Troy Vaval appeals from his conviction and sentence after pleading guilty before Judge Amon. Appellant participated in a scheme to rob 'and carjack a purported illegal gun buyer, actually a confidential informant carrying federal funds. On appeal, appellant principally argues that: (i) he should be permitted to withdraw his guilty plea because the district court violated Fed.R.Crim.P. ll(b)(l)(K) by failing to inform him of mandatory restitution; and (ii) he should be resentenced before a different judge or permitted to withdraw his guilty plea because the government’s arguments at sentencing violated the plea agreement. 1 We conclude that the failure to inform him of mandatory restitution in the amount of $6500 was not plain error because it would not have affected his decision to plead guilty. However, we also conclude that the government breached the plea agreement by engaging in sentence advocacy, and we therefore vacate appellant’s sentence and remand for resen-tencing.
BACKGROUND
a) The Indictment
Appellant was charged with carjacking, 18 U.S.C. § 2119(1) (Count I), robbery of federal money using a dangerous weapon, 18 U.S.C. § 2114(a) (Count II), and possession of a firearm with an obliterated serial number, 18 U.S.C. §§ 922(k), 924(a)(1)(B), 3551 et seq. (Count VI), by a felon, 18 U.S.C. §§ 922(g)(1), 924(a)(2), 3551 et seq. (Count V). The indictment also charged two co-defendants.
The government alleged that on January 2, 2003, appellant met with a confidential informant (“Cl”) in Queens, New York after. having promised to sell the Cl firearms. Appellant told the Cl to follow him into an alley, where the Cl was ambushed by appellant and three other individuals using two guns, one of them a Tec-9. Appellant took $6500 of federally-supplied “buy money” and a gold chain from the Cl; another attacker took his wallet and rings. Appellant then told his co-defendants to put the Cl in the Cl’s car and take the *149 keys. Appellant got into his own car; two of the other three attackers drove the Cl’s car further into the alley and were in the process of taking off the Cl’s pants when the police arrived. Before his arrest, appellant attempted to flee, driving at high speeds down a service road, on sidewalks, and in the middle of roads toward oncoming traffic.
b) The Plea Agreement
Appellant pleaded guilty to Count II of the indictment — robbery of federal property with a dangerous weapon, 18 U.S.C. § 2114(a) — pursuant to a plea agreement. The agreement stated that the maximum term of imprisonment was 25 years, the maximum fine was $250,000, and restitution was “N/A” under 18 U.S.C. § 3663. The remaining counts were to be dismissed. The agreement further stated that the government “will advise the Court and the Probation Department of information relevant to sentencing, including criminal activity engaged in by the defendant, and such information will be used by the Court in determining the defendant’s sentence.” However, the government also agreed that “based upon information now known to” the U.S. Attorney’s Office, it would “take no position concerning where within the Guidelines range determined by the Court the sentence should fall,” and “make no motion for an upward departure.” The government would not be bound by these two provisions if “information relevant to sentencing” became known to it after the date of the plea agreement, or if it determined that appellant violated the agreement.
c) The Guilty Plea
Appellant signed the plea agreement and pleaded guilty on September 9, 2003. At the plea colloquy, the court did not mention restitution but did tell appellant that he was subject to a mandatory $100 special assessment and a maximum fine of $250,000. Appellant, through counsel, asked “to be assured ... that the U.S. Attorney agreed not to move for an upward departure, and not to argue where in the guideline range he should be sentenced.” The government agreed to this characterization of the plea agreement. Appellant then stated that he “planned” the scheme to steal federal money, that two other individuals were involved, and that a co-defendant pointed a Tec-9 during the robbery. The court accepted the plea.
d) The Presentence Report
The Presentence Report (“PSR”) recommended an offense level of 32, a Criminal History Category (“CHC”) of II, and, therefore, a Guidelines range of 135 to 168 months. It also stated, correctly, that restitution of $6500 was mandatory. The PSR’s offense level was higher than that specified in the plea agreement, because it included a two level enhancement for fleeing from the police in a dangerous manner. The PSR’s recommended CHC was lower than that of the plea agreement — II rather than III — because the plea agreement CHC had been calculated incorrectly to include outdated crimes. Finally, the PSR emphasized appellant’s supervisory role and seemed to show that five participants were involved in the crime, justifying a three level role adjustment; nevertheless, the PSR recommended only the two level role adjustment that had been recommended in the plea agreement. Appellant did not object to any aspects of the PSR.
