Frank Ready pled guilty to wire fraud under 18 U.S.C. § 1343. His plea agreement included a waiver of his right to appeal his sentence. His sentence included a penalty of restitution. On appeal, he claims that the restitution penalty wás imposed illegally. The Government argues that Ready’s waiver of his right to appeal bars this challenge, and that in any ease his claim fails on the merits.
After the parties filed their appellate briefs but prior to oral argument, we decided
United States v. Yemitan,
We conclude that the waiver contained in Ready’s plea agreement does not, under the circumstances presented, operate as a waiver of Ready’s right to appeal his restitution penalty. Reaching the merits of Ready’s challenge to his sentence, we also decide that the restitution penalty was legally and properly imposed. We discuss in this opinion only our conclusion that Ready did not waive his right to appeal. Ready’s substantive challenges to his restitution penalty raise no new legal issues, and we reject them in a summary order also issued today.
I
There are two plea agreements in this case. One of them contains a waiver of Ready’s right to appeal; the other does not. Ready entered into the first plea agreement with the Office of the United States Attorney for the Northern. District of New York, pleading guilty to Count Five of a five-count indictment that charged him with a scheme to defraud the federal government (the “New York plea agreement”). Count Five concerned a telephone conversation that furthered the scheme, in violation of the wire fraud statute, 18 U.S.C. § 1343. In pleading guilty to this count, Ready agreed to pay about $16,000 in restitution. He and the Government explicitly “reserve[d] the right to appeal any sentence imposed in this matter.”
About six months later, Ready was charged in the District of Maryland with two additional counts of wire fraud, relating to a similar scheme to defraud the United States and several private companies. In an agreement with the United States Attorney’s Office. for that district, he pled guilty to both counts (the “Maryland plea agreement”). This agreement, analyzed below, contains the disputed waiver of Ready’s right to appeal.
Paragraph 2 of the Maryland plea agreement (drafted as a letter to Ready’s counsel) sets out the possible punishment:
The maximum sentence provided by statute for the offense to which your client is pleading guilty is as follows: Five years imprisonment per count and a fine of $250,000 per count, followed by a term of supervised release of three years: ' In addition, your client must pay $100 as a special assessment under 18 U.S.C. Section 3013, which will be due and should be paid at time of sentencing unless otherwise ordered by the Court. This Court may also order your client to make restitution pursuant to 18 Ú.S.C. Sections 3663 and 3664.
Ready agreed in paragraph 3B that the applicable offense level for sentencing' under the Guidelines was 22. In paragraph 4, the Government expressly withheld any assurance that it would recommend a particular prison term within the Guidelines range, or that it would recommend a particular level of restitution:
At your client’s sentencing this Office will make any recommendation regarding the sentence in the guideline range it deems appropriate; and make any recommenda *554 tion regarding restitution it deems appropriate.
Ready’s Maryland plea agreement did not recite his acceptance of a specific restitution amount. .
Paragraph 5 contains the waiver of Ready’s right to appeal:
Your client and the United States knowingly and expressly waive all rights conferred by 18 U.S.C. Section 3742 to appeal whatever sentence is imposed, including any issues that relate to the establishment of the guideline range, reserving only the right to appeal from a sentence resulting from an adjusted base offense level of greater than twenty-three. 1
Finally, paragraph 6 limits Ready’s ability to withdraw from his guilty plea:
If the Court should impose any sentence up to the maximum established by statute, your client cannot, for that reason alone, withdraw his guilty plea, and will remain bound to fulfill all of his obligations under this agreement.
(Emphasis added.)
Ready’s two pleas were consolidated before Judge McAvoy in the Northern District of New York. Before accepting the pleas, the district court duly advised Ready that he was waiving a panoply of rights by pleading guilty, and ascertained from Ready that he understood “the consequences of pleading guilty.”' However, the court did not include the right to appeal in its list of the rights waived by Ready.
