Theodore Wiggins v. United States, 900 F.3d 618

Wiggins was charged with conspiracy to distribute cocaine (Count 1) and distribution of cocaine base (Count 8); enhancements based on two prior drug felonies exposed him to a mandatory life sentence on Count 1.
The government made two pretrial plea offers: (1) a binding 15-year sentence; (2) a plea to a lesser offense carrying 10 years to life with the government limited to arguing within the Sentencing Guidelines. Wiggins rejected both.
At trial a jury convicted Wiggins; the district court applied the enhancements and imposed a mandatory life sentence on Count 1 and 30 years on Count 8 (concurrent). This Court affirmed on direct appeal.
Wiggins filed a timely 28 U.S.C. § 2255 claim alleging counsel ineffectively failed to advise him that conviction would carry a mandatory life term; counsel had given Wiggins incorrect, lower exposure estimates.
The district court granted relief, crediting Wiggins’s claim of prejudice but found it not credible that he would have accepted the binding 15-year offer; it ordered the government to reoffer only the second plea (10 years to life). Wiggins pleaded to a lesser offense and was resentenced to 20 years.
Wiggins appealed the district court’s remedy (challenging that only one plea was reinstated); the government moved to dismiss as untimely. The Court held the appeal timely and affirmed the district court’s remedy.

Issue	Plaintiff's Argument	Defendant's Argument	Held
Was Wiggins’s appeal timely?	Appeal from the § 2255 remedy was timely after resentencing.	Appeal was untimely because it was not filed within 60 days of the § 2255 order or plea.	Timely: § 2255 order wasn’t final until resentencing; appeal filed within 60 days after resentencing.
Did Wiggins waive or moot his right to challenge the district court’s remedy by pleading the reinstated plea?	No—he preserved the right; the § 2255 order wasn’t final until resentencing.	By accepting the plea, Wiggins lost any claim about the § 2255 remedy; claim is moot/waived.	No waiver/mootness: finality occurs at resentencing, so challenge remains live.
Was the district court’s remedy (reoffering only one plea) an appropriate remedy for counsel’s ineffective assistance?	Wiggins argued both original plea offers should have been reoffered because he would have accepted either if properly advised.	Government supported district court’s discretion to tailor remedy and offered only one plea reoffer was appropriate.	Affirmed: district court did not clearly err; credibility findings supported that Wiggins would not have accepted the binding 15-year offer.
Standard of review for remedy and factual findings?	N/A—party positions implicit.	N/A.	Legal conclusions reviewed de novo; factual/credibility findings reviewed for clear error; no clear error here.

Andrews v. United States, 373 U.S. 334 (finality of § 2255 orders depends on resentencing)
Lafler v. Cooper, 566 U.S. 156 (remedy for deficient plea advice may include requiring prosecution to reoffer plea)
United States v. Stitt, 459 F.3d 483 (district § 2255 vacatur not final until resentencing)
United States v. Olano, 507 U.S. 725 (definition of waiver)
United States v. Evans, 690 F.3d 940 (mootness where parties lack a personal stake)