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
*
Of the Northern District of California, sitting by
designation.
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. Yeje-
Cabrera, 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
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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.
1
Rule 410 provides in relevant part: "[E]vidence of the
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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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
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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.2 Smith was to be the government's sole civilian
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
2
This information was not entirely new, although its
source was. Newbert's wife had told him, prior to his plea, that
the cocaine may have been Smith's.
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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
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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.").3 In this case, the "under circumstances
constituting a breach" clause is clearly ambiguous. The agreement
3
This is not only because ambiguities in contracts are
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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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 self-
defining. 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
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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
4
The court in Molinaro did not discuss the grounds for
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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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
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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.5 Cf. United States v. Barron, 172 F.3d 1153,
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
5
Newbert's original plea is not dispositive of his guilt.
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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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.").
6
The prosecution has another attack, which again
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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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
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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).7 But even if policy is neutral, the
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
7
The claim would not necessarily succeed. Rule 410 does not
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).
8
See Am. Honda Motor Co., Inc. v. Richard Lundgren, Inc., 314
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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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.
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