at sentencing cannot meaningfully be reviewed on the
existing record, they cannot underpin a miscarriage-of-justice
claim sufficient to upset an appellate waiver. We have said before
— and today reiterate — that it would be absurd to conclude that
the enforcement of a waiver would work a miscarriage of justice
when "we would decline to hear [the defendant's] claims on direct
appeal." United States v. Torres-Estrada, 817 F.3d 376, 379 (1st
Cir. 2016). If the simple fact that a defendant can muster claims
that might ordinarily be cognizable on appeal was enough to nullify
a valid waiver-of-appeal provision, then waiver-of-appeal
provisions would be little more than empty vessels. See United
States v. Edelen, 539 F.3d 83, 87 (1st Cir. 2008).
"Triggering the miscarriage of justice exception
requires, at a bare minimum, an increment of error more glaring
than routine reversible error." Nguyen, 618 F.3d at 75. Thus, a
defendant will rarely, if ever, carry his burden of showing a
miscarriage of justice based on an ineffective assistance of
counsel claim falling within the Mala rule.
This makes perfect sense: whether the miscarriage-of-
justice exception applies is a fact-specific inquiry, involving a
multitude of considerations, such as "the clarity of the error,
its gravity, its character . . . , the impact of the error on the
defendant, the impact of correcting the error on the government,
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and the extent to which the defendant acquiesced in the result."
Teeter, 257 F.3d at 26. In the end, the exception requires "an
error of significant or constitutional dimension [that] is clear."
United States v. Del Valle-Cruz, 785 F.3d 48, 56 (1st Cir. 2015)
(emphasis added).
Absent some footing in the record, we cannot determine
whether enforcing the waiver would result in a miscarriage of
justice. After all, the clarity of an alleged error — or its lack
of clarity — is revealed only by measuring the appellant's argument
against the record. See United States v. Santiago, 769 F.3d 1, 10
(1st Cir. 2014) (identifying "error" as "clear" based on review of
sentencing transcript and written judgment); United States v.
Rivera-López, 736 F.3d 633, 636 (1st Cir. 2013) (declining to
"speculate" regarding information "not before us on th[e] appeal"
in addressing claim of error). And without adequate indicia in
the record concerning the impact of an alleged error, there is no
reliable way for us to tell whether and to what extent an
appellant's claim of unfairness is woven entirely out of strands
of speculation and surmise. See O'farrill-López, 991 F.3d at 50
(rejecting miscarriage-of-justice argument because "impact of the
challenged action . . . [wa]s wholly conjectural").
Where, as here, the claimed error is a fact-specific
claim of ineffective assistance of counsel raised for the first
time on appeal and falling within the Mala rule, the requisite
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degree of clarity will almost always be lacking. See United States
v. Torres-Oliveras, 583 F.3d 37, 42-43 (1st Cir. 2009) (rejecting
reliance on miscarriage-of-justice exception based on ineffective
assistance of counsel where record inhibited assessment of whether
attorney's action was erroneous or "strategic" and whether the
"sentence would have been different"). The upshot, then, is that
when an ineffective assistance of counsel claim cannot be
adequately adjudicated based on the existing record, reliance on
that claim to show a miscarriage of justice will be fruitless.
To say more would be to paint the lily. Ineffective
assistance of counsel claims — not raised in the district court
and not within an exception to Mala — cannot overcome an otherwise
enforceable appeal waiver. So it is here: we conclude that the
defendant's allegations that he received ineffective assistance of
counsel fall within the Mala rule and, thus, cannot surmount his
waiver of appeal.
D
There is one loose end. Enforcement of a waiver-of-
appeal provision ordinarily requires dismissal of the appeal. When
an appellant asserts that counsel's ineffective assistance
invalidates his plea agreement, though, the claim usually may be
addressed notwithstanding a waiver-of-appeal provision in the plea
agreement. Rudimentary logic teaches that a waiver of appeal will
typically fall by the wayside when an appellant "challenges the
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validity of the plea itself." United States v. Ramos-Mejía, 721
F.3d 12, 14 (1st Cir. 2013) (citing Chambers, 710 F.3d at 27); cf.
Teeter, 257 F.3d at 25 n.9 (suggesting that circumstances in which
"plea proceedings were tainted by ineffective assistance of
counsel" could warrant setting aside waiver based on miscarriage-
of-justice exception). If a plea agreement is invalid, then its
components — including any waiver-of-appeal provision — are
necessarily void as well. See Ramos-Mejía, 721 F.3d at 14.
Here, however, a different outcome is required because
the ineffective-assistance claim that targets the plea is brought
for the first time on appeal and falls squarely within the Mala
rule. When an ineffective-assistance claim is raised for the first
time on direct appeal and does not trigger any exception to the
Mala rule, we have two options: we may either dismiss the appeal
without prejudice, thus allowing the defendant to bring his claim
in a collateral proceeding, see, e.g., Padilla-Galarza, 990 F.3d
at 94; or — under "special circumstances" — we may remand the claim
to the district court for an evidentiary hearing, United States v.
Vega Molina, 407 F.3d 511, 531 (1st Cir. 2005). Because no special
circumstances are apparent here, dismissal of both claims is the
appropriate remedy. The defendant may seek to address his "newly
minted ineffective assistance of counsel claim[s]" through "a
collateral proceeding brought in the district court under 28 U.S.C.
§ 2255." Padilla-Galarza, 990 F.3d at 94. At that time, the
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district court also can address the defendant's piggybacked claim
that the ineffective assistance of his counsel regarding the
discovery materials undermined his guilty plea.
III
We need go no further. Waivers of appeal are important
tools in the plea-bargaining process. This case, however, is less
about waivers of appeal and more about the Mala rule: a "fact-
specific claim[] of ineffective assistance [of counsel] cannot
make [its] debut on direct review" when the record is
insufficiently "developed to allow reasoned consideration of the
claim." Mala, 7 F.3d at 1063. For the reasons elucidated above,
we dismiss the appeal; without prejudice, however, to the right of
the defendant, should he so elect, to prosecute his ineffective
assistance of counsel claims in a collateral proceeding under 28
U.S.C. § 2255.
Dismissed without prejudice.
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