In the

United States Court of Appeals For the Seventh Circuit ____________________ Nos. 24-2355 & 24-2401 UNITED STATES OF AMERICA, Plaintiff-Appellee, v.

KENIN EDWARDS, Defendant-Appellant. ____________________

Appeals from the United States District Court for the Central District of Illinois. No. 21-CR-10012-JES-JEH — James E. Shadid, Judge. ____________________

ARGUED MAY 15, 2025 — DECIDED JULY 31, 2025 ____________________

Before RIPPLE, KIRSCH, and KOLAR, Circuit Judges. KIRSCH, Circuit Judge. Kenin Edwards was sentenced to 21 months’ imprisonment for tax fraud. The procedural road leading to his sentence was rocky, to say the least. Edwards would come to be represented by four attorneys between his indictment and sentencing. Along the way, he repeatedly de- layed his trial before eventually reaching an agreement to plead guilty. After his guilty plea, things still did not proceed smoothly, however, as Edwards fired his final attorney on the 2 Nos. 24-2355 & 24-2401

eve of sentencing, decided to proceed pro se, recanted his ad- mission of guilt, sought to vacate his plea, challenged stipula- tions made in his plea agreement, and flooded the court with frivolous motions. Though the government had agreed to rec- ommend a split sentence of five months in exchange for Ed- wards’s guilty plea, it sought 21 months at sentencing given everything that had transpired since. Edwards now wants to take it all back. He asks to be re- sentenced with the benefit of his plea agreement and its sen- tencing recommendation of five months. To justify this, he claims that his Sixth Amendment rights were violated when the district court disqualified one of his attorneys for a conflict of interest and when it, in his view, forced Edwards to pro- ceed pro se at sentencing. He also says that the government, not he, breached the plea agreement by recommending a higher sentence. The merits of these arguments are highly questionable. But we dismiss his appeal without reaching them because Edwards waived his right to appeal in his plea agreement. I Kenin Edwards was a contractor for logging businesses, working as a middleman between landowners and third- party timber purchasers. He helped negotiate contracts be- tween these parties and earned a commission for each suc- cessful deal he brokered. As one normally does, Edwards filed state and federal tax returns each year for this venture. The issue is that Edwards underreported his income to the tune of nearly $2.8 million over four years, causing a tax loss of over $200,000. As a result of this scheme, Edwards was indicted on 14 counts of wire, mail, and tax fraud. 18 U.S.C. §§ 1341 & 1343; 26 U.S.C. § 7206(1). Nos. 24-2355 & 24-2401 3

Edwards initially retained two attorneys to mount his de- fense: Robert Hanauer and Anthony Cameron. Two years and a series of unremarkable continuances later, a timeline for Ed- wards’s trial had finally solidified. Just two weeks before trial was to start, though, things took a turn when Hanauer and Cameron filed a motion to withdraw as counsel because Ed- wards had discharged them. At a hearing on the motion, Ed- wards explained that certain exculpatory materials seized during the search of his home were never returned to him or properly documented by the government. Hanauer and Cam- eron, however, stated they had no reason to dispute the gov- ernment’s contrary assertions and declined to file a motion accusing the government of discovery violations. The govern- ment argued that this was a blatant attempt by Edwards to delay trial. But finding a genuine breakdown in trial strategy between Edwards and his attorneys, the district court indi- cated it would permit Hanauer and Cameron to withdraw if Edwards retained new counsel within 21 days. The court set a status conference for two days after this 21-day deadline. Attorney William Anderson entered an appearance for Edwards on day 20. This was not a surprise; the parties had discussed the possibility of Anderson taking over as counsel at the most recent hearing. The morning of the scheduled sta- tus conference, the government filed a motion to disqualify Anderson. The court granted Hanauer and Cameron’s re- newed motion to withdraw and set a hearing on Anderson’s disqualification. Anderson had previously represented a key government witness—a fact which Edwards was well aware of, since he had arranged that representation. What’s more, Edwards had listed Anderson as a potential witness in his up- coming criminal trial. Finding a clear conflict that outweighed 4 Nos. 24-2355 & 24-2401