Later in the hearing, the court asked Ready’s trial lawyer if he had “advised Mr. Ready of his rights, the nature of the charges and consequences of pleading guilty.” Ready’s counsel said that he had, and specified that “I have advised him that ... pursuant to the plea agreement in Maryland, he gives up his right to appeal any sentence that might be rendered here pursuant to that agreement.”
At the end of. the hearing, in a short colloquy with Ready’s counsel, the court stated that Ready had not fully waived his right to appeal:
The CouRT: [Addressing Ready.] You have the right to appeal this sentence to certain limited circumstances—
Ready’s Lawyer: I don’t believe that’s correct, according to the plea agreement, your Honor.
The Court: Ye[s]. The plea agreement talks about certain things with respect to the sentence. But if I impose an illegal sentence on him, he certainly would have the right to appeal that. So you should consult with your attorney before hitting him. in the ribs again as to any appeal.
The court sentenced Ready based on an offense level of 22, as the Maryland plea agreement contemplated. Ready’s criminal history category of VI yielded a Guidelines imprisonment range of 84 to 105 months, and a fine range of $7,500 to $75,000. He was sentenced to a total of 100 months in prison. No fine was imposed “because of the defendant’s inability to pay.”
The court imposed a restitution penalty of approximately $308,000. Of that, $16,000 was the amount agreed to in the New York plea agreement, and $292,000 was the amount attributed to the Maryland indictment. The court drew the $292,000 figure from the presentencing report, which listed the losses suffered by five corporate victims of Ready’s scheme. Ready claims that the court failed to “consider” his “financial resources ... and earning ability” before imposing restitution, as required by 18 U.S.C. § 3664(a). The restitution penalty, he says, was therefore imposed illegally. But if. Ready completely waived his right to appeal the restitution imposed pursuant to the Maryland plea agreement, then he cannot contest the legality of the $292,000 portion of the restitution penalty.
II
A criminal defendant has no constitutional right to an appeal.
Jones v. Barnes,
The right to appeal a criminal conviction and sentence is statutory. Prior to the passage of the Sentencing Reform Act of 1984 (the “1984 Act”), which brought us the Sentencing Guidelines, criminal appeals were taken pursuant to 28 U.S.C. § 1291. That statute simply allows appellate courts to hear appeals from “all final decisions of the district courts.” The right to appeal a sentence under § 1291 was limited to sentences that were. imposed above statutory limits, that were the result of material misinformation, or that were based on a constitutionally impermissible factor.
United States v. Tucker,
The 1984 Act “expanded appellate review.”
Colon,
Along with the other circuits that have considered the question, we have held that a defendant’s right to appeal his sentence may be waived in a plea agreement.
See Yemitan,
But no circuit has held that these contractual waivers are enforceable on a basis that is unlimited and unexamined.
See, e.g., Yemitan,
In deciding whether to enforce an individual’s waiver of a right, courts ask whether the right implicates institutional and societal values that transcend the individual’s interests. Recently, the Supreme Court has held that, even as to evidentiary rulings, a defendant may be deemed incapable of waiving a right that has an overriding impact on public interests:
[Tjhere may be some evidentiary provisions that are so fundamental to the relia *556 bility of the fact-finding process that they may never be waived without irreparably discredit[ing] the federal courts.
United States v. Mezzanatto,
— U.S. —, —,
No doubt there are limits to waiver; if the parties stipulated to trial by 12 orangutans the defendant’s conviction would be invalid notwithstanding his consent, because some minimum of civilized procedure is required by community feeling regardless of what the defendant wants or is willing to accept.
Id.
(quoting
United States v. Josefik,
As for the right to appeal, we have recognized that appellate review under the Guidelines, important as it is for individual defendants, also serves an important public interest in avoiding the sentencing disparities that were seen to be a great problem with the pre-Guidelines system.
See Colon,
Accordingly, we must scrutinize waivers closely and apply them narrowly. To this end, we use two familiar mechanisms. First, we assure that the waiver of this important right is knowing and voluntary.
