United States v. Villodas-Rosario

United States Court of Appeals
For the First Circuit

No. 15-1981

UNITED STATES OF AMERICA,

Appellee,

v.

ANGEL L. VILLODAS-ROSARIO,

Defendant, Appellant.

APPEAL FROM THE UNITED STATES DISTRICT COURT
FOR THE DISTRICT OF PUERTO RICO

[Hon. José Antonio Fusté, U.S. District Judge]

Before

Howard, Chief Judge,
Selya and Lipez, Circuit Judges.

Jonathan G. Mermin and Preti, Flaherty, Beliveau & Pachios,
LLP, on brief for appellant.
Rosa Emilia Rodríguez-Vélez, United States Attorney, Mariana
E. Bauzá-Almonte, Assistant United States Attorney, and Francisco
A. Besosa-Martínez, Assistant United States Attorney, on brief for
appellee.

August 20, 2018
 LIPEZ, Circuit Judge. Appellant Angel L. Villodas-

Rosario appeals his sentence, claiming that it is both procedurally

and substantively unreasonable. He asserts that he may bring these

challenges because the waiver-of-appeal provision in his plea

agreement should not be enforced under the tripartite framework of

United States v. Teeter, 257 F.3d 14 (1st Cir. 2001). The

government urges us to dismiss the appeal based on the plain-error

analysis set forth in United States v. Borrero-Acevedo, 533 F.3d

11 (1st Cir. 2008).

These competing arguments mirror the confusion in our

precedent as to the proper standard for evaluating the

enforceability of an appellate waiver. Although we explain this

confusion below, we ultimately conclude that, even under the more

defendant-friendly Teeter approach, Villodas-Rosario's waiver of

appeal must be enforced. Accordingly, we dismiss his appeal.

I.

Villodas-Rosario pleaded guilty pursuant to a plea

agreement to one count of knowingly possessing a firearm in

furtherance of a drug trafficking crime, in violation of 18 U.S.C.

§ 924(c)(1)(A)(i). The plea agreement contained several key

provisions. First, the government agreed to dismiss a related

charge for possession of a machine gun, which carried a mandatory

minimum of 30 years' imprisonment. Second, the parties agreed

that the guideline sentence recommendation on the remaining charge

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was 60 months, which was the statutory mandatory minimum. Third,

the agreement permitted the government to recommend a sentence not

to exceed 17 years of imprisonment and Villodas-Rosario to advocate

for a sentence as low as 8 years of imprisonment. Finally,

Villodas-Rosario agreed "to waive and surrender his right to appeal

the judgment and sentence in this case if the Court accept[ed]

[the agreement] and sentence[d] him according to its terms,

conditions, and recommendations."

At the change-of-plea hearing, the district court

explained to Villodas-Rosario the rights that defendants waive by

pleading guilty. In the context of describing the rights of

defendants who are generally in Villodas-Rosario's position, the

court stated:

You should know that sentences imposed in this court for
this kind of case can be appealed by both sides. You
can appeal. The government can appeal. Both sides can
exercise the right to appeal. Sometimes Plea Agreements
require that a defendant waive the right to appeal under
some circumstances. Do you understand that?

The court did not go beyond this general explanation to describe

Villodas-Rosario's specific appellate waiver provision or to

inquire into his understanding of the appellate rights he was

giving up by accepting the plea agreement. After delivering the

explanation, the court accepted Villodas-Rosario's guilty plea.

Subsequent to the plea hearing but prior to sentencing,

Villodas-Rosario became concerned about the affidavit of the sole

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police officer who conducted surveillance in this case. For

example, the officer signed into the precinct to work on only one

of the three days on which she supposedly conducted surveillance,

and appellant claims that the log book records for the vehicles

allegedly used by the officer were unavailable. Nevertheless, the

officer's affidavit was used to establish probable cause for the

search warrant that led to the discovery of weapons and drugs in

Villodas-Rosario's possession. Despite these concerns, Villodas-

Rosario never filed a motion challenging the validity of the

affidavit. Instead, defense counsel discussed these concerns with

the prosecutor out of "courtesy." The prosecutor, in turn, agreed

to lower the government's sentencing recommendation to "at least

ten (10) years."

