United States v. Borrero-Acevedo

United States Court of Appeals
For the First Circuit

No. 06-2655

UNITED STATES OF AMERICA,

Appellee,

v.

JUAN BORRERO-ACEVEDO,

Defendant, Appellant.

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

[Hon. Daniel R. Domínguez, U.S. District Judge]

Before

Lynch, Chief Judge,
O'Connor,* Associate Justice,
and Torruella, Circuit Judge.

Johnny Rivera González for appellant.
Thomas F. Klumper, Assistant United States Attorney, with whom
Rosa Emilia Rodríguez-Vélez, United States Attorney, and Nelson
Pérez-Sosa, Assistant United States Attorney, were on brief for
appellee.

July 10, 2008

*
The Hon. Sandra Day O'Connor, Associate Justice (Ret.) of
the Supreme Court of the United States, sitting by designation.
 LYNCH, Chief Judge. We apply, for the first time, the

Supreme Court's recent plain error decisions to a defendant's

unpreserved claim of Rule 11(b)(1)(N) error as to a waiver of

appeal clause at the change-of-plea hearing. See United States v.

Dominguez Benitez, 542 U.S. 74 (2004); United States v. Vonn, 535

U.S. 55 (2002); cf. United States v. Teeter, 257 F.3d 14 (1st Cir.

2001).

In doing so, we join the other circuits to have

considered the question and hold that the plain error standard

applies to unpreserved claims of violations of Fed. R. Crim. P.

11(b)(1)(N), albeit our understanding of the plain error rule seems

to differ from some. See, e.g., United States v. Murdock, 398 F.3d

491, 496 (6th Cir. 2005); United States v. Arellano-Gallegos, 387

F.3d 794, 797 (9th Cir. 2004). The defendant must show, as part of

his demonstration that his substantial rights were affected, a

reasonable probability that he would not have entered the plea had

the error not been made.

We conclude that defendant has not met his burden, and

the waiver of appeal clause at issue here is to be enforced. As a

result, we do not reach defendant's underlying arguments that the

plea is invalid for other reasons.

I.

On July 20, 2005, in a one-count indictment covering him

and eleven co-defendants, Juan Borrero-Acevedo was charged with

-2-
conspiracy to possess with intent to distribute five kilograms or

more of cocaine and one kilogram or more of a mixture or substance

containing a detectable amount of heroin, in violation of 21 U.S.C.

§§ 841(a)(1), 841(b)(1)(A), 846. The indictment identified Borrero

as one of the suppliers for the conspiracy's drug points. After

initially pleading not guilty, Borrero filed a motion to change his

plea, which was referred to a magistrate judge.

The change-of-plea hearing was conducted on June 9, 2006,

by a magistrate judge. Borrero entered a guilty plea pursuant to

Fed. R. Crim. P. 11(c)(1)(A) and (B) and an agreement with the

government. The plea agreement stated, and the government

testified at the hearing, that at trial the government would have

presented evidence establishing that, from 1999 to the date of the

indictment, the defendant participated in the distribution of

cocaine and heroin in the La Via sector at Aguadilla, Puerto Rico.

During this time, defendant was considered a supply source for

heroin in La Via and was involved in at least one drug transaction

there. He conspired to sell between 700 grams and one kilogram of

heroin in furtherance of the conspiracy.

Borrero benefitted from the plea agreement he had reached

with the government. Based on the charges in the indictment,

Borrero was subject to a minimum ten-year sentence. Pursuant to

the plea agreement, the government recommended an eighty-seven

month prison term, which was the sentence the court imposed. The

-3-
plea agreement contained a simple and easily understood waiver of

appeal. This waiver stated: "The defendant hereby agrees that if

this Honorable Court accepts this agreement and sentences him

according to its terms and conditions, defendant waives and

surrenders his right to appeal the judgment and sentence in this

case."

In 1999, Congress added to Rule 11 what would become

section (b)(1)(N), which requires the court both to inform the

defendant of and to determine that the defendant understands "the

terms of any plea-agreement provision waiving the right to appeal

or to collaterally attack the sentence."1 Fed. R. Crim. P.

11(b)(1)(N). The purpose of the amendment was to ensure that

waivers of appellate rights are knowing and voluntary. See id. 11

advisory committee's note ("1999 Amendments"). When Rule

11(b)(1)(N) was added, it became subject to the terms of Fed. R.

Crim. P. 11(h) that "[a] variance from the requirements of this

rule is harmless error if it does not affect substantial rights."

1
The provision states:

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 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).

-4-
This language is similar to the harmless error rule in Fed. R.

Crim. P. 52(a).

