United States v. McKay: Preserved Objection Allows New Appellate Arguments; Vague “Third-Party Risk” Condition Vacated

1. Introduction

In United States v. Dennis McKay (7th Cir. May 20, 2026), the Seventh Circuit addressed two recurring supervised-release disputes: (1) what is required to preserve appellate review of a supervised-release condition when the defendant did not object in writing before sentencing, and (2) whether the standard “third-party risk” notification condition—allowing a probation officer to require disclosure of an undefined “risk” to unspecified third parties— is impermissibly vague.

McKay pleaded guilty to three counts of Hobbs Act robbery, 18 U.S.C. § 1951(a), and one count of discharging a firearm during a crime of violence, 18 U.S.C. § 924(c)(1)(A)(iii). The Presentence Investigation Report recommended Special Condition 13, authorizing a probation officer to compel McKay to notify third parties of a “risk” the officer determines he poses. McKay did not object to that condition in his sentencing memorandum (though he objected to other conditions). At sentencing, however, when the district judge specifically asked counsel to address the “third-party risk” concern, defense counsel stated the condition was unwarranted because there was “no consistent threat of violence towards others.”

On appeal, McKay challenged Special Condition 13 on vagueness, First Amendment, and non-delegation grounds. The government argued waiver: that McKay’s failure to object earlier, and his failure to articulate the specific legal theories at sentencing, foreclosed review.

2. Summary of the Opinion

The Seventh Circuit held that McKay did not waive his challenge. His on-the-record statement that the condition was “unwarranted,” made in response to the district court’s direct inquiry, was an adequate objection. Relying on Yee v. City of Escondido, 503 U.S. 519 (1992) and Seventh Circuit authority, the court further held that once a claim is preserved, a party may raise new arguments on appeal supporting that preserved claim, so long as the appellate theories do not depend on new facts or evidentiary development.

Reaching the merits under de novo review, the court vacated Special Condition 13 as vague under established circuit precedent addressing nearly identical “risk notification” language, and remanded for reconsideration and clarification. The panel also directed the Clerk to distribute the opinion to each Chief Probation Officer in the circuit, urging probation offices to draft such conditions “in concrete terms.”

3. Analysis

A. Precedents Cited

1) Preservation, waiver/forfeiture, and the “claim vs. argument” distinction

  • Fed. R. Crim. P. 51(b) (quoted for the baseline rule): a party preserves an issue by timely informing the court of the objection and its grounds.
  • United States v. Hunt, 930 F.3d 921 (7th Cir. 2019): provides the core definition—waiver is an intentional relinquishment of a known right.
  • United States v. Butler, 777 F.3d 382 (7th Cir. 2015): cited for the criminal-case inclination to construe waiver principles “liberally in favor of the defendant,” emphasizing careful, fact-specific application.
  • United States v. Flores, 929 F.3d 443 (7th Cir. 2019): the central Seventh Circuit framework for when failure to object to supervised-release conditions becomes waiver. In Flores, advance notice plus selective written objections, silence at sentencing, and affirmative waiver of explanation combined to show a “deliberate and informed decision” not to object.
    McKay distinguishes Flores on a pivotal fact: when asked directly about Special Condition 13, McKay objected on the record, and the district court did not demand further specification.
  • Yee v. City of Escondido, 503 U.S. 519 (1992): supplies the opinion’s key doctrinal move. The Supreme Court held that “[o]nce a federal claim is properly presented, a party can make any argument in support of that claim.” The Seventh Circuit imports this distinction into sentencing-condition litigation: preserve the challenge, and additional appellate legal theories may follow.
  • Lawson v. Sun Microsystems, Inc., 791 F.3d 754 (7th Cir. 2015), United States v. Otradovec, 72 F.4th 794 (7th Cir. 2023), United States v. Billups, 536 F.3d 574 (7th Cir. 2008), and Bew v. City of Chicago, 252 F.3d 891 (7th Cir. 2001): collectively stand for the proposition that “no rule prohibits appellate amplification of a properly preserved issue.”
    In particular, United States v. Billups, 536 F.3d 574 (7th Cir. 2008) is used as an analogy: a defendant preserved the claim (prior conviction not a crime of violence) but advanced a new statutory-definition-based twist on appeal; the court treated it as permissible “additional authority,” not forfeiture.
  • United States v. Anderson, 948 F.3d 910 (7th Cir. 2020) and United States v. Tjader, 927 F.3d 483 (7th Cir. 2019): the government relied on these as examples where new appellate grounds were treated as waived. McKay narrows them, explaining they are best understood through Flores—cases featuring indicia of strategic silence or intentional forgoing of objections—rather than as rejections of Yee’s claim/argument distinction.
  • Arnold v. United Airlines, Inc., 142 F.4th 460 (7th Cir. 2025), Packer v. Trustees of Indiana Univ. Sch. of Med., 800 F.3d 843 (7th Cir. 2015), and Puffer v. Allstate Insurance Co., 675 F.3d 709 (7th Cir. 2012): cited as counterexamples—waiver can apply when the new appellate theory turns on new factual/evidentiary assertions that should have been tested in the district court first.
    The panel uses these to draw a boundary: Yee does not license new fact-bound theories; it supports new legal arguments on a preserved claim.