At sentencing, the government recommended a sentence of

"at least 120 months," well below the maximum term set forth in

the plea agreement and consistent with the informally promised

recommendation. In fact, both the government and defense counsel

confirmed during the sentencing hearing that the 120-month

recommendation was "with the understanding that if Your Honor

sentences within the range of eight to 17 [years], then the

defendant waives his right to appeal" under the plea agreement.

During sentencing, the district court expressly

considered relevant factors specified by 18 U.S.C. § 3553(a),

including: 1) the drugs, paraphernalia, cash, and multiple

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firearms discovered during Villodas-Rosario's arrest; 2) the

presence of an automatic firearm; 3) Villodas-Rosario's criminal

history; and 4) Villodas-Rosario's history of substance abuse.

The district court also noted that the defense essentially

"stipulated on [its] own some sort of voluntary variance, if you

will, by way of recommendation," since Villodas-Rosario agreed to

advocate for at least 96 months' imprisonment despite the minimum

guidelines sentence of 60 months. After the allocution, the

district court sentenced Villodas-Rosario to 144 months'

imprisonment -- a sentence within the plea agreement's appellate

waiver range.

On appeal, Villodas-Rosario asks that his sentence be

vacated and the case remanded for resentencing. First, Villodas-

Rosario contends that his plea agreement's appellate waiver is

unenforceable because "the trial court did nothing to ensure that

Villodas-Rosario was freely and intelligently waiving his right to

appeal his sentence; on the contrary, it assured him that he did

have the right to appeal his sentence." Second, if this court

finds that the waiver is unenforceable, Villodas-Rosario contends

that his sentence was both procedurally unreasonable -- due to the

district court's supposed failure to explain the reasons for the

variance -- and substantively unreasonable. The government argues

that we should enforce the appellate waiver set forth in the plea

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agreement and not address the sentencing arguments that Villodas-

Rosario raises.

II.

Villodas-Rosario and the government, relying on

different strands of our court's precedent, disagree about the

appropriate standard for determining whether to enforce an

appellate waiver. As we explain in Section II.B, we should enforce

Villodas-Rosario's waiver regardless of which of the two standards

we apply. Nonetheless, the parties' competing arguments highlight

a tension in our cases that warrants careful examination. We thus

begin our discussion by reviewing the development of our case law

on appellate waiver enforcement.

A. Waiving the Right to Appeal

In 1999, Rule 11(c)(6) of the Federal Rules of Criminal

Procedure was amended to require that, "during a change-of-plea

hearing, the presiding judge 'must address the defendant

personally in open court and inform the defendant of, and determine

that the defendant understands . . . the terms of any provision in

a plea agreement waiving the right to appeal.'" Teeter, 257 F.3d

at 22 (quoting Fed. R. Crim. P. 11(c)(6) (1999)).1 In the

1
In a 2002 amendment, Rule 11 was reorganized and this
requirement became what is known today as Rule 11(b)(1)(N), but
the substance of the rule remained largely the same. The current
text of Rule 11(b)(1)(N) reads, in relevant part: "Before the court
accepts a plea of guilty or nolo contendere, the defendant may be
placed under oath, and the court must address the defendant

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explanatory notes for the 1999 amendments, the advisory committee

clarified that it was adding the requirement to inquire into

waivers of appellate rights only to "reflect the increasing

practice of including [appellate waiver] provisions in plea

agreements[.]" Fed. R. Crim. P. 11(c)(6), advisory committee's

note to 1999 amendments. The committee explicitly disavowed any

inference that it thought such appellate waivers were, in fact,

enforceable, stating that it "t[ook] no position on the underlying

validity of such waivers." Id.