e) The Sentencing
At sentencing, the government noted that both the plea agreement and the PSR had erroneously given appellant a two-level rather than a three-level role adjustment. Noting that its mistake was caused *150 by a misunderstanding of the law, the government stated:
Judge, I did agree to the two level enhancement in the plea agreement for a role adjustment. I was speaking to the probation officer before court today. I wanted to point out to the Court that although the probation officer also only gave two points for the adjustment of role offense, ... as the Court will recall the testimony at [the co-defendant’s] trial did bring out that actually including the defendant there were five participants in this crime. So, technically, I think that it would be three levels added instead of two for the role adjustment.
Appellant objected, claiming that this statement violated the plea agreement.
The district court decided to use the Guidelines calculations specified in the PSR, because the role adjustment issue was not raised in a timely fashion and because it believed that the added level would not affect appellant’s sentence. Having set the Guidelines range at 135 to 168 months, the court then gave the parties a chance to speak. Appellant’s counsel asked for a sentence at the bottom of the range, while appellant apologized for his conduct and asked for leniency. The government, after noting that it had “waived the government’s right in the plea agreement to ask for an upward departure or to ask the Court to sentence the defendant in a particular place in the range of the guidelines,” stated:
I would like to point out a couple of things to the Court. Again, in the plea agreement we believed that the defendant was in [CHC] three. It turns out that he is in [CHC] two. I find this defendant’s criminal history appalling. And the fact that he can sit here today and say that he made a mistake, I find completely disingenuous. Because it is a mistake that he has made over and over and over again in terms of robbing people at gun point and using violence to commit robberies. I understand that the guidelines preclude us from looking at or calculating certain offenses. But certainly this is not this defendant’s first or second offense.
Also, the instant conduct shows that this defendant was the ring leader of this crime. He punched the victim in the face. He orchestrated three people who were armed with guns. One was an Intratek AB-10 semi automatic assault weapon. To be lying in wait for a victim, to rob him, to abduct him. There was testimony at the trial brought out that he was going to be killed. I just ask the Court to consider all of that when making the Court’s decision about where to sentence this defendant.
Appellant objected that the government was violating its agreement not to take any position about where within the Guidelines range appellant should be sentenced and asked that the government’s remarks be stricken. The government responded that “we don’t make a promise that we will be silent at sentencing” but only not to move for an upward departure or to ask for a particular sentence within a range. The government noted that “based on the information that I had at [the] time [of the plea agreement] I believed that the defendant was going to be in a [CHC] category three. He is in a category two. I think, technically, I could make an upward departure which I am not.”
The court said that it understood appellant’s concern about the arguments made by the government, but that
I sat through the trial [of appellant’s co-defendants], The government’s remarks do not change any view that the Court had of this case coming out here.
So whether the government is correct or not, whether their interpretation of *151 your agreement is correct, I don’t think there is any prejudice as a result of it.
I think that I have given Mr. Vaval the serious benefit here by not litigating an issue about the extra [role adjustment] point.
The court noted that it had always believed that this was an “extremely serious matter” and a “sentence at the top of the guidelines range” is required for punishment and deterrence. 2 The court sentenced appellant to the top of his Guidelines range — 168 months — and ordered $6500 in restitution, but no fine.
DISCUSSION
We turn now to appellant’s arguments regarding the withdrawal of his plea because of a Rule 11 violation or resentenc-ing because of a plea agreement breach by the government.
a) The Rule 11 Violation
Rule ll(b)(l)(K) required the district court to “inform the defendant of, and determine that the defendant understands ... the court’s authority to order restitution.” It is undisputed that the court’s failure to do so violated Rule 11. Nevertheless, we conclude that appellant may not withdraw his plea.
Appellant did not object to the Rule 11 violation, and we therefore review it for plain error under Fed.R.Crim.P. 52(b). Appellant bears the burden of establishing such an error.
