Of the Northern District of California, sitting by *

designation.

United States Court of Appeals

For the First Circuit

No. 07-1387

UNITED STATES OF AMERICA,

Appellant,

v.

WINSLOW NEWBERT,

Defendant, Appellee.

APPEAL FROM THE UNITED STATES 

DISTRICT COURT FOR THE DISTRICT OF MAINE

[Hon. John A. Woodcock, Jr., U.S. District Judge]

Before

Boudin, Chief Judge,

Lynch, Circuit Judge,

and Schwarzer, Senior District Judge. *

F. Mark Terison, Senior Litigation Counsel, with whom Paula D.

Silsby, United States Attorney, was on brief, for appellant.

Richard L. Hartley for appellee.

October 11, 2007
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LYNCH, Circuit Judge. In this case we decline to enforce

a defendant's waiver of rights contained in a plea agreement.

It has become common for the prosecution to require that

plea agreements which defendants enter contain a waiver of

constitutional and statutory rights. The Supreme Court has, in

specific contexts, upheld the practice. See, e.g., United States

v. Ruiz, 536 U.S. 622, 629-33 (2002) (defendant can waive right to

government's required disclosure of evidence related to any

affirmative defense or impeachment of witnesses); United States v.

Mezzanatto, 513 U.S. 196, 210 (1995) (defendant can waive right

under the rules of evidence to exclude guilty pleas, plea

discussions, and related statements); see also Halbert v. Michigan,

545 U.S. 605, 624 n.8 (2005) (recognizing that defendant can waive

right to all forms of appeal); Ricketts v. Adamson, 483 U.S. 1, 10

(1987) (defendant can effectively waive double jeopardy protection

by signing and then breaching plea agreement); Brady v. United

States, 397 U.S. 742, 748 (1970) (noting that a guilty plea

necessarily is a waiver of the right against self-incrimination and

the right to trial by jury).

This court, following suit, will enforce knowing and

voluntary waivers by defendants in plea agreements of their rights

to appeal, except when it would work a miscarriage of justice.

United States v. Teeter, 257 F.3d 14, 23-25 (1st Cir. 2001). We

have also suggested that we will enforce defendants' waivers in
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plea agreements or during plea colloquies of their Fifth Amendment

right against self-incrimination, United States v. Conway, 81 F.3d

15, 16-17 (1st Cir. 1996), their right to collaterally attack their

convictions through habeas proceedings, United States v. Ciampi,

419 F.3d 20, 25-27 (1st Cir. 2005), their rights to trial by jury

and assistance of counsel, United States v. Frechette, 456 F.3d 1,

12-14 (1st Cir. 2006), and their right to receive any exculpatory

information in the government's possession, United States v. YejeCabrera, 430 F.3d 1, 24 (1st Cir. 2005). Further, we have

repeatedly recognized that an unconditional guilty plea is

inherently a waiver of all non-jurisdictional claims predating the

plea. See, e.g., United States v. Rodriguez-Castillo, 350 F.3d 1,

3-4 (1st Cir. 2003); see also Acevedo-Ramos v. United States, 961

F.2d 305, 307-08 (1st Cir. 1992) (statute of limitations defense

waived); United States v. Wright, 873 F.2d 437, 442 (1st Cir. 1989)

(challenge to voluntariness of confession waived).

This case concerns a type of waiver our court has not

addressed before. This waiver has several distinct components. It

occurs only when the defendant is, by terms of the agreement, in

breach of the plea agreement. The alleged breach involved is the

defendant's motion to withdraw his plea, which has been granted by

the district court. The waiver affects the defendant's later

rights in the trial court after withdrawal of the plea, and not in

the court of appeals. What are waived are that defendant's rights
Rule 410 provides in relevant part: "[E]vidence of the 1

following is not . . . admissible against the defendant who made

the plea . . .: (1) a plea of guilty which was later withdrawn; .

. . (3) any statement made in the course of any proceedings under

Rule 11 of the Federal Rules of Criminal Procedure . . .; or (4)

any statement made in the course of plea discussions with an

attorney for the prosecuting authority . . . which result in a plea

of guilty later withdrawn." Fed. R. Evid. 410.