Indeed, at the time Rule 11 was amended to address plea

agreement appellate waivers, our court had not yet spoken on their

validity. In 2001, Teeter presented us with the opportunity to do

so. At the time Teeter was decided, nine other circuits had

already addressed the issue, and all nine had upheld the use of

such waivers. See 257 F.3d at 23 (compiling cases). In light of

this consensus, and "reluctant to brush aside this collective

wisdom[,]" we followed our sister circuits in holding that, "under

ordinary circumstances," such waivers "are valid in theory." Id.

We were concerned, however, about the risks presented by defendants

giving up their appellate rights before sentencing. "To ameliorate

personally in open court. During this address, the 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).

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these risks, we deem[ed] it appropriate that such waivers meet

stringent criteria." Id. Hence, we held that appellate waivers

are binding so long as: (1) "the written plea agreement signed by

the defendant contains a clear statement elucidating the waiver

and delineating its scope"; (2) the district court ensures that

"the defendant freely and intelligently agreed to waive her right

to appeal her forthcoming sentence" by inquiring "specifically at

the change-of-the-plea hearing into any waiver of appellate

rights"; and (3) the denial of the right to appeal would not "work

a miscarriage of justice." Id. at 24-25; see also United States

v. Edelen, 539 F.3d 83, 85 (1st Cir. 2008).

As to the second prong, Teeter explained that, while an

inquiry at the change-of-plea hearing would ensure an intelligent

waiver, such an inquiry was not a necessary condition. If the

record as a whole revealed that the defendant understood the waiver

at the time he entered the plea, an inadequate inquiry would not

invalidate the waiver. Teeter, 257 F.3d at 24 (explaining that

failure to inquire "may serve to invalidate the waiver, depending

upon what the record shows as to the defendant's knowledge (that

is, whether the defendant, notwithstanding the absence of a

particularized inquiry, understood the full significance of the

waiver)").

The Teeter inquiry requirement was explicitly inspired

by, but not dependent on, Rule 11. We were "[m]indful that Rule

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11[] . . . specifically recognize[d] the importance of the change-

of-plea hearing to any waiver of appellate rights," and we noted

that "the advisory committee made it pellucid that such an inquiry,

properly performed, offer[ed] considerable assurance of the

defendant's knowledge and volition." Id. While Teeter favorably

referenced the policy motivations of Rule 11(b)(1)(N), other

circuits had adopted tests similar to the one in Teeter --

including the requirement that judges inquire into a defendant's

waiver of appellate rights at the change-of-plea hearing -- years

before the 1999 amendments added such a requirement to the Federal

Rules of Criminal Procedure. See, e.g., United States v. Bushert,

997 F.2d 1343, 1351 (11th Cir. 1993).

Importantly, the Teeter prong-two inquiry and the Rule

11(b)(1)(N) inquiry -- although accomplished by a single colloquy

between court and defendant -- serve two distinct purposes. A

defendant invoking Teeter seeks relief from an appellate waiver in

order to appeal his conviction, his sentence, or both. The

decision whether to enforce an appellate waiver is thus a threshold

question. We cannot consider the underlying merits of a

defendant's appeal until we decide whether a defendant has validly

waived his appellate rights. A defendant alleging Rule 11

violations seeks to vacate the entire plea. The decision whether

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to enforce an appellate waiver necessarily precedes the

consideration of such claims.2

This distinction between a Teeter inquiry and a Rule 11

inquiry is highlighted by the remedy prescribed by Teeter when an

appellate waiver is deemed unenforceable. In such cases, we "sever

the waiver of appellate rights from the remainder of the plea

agreement, allowing the other provisions to remain in force."

Teeter, 257 F.3d at 27. After severing, we go on to consider the

merits arguments the defendant raises relating to his conviction

or sentence. In other words, contravening the requirements of

Teeter does not render invalid a defendant's guilty plea. That

Teeter treats the enforcement of an appellate waiver as a separate

question from the validity of a plea demonstrates that the Rule 11

and Teeter requirements are distinct, each tailored to a different

request for relief.