Edwards’s interest in retaining Anderson, the court granted the motion and disqualified Anderson. Edwards promptly retained his fourth and final attorney, Peter Lynch. His trial was continued twice more before the parties finally entered into a plea agreement. Pursuant to the agreement, Edwards pleaded guilty to one count of filing a false and fraudulent tax return in violation of 26 U.S.C. § 7206(1). He also acknowledged that he had underreported his taxes for four years and stipulated to the total tax loss amount. Based on these admissions, the government recom- mended a two-level reduction for acceptance of responsibility under U.S.S.G. § 3E1.1. Reflecting these terms, the parties anticipated that Ed- wards’s advisory Guidelines range would be 10 to 16 months. Accordingly, the government “agree[d] to recommend no higher than a split sentence of 5 months of imprisonment and 5 months of home confinement” and a “fine of no more than $10,000.” If Edwards was not eligible for the reduction for zero criminal history points, as expected, the government “agree[d] to recommend no higher than a split sentence at the low end of” his ultimate Guidelines range. Separately, the plea agreement allowed the government to “chang[e] its po- sition” on whether to recommend a reduction for acceptance of responsibility “if new evidence to the contrary [was] dis- covered or if [Edwards] later demonstrate[d] a lack of ac- ceptance of personal responsibility.” In exchange for these recommendations, Edwards “waive[d] all rights to appeal and/or collaterally attack his conviction and sentence.” The waiver “[did] not apply to a claim that [Edwards] received ineffective assistance of coun- sel.” During his change of plea hearing, Edwards swore to the Nos. 24-2355 & 24-2401 5

statements in the plea agreement, acknowledged that he un- derstood he was waiving his appeal rights, and said he was satisfied with Lynch’s representation. The probation office filed a revised presentence report one week before sentencing. That same day, Lynch moved to withdraw as Edwards’s counsel due to an increasingly dete- riorating attorney-client relationship. He asked the court to continue sentencing so Edwards could prepare objections to the revised presentence report; as the probation office noted, Lynch had not submitted any objections to its initial report. According to Lynch, Edwards had discharged him and in- tended to file pro se motions and represent himself. The gov- ernment objected to both motions unless Edwards proceeded pro se and submitted to a hearing under Faretta v. California, 422 U.S. 806 (1975), to ensure his waiver of his Sixth Amend- ment right to counsel was knowing and intelligent. The court set a hearing on the motion to withdraw just before sentenc- ing was scheduled to take place so that, depending on the court’s decision, sentencing could proceed as planned. Edwards submitted a pro se motion the day before these hearings. In it, he renewed his allegations of discovery viola- tions by the government that hindered his defense, asserted his innocence, and sought to withdraw his guilty plea. He also included objections to the presentence report that Lynch had neglected to submit. At the hearing on the motion to with- draw, Edwards confirmed that he wanted to discharge Lynch. The court conducted a Faretta colloquy to further verify Ed- wards’s desire for self-representation and walk him through the requirements and risks. Satisfied with Edwards’s re- sponses, the court granted his request to proceed pro se, set a schedule on the motion to withdraw his guilty plea, and 6 Nos. 24-2355 & 24-2401

stayed the sentencing hearing. It informed Edwards that he would likely be proceeding pro se at sentencing if he was un- able to withdraw his plea. But the court emphasized that it would reconsider its position if Edwards obtained another at- torney to represent him at sentencing without seeking a con- tinuance. Left to his own devices, Edwards inundated the court with filings. He repeatedly asserted his innocence, contradicted his admissions of guilt and stipulations in his plea agreement, and complained of the same purported discovery violations by the government as well as Lynch’s handling of them. He filed about a dozen additional motions or petitions with a va- riety of frivolous requests—one even sought to disqualify the district judge for his apparent bias against Edwards. As a re- sult of this behavior, the government determined that Ed- wards was no longer entitled to a reduction based on ac- ceptance of responsibility. Edwards characterized this as an anticipatory breach of the plea agreement. The district court denied Edwards’s motion to withdraw his guilty plea and, rejecting his anticipatory breach argu- ment, found his actions an obvious breach of the plea agree- ment instead. After several additional continuances and one more motion to withdraw his guilty plea, the case finally pro- ceeded to sentencing. Without the reduction for acceptance of responsibility, Edwards’s Guidelines range was 15 to 21 months’ imprisonment. Throughout sentencing, Edwards re- peated the same refrain of objections and claims of innocence. Given Edwards’s repeated obstructive conduct, the govern- ment recommended a sentence of 21 months and a fine of $25,000. The court sentenced him to 21 months, with a $10,000 Nos. 24-2355 & 24-2401 7

