United States v. Sakellarion, 2011 U.S. App. LEXIS 17213

Sakellarion cooperated with investigators in a cocaine distribution scheme and entered a Rule 11(c)(1)(C) plea agreement that required the court to sentence about 50% below the low end of the guidelines or statutory minimum, whichever greater, based on government motion for a downward departure.
The district court accepted the plea, including a waiver of Sakellarion's appellate rights, and imposed a sentence pursuant to the agreement.
A key dispute centered on Sakellarion’s criminal history: the PSR counted a 2000 battery conviction, which Sakellarion argued did not qualify for criminal history points.
Hearing after hearing focused on whether the 2000 conviction should count and whether Sakellarion could be eligible for the safety-valve reduction, with the government later offering to renegotiate the sentence.
Due to repeated positive drug tests (opiate and morphine) and arguments over testing reliability, the government declined to amend the plea, and Sakellarion was sentenced under the original agreement to 60 months.
Sakellarion appealed, but the government moved to enforce the appellate waiver contained in the plea agreement.

Issue	Plaintiff's Argument	Defendant's Argument	Held
Is the appellate waiver enforceable to bar Sakellarion's appeal?	Waiver is valid, knowing and voluntary, and covers appellate challenges.	Bad-faith government conduct in not amending the agreement undermines the waiver.	Yes; appellate waiver enforceable and appeal must be dismissed.
Does a government breach of a supplemental agreement void the appellate waiver?	Waiver stands despite any breach of the supplemental agreement.	Breach nullifies the waiver and allows appeal on bad-faith grounds.	No; waiver remains enforceable and appeal is still dismissal.
If the guilty plea were voided, could Sakellarion obtain meaningful appellate review of the bad-faith claim?	Not directly; appellate review would be limited or unavailable given the waiver and the government's discretion.	There should be a pathway to review the government’s alleged bad faith.	Even if the plea were set aside, the waiver and discretionary review limitations would still foreclose meaningful appellate relief.

United States v. Sines, 303 F.3d 793 (7th Cir. 2002) (voluntary appellate waiver valid and enforceable)
United States v. Woods, 581 F.3d 531 (7th Cir. 2009) (enforcement of appellate waivers when terms are clear)
United States v. Hare, 269 F.3d 859 (7th Cir. 2001) (appellate waiver enforcement framework)
United States v. Aslan, 644 F.3d 526 (7th Cir. 2011) (express and unambiguous waivers require knowing and voluntary entry)
United States v. Mason, 343 F.3d 893 (7th Cir. 2003) (waiver falls with the bargain; unenforceability limited to unenforceable agreements)
United States v. Whitlow, 287 F.3d 638 (7th Cir. 2002) (a mere claim of breach does