See United States v. Robinson, 8
F.3d 418, 421 (7th Cir.1993); see
also Yemitan,
Ill
In plea agreements, “[w]aivers of constitutional rights not only must be voluntary but must be knowing, intelligent acts done with sufficient awareness of the relevant circumstances and likely consequences.”
Brady v. United States,
A majority of circuits that have addressed this issue have either ruled or intimated that the district court should specifically flag the defendant’s waiver of the right to appeal at the Rule 11 plea agreement hearing.
3
We agree that a waiver of the right to appeal should only be enforced by an appellate court if the record “clearly demonstrates” that the waiver was both knowing (in the sense that the defendant fully understood the potential consequences of his waiver) and voluntary.
See Schmidt,
After reviewing the transcript of the Rule 11 hearing, we conclude that Ready did not knowingly waive his right to appeal a restitution order that is imposed in violation of 18 U.S.C. § 3664(a). At the hearing, the district court explained to Ready that it would soon be “advis[ing] you of your rights as to whether or not you are pleading guilty freely and voluntarily with an understanding of the charges made against you and the consequences of pleading guilty.” When the court enumerated the rights that Ready was waiving, however, it did not mention the right to appeal or explain the consequences of waiving this right. Ready’s lawyer had advised Ready that “he gives up his right to appeal any sentence that might be rendered here pursuant to [the plea] agreement,” and so advised the court. In response, the court explained that it understood the waiver to be a limited one: “But if I impose an illegal sentence on him, he certainly would have the right to appeal that.” Since the court stated that the waiver only applied to legally imposed sentences, it would have been entirely reasonable for Ready to believe (with the judge) that he was not waiving his right to appeal a sentence that was imposed illegally. *558 This understanding is consistent with the comment of Ready’s counsel that he could not appeal a sentence imposed “pursuant to [the plea] agreement,” since it would have been reasonable for Ready to believe that his plea agreement, written by Government lawyers and scrutinized by his own lawyer, did not authorize an illegally imposed sentence.
As in
Baty,
then, “there was no satisfactory explanation to [Ready that] the consequences of [his] waiver of [his] right to appeal” included the waiver of an illegally imposed sentence.
See
[A] defendant’s waiver of her right to appeal deserves, and, indeed, requires the special attention of the district court. When a defendant waives her right to appeal, she gives up the very valuable right to correct a district court’s unknown and unannounced sentence.... It is up to the district court to insure that the defendant fully understands her right to appeal and the consequences of waiving that right.
Id. Here, the record does not instill confidence that Ready understood his waiver to include the waiver of his right to appeal a restitution penalty imposed in violation of 18 U.S.C § 3664(a). We therefore hold that his waiver was not knowing, for the purposes of this appeal.
IV
We construe a criminal defendant’s waiver of appellate rights narrowly. See supra section II. Applying that rule to this case, we conclude that the waiver in Ready’s Maryland plea agreement did not include his right to appeal an illegally imposed restitution penalty.
As we said in
Yemitan,
“[p]lea agreements are construed according to contract law principles.”
As the Fourth Circuit has recognized, in interpreting plea agreements,
courts have necessarily drawn on the most relevant body of developed rules and principles of private law, those pertaining to the formation and interpretation of commercial contracts. But the courts have recognized that those rules have to be applied to plea agreements with two things in mind which may require their tempering in particular cases. First, the defendant’s underlying “contract” right is constitutionally based and therefore reflects concerns that differ fundamentally from and run wider than those of commercial contract law. Second, with respect to federal prosecutions, the courts’ concerns run even wider than protection of the defendant’s individual constitutional rights — to concerns for the honor of the government, public confidence in the fair administration of justice, and the effective administration of justice in a federal scheme of government.
United States v. Harvey,
Several rules of interpretation, consistent with general contract law principles,
*559
are suited to the delicate private and public interests that are implicated in plea agreements. First, courts construe plea agreements strictly against the Government. This is done for a variety of reasons, including the fact that the Government is usually the party that drafts the agreement, and the fact that the Government ordinarily has certain awesome advantages in bargaining power.