It is undisputed here that the magistrate judge failed to

comply with the requirements of Rule 11(b)(1)(N) during the

colloquy with the defendant at the change-of-plea hearing. The

prosecutor also failed to point out the waiver during the

colloquy.2

Borrero could have attempted, based on this omission, to

withdraw his guilty plea in the trial court before sentencing. See

id. 11(d)(2)(B). Had he done so, he would have had to show only a

"fair and just reason for withdrawal." Id.; see also, e.g., United

States v. Newbert, 504 F.3d 180, 183-84 (1st Cir. 2007) (affirming

decision of trial court not to enforce waiver of rights where

defendant had been permitted to withdraw his plea under Rule

11(d)(2)(B)). Having raised the omission for the first time on

appeal, Borrero faces a much tougher standard.

Borrero argues that the magistrate judge's failure to ask

him specifically about the waiver of appeal means that he is not

bound by this waiver. Not so.3 Borrero's primary argument is that

2
As a matter of efficiency and securing finality,
prosecutors would be well-advised to call such omissions to the
attention of the court at change-of-plea hearings.
3
In its initial brief, the United States took the position
that because there had been no mention of the appellate waiver at
the plea colloquy, the waiver could not be enforced. This court is
not bound by a party's concessions. See United States v. Mescual-
Cruz, 387 F.3d 1, 8 n.2 (1st Cir. 2004). The court directed the

-5-
it would be unjust to hold him to the waiver of appeal because this

would block him from making his argument on the merits, which is

that insufficient attention was paid 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.

II.

Vonn resolved a circuit split4 on the standard for

evaluating Rule 11 errors. It held that a defendant who has not

preserved his claim of Rule 11 error and wishes to be relieved of

his guilty plea on appeal must satisfy the plain error standard of

Fed. R. Crim. P. 52(b). Vonn, 535 U.S. at 58-59.

In order to show plain error, a defendant must

demonstrate that there is "(1) 'error,' (2) that is 'plain,' and

(3) that 'affect[s] substantial rights.' If all three conditions

are met, an appellate court may then exercise its discretion to

notice a forfeited error, but only if (4) the error 'seriously

affect[s] the fairness, integrity, or public reputation of judicial

proceedings.'" Johnson v. United States, 520 U.S. 461, 467 (1997)

parties to file supplemental briefs on the waiver issue, calling
their attention to the case law on point. Thereafter, the United
States filed a supplemental brief reversing its position and
arguing that defendant was bound by his appellate waiver because he
had not met the third prong of the plain error test.
4
Before Vonn, this court had held that unpreserved claims
of Rule 11 error were subject to plain error review under Rule
52(b), and not harmless error review. See United States v. Gandia-
Maysonet, 227 F.3d 1, 5 (1st Cir. 2000). Vonn agreed with the
position. Vonn, 535 U.S. at 61, 62 n.4.

-6-
(quoting United States v. Olano, 507 U.S. 725, 732 (1993))

(alterations in original).

As we noted in United States v. Mescual-Cruz, 387 F.3d 1

(1st Cir. 2004), the decision in Vonn also clarified two areas as

to application of the plain error rule to Rule 11 errors. First,

the burden is on the defendant to make the required showings. Id.

at 7. As Vonn noted, this placement of burdens is necessary to

give the defendant an incentive to bring an obvious Rule 11 error

to the court's attention when it occurs. Vonn, 535 U.S. at 73.

Second, an appellate court may consider the whole record when

considering the effect of the Rule 11 error on defendant's

substantial rights, and not simply the record of the plea colloquy.

Mescual-Cruz, 387 F.3d at 7.

Vonn, by its terms, is not restricted to particular types

of Rule 11 errors. This court has applied Vonn's plain error rule

to claimed Rule 11 errors regarding defendant's understanding of

his possible sentencing exposure, United States v. Jimenez, 512

F.3d 1, 3 (1st Cir. 2007); defendant's understanding of the charges

and the factual basis for the plea, United States v. Smith, 511

F.3d 77, 85 (1st Cir. 2007); defendant's understanding of a package

plea agreement, Mescual-Cruz, 387 F.3d at 7; and a lack of

explanation of the interstate commerce elements of the crime to

which defendant was pleading guilty, United States v. Cruz-Rivera,

357 F.3d 10, 12-13 (1st Cir. 2004). As we read Vonn, it provides

-7-
no basis for applying a standard other than plain error to a

court's failure to address a waiver of appeal (or a waiver of the

right to collaterally attack a sentence) as required by Rule

11(b)(1)(N). Indeed, other circuits have applied the plain error

test articulated in Vonn to claims involving violations of Rule

11(b)(1)(N). See, e.g., United States v. Sura, 511 F.3d 654, 658

(7th Cir. 2007); Murdock, 398 F.3d at 496; Arellano-Gallegos, 387

F.3d at 796; United States v. Edgar, 348 F.3d 867, 871 (10th Cir.