In sum, after Teeter, a First Circuit district court's

plea colloquy about an appellate waiver fulfills two independent

purposes: it simultaneously satisfies Rule 11's requirement for

the valid acceptance of a plea and Teeter's second prong for the

enforcement of an appellate waiver. Accordingly, even if Rule

2
In some cases, a defendant may seek to invalidate his plea
after he is successfully released from an appellate waiver. A
defendant may even seek to invalidate his plea on the basis of a
Rule 11(b)(1)(N) error. The issues of appellate waiver enforcement
and whether a plea should be invalidated are not mutually
exclusive, but will arise sequentially.

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11(b)(1)(N) were repealed, Teeter's inquiry requirement would

remain unchanged.

That said, since our decision in Teeter, we have failed

to continuously stress that Rule 11(b)(1)(N) and the second prong

of Teeter, with their shared directive to inquire into the

defendant's understanding of an appellate waiver, created two

separate, albeit related, obligations.3 Indeed, we effectively

blended the two areas of law in Borrero-Acevedo, the case on which

the government relies to argue that Villodas-Rosario's appeal

should be dismissed.

In Borrero-Acevedo, we looked to the Supreme Court's

decisions in United States v. Dominguez Benitez, 542 U.S. 74

(2004), and United States v. Vonn, 535 U.S. 55 (2002), which held

that a defendant seeking to vacate a conviction based on an

unpreserved Rule 11 error "must show a reasonable probability that,

but for the error, he would not have entered the plea." Dominguez

Benitez, 542 U.S. at 83; see also Vonn, 535 U.S. at 72-74. Although

the defendant in Borrero-Acevedo challenged the adequacy of the

district court's inquiry about his waiver of appeal, it appears

that he invoked the deficient inquiry only to challenge the

enforcement of his waiver. The defendant sought to invalidate his

3
As previously discussed, the notes to Rule 11 explicitly
state that "the Committee takes no position on the underlying
validity of such waivers."

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guilty plea on other, non-Rule 11(b)(1)(N) grounds. See Borrero-

Acevedo, 533 F.3d at 15 (describing the appellant's arguments on

the merits as a challenge to "whether his plea was voluntary[,]

given that it was part of a package deal and he might have been

coerced into pleading guilty by a co-defendant"). Nonetheless, we

characterized the flawed plea colloquy in Borrero-Acevedo as an

unpreserved Rule 11(b)(1)(N) error and concluded that -- pursuant

to Dominguez Benitez and Vonn -- we should apply plain error review

in determining whether to enforce the appellate waiver. Hence, we

held that a defendant who seeks non-enforcement of an appellate

waiver must show that, but for an erroneous plea colloquy

pertaining to the waiver, "he would otherwise not have pled

guilty." Borrero-Acevedo, 533 F.3d at 18.

In so holding, we may have mistakenly incorporated Rule

11 standards into the second prong of Teeter's analysis for

appellate waiver enforcement. The Supreme Court's requirement

that a defendant "must show a reasonable probability that, but for

the error, he would not have entered the plea," was articulated in

the context of "a defendant who seeks reversal of his conviction

after a guilty plea." Dominguez Benitez, 542 U.S. at 83. If

imported into the realm of appellate waiver enforcement, the

Dominguez Benitez plain error standard would be significantly more

demanding than the standard set forth in Teeter. Nevertheless,

where a defendant such as Villodas-Rosario raises an omission in

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the plea colloquy inquiry as a basis for the non-enforcement of an

appellate waiver, the conviction itself is not at issue. Arguably,

then, Teeter's tripartite test, and not the plain-error standard

articulated in Dominguez Benitez and Vonn, should remain the

standard used to assess the enforceability of appellate waivers.

In this case, however, -- as explained below -- we need

not reconcile any inconsistency between Teeter and Borrero-

Acevedo.

B. Plea Colloquy Error

Villodas-Rosario avers that his appellate waiver is

unenforceable because the district court's plea colloquy failed to

ensure that he entered into it knowingly and voluntarily. He

argues that the district court not only failed to specifically

address the terms of his appellate waiver, but it also

affirmatively misled him by stating "you can appeal."

