United States v. Young, 908 F.3d 241

Dean Young, a veteran, pleaded guilty to one count of wire fraud for obtaining inflated VA benefits by exaggerating service-related back injuries and PTSD.
The plea agreement and parties stipulated a loss/restitution amount of $201,521.41, representing VA overpayments attributable to his back injury (PTSD-related benefits were excluded as part of the compromise).
The stipulated loss figure was used to calculate the Sentencing Guidelines range; the district court sentenced Young to 21 months (midrange) and ordered restitution of $201,521.41.
On appeal Young challenged the loss/restitution calculation, arguing a lower loss ($126,630.41) should apply based on an earlier start date for fraudulent claims, which would reduce his guideline calculation by two levels.
Young did not object in district court to the stipulated loss amount; the parties negotiated the split between back-injury and PTSD tracks to avoid trial and Young actively participated in the compromise.
The Seventh Circuit affirmed, holding Young waived appellate review of the stipulated loss because he knowingly and intentionally relinquished the right to litigate the loss amount as part of a strategic plea compromise.

Issue	Plaintiff's Argument	Defendant's Argument	Held
Whether Young may challenge the loss amount used for Guidelines and restitution on appeal	Government: the agreed $201,521.41 loss governs sentencing and restitution	Young: the appropriate loss should be $126,630.41 based on an earlier start to fraudulent claims	Affirmed: Young waived the challenge by stipulating to the $201,521.41 loss in the plea and at sentencing
Whether the failure to object in district court merits plain-error review	Government: no plain-error review because issue was waived, not forfeited	Young: requests plain-error review to alter loss and guideline range	Denied: appellate review unavailable because the error was intentionally waived
Whether a plea-stipulated allocation of loss extinguishes later challenges to conduct and loss	Government: plea stipulation and PSR adoption preclude relitigation	Young: seeks relitigation of when fraud began and proper loss allocation	Held: stipulation and adoption in PSR, sentencing memo, and hearing constitute waiver of later challenge
Whether counsel was deficient for not objecting to the stipulated loss	Government: counsel reasonably pursued strategic compromise to exclude PTSD losses and avoid trial	Young: implies counsel should have preserved the alternative loss theory	Held: counsel was not deficient; strategic waiver was reasonable and intentional

Newman v. United States, 148 F.3d 871 (7th Cir.) (stipulation in plea can waive later challenge to conduct and loss)
Sunmola v. United States, 887 F.3d 830 (7th Cir.) (restitution calculation reviewed for abuse of discretion)
Brodie v. United States, 507 F.3d 527 (7th Cir.) (distinguishes waiver from forfeiture; waiver extinguishes appellate review)
Garcia v. United States, 580 F.3d 528 (7th Cir.) (knowing strategic decision to forgo argument indicates waiver)
Allen v. United States, 529 F.3d 390 (7th Cir.) (counsel not deficient when tactical choice leads to waiver)
Fuentes v. United States, 858 F.3d 1119 (7th Cir.) (objecting to parts of PSR but not guideline range reflects intentional relinquishment)
Flores-Sandoval v. United States, 94 F.3d 346 (7th Cir.) (stipulating to plea conduct waives subsequent challenges to that conduct)