United States v. Vonn,
*152 Appellant has not met this burden. Significantly, the PSR informed appellant before sentencing that restitution of $6500 was mandatory. At sentencing, appellant stated that he had read the PSR and was aware of its contents. Nevertheless, appellant never objected to the ordering of restitution or attempted to withdraw his plea prior to imposition of sentence. He also failed to object when the restitution order was actually imposed.
Where a defendant, before sentencing, learns of information erroneously omitted in violation of Rule 11 but fails to attempt to withdraw his plea based on that violation, there can be no “reasonable probability that, but for the [Rule 11 violation], he would not have entered the plea,” and the plain error standard is not met.
Id.; see United States v. Sanchez-Cruz,
In the instant matter, this conclusion is bolstered by the fact that at the Rule 11 proceeding, the court informed appellant that by pleading guilty, he would subject himself to a maximum fíne of $250,000.
Cf United States v. Molzen,
We therefore conclude without difficulty that there is no reasonable probability that being told at the plea hearing of mandatory restitution of $6500 would have affected appellant’s decision to plead guilty.
b) The Breach of the Plea Agreement
Appellant argues that the government breached the plea agreement by its argumentative relating of the facts of appellant’s crime and the seriousness of his criminal history. We agree.
“We review interpretations of plea agreements de novo and in accordance with principles of contract law.”
United States v. Riera,
To be sure, the government acknowledged at sentencing that the plea agreement prohibited it from seeking an upward departure or taking a position on the appropriate sentence within the applicable Guidelines range. It also stated that it did not intend to violate those provisions of the agreement. Such statements do not, however, insulate the government against a finding of breach if in fact what was said constituted an argument about where within the range to sentence appellant and/or whether to upwardly depart. See id. at 637.
The government was permitted by the plea agreement to “advise” the court of “information relevant to sentencing, including criminal activity engaged in by the defendant,” but some of its statements did not fall within this category of permissible behavior. 4 For example, the government volunteered highly negative characterizations of appellant’s criminal history as “appalling” and his purported contrition as “disingenuous.” Such characterizations are not “information” protected by the agreement. The government also noted that “the guidelines preclude us from looking at or calculating certain offenses.” It then went on to do just'that by stating, “[b]ut certainly this is not this defendant’s first or second offense.”
The facts of appellant’s present crimes had already been fully canvassed during sentencing, in the PSR, and at the trial of appellant’s co-defendants before the same judge. Nevertheless, just before sentencing, the government felt the need to provide the vivid detail quoted earlier. The government also suggested that “I think, technically, I could make an upward departure [argument]” and reiterated that it had thought appellant’s CHC was III rather than II at the time of the agreement. It is difficult to draw a principled distinction between the government actually moving for an upward departure and stating that it “technically'’ could move for such a departure and then adding arguments that would support such a departure.
Moreover, the offending statements by the government occurred after the court had determined appellant’s Guidelines range. At that point, the only remaining issues were whether to depart or where within the range to sentence appellant, and the government’s statements had no relevance other than to address those issues. Indeed, at the conclusion of the statements in question, the government stated, “I just ask the Court to consider all of that when making the Court’s decision about where to sentence this defendant.”
Our holding that the government breached its plea agreement obligations is fully consistent with our decision in
Riera,
The distinction between this case and Riera is in the severity and context of the government’s breach. The government’s conduct in this case went far beyond a few ill-advised words.
This case also differs from Riera because the government’s letter there served a useful purpose — as specifically permitted by the plea agreement, the provision of requested legal and factual information to the court — which is an essential function of the government at sentencing. In such circumstances, rather than deter the provision of necessary information, we may forgive “a few ill-advised descriptive words.” Id. at 135. Here, all relevant legal and factual information had already been provided to the court, and the government’s statements served no purpose other than to advocate that the court upwardly depart or impose a high sentence within the Guidelines range.
c) The Remedy for Breach of the Plea Agreement
In general, “[t]he remedy for a breached plea agreement is either to permit the plea to be withdrawn or to order specific performance of the agreement.”
United States v. Brody,
1. Types of Breaches That Require Remedies
We have said that not every breach requires a remedy. Rather, the need for a remedy depends on the “nature of the broken promise and the facts of each particular case.”
