United States v. Dennis McKay

── United States v. Dennis McKay ── Court: Court of Appeals for the Seventh Circuit Date: May 20, 2026 Category: General In the United States Court of Appeals For the Seventh Circuit ____________________ No. 24-2015 UNITED STATES OF AMERICA, Plaintiff-Appellee, v. DENNIS MCKAY, Defendant-Appellant. ____________________ Appeal from the United States District Court for the Northern District of Illinois, Eastern Division. No. 1:17-cr-00729-1 — Andrea R. Wood, Judge. ____________________ ARGUED JANUARY 30, 2026 — DECIDED MAY 20, 2026 ____________________ Before BRENNAN, Chief Judge, and ROVNER and HAMILTON, Circuit Judges. HAMILTON, Circuit Judge. Defendant-appellant Dennis McKay challenges one condition of his future supervised release. Before and during his sentencing hearing, defendant did not affirmatively object to that condition. When the district court specifically asked the parties to justify the condition, however, defense counsel said it was unwarranted. The government argues that defendant has waived his legal 2 No. 24-2015 arguments on appeal by not raising them before the district court. We conclude that defendant lodged an adequate objection to the condition by saying on the record that it was unwarranted. And Yee v. City of Escondido, 503 U.S. 519 (1992), and our own precedents on preserving sentencing issues for appeal allow a party to make new arguments on appeal that support a properly preserved challenge. Defendant’s legal challenges to the supervised release condition at issue are not waived. The challenged condition would require defendant to notify third parties of a “risk” he poses as determined by a probation officer. In other cases, this court has vacated that same condition as impermissibly vague. Both parties agree that if we reach the merits of defendant’s argument, remand is appropriate. We therefore vacate the challenged supervised release condition and remand the case to the district court for further proceedings. I. Factual & Procedural Background In June 2023, defendant Dennis McKay pled guilty to several charges: three counts of Hobbs Act robbery affecting commerce in violation of 18 U.S.C. § 1951(a) and one count of discharging a firearm in connection to a crime of violence in violation of 18 U.S.C. § 924(c)(1)(A)(iii). In his plea agreement, defendant also stipulated to having commi ed four additional robberies and to possessing a firearm as a felon. Before defendant’s sentencing hearing, the U.S. Probation Office for the Northern District of Illinois prepared a Presentence Investigation Report. The PSR recommended the following condition, Special Condition 13, of supervised release: No. 24-2015 3 If the probation officer determines that you pose a risk to another person (including an organization or members of the community), the probation officer may require you to tell the person about the risk, and you must comply with that instruction. Such notification could include advising the person about your record of arrests and convictions and substance use. The probation officer may contact the person and confirm that you have told the person about the risk. As justifications for the recommended conditions, the PSR cited compliance with statutory factors of deterrence, protection of the public, providing the defendant with effective correctional treatment, and the probation officer’s duty to stay informed of defendant’s conduct and compliance. Defendant McKay then filed his sentencing memorandum, which contained wri en objections to two other conditions of supervised release but no objection to Special Condition 13. At defendant’s sentencing hearing, the district judge confirmed with his co