Rule 11(f) provides: "The admissibility or inadmissability of

a plea, a plea discussion, and any related statement is governed by

Federal Rule of Evidence 410." Fed. R. Crim. P. 11(f).

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under Federal Rule of Evidence 410 and Federal Rule of Criminal

Procedure 11(f) not to have his plea agreement or associated

statements admitted into evidence in later proceedings.1

Here, defendant Winslow Newbert originally pleaded

guilty; he was later permitted to withdraw his plea by the court

based on post-plea new plausible evidence of innocence. United

States v. Newbert (Newbert I), 471 F. Supp. 2d 182, 199 (D. Me.

2007). The government contended that by successfully withdrawing

his plea, Newbert was in breach of his plea agreement and thus had

waived his Rule 410 rights. The district court disagreed that

defendant was in breach of the agreement and refused to enforce the

waiver. Thus, on motion in limine, the court barred the government

from using evidence excluded by Rule 410. United States v. Newbert

(Newbert II), 477 F. Supp. 2d 287, 294 (D. Me. 2007). 

The prosecution took this interlocutory appeal from the

pre-trial ruling excluding this evidence. See 18 U.S.C. § 3731.

We affirm, finding no error in the court's construction of the

agreement and in its exclusion order.
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I.

During a February 2002 search of Newbert's home, the

police discovered, among other things, 18.3 grams of cocaine.

Based on this evidence, Newbert pleaded guilty in June 2006 to a

single violation of 21 U.S.C. § 841(a)(1), possession with intent

to distribute a controlled substance. His plea agreement with the

government included waivers of his rights to appeal and to a speedy

trial; it also included the following provision, at issue in the

present case:

If defendant fails to enter a guilty plea or seeks and is

allowed to withdraw his plea of guilty entered pursuant

to this Agreement, under circumstances constituting a

breach of this Agreement, or if Defendant's guilty plea

is rejected due to Defendant's conduct constituting a

breach of this Agreement, he hereby waives any rights

that he has under Rule 410 of the Federal Rules of

Evidence and Rule 11(f) of the Federal Rules of Criminal

Procedure. Defendant understands that by waiving such

right, the following would be admissible against him in

any subsequent prosecution for the conduct underlying the

charges in the case: (a) the fact that he pleaded guilty

in this case; (b) all statements made in the course of

the guilty plea; and (c) all statements made during the

course of plea discussions.

Newbert II, 477 F. Supp. 2d at 290 (quoting clause 5 of the plea

agreement).

Less than two months later, Newbert moved to withdraw his

guilty plea. He argued that his plea had been based on a desire to

protect his wife and his friend James Michael Smith, but he had

since learned that his wife had moved in with Smith and that Smith

was preparing to testify against him. Further, one of his
This information was not entirely new, although its 2

source was. Newbert's wife had told him, prior to his plea, that

the cocaine may have been Smith's.

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daughters had informed Newbert that she had seen Smith place a pill

bottle in Newbert's house near where the cocaine was found shortly

before the February 2002 police search; his other daughter told him

that Smith had confessed to her that it was his cocaine the police

had discovered. Smith was to be the government's sole civilian 2

witness against Newbert, and the government had no physical

evidence linking the cocaine to Newbert other than the location of

its discovery. 

The court ruled that Newbert's guilty plea had been

knowing, intelligent and voluntary, but that there was nevertheless

a "fair and just" reason to allow Newbert to withdraw his plea.

Newbert I, 471 F. Supp. 2d at 199; see also Fed. R. Crim. P.

11(d)(2)(B). The court reasoned that Newbert had presented not

only new evidence as to his innocence, but also a plausible

explanation for why he would have pleaded guilty in the first place

-- and why his motivation to do so had since changed. Newbert I,

471 F. Supp. 2d at 199. Further, Newbert had moved quickly to

withdraw his plea before his sentencing, and the court emphasized

that the government would suffer no prejudice as a result. It was

the government that had waited for more than three years to indict

Newbert in the first place, and the government's case relied

primarily on law enforcement witnesses and experts, whose memories
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were assumed to be more reliable than those of civilian witnesses.