2003).

In Dominguez Benitez, the Supreme Court set the standards

that a defendant complaining of an unpreserved Rule 11 error must

meet on the third prong of the plain error test. In Dominguez

Benitez, the judge had failed to warn the defendant, as required by

Fed. R. Crim. P. 11(c)(3)(B), that he could not withdraw his plea

if the court did not accept the government's sentencing

recommendation, an obvious error. Dominguez Benitez, 542 U.S. at

78. The question on which the Court granted review was the showing

that must be made by a defendant alleging a violation of Rule 11

under the plain error standard. The Court held that a defendant is

"obliged to show a reasonable probability that, but for the [Rule

11] error, he would not have entered the plea." Id. at 76; see

also Hill v. Lockhart, 474 U.S. 52, 59 (1985) (to demonstrate

prejudice in an ineffective assistance of counsel claim, defendant

must "show that there is a reasonable probability that, but for

-8-
counsel's errors, he would not have pleaded guilty and would have

insisted on going to trial"). It is not enough to ask whether the

defendant understood the rights at issue when he entered his guilty

plea; courts must consider the effect of an omitted warning on the

defendant's decision to plead guilty. Dominguez Benitez, 542 U.S.

at 84. The Court also stated that the defendant's showing of

prejudice should be causally tied to the precise Rule 11 error

alleged. Id. at 85. The Court did not suggest it would vary the

rule depending on the type of Rule 11 violation alleged.

The "reasonable probability" standard for showing

prejudice on plain error review of Rule 11 violations is less

onerous than a requirement that a defendant prove by a

preponderance of the evidence that but for the error, things would

have been different. See id. at 83 n.9. One rationale for using

the "reasonable probability" standard for Rule 11 plain error

review, instead of a more burdensome standard, may be the

recognition that a defendant will "rarely, if ever be able to

obtain relief for Rule 11 violations under [28 U.S.C.] § 2255."

Id.; see also Vonn, 535 U.S. at 63-64; United States v. Timmreck,

441 U.S. 780, 783-84 (1979).

We have enforced the Dominguez Benitez rule before in

considering unpreserved claims that the district court committed

Rule 11 error in accepting a plea. See, e.g., United States v.

Caraballo-Rodriguez, 480 F.3d 62, 76 (1st Cir. 2007); United States

-9-
v. Matos-Quiñones, 456 F.3d 14, 23 (1st Cir. 2006); United States

v. Delgado-Hernandez, 420 F.3d 16, 28 (1st Cir. 2005).

III.

The question here is not whether the waiver of appeal

clause in the plea agreement was initially valid, but whether

defendant, who could have but did not raise the issue in the

district court, where it could easily have been remedied, has met

the plain error standard.

Applying Vonn, it is clear that the defendant has

established the first two prongs of the plain error rule. The

magistrate judge committed error in his failure to comply with the

clear terms of Rule 11(b)(1)(N), and that error was both obvious

and plain. Murdock, 398 F.3d at 497; Edgar, 348 F.3d at 871-72;

accord Teeter, 257 F.3d at 24.

The third prong of the test asks whether defendant has

shown that his substantial rights were affected. We start the

analysis of the third prong with the plea agreement and the plea

colloquy. Relevant considerations include, inter alia, the clarity

of the plea agreement itself, defendant's signature on the

agreement and his attestations, defendant's statements at the

change-of-plea hearing, statements by counsel for both the

defendant and the government at the hearing, and the nature of the

questioning done by the judge at the hearing.

-10-
 The waiver of appeal clause was clear and self-evident on

its face. Borrero initialed every page of the plea agreement and

signed his name at the bottom to indicate that he had "read the

Plea Agreement and carefully reviewed every part of it with my

attorney," and that he fully understood and was voluntarily

agreeing to it.

At the plea colloquy, Borrero stated that he was thirty-

eight years old, had an eleventh grade education, was mentally

competent, and was suffering from no disability. Borrero also

stated affirmatively that (a) he had the opportunity to review and

discuss the plea agreement with his attorney; (b) he did not need

additional time to discuss the agreement with his attorney; (c) he

understood all the terms of the plea agreement and no one had made

any promises to him that were not contained in the agreement; (d)

he understood that the court could accept or reject the agreement,

that sentencing was within the court's discretion, and what the

statutory minimum and maximum penalties were; and (e) he had

discussed with his attorney and understood that he was waiving

various constitutional rights. Additionally, his attorney stated

that Borrero was fully competent; that he had met with Borrero on

multiple occasions to discuss the case and his defense; and that he

had provided a sentence-by-sentence translation of the plea

agreement into Spanish for Borrero.