As discussed, Villodas-Rosario relies on Teeter in

seeking release from his appellate waiver. See 257 F.3d at 27.

Notably, he does not cite Rule 11(b)(1)(N) in his briefs,

presumably because he is not seeking to vacate his plea. The

government counters that we should enforce the waiver because

Villodas-Rosario has not met the standard set by Borrero-Acevedo:

a showing that, but for the district court's deficient explanation,

he would not have entered the plea. See 533 F.3d at 18.

Notwithstanding this important debate concerning the correct

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analysis, we do not resolve this dispute because Villodas-

Rosario's effort to escape the appellate waiver is unavailing even

under the more defendant-friendly Teeter test.

The first prong of the tripartite Teeter test -- the

clarity of the written waiver provision -- is not contested. The

plea agreement clearly stated that Villodas-Rosario relinquished

the right to appeal if he was sentenced within the agreed-upon

range. It is also beyond debate that the district court failed to

satisfy the second prong's instruction to "inquire specifically at

the change-of-the-plea hearing into any waiver of appellate

rights." Teeter, 257 F.3d at 24. The court's general statements

about appellate waivers were insufficient to ensure Villodas-

Rosario's understanding of his specific waiver. However, an

inadequate colloquy does not end our evaluation of the second

prong. Instead, enforcement of the waiver ultimately depends "upon

what the record shows as to the defendant['s] knowledge (that is,

whether the defendant, notwithstanding the absence of a

particularized inquiry, understood the full significance of the

waiver)." Id.

Villodas-Rosario suggests that the district court's

statement "you can appeal" necessarily prevents a finding that he

knew otherwise. To the contrary, we previously have observed that,

"[w]hile broad assurances to a defendant who has waived her

appellate rights (e.g., 'you have a right to appeal your sentence')

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are to be avoided[,] . . . they do not effect a per se nullification

of a plea-agreement waiver of appellate rights." Teeter, 257 F.3d

at 25.

Nowhere does Villodas-Rosario assert that he, in fact,

unknowingly waived his appellate rights. He argues only that the

district court's colloquy was erroneous and misleading. Indeed,

at Villodas-Rosario's sentencing, his counsel acknowledged that

his plea agreement contained a provision that waived his right to

appeal his sentence if he was sentenced "within the range of eight

to 17" years. Neither Villodas-Rosario nor his counsel indicated

any objection to, or concern about, the terms of the waiver after

they were openly discussed.4 Although the relevant knowledge under

Teeter is what Villodas-Rosario knew about the appellate waiver at

the time the plea was accepted, we look to the whole record to

determine what he understood about the waiver when he entered the

plea. See 257 F.3d at 24; see also Borrero-Acevedo, 533 F.3d at

16.

Our review persuades us that Villodas-Rosario understood

at the time he entered his plea that he agreed to forego the right

to appeal if his sentence fell within the provided-for range. The

record does not indicate when he would have allegedly learned of

4
Although the district court reiterated at the end of
sentencing that Villodas-Rosario could appeal, Villodas-Rosario
does not contend that this statement had any effect on whether his
waiver was knowing and voluntary.

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the specifics of his appellate waiver after entry of the plea but

before sentencing. Yet Villodas-Rosario's counsel at the

sentencing hearing -- without prompting by the court and in his

client's presence -- reiterated the defendant's agreement to the

specific appellate waiver provision. Even at that point, when an

opportunity remained to object before his sentence was imposed,

Villodas-Rosario expressed no concern about the waiver. Given the

clarity of the written provision, the lack of objection at any

time to the meaning of the appellate waiver, and defense counsel's

representations to the court, we think it is a fair conclusion

that Villodas-Rosario understood the terms of the appellate waiver

when he entered his plea. His waiver was knowing and voluntary as

required by the first and second Teeter prongs.