Id. Further, "[t]here [was] no suggestion that critical witnesses

[were] unavailable, that evidence [had] been lost, or that any

similar prejudice would obtain." Id. "Ultimately," the court

concluded, "because a man's reputation and freedom hang in the

balance, . . . the better course is to allow a jury to determine"

whether or not Newbert is in fact guilty. Id.

The government was not pleased with this result and

quickly filed a motion to reconsider the order granting the

withdrawal; when that motion was denied, the government filed a

motion to reopen the hearing on withdrawal to present further

evidence. That motion was also denied. Trying a different tack,

the government moved in limine for a ruling that Newbert's guilty

plea and all related statements could be introduced against him at

his trial, based on the waiver language in Newbert's plea

agreement. Newbert filed a competing motion in limine to exclude

this evidence.

The district court ruled that Newbert was not in breach

of his plea agreement when he withdrew his plea and thus that

Federal Rule of Evidence 410 still applied in full. Newbert II,

477 F. Supp. 2d. at 288. The court referred to contract law

principles and noted that the clause assumed that some withdrawals

of guilty pleas would not constitute a breach. Id. at 290-91.

Rejecting the government's argument, repeated before this court,
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that only guilty plea withdrawals based on government error or

agreed to by the government would not breach the agreement, the

judge concluded that if "the defendant's post-plea evidence is

sufficient to substantially affect the basis upon which the

defendant entered the plea agreement, a motion to withdraw cannot

constitute a breach of this agreement." Id. at 293. This, the

judge noted, was the logical corollary of the government's argument

that withdrawal would not be in breach if the government "agrees

that new evidence establishes the defendant's innocence," for "the

phrase must be interpreted evenly to allow for withdrawal without

breach when the defendant presents post-plea evidence of innocence

and the Court concurs, even if the government does not." Id. at

294.

II.

We review the district court's order excluding evidence

for abuse of discretion. White v. N.H. Dept. of Corrections, 221

F.3d 254, 262 (1st Cir. 2000). Here the exclusion is based on

construction of the plea agreement. A construction of the

agreement based on an error of law would constitute an abuse of

discretion. To the extent the district court's conclusion involved

questions of law as to the construction of the agreement, our

review is de novo. United States v. Clark, 55 F.3d 9, 11 (1st Cir.

1995). This includes the question of whether there was a breach of

the agreement. United States v. Doe, 233 F.3d 642, 643-44 (1st
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Cir. 2000); Clark, 55 F.3d at 11; United States v. Atwood, 963 F.2d

476, 478 (1st Cir. 1992). To the extent the court made factual

findings, such as the interpretation of ambiguous terms in light of

the intent and conduct of the parties, our review of the underlying

factual findings is for clear error. Clark, 55 F.3d at 11. The

court made no error of fact or law, and there was no abuse of

discretion.

Rule 410 of the Federal Rules of Evidence, and Rule 11(f)

of the Federal Rules of Criminal Procedure by incorporation, is the

legacy of Kercheval v. United States, 274 U.S. 220 (1927), in which

the Supreme Court recognized that allowing a withdrawn guilty plea

to be used against a defendant defeats the purpose of allowing the

withdrawal in the first place. Id. at 224 ("Giving to the

withdrawn plea any weight is in principle quite as inconsistent

with the prior order [allowing withdrawal of the plea] as it would

be to hold the plea conclusive."); Fed. R. Evid. 410 note (citing

Kercheval). As the order allowing the withdrawal is an exercise of

the court's sound discretion, to effectively negate that order

would not only harm the defendant's rights, but would also

undermine the conclusiveness of the court's ruling. See Kercheval,

274 U.S. at 224; 23 Wright & Graham, Federal Practice and

Procedure: Evidence § 5342 (1980); see also 1A Wright, Federal

Practice and Procedure: Criminal § 171 (3d ed. 1999) (discussing

the policies underlying Rule 11 as including ensuring the court's
This is not only because ambiguities in contracts are 3

traditionally interpreted against the drafter, Restatement (Second)

of Contracts § 206 (1981), but also because plea agreements

implicate broader societal interests, some of constitutional

magnitude, Giorgi, 840 F.2d at 1026 (citing United States v.

Harvey, 791 F.2d 294 (4th Cir. 1986)).