-11-
 As to Borrero's burden to show prejudice, we look to the

"entire record, not to the plea proceedings alone." Dominguez

Benitez, 542 U.S. at 80; see also Caraballo-Rodriguez, 480 F.3d at

76. Here the government had a strong case and Borrero had

compelling reasons to make a deal and reduce his sentencing

exposure. Borrero received the exact sentence recommended by the

plea agreement. Borrero, with good reason, does not even attempt

an argument that he would not have entered the plea had he been

aware he was waiving his appellate rights. Indeed, it is hard to

see how the omission of the appellate waiver warning from the bench

had any effect on his decision to plead guilty. See Dominguez

Benitez, 542 U.S. at 85; Caraballo-Rodriguez, 480 F.3d at 76.

Whether or not Borrero's decision to plead guilty was foolish (and

it does not seem to be), the "point . . . is not to second-guess a

defendant's actual decision." Dominguez Benitez, 542 U.S. at 85.

Some courts have held that where there is no discussion

of an appellate waiver clause at the plea hearing and there is an

absence of "any indication on the record that the defendant

understood that he had a right to appeal and he was giving up that

right," that will suffice to satisfy the third prong of the plain

error test. Murdock, 398 F.3d at 497; see also Arellano-Gallegos,

387 F.3d at 797 (same). This view is, we think, inconsistent with

both Vonn and Dominguez Benitez. It is defendant's burden to show

that the waiver of appellate rights was deficient and that he would

-12-
otherwise not have pled guilty. If the record contains no evidence

in defendant's favor, his claim fails. See Dominguez Benitez, 542

U.S. at 82; Vonn, 535 U.S. at 62-63; cf. Edgar, 348 F.3d at 872-73.

There may well be cases where a defendant can show he did

not understand that he was waiving his appellate rights, and that

had he understood the appellate waiver clause, he would not have

pled guilty. A panel in the Seventh Circuit, over a dissent, found

that to be the situation in United States v. Sura, which also

involved a Rule 11(b)(1)(N) error. But there were other indicia in

that case not present here: the seventy-one-year-old defendant, who

was undergoing mental health treatment, gave confused responses to

the district court, and the appellate court said it doubted, on the

record, whether he would have entered the plea "had he realized

that he was losing his chance to challenge the district court's

sentencing decision, which was based primarily on crimes unrelated

to the crime of conviction and gave little weight to Sura's

individual circumstances." Sura, 511 F.3d at 662. Nothing of the

sort exists here. Borrero has not shown that he did not know or

understand that he had waived his appellate rights or that he would

not have pled guilty had he realized he was waiving his appellate

rights.

We do not reach Borrero's underlying merits argument

about this being a package plea. "[A]n inquiry into the merits is

exactly what a waiver of appeal blocks." Id. at 668 (Easterbrook,

-13-
J., dissenting). As the Supreme Court said in Dominguez Benitez,

relief from a guilty plea "will be difficult to get, as it should

be." Dominguez Benitez, 542 U.S. at 83 n.9.

There is one final point. In light of Vonn and Dominguez

Benitez, one might question what is left of this circuit's former

rule on enforceabililty of waiver of appeal clauses, announced in

United States v. Teeter. In Teeter, we held that pre-sentence

waivers of appellate rights were valid in theory, but given the

attendant dangers, we would require such waivers to meet stringent

conditions:

Our basic premise, therefore, is that if
denying a right of appeal would work a
miscarriage of justice, the appellate court,
in its sound discretion, may refuse to honor
the waiver. As a subset of this premise, we
think that the same flexibility ought to
pertain when the district court plainly errs
in sentencing.

Teeter, 257 F.3d at 25 (footnote omitted); see also Newbert, 504

F.3d at 189 (Boudin, J., concurring) (defendant may be relieved of

a waiver of the right to appeal by district judge where enforcing

the waiver would effect a miscarriage of justice).

More precisely, the 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. The question may well be a hypothetical one; it is not

-14-
clear such situations would exist where a defendant could not also

meet all four prongs of the plain error rule.

In Timmreck, the Supreme Court left room for a defendant

on collateral review to show that the Rule 11 proceeding either

constituted a "complete miscarriage of justice" or was

"inconsistent with the rudimentary demands of fair procedure."

Timmreck, 441 U.S. at 783 (quoting Hill v. United States, 368 U.S.

424, 427 (1962)) (internal quotation marks omitted). This suggests

such exceptions might also be available on direct review. The

Supreme Court has not directly addressed this question in the

context of Rule 11 errors regarding appellate waiver clauses, and

we do not address it here. If such a case exists in fact, and not

in hypothetical, we will address the issue then.

We enforce the waiver of appeal and dismiss the appeal.

-15-