Long v. United States, 847 F.3d 916

Background

Police found Willie Long asleep at the wheel in a McDonald's drive-through; officer smelled marijuana after Long opened the door and observed a gun on the floorboard. Inventory search recovered marijuana, ecstasy, scales, baggies, and phones.
Long, with appointed counsel H. Jay Stevens, pled guilty to being a felon in possession of a firearm; plea agreement included an express waiver of appeal and collateral attack.
After the PSR assessed a 4-level enhancement for possession of a firearm in connection with another felony (marijuana), Long sought to withdraw his plea; Stevens had declined to file a suppression motion and later withdrew; new counsel Michael Rehak advised against withdrawal and Long proceeded to sentencing and received 51 months.
Long filed a timely pro se 28 U.S.C. § 2255 motion claiming Stevens provided ineffective assistance by failing to file a suppression motion, failing to investigate, and not fully explaining the waiver; district court denied relief without an evidentiary hearing based on the waiver.
On appeal, Long argued the district court erred by refusing an evidentiary hearing; he asserted he could circumvent the collateral-attack waiver because counsel was ineffective in negotiating the plea agreement.
The Seventh Circuit affirmed, holding Long’s allegations were vague/conclusory, failed to show a meritorious suppression claim or what additional investigation would have produced, and failed to prove prejudice necessary under Strickland.

Issues

Issue	Plaintiff's Argument	Defendant's Argument	Held
Whether a collateral-attack waiver bars Long's § 2255 ineffective-assistance claim	Long: waiver can be bypassed because counsel was ineffective in negotiating the plea (failed to move to suppress or investigate)	Government: waiver is valid; Long admitted facts at plea and sentencing; allegations are conclusory and do not show counsel's negotiation was ineffective	Waiver bars relief because Long alleged no facts that, if true, would entitle him to relief; claim is vague and conclusory
Whether Stevens performed deficiently by declining to move to suppress	Long: Stevens ignored Fourth Amendment issues and failed to file suppression motion	Government: arrest report and plea admissions show caretaking stop and probable cause after smell of marijuana; suppression would have failed	No deficient performance shown — motion to suppress lacked merit under facts available to counsel
Whether Stevens failed to investigate adequately	Long: counsel should have obtained camera footage and interviewed witnesses	Government: Long fails to allege what investigation would have produced; counsel need only a reasonable investigation	Allegations too vague; petitioner must state what investigation would have uncovered; Long did not meet that burden
Whether Long suffered Strickland prejudice (would not have pled guilty)	Long: would have gone to trial but for counsel’s errors	Government: Long later declined to withdraw plea after new counsel advised against it; objective evidence shows he chose to keep plea	No prejudice shown; objective record (choice not to withdraw plea) rebuts claim he would have insisted on trial

Key Cases Cited

Hurlow v. United States, 726 F.3d 958 (7th Cir. 2013) (waivers cannot be invoked against claims that counsel was ineffective in negotiating the plea)
Strickland v. Washington, 466 U.S. 668 (1984) (two-part test for ineffective assistance: deficient performance and prejudice)
Cieslowski v. United States, 410 F.3d 353 (7th Cir. 2005) (when alleging failure to move to suppress, petitioner must show the motion was meritorious)
Martin v. United States, 789 F.3d 703 (7th Cir. 2015) (district court need not hold evidentiary hearing where allegations are vague, conclusory, or contradicted by the record)
Mosby v. United States, 541 F.3d 764 (7th Cir. 2008) (probable cause based on smell of marijuana justified vehicle search)