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oversight of plea agreements and the prevention of abuse of the

plea agreement process). Further, providing some protection for

defendants from pleas gone awry fosters plea bargaining by

encouraging openness and honesty during plea negotiations. Fed. R.

Evid. 410 note. These Rules thus protect important rights and

interests, but their protection can be waived by defendants.

Mezzanatto, 513 U.S. at 806. The question presented here is

whether Newbert's successful motion to withdraw his guilty plea,

based on post-plea evidence of actual innocence, constitutes a

breach of his plea agreement such that he has waived his Rule 410

and Rule 11(f) rights.

Basic contract principles apply to the construction of

plea agreements. Clark, 55 F.3d at 12; Atwood, 963 F.2d at 479.

Ambiguities in plea agreements are construed against the

government. United States v. Giorgi, 840 F.2d 1022, 1026 (1st Cir.

1988) ("[W]e find that the costs of an unclear agreement must fall

upon the government. . . . [W]e hold that the government must

shoulder a greater degree of responsibility for lack of clarity in

a plea agreement."). In this case, the "under circumstances 3

constituting a breach" clause is clearly ambiguous. The agreement
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contains no definitions for when the withdrawal of a plea allowed

by a court could constitute a breach. The district court aptly

noted that the phrase "under circumstances constituting a breach"

when applied to successful withdrawals of pleas is also not selfdefining. Newbert II, 477 F. Supp. 2d at 291. This clause by its

terms does not purport to govern situations where a defendant has

violated other terms of a plea agreement, such as a failure to

testify or to testify honestly.

The government's construction of the agreement is that

the "under circumstances constituting a breach" of the agreement

language was meant to exclude situations in which government

conduct was the cause of the defendant's successful motion to

withdraw the plea, as well as situations in which the government

agreed to withdrawal of the plea, such as when new evidence has

convinced the government of the defendant's innocence. This

argument from the negative makes an inherent assumption that every

successful motion to withdraw is a breach unless the government

provokes it or agrees to it. The government reads into the clause

language which is not there. Taken literally, the government's

position would lead to the absurd conclusion that where a court,

over the government's opposition, had found a plea not knowing,

intelligent, and voluntary and vacated the plea, a defendant could

nonetheless be in breach of the agreement and thus deemed to have

waived the defendant's Rule 410 right to exclude evidence
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concerning that defective plea. See Mezzanatto, 513 U.S. at 210 (a

waiver of a defendant's Rule 410 right will not be enforced if

found to be unknowing or involuntary). If the government had such

a clear idea of what the breach language did or did not cover, it

could have said as much in the agreement itself. Instead, not only

does the government fail to acknowledge that it must bear the cost

of ambiguities in the plea agreement, it also firmly and

incorrectly argues that the ambiguous language should be construed

against the defendant. It is the prosecution's locution which is

odd. 

Thus with unintended irony, the prosecution argues on

appeal that the district court read into the agreement language

which is not there. It says the court construed the term "under

circumstances constituting a breach" to mean "circumstances

generated by the defendant, not necessarily agreed to by the

government." But the court did not make that construction at all.

The court's full statement is instructive: "The question here is

what circumstances generated by the defendant, not necessarily

agreed to by the government, should not be considered a breach."

Newbert II, 477 F. Supp. 2d at 292. The court was responding to

the one-sided interpretation of the government, noting that the

government could not be the sole arbiter of when a judicially

sanctioned withdrawal would or would not constitute a breach;

"rather, [that decision] must rest with the court," which will
The court in Molinaro did not discuss the grounds for 4

Molinaro's withdrawal of his guilty plea or explain why this

withdrawal constituted a breach under the terms of his agreement.

See 11 F.3d at 864.

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sometimes be swayed by defendant's arguments even if the government

is not. Id. at 293.

The government argues its construction is mandated by

prior case law. Not so. In United States v. Swick, 262 F.3d 684

(8th Cir. 2001), and United States v. Young, 223 F.3d 905 (8th Cir.