C. Miscarriage of Justice

The remaining question under Teeter -- the third prong

-- is whether "denying a right to appeal would work a miscarriage

of justice." 257 F.3d at 25. If such a miscarriage of justice

would occur, we, in our discretion, "may refuse to honor the

waiver." Id.; see also Sotirion v. United States, 617 F.3d 27, 37

(1st Cir. 2010) (holding that, even under the Borrero-Acevedo

analysis, a defendant "must nevertheless be afforded the

opportunity to demonstrate that enforcement of the waiver would

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work a miscarriage of justice").5 We permit appellants to make

miscarriage of justice challenges because "appellate waivers are

made before any manifestation of sentencing error emerges," and so

"appellate courts must remain free to grant relief from them."

Sotirion, 617 F.3d at 36 (quoting Teeter, 257 F.3d at 25) (internal

quotation marks omitted). Although appellate waivers bring

finality to proceedings, they "are not intended to leave defendants

'totally exposed to future vagaries (however harsh, unfair, or

unforeseeable).'" Id. (quoting Teeter, 257 F.3d at 25). That

said, the miscarriage of justice exception is designed "only for

'egregious cases' and is to be applied 'sparingly and without undue

generosity.'" Id. (quoting Teeter, 257 F.3d at 25, 26). The

standard is "demanding enough to prevent defendants who have agreed

to waive their right to appeal from successfully pursuing garden-

variety claims of error." Teeter, 257 F.3d at 26.

Villodas-Rosario argues that "it would be a miscarriage

of justice for this Court to deny him the right to appeal his

5
Borrero-Acevedo questioned, without deciding, whether the
"miscarriage of justice" prong of Teeter survived its
characterization of the proper test for enforcement of appellate
waivers. See Borrero-Acevedo, 533 F.3d at 19 ("[T]he question
after Vonn and Dominguez Benitez is whether there is any
discretionary power left in this court to decline to enforce a
waiver of appeal clause where we conclude that enforcing the waiver
would be a miscarriage of justice."). In a subsequent case,
Sotirion, we held that the miscarriage of justice analysis
articulated in Teeter survived even under the Borrero-Acevedo
standard. See Sotirion, 617 F.3d at 37.

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sentence after the district court expressly advised him that he

did have that right." In other words, Villodas-Rosario's

miscarriage-of-justice claim attempts to reargue the plea colloquy

error that we have already addressed. But the third prong of

Teeter, unlike the first two prongs, is not about the knowing and

voluntary nature of the waiver. See Sotirion, 617 F.3d at 37.

Instead, miscarriage-of-justice analysis provides the court with

an opportunity to release a defendant from an appellate waiver

when errors unrelated to the validity of the waiver are so

egregious that barring the defendant's ability to appeal would

work a "miscarriage of justice." As we have said, there are

"dangers posed by a prospective waiver of the right to challenge

errors that have not yet occurred." Id. (emphasis added). We

gave examples of such errors in Teeter: the use of

"constitutionally impermissible factors (say, race or ethnicity)"

at sentencing, the imposition of a "sentence exceeding the maximum

penalty permitted by law," or the imposition of a sentence that

"violates a material term of the plea agreement[.]" 257 F.3d at

25 nn.9 & 10 (internal citations omitted).

The errors claimed by Villodas-Rosario in the merits

portion of his briefing -- the sentence was both procedurally and

substantively unreasonable -- do not begin to suggest a viable

miscarriage-of-justice claim. Procedurally, Villodas-Rosario's

assertion that the district court failed to justify its imposition

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of a sentencing variance is no more than a "garden-variety" claim

specifically barred by an appellate waiver. See Sotirion, 617

F.3d at 38 (quoting Teeter, 257 F.3d at 26). So too with Villodas-

Rosario's substantive challenge to the district court's

discretionary weighing of appropriate sentencing factors. See

United States v. Madera-Ortiz, 637 F.3d 26, 31 (1st Cir. 2011).

Thus, we enforce Villodas-Rosario's appellate waiver, and we

decline to reach the merits of his challenge to his sentence.

Appeal Dismissed.

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