United States v. Jeremy F. Viles, 668 F. App'x 371

Defendant Jeremy F. Viles pleaded guilty in S.D.N.Y. to mail fraud pursuant to a plea agreement stipulating a Guidelines range of 27–33 months.
The plea agreement contained an appeal waiver but expressly preserved claims of ineffective assistance of counsel.
Viles contends counsel misadvised him about the sentencing exposure by including three prior convictions in the criminal-history calculation when those convictions, he argues, should have been treated as part of the instant offense.
He was sentenced to the bottom of the stipulated range (27 months).
The Second Circuit accepted direct-review consideration of the ineffective-assistance claim because Viles had new appellate counsel and the record was fully developed, and reviewed the claim de novo.
The panel concluded Viles failed to show prejudice from any alleged deficient performance and affirmed the district court judgment.

Issue	Plaintiff's Argument	Defendant's Argument	Held
Whether counsel was ineffective in advising Viles to accept the plea based on a stipulated Guidelines range that relied in part on prior convictions Viles says were part of the offense	Counsel misled Viles about sentencing exposure by treating prior convictions as separate, causing an uninformed plea; Viles would have gone to trial but for the advice	Counsel’s advice did not prejudice Viles: plea reflected known risks, included benefits (two-level reduction and stipulated lower loss amount), and the court was not bound by the stipulated range	Court held Viles failed to show prejudice under Strickland/Hill; the record shows no reasonable probability he would have declined the plea and gone to trial, so affirming conviction

United States v. Morris, 350 F.3d 32 (2d Cir. 2003) (standards for addressing ineffective-assistance claims on direct appeal)
United States v. Yauri, 559 F.3d 130 (2d Cir. 2009) (when direct-review consideration of ineffectiveness claims is appropriate)
United States v. Williams, 205 F.3d 23 (2d Cir. 2000) (framework for when appellate courts may hear ineffectiveness claims)
United States v. Guang, 511 F.3d 110 (2d Cir. 2007) (de novo review of ineffective-assistance claims on direct appeal)
United States v. Arteca, 411 F.3d 315 (2d Cir. 2005) (plea-negotiation ineffectiveness and prejudice inquiry)
Hill v. Lockhart, 474 U.S. 52 (1985) (prejudice standard when ineffective assistance affects guilty plea decision)
Ventura v. Meachum, 957 F.2d 1048 (2d Cir. 1992) (whether inaccurate sentencing information would have changed plea decision)
Strickland v. Washington, 466 U.S. 668 (1984) (deficient performance and prejudice test for ineffective assistance)
United States v. Gordon, 156 F.3d 376 (2d Cir. 1998) (disparity between advised and actual exposure as objective evidence of prejudice)
United States v. Khedr, 343 F.3d 96 (2d Cir. 2003) (direct-review standards and exceptions for ineffectiveness claims)