2000), the Eighth Circuit considered only whether waivers of Rule

410 rights were knowing and voluntary; no claims of actual

innocence were raised, nor any questions of interpretation. In

Young, the defendant breached his agreement by absconding before

his plea hearing. 223 F.3d at 907. In Swick, the defendant

withdrew his plea apparently without much explanation. 262 F.3d at

686 (noting that the district court "act[ed] out of what appears to

us to be an abundance of discretion" in granting the withdrawal

motion). In neither case did the defendants dispute that their

actions constituted a breach. The government also cites to United

States v. Molinaro, 11 F.3d 853 (9th Cir. 1993), but again in that

case the defendant's withdrawal of his plea was not based on a

claim of actual innocence.4

The prosecution misreads the district court as having

held that every time it is arguable that defendant would not

otherwise have entered the plea had he known then what he later
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knew, then the withdrawal of a plea cannot be a breach of the

agreement. That was not the court's holding. The district court

enunciated a number of limiting principles on its decision that

defendant was not in breach, emphasizing the restrictions it had

already employed in deciding whether to permit withdrawal of the

plea:

[T]he defendant must first be successful in his motion to

withdraw his guilty plea, a motion fraught with

difficulty; the defendant must also demonstrate that the

basis of the motion is evidence that he discovered only

after he entered his guilty plea, that he could not,

acting with due diligence, have discovered the evidence

before entering into the guilty plea, that the evidence

establishes a plausible basis for concluding that the

defendant was not guilty of the crime to which he pleaded

guilty, and that the evidence would have materially

affected his decision as to whether to plead guilty.

Newbert II, 477 F. Supp. 2d at 294. As the court noted, "[t]hese

significant limitations are rarely met, but they happen to be met

in this case." Id. It was only as one of several limiting

principles that the court noted that Newbert had a credible claim

that he would never have entered the plea agreement if he had had

the post-plea evidence available at the time he entered the plea.

Moreover, the prosecution's argument spins out from our

statement in Clark that the government was in breach of a plea

agreement even though the government "would not have made this

agreement had it known then what it knows now." 55 F.3d at 113.

In that case, the government learned post-plea that the defendant

might have obstructed justice, and as a result it effectively
Newbert's original plea is not dispositive of his guilt. 5

Thore v. Howe, 466 F.3d 173, 185 (1st Cir. 2006) ("[T]here are a

number of reasons why a defendant might choose to plead guilty.").

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argued against the sentencing reduction it had promised in the plea

agreement not to oppose. There is an important difference between

new information suggesting the defendant deserves a stronger

sentence and new information suggesting the defendant might

actually be innocent. Cf. United States v. Barron, 172 F.3d 1153, 5

1158 (9th Cir. 1999) ("What is at stake for the defendant is his

liberty. . . . What is at stake for the government is its interest

in securing just punishment for violation of the law and its

interest that an innocent act not be punished at all."). This

difference limits the application of contract law principles to

plea agreements; the analogy between plea agreements and commercial

contracts is not exact, and the parties do not necessarily bear

equal obligations. See United States v. Gonzalez-Sanchez, 825 F.2d

572, 578 (1st Cir. 1987) ("Contractual principles apply [to plea

agreements] insofar as they are relevant in determining what the

government 'owes' the defendant."); United States v. Baldacchino,

762 F.2d 170, 179 (1st Cir. 1985) (same); see also United States v.

Harvey, 791 F.2d 294, 300 (4th Cir. 1986) ("[T]he defendant's

underlying 'contract' right is constitutionally based and therefore
The prosecution has another attack, which again 6

fundamentally misapprehends the ruling by the district court. The

prosecution argues that the reasons the court gave for allowing the

motion to withdraw are irrelevant to whether the defendant is in

breach. As a matter of logic, this is nonsensical. The two

questions are inherently interrelated. As a matter of basic

contract law, it is incorrect. Contracts may fail for a variety of

reasons, including mistake, impracticability of performance, and

frustration of purpose. Restatement (Second) of Contracts §§ 152,

261, 265 (1981). These contract law principles run parallel to,

but are not fully coextensive with, the reasons for which a federal

judge may decide that the government or defendant is not in breach

of a plea agreement. See, e.g., United States v. Bradley, 381 F.3d

641, 648 (7th Cir. 2004) (invalidating plea agreement based on

mutual mistake); United States v. Bunner, 134 F.3d 1000, 1004-05

(10th Cir. 1998) (invalidating plea agreement based on frustration

of purpose).