fine. Edwards filed several meritless post-judgment motions before initiating this appeal. II Edwards no longer wishes to vacate his plea, despite his repeated and vehement insistence to the contrary in the dis- trict court. Rather, he asks us to vacate the district court’s judgment and remand for resentencing according to the plea agreement’s terms. He supplies three justifications for this re- quest. The first two stem from purported violations of his Sixth Amendment rights, once when the district court dis- qualified Anderson and again when it allegedly forced him to proceed pro se at sentencing. In his third argument, Edwards says the government breached its obligations under the plea agreement by failing to recommend a split sentence of five months as contemplated by its terms. According to Edwards, remand is warranted if we agree with him on any one of these issues. The problem is that Edwards bargained away his appeal rights in his plea agreement. Not to worry, he says, because each of his claims is excepted from his appeal waiver. We dis- agree and find Edwards bound by the waiver he agreed to. “Appeal waivers in plea agreements are typically enforce- able.” United States v. Adkins, 743 F.3d 176, 192 (7th Cir. 2014). That said, “no appeal waiver serves as an absolute bar to all appellate claims.” Garza v. Idaho, 586 U.S. 232, 238 (2019). Ra- ther, given the contractual nature of plea agreements, an ap- peal waiver only bars review of claims that fall within its scope. Id. (“That an appeal waiver does not bar claims outside its scope follows from the fact that, although the analogy may not hold in all respects, plea bargains are essentially 8 Nos. 24-2355 & 24-2401

contracts.”) (cleaned up). Additionally, certain claims are ex- cepted from appeal waivers. “Most fundamentally,” defend- ants may bring an appeal challenging “whether the waiver it- self is valid and enforceable—for example, on the grounds that it was unknowing or involuntary.” Id. at 239. In addition to these contractual limits, there are other checks on the waiver of appeal “imposed by judicial interpre- tations of the due process clause.” United States v. Bownes, 405 F.3d 634, 637 (7th Cir. 2005). While traditional principles of contract law apply to plea agreements, their application must be “tempered by recognition of limits that the Constitution places on the criminal process.” Id. at 636; see also Adkins, 743 F.3d at 192 (“Although we construe plea agreements as con- tracts, we regard plea agreements as unique contracts in which special due process concerns for fairness and the ade- quacy of procedural safeguards obtain.”) (quotations omit- ted). In respect of these limits, our cases have carved out sev- eral paradigmatic exceptions to appeal waivers. These permit challenges to an illegal sentence (i.e., one based on constitu- tionally impermissible criteria or in excess of statutory maxi- mums), a judicial process devoid of “some minimum of civi- lized procedure,” and ineffective assistance of counsel in ne- gotiating the plea agreement. Bownes, 405 F.3d at 637 (quota- tion omitted). A Edwards contends that his Sixth Amendment claims are the type of challenge that always falls outside the scope of an appeal waiver. We disagree. Nos. 24-2355 & 24-2401 9

1 We turn first to Edwards’s claim that the district court vi- olated his Sixth Amendment right to choose his counsel when it disqualified Anderson for an apparent conflict. To argue that this claim overcomes his appeal waiver, Edwards points to our recent decision in Elliott v. United States, 110 F.4th 974 (7th Cir. 2024), where we extended the ineffective assistance exception to include a defendant’s claim that the district court violated his right to conflict-free counsel. Id. at 980–82. Ed- wards asks us to expand the exception once again to include his choice of counsel claim because it also implicates his right to effective representation under the Sixth Amendment. This request misunderstands the principles undergirding the inef- fective assistance exception. No doubt, a Sixth Amendment claim of ineffective assis- tance of counsel is one of the foremost exceptions to appeal waivers. Hurlow v. United States, 726 F.3d 958, 964–66 (7th Cir. 2013). But defendants cannot regain their appeal rights with a run-of-the-mill claim of ineffective assistance. Rather, this ex- ception is limited to claims that counsel was ineffective dur- ing the negotiations of the plea agreement itself. See Jones v. United States, 167 F.3d 1142, 1145 (7th Cir. 1999). The exception comes from a recognition of the due process concerns with barring claims that stem from “the very product of the alleged ineffectiveness.” Id. The ineffective assistance exception is a “particularly strik- ing example of the divergence between the legal principles that govern plea agreements and those that govern ordinary contracts.” Bownes, 405 F.3d at 637. While we ordinarily bind contracting parties to their lawyers’ mistakes, defendants en- tering plea agreements are entitled to effective assistance of 10 Nos. 24-2355 & 24-2401

counsel under the Sixth Amendment. Id. And, critically, a waiver “cannot be ‘knowing and voluntary’ if it resulted from ineffective assistance of counsel.” Hurlow, 726 F.3d at 967–68. To put it plainly, defendants can bring these claims because plea agreements (and their appeal waivers) are invalid and must be set aside if they are the result of ineffective assistance. In Elliott, we recognized that the Sixth Amendment’s guar- antee of effective assistance includes the right to conflict-free counsel, such that Elliot’s claim “necessarily implicate[d] his … right to effective assistance of counsel.” 110 F.4th at 981. Elliott argued on appeal that the district court concealed in- formation about his counsel’s serious conflict of interest, de- priving him of the opportunity to make an informed decision to waive the conflict. Id. at 976. Because he was represented by this conflicted counsel when he pleaded guilty and waived his appeal rights, Elliott’s claim called into question the know- ing and voluntary nature of his appeal waiver, allowing us to find it covered by the ineffective assistance exception. Id. at 981–82 & n.13. Edwards’s argument that we should further expand the exception to include his choice of counsel claim is, on its face, a reasonable request. A defendant’s choice of counsel can “se- riously impact” his decision to plead guilty and affect its vol- untary and intelligent nature. United States v. Smith, 618 F.3d 657, 663 (7th Cir. 2010) (quotation omitted). The issue for Ed- wards is that his choice of counsel claim does not attack the voluntary and intelligent character of his plea or otherwise challenge the validity of his plea agreement. Quite the oppo- site: Edwards specifically requests that we leave his guilty plea intact and remand for resentencing according to the agreement’s terms. Nos. 24-2355 & 24-2401 11

Edwards correctly notes that, if meritorious, his choice of counsel claim implicates a structural error where prejudice is presumed. See United States v. Gonzales-Lopez, 548 U.S. 140, 150 (2006). But this does not permit our review. The presump- tion of prejudice to a defendant does not bear on his ability to waive a claim. On the contrary, defendants can—and do— waive structural errors all the time. Jackson v. Bartow, 930 F.3d 930, 934 (7th Cir. 2019). To avail himself of the ineffective as- sistance exception, a defendant must allege that the purported Sixth Amendment violation made his plea unknowing or in- voluntary such that it “render[s] the plea agreement (and the waiver contained therein) invalid.” Elliott, 110 F.4th at 982 n.13. Indeed, “[t]he sole type of ineffectiveness claim we have said that a defendant may not waive is an ineffectiveness claim having to do with the waiver (or the plea agreement as a whole) and its negotiation.” United States v. Smith, 759 F.3d 702, 707 (7th Cir. 2014). Edwards makes no such contention, so his appeal waiver bars this claim. 2 We can dismiss Edwards’s claim that the district court forced him to proceed pro se at sentencing for much the same reason. Of course, at its core the Sixth Amendment guarantees criminal defendants the right to counsel. U.S. Const. amend. VI; Garza, 586 U.S. at 237. And it is well-established that this right extends to sentencing. Lafler v. Cooper, 566 U.S. 156, 165 (2012). But we have repeatedly enforced appeal waivers and “dismissed appeals contending that the defendant was de- prived of the effective assistance of sentencing counsel.” Smith, 759 F.3d at 707. This is because, as discussed, the inef- fective assistance claim must relate directly to the waiver or its negotiation to benefit from the exception. A claim that 12 Nos. 24-2355 & 24-2401

counsel performed deficiently at sentencing does not impact the validity of a prior waiver of appeal rights. The same logic forecloses Edwards’s claim that he was deprived of counsel at sentencing. Briefly, we note that we would be facing a different ques- tion if Edwards’s claim involved the total deprivation of counsel without a Faretta colloquy. Such a Sixth Amendment violation would necessitate a different calculus of the due process interests to determine whether they justified a waiver exception. But that is not the situation presented here. The court conducted a thorough Faretta colloquy to assess Ed- wards’s repeated, insistent requests to discharge his counsel and represent himself at sentencing. Edwards’s claim simply does not rise to the level of “matters that implicate the funda- mental fairness of the proceeding,” Smith, 759 F.3d at 707, nor does it fall within one of the other recognized and limited ex- ceptions to appeal waivers. This claim is waived. B Finally, Edwards argues that the government breached the plea agreement with its sentencing recommendation. Whether breach claims survive an appeal waiver is a difficult question, made more complicated by an array of inconsistent case law. Broadly speaking, our cases approach the issue in one of two ways. To start, we have routinely entertained a defendant’s breach claim despite his appeal waiver. Most often, we have employed what can best be described as a two-step process, first determining whether the government actually breached the plea agreement and, if it did not, then enforcing the waiver and dismissing the appeal. E.g., United States v. Nos. 24-2355 & 24-2401 13

Malone, 815 F.3d 367, 370 (7th Cir. 2016); United States v. Match- opatow, 259 F.3d 847, 852–53 (7th Cir. 2001); United States v. Linder, 530 F.3d 556, 564–65 (7th Cir. 2008). * Our rationale in these cases has generally sounded in contract law—because one party may void a contract if the other party materially breaches, we’ve reasoned, an “otherwise-valid appellate waiver does not preclude our review of [a] claim of material breach.” Malone, 815 F.3d at 370; see also United States v. Craig, 142 F.4th 192, 198–99 (4th Cir. 2025) (if government breaches plea agreement, defendant may seek specific performance on appeal despite appeal waiver because he “was deprived of the benefit of his bargain” and remand “makes him whole”); Gonzalez, 16 F.3d at 989–90 (government’s breach releases de- fendant from his reciprocal promise not to appeal). Simultaneously, another line of cases holds that appeal waivers foreclose these claims altogether. In United States v. Whitlow, 287 F.3d 638 (7th Cir. 2002), we held that a defendant cannot appeal the issue of breach if the district court has al- ready decided that no breach occurred, as it would be unten- able to assume “that a claim of breach allows appeal.” Id. at 640. Rather, the waiver of appeal “determines who will be the

* Ten of our sister circuits have concluded that appeal waivers are unenforceable when the government breaches the plea agreement. United States v. Arevalo, 628 F.3d 93, 98 (2d Cir. 2010); United States v. Schwartz, 511 F.3d 403, 405 (3d Cir. 2008); United States v. Tate, 845 F.3d 571, 574 (4th Cir. 2017); United States v. Keresztury, 293 F.3d 750, 756 (5th Cir. 2002); United States v. Keller, 665 F.3d 711, 718–19 (6th Cir. 2011) (breach must be material); United States v. Sayles, 754 F.3d 564, 568 (8th Cir. 2014); United States v. Gonzalez, 16 F.3d 985, 989–90 (9th Cir. 1993); United States v. Rodriguez-Rivera, 518 F.3d 1208, 1212 (10th Cir. 2008); United States v. Hunter, 835 F.3d 1320, 1324 (11th Cir. 2016); United States v. Thomas, 999 F.3d 723, 728–29 (D.C. Cir. 2021) (analyzing breach despite waiver). 14 Nos. 24-2355 & 24-2401

judge of a claim that breach has occurred.” Id. We relied in part on a decision from one year earlier, United States v. Hare, 269 F.3d 859 (7th Cir. 2001), in which we said that an appeal waiver “means that the final decision will be made by one Ar- ticle III judge rather than three Article III judges.” Id. at 861. In short, Whitlow and Hare establish that a defendant’s appeal waiver precludes a court of appeals from considering his claim of breach. United States v. Sakellarion, 649 F.3d 634, 639 (7th Cir. 2011) (“Stated otherwise, a mere ‘claim of breach’ does not void a waiver because that would make all appellate waivers unenforceable as ‘talk is cheap.’”) (quoting Whitlow, 287 F.3d at 640). For some time, we have recognized this “apparent ten- sion” in our approach to consideration of breach claims de- spite appeal waivers, United States v. Haslam, 833 F.3d 840, 845 (7th Cir. 2016), but have yet to reconcile it. Nor do we today— as discussed below, Edwards’s claim would be barred by his appeal waiver under either of the predominant standards. Re- solving this tension would not alter today’s outcome. In this case, it is plain that the government did not commit a breach. According to Edwards, the government breached the plea agreement when it recommended a 21-month prison sentence and a fine of $25,000. He says the agreement uncon- ditionally obligated the government to recommend no more than a split sentence of five months and a $10,000 fine. The lone exception to this condition, Edwards argues, was if he didn’t receive a zero-point offender reduction; in that case, the government was to recommend a split sentence at the low end of the ultimate Guidelines range. To evaluate a claim of breach, we look to the “plain lan- guage of the plea agreement.” United States v. Quintero, 618 Nos. 24-2355 & 24-2401 15 F.3d 746, 751 (7th Cir. 2010). “[W]e interpret a plea agreement based on the parties’ reasonable expectations and construe ambiguities against the government as the drafter.” United States v. Munoz, 718 F.3d 726, 729 (7th Cir. 2013). If the agree- ment is unambiguous, we hold the parties to its literal terms. United States v. Hallahan, 756 F.3d 962, 974 (7th Cir. 2014). Im- portantly, we must “eschew” any interpretation of the agree- ment’s provisions “that make[s] them unreasonable.” Id. We will not presume the contract “to have imposed an absurd” condition on one of the parties. Id. (quotation omitted). The interpretation Edwards advocates for lends itself to- ward absurdity. Read in isolation, the provision of the plea agreement outlining the government’s planned sentencing recommendation could theoretically be thought to bind the government as Edwards contends. But, as with other con- tracts, we must look to the “structure of the plea agreement” to illuminate the proper meaning of its terms. United States v. Bowler, 585 F.2d 851, 854 (7th Cir. 1978). In another provision, the government was given carte blanche to recant its recom- mendation for a reduction based on Edwards’s acceptance of responsibility under U.S.S.G. § 3E1.1. To hold the government to a sentencing recommendation based on Edwards’s antici- pated Guidelines range, regardless of any subsequent con- duct costing him the acceptance of responsibility reduction, would render that provision meaningless. United States v. Schilling, 142 F.3d 388, 395 (7th Cir. 1998) (“A plea agreement, like any contract, should be construed as a whole, so that var- ious provisions of the contract are harmonized and none are rendered meaningless.”) (quotations omitted). Losing the two-level reduction under § 3E1.1 would—and did—auto- matically increase Edwards’s Guidelines range. The govern- ment adjusted its sentencing recommendation accordingly. 16 Nos. 24-2355 & 24-2401

On any reasonable interpretation of the agreement, this was not a breach. Under either Whitlow or the two-step process, then, Ed- wards would be unable to obtain appellate review of his breach claim. As with his other claims, dismissal is required. DISMISSED