See Carnine,
Second, we construe the agreement against a general background understanding of legality. That is, we presume that both parties to the plea agreements contemplated that all promises made were legal, and that the non-contracting “party” who implements the agreement (the district judge) will act legally in executing the agreement.
See Walsh v. Schlecht,
Finally, as we pointed out in
Yemitan,
courts may apply general fairness principles to invalidate particular terms of a plea agreement.
We apply these principles to Ready’s plea agreement. When construed strictly against the Government and against a background presumption of legality, the waiver language does not allow the inference that the parties intended it to preclude the appeal of an illegally imposed restitution penalty. First, paragraph 2 of the agreement explicitly applies the background presumption of legality to Ready’s restitution penalty: “Th[e] Court may also order your client to make restitution pursuant to 18 U.S.C. Sections 3663 and 3661.” (Emphasis added.) Though Ready’s waiver of his appellate rights in paragraph 5 is admittedly broad (waiver of right to appeal “whatever sentence is imposed”), it does not distinctly negate paragraph 2’s statement that restitution will be imposed in accordance with the restitution statute. There is thus an ambiguity (at the least) as to the parties’ intent with regard to restitution penalties imposed illegally. Construing this ambiguity strictly against the Government, we must presume that on the issue of restitution, the parties intended the phrase, “whatever sentence is imposed,” to mean “whatever sentence is imposed by law.”
Second, there is an ambiguity in paragraph 5 as to whether the term “sentence” includes the restitution penalty. Paragraph 5 states:
*560 [The defendant] and the United States knowingly and expressly waive all rights conferred by 18 U.S.C. Section 3742 to appeal whatever sentence is imposed, including any issues that relate to the establishment of the guideline range, reserving only the right to appeal from a sentence resulting from an adjusted base offense level of greater than twenty-three.
(Emphasis added.) The word “sentence” is thus used twice, once in the waiver and then in the reservation. It is express that the “sentence” referenced in the reservation is the sentence that “result[s] from an adjusted base offense level,” which would include the prison sentence and the fine. But the word “sentence,” as used in the reservation, would not include restitution, because restitution penalties are not linked in any way with Guidelines base offense levels. And there is no indication that the word “sentence” is intended to mean a different thing when used earlier in the paragraph (in the phrase “whatever sentence is imposed”). Nor is there anything in the plea agreement to suggest that the defendant agreed not to appeal “whatever restitution is imposed,” including, for instance, an unlimited restitution penalty (which might in any case be an unconscionable agreement). It is thus ambiguous whether paragraph 5’s reference to “whatever sentence is imposed” includes the restitution penalty imposed. Once again, this ambiguity must be construed strictly against the Government.
The use of the term “sentence” in paragraph 4 of the agreement confirms the impression that the term was not intended to include restitution. That provision states that the Government
will make any recommendation regarding the sentence in the guideline range it deems appropriate; and make any recommendation regarding restitution it deems appropriate.
(Emphasis added.) Under a straightforward reading of this passage, the “sentence” is an idea separate from “restitution.” Paragraph 6 adds more support:
If the Court should impose any sentence up to the maximum established by statute, [the defendant] cannot, for that reason alone, withdraw his guilty plea, and will remain bound to fulfill all of his obligations under this agreement.
(Emphasis added.) Prison terms and fines are frequently limited by statutes, but restitution amounts are not. The term “any sentence” in paragraph 6 thus seems to exclude restitution, or any imposition that is not subject to a statutory maximum. For all of these reasons, we conclude that the waiver of Ready’s right to appeal his “sentence” did not include a waiver of his right to appeal his restitution penalty.
We hold that Ready did not waive the right to bring this appeal. The merits of that appeal raise no new issues, and are resolved by summary order issued on the same day as this opinion.
Notes
. The reference to an offense level of 23 appears to be a mistake, since the Government had agreed in paragraph 3B that the proper offense level was 22.
. Though this Court has never ruled on the issue explicitly, statements in our past decisions make it clear that we would not accept an involuntary or “unknowing” waiver of the right to appeal.
See Yemitan,
.
Compare Schmidt,