Brody,
(i) Lack of Prejudice Generally Irrelevant
Whether a breach by sentence advocacy caused prejudice in the form of an increased sentence is irrelevant to the need for a remedy. In
Santobello,
the government violated an agreement not to make a sentencing recommendation, and the Supreme Court accepted at face value the sentencing court’s statement “the prosecutor’s recommendation did not influence him.”
(ii) Curative Performance Exception
Under our caselaw, the principal type of plea agreement breach by the government that does not require a remedy is one that has been previously cured by specific performance. Thus, where the government breaches an affirmative obligation of a plea agreement provision at sentencing but then complies with that provision at a post-sentencing Rule 35 hearing, no further remedy for the initial breach is required on appeal. This is so because the defendant has already effectively received his remedy — performance.
For example, in
Brody,
the government agreed to inform the court at sentencing of the defendant’s cooperation with authorities but failed to do so. We ordered no remedy for the breach, however, because the government complied with the breached provision at a Rule 35 motion for a reduced sentence.
(iii) De Minimis Breach Exception
There is also a very limited exception to the need for a remedy for a plea agreement breach by the government where the violation is so minor that it does not cause the defendant to suffer any meaningful detriment.
See Brody,
(iv) The Present Case
In this case, the government’s violation constituted a breach that requires a remedy. The promises not to move for an upward departure or to argue where to sentence appellant within his Guidelines range were, along with the dropping of five counts of the indictment, unquestionably the centerpiece of the agreement. Because the government violated essential provisions of the plea agreement, and because no specific performance of the agreement was (or could be) granted to appellant through a Rule 35 proceeding, we must order a remedy.
2. Choice of Remedy — Resentencing or Withdrawal of Plea
Where a plea agreement is breached, the choice between the remedies of resentencing or plea withdrawal “is generally a discretionary one guided by the circumstances of each case.”
United States v. Palladino,
CONCLUSION
Because there is no reasonable probability that appellant would not have pleaded guilty had he known that he was subject to mandatory restitution, the Rule 11 violation in this case does not constitute plain error. However, the government violated its plea agreement, and this breach requires the remedy of resentencing before a different district judge.
Notes
. Appellant also claims on appeal that his counsel was ineffective because of her failure to object to the Rule 11 violation and her failure to file a “Sentencing Memorandum.” We disagree. Even if we assume that counsel’s actions "fell below an objective standard of reasonableness,”
Strickland v. Washington,
. As to the seriousness of the case, the court stated further that:
There was violence here. It is one of the most serious cases that I have seen where a gun is pulled on someone. The whole circumstances that I heard at the trial, and that were accurately reported in the presen-tence report are extremely disturbing. Mr. Vaval has a very serious criminal history .... I had people with [CHC] two with far less serious charges than these. You can get in [CHC] two with certain traffic offenses. These are very serious criminal charges.
. Although we have held that the failure to inform a defendant at a plea hearing of the possibility of restitution where such restitu-lion is ultimately imposed is not harmless error,
e.g., United States v. Harrington,
. Appellant argues that the government breached the agreement by noting that the plea agreement and PSR mistakenly recommended a two-point rather than a three-point role adjustment. These statements were not a breach by the government because they constituted “information relevant to sentencing,” and the government did not argue that this information should affect the court's sentencing decision.
See United States v. Peglera,
. Although we did not “perceive any possible prejudicial effect caused by the prosecutor's breach,” but this was not because the memorandum did not affect the sentence; it may well have done so.
Casamento,
. In Paradiso, the agreement required that the defendant's sentences on the counts of two separate indictments be imposed concurrently rather than consecutively, but the purpose of that requirement, as evidenced by the intent of the parties, was to ensure that the sentence would be no longer than ten years — the maximum on one of the counts. Id. at 30-31. The district court imposed consecutive sentences of 8 years' imprisonment on one count of the first indictment and 2 years' probation on the single count of the second indictment in technical violation of the binding plea agreement's guarantee that the sentences would be imposed concurrently. Id. We upheld the sentence because it satisfied the purpose of the agreement — to keep the defendant's sentence under 10 years. Id.