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reflects concerns that differ fundamentally from and run wider than

those of commercial contract law.").6

The government's underlying quarrel is with the court's

decision to allow defendant's motion to withdraw the plea. That

issue is not before us, nor could it be. See 18 U.S.C. § 3731

(describing limited circumstances when the government may seek an

interlocutory appeal, which do not include withdrawals of pleas).

In pressing this dispute here, the prosecution is attempting an end

run around the limits of interlocutory appeal.

Indeed, adoption of the government's argument could

create undesirable incentives in the system. Cf. Mezzanatto, 513

U.S. at 211 (Ginsburg, J., concurring) ("It may be . . . that a

waiver to use [plea-related] statements in the case in chief would

more severely undermine a defendant's incentive to negotiate, and

thereby inhibit plea bargaining.").
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The judgment of the district court is affirmed.

Concurring opinion follows.
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BOUDIN, Chief Judge, concurring. The plea agreement

provided that the defendant "agrees to plead guilty to the

indictment" charging him with possessing cocaine with intent to

distribute; in exchange the government agreed to recommend a

reduced sentence. So the government perhaps has a plausible

argument that the agreement, which was to plead guilty on specific

terms and understandings, was breached when the defendant chose--

however legitimately--to withdraw his plea and go to trial. 

Yet because of the vague qualifier on the waiver ("under

circumstances constituting a breach of this Agreement"), the

language is less airtight than it might have been; and ambiguity

counts against the drafter who, in this case, has greater

bargaining power and more expertise. Even if the qualifying

language was inserted to help the defendant, as the government

claims, it muddles the meaning. So, on a strict reading of the

plea language, the interpretation issue can reasonably be resolved

against the government.

Policy might at first also suggest that the waiver clause

be narrowly construed, tipping the balance decisively against the

government. That the government might use the admissions against

the defendant would surely discourage an otherwise proper

withdrawal of a guilty plea. Yet the government has some basis for

asking for such a waiver (apart from discouraging withdrawals).

Otherwise, a defendant might claim that information provided in the
The claim would not necessarily succeed. Rule 410 does not 7

in terms apply to fruits and one circuit has said the fruits

doctrine would not apply. See United States v. Rutkowski, 814 F.2d

594, 599 (11th Cir. 1987).

See Am. Honda Motor Co., Inc. v. Richard Lundgren, Inc., 314 8

F.3d 17, 21 (1st Cir. 2002) (stipulation); United States v. Teeter,

257 F.3d 14, 25-26 (1st Cir. 2001) (waiver of right to appeal).

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plea agreement tainted evidence that the government had

independently derived. Cf. United States v. Poindexter, 951 F.2d

369, 394-95 (D.C. Cir. 1991). But even if policy is neutral, the 7

present language leaves unclear whether it applies to a plea

withdrawal approved by the court based on new evidence.

Because the government may well redraft its language, a

further point ought to be stressed. Even if the withdrawal motion

were plainly a breach of the agreement, the district court would

not be required automatically to enforce the waiver. The waiver

concerned trial rights--here, the right under Rule 410 to exclude

plea discussions and related statements. For good cause, the

district court can relieve a defendant of such a waiver--just as it

can relieve parties from a stipulation or refuse to honor a plea

agreement's waiver of the right to appeal when the waiver would

effect a "miscarriage of justice."8

In the present circumstances, the district judge thought

that the withdrawal of the plea was adequately justified. The

defendant had previously conceded that he had possessed and sold

cocaine, and admission of these statements would largely have
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undercut the utility of the new trial that the court was

permitting. And, the waiver clause was less than pellucid. In

these circumstances, a refusal to enforce the waiver would arguably

have been justified even if "the contract" were read in the

government's favor.

Defendants often have second thoughts about guilty pleas,

withdrawals impose costs and sometimes seriously prejudice

government interests, and the government properly resists

promiscuous efforts to disavow such agreements. But a claim of

innocence supported by new evidence is not lightly ignored by

judges. Where a trial judge has endorsed a plausible motion to

withdraw a plea on such a ground, the government--in considering

appeal--should consider that the principle established may turn out

to be one not much to its liking.