2) Standard of review and vagueness doctrine

  • United States v. Russell, 140 F.4th 430 (7th Cir. 2025) and United States v. Sandidge, 863 F.3d 755 (7th Cir. 2017): cited for the de novo standard of review once the condition’s validity is properly before the court.
  • United States v. Shannon, 851 F.3d 740 (7th Cir. 2017): provides the operative vagueness test for supervised release conditions—whether a person of reasonable intelligence has sufficient notice of what is required—and highlights the “principal concern” of unknowingly running afoul of a legal requirement.
  • A line of Seventh Circuit cases invalidating nearly identical “risk notification” conditions as vague: United States v. Thompson, 777 F.3d 368 (7th Cir. 2015); United States v. Kappes, 782 F.3d 828 (7th Cir. 2015); United States v. Guidry, 817 F.3d 997 (7th Cir. 2016); United States v. Bickart, 825 F.3d 832 (7th Cir. 2016); United States v. Canfield, 893 F.3d 491 (7th Cir. 2018); United States v. Greco, 938 F.3d 891 (7th Cir. 2019); and again Russell, 140 F.4th 430 (7th Cir. 2025).
    These precedents collectively emphasize that undefined terms like “risk,” coupled with open-ended identification of who must be notified, give insufficient guidance and risk arbitrary enforcement.

B. Legal Reasoning

1) Why McKay’s objection was sufficient

The court treated McKay’s oral objection—made when the judge specifically invited justification—as a timely objection under Rule 51(b). Unlike Flores, the record did not show a “deliberate and informed decision” to forgo the challenge; rather, the defense objected at the very moment the condition was being vetted and adopted. The district judge’s own remarks reinforced this understanding: she noted the condition “wasn’t objected to initially” but she wanted to hear from defense counsel after hearing from Probation and the government.

2) Why new legal theories (vagueness, First Amendment, non-delegation) were allowed on appeal

The panel’s doctrinal clarification is that appellate courts should distinguish between (a) preserving a claim (here, “Special Condition 13 is unwarranted/invalid”) and (b) the specific arguments that can support that preserved claim. Under Yee v. City of Escondido and Seventh Circuit cases such as Lawson, Otradovec, Billups, and Bew, a defendant may add new legal reasoning on appeal that “supports a claim made before the district court” and “grow[s] out of the facts presented.”

The limiting principle is practical and institutional: if a new appellate theory depends on new facts, evidence, or a trial-level record that was never developed, waiver/forfeiture concerns become stronger (as illustrated by Arnold, Packer, and Puffer). McKay’s appellate theories were “pure questions of law” about the text of the condition and constitutional doctrine; they did not require additional factfinding.

3) Why Special Condition 13 was vacated

The opinion’s merits analysis is intentionally streamlined because existing circuit law already condemns materially identical language. Special Condition 13 allowed a probation officer to decide whether McKay “pose[s] a risk” and then require notification of another “person” (including broad community categories), without defining “risk” or identifying the relevant persons or categories with sufficient precision. Under United States v. Shannon, a supervised-release condition must give fair notice so the defendant does not unknowingly violate it; under the repeated holdings in United States v. Thompson, United States v. Kappes, United States v. Guidry, United States v. Bickart, United States v. Canfield, United States v. Greco, and Russell, the undefined “risk” notification condition fails that requirement.

The court therefore vacated the condition and remanded for the district court to “define with greater specificity the identities or categories of individuals and the types of risks” to which any notification requirement would apply (quoting United States v. Canfield).

C. Impact

  • Preservation doctrine in supervised-release litigation: The decision strengthens defendants’ ability to obtain merits review when they make a clear, on-the-record objection at sentencing—even if they did not object in writing beforehand—and clarifies that additional appellate legal theories can be permissible “amplifications” of a preserved claim. Practically, counsel who object generally (“unwarranted”) may still litigate constitutional and doctrinal objections on appeal, so long as the claim itself was preserved and the theories are legal rather than fact-dependent.
  • Drafting and administration of supervised-release conditions: The panel’s directive to circulate the opinion to Chief Probation Officers signals an institutional push to end reliance on boilerplate “risk” notification language. Expect more tailored PSR recommendations specifying (i) what “risk” means (e.g., risk of financial fraud, risk of contact with minors), and (ii) who must be notified (e.g., specific categories like employers with access to client funds), thereby reducing vagueness and delegation concerns.
  • Future constitutional challenges: Although the court resolved the case on vagueness grounds, its willingness to allow new appellate arguments once a claim is preserved will likely increase appellate consideration of First Amendment compelled-speech and non-delegation objections to supervised-release conditions—at least where the theories are legal and do not require new evidence.

4. Complex Concepts Simplified

  • Waiver vs. forfeiture: Waiver is an intentional giving up of a right (you chose not to raise it). Forfeiture is a failure to raise it in time (you missed it). Waiver is typically more fatal to appellate review. McKay treats the record as lacking the intentionality required for waiver.
  • “Claim” vs. “argument” (from Yee): A claim is what you are asking the court to decide (e.g., “this condition is invalid”). An argument is a reason why you should win (e.g., “it’s vague,” “it delegates too much,” “it compels speech”). Preserve the claim, and you may be able to refine or add legal arguments on appeal.
  • Vagueness: A rule is unconstitutionally vague if ordinary people cannot tell what it requires, creating a risk of accidental violation or arbitrary enforcement. Here, “pose a risk” and who must be told were left too open-ended.
  • Non-delegation (in supervised release): Courts may not hand probation officers unfettered power to define the scope of a defendant’s obligations. Although not reached, the concern is that an undefined “risk” standard can effectively allow probation to set the rule rather than enforce a court-defined rule.
  • First Amendment compelled speech: A condition requiring a defendant to tell others about alleged “risk” can raise compelled-speech issues. The court did not decide this point because vagueness was sufficient to vacate.

5. Conclusion

United States v. McKay does two significant things. First, it clarifies preservation: when a defendant objects on the record that a supervised-release condition is unwarranted, the claim is preserved, and under Yee v. City of Escondido the defendant may press additional legal theories on appeal that support that preserved claim—especially where the theories are purely legal. Second, it continues the Seventh Circuit’s firm line against the boilerplate “third-party risk” notification condition, vacating Special Condition 13 as impermissibly vague and remanding for concrete tailoring. The opinion’s distribution order underscores that this is not merely a case-specific correction but a circuit-wide directive to draft clearer, more bounded supervised-release conditions.