Jerry L. Vinyard v. United States, 804 F.3d 1218

Jerry Vinyard pled guilty to conspiracy to manufacture and distribute methamphetamine; plea and stipulation admitted involvement and >500 grams.
At sentencing Judge Gilbert raised concerns after Vinyard briefly questioned the presentence report; Vinyard consulted counsel, then declined to contest relevant conduct and was sentenced to the 240-month mandatory minimum.
Judge Gilbert sua sponte vacated the plea and sentence, released Vinyard on bail, then revoked that release and vacated the plea again; this prompted the government to seek and obtain a mandamus from the Seventh Circuit directing reinstatement of the May 3, 2007 judgment.
On remand the case was assigned to Judge Stiehl, who denied Vinyard’s motion to withdraw his plea as outside the limited mandamus remand and entered judgment; Vinyard could appeal or pursue §2255 relief.
New counsel (Gross) advised Vinyard to pursue a §2255 collateral attack rather than a direct appeal, reasoning the record was inadequate for direct appeal and ineffective-assistance claims required collateral development; Vinyard followed that advice and missed the direct appeal window.
Vinyard filed a §2255 alleging Gross was ineffective for advising against a direct appeal; the district court denied relief, finding Gross’s advice strategic and not objectively unreasonable and that Vinyard showed no Strickland prejudice.

Issue	Plaintiff's Argument	Defendant's Argument	Held
Whether counsel was constitutionally ineffective for advising Vinyard to forgo a direct appeal and pursue §2255	Gross’s advice was legally erroneous because voluntariness of a guilty plea generally must be raised on direct appeal first (Bousley); advising collateral-only caused procedural default	Gross made a strategic, reasonable decision: the trial record offered no basis to attack the plea on direct appeal and §2255 was the proper vehicle for claims requiring extra-record development	Counsel’s advice was not deficient; proceeding by §2255 was reasonable and not the sort of abandonment that triggers a Flores-Ortega prejudice presumption
Whether Vinyard established prejudice under Strickland	Because Gross’s advice foreclosed appeal, Vinyard was presumptively prejudiced and should be restored the right to direct appeal	No presumption applies because Vinyard knowingly agreed not to appeal; he wasn’t abandoned and must show a reasonable probability of a different outcome	No prejudice shown; Flores-Ortega presumption does not apply where defendant and counsel discussed and agreed on strategy

Strickland v. Washington, 466 U.S. 668 (ineffective assistance two-prong test: deficient performance + prejudice)
Bousley v. United States, 523 U.S. 614 (voluntariness of guilty plea ordinarily must be challenged on direct review unless claim depends on facts outside the record)
Massaro v. United States, 538 U.S. 500 (ineffective-assistance claims generally may be raised in collateral proceedings without being presented on direct appeal)
Roe v. Flores-Ortega, 528 U.S. 470 (counsel's failure to file requested appeal presumes prejudice; consultation requirement for appeals)
Evitts v. Lucey, 469 U.S. 387 (right to effective assistance on first appeal as of right)
United States v. Vinyard, 539 F.3d 589 (7th Cir. 2008) (mandamus directing reinstatement of original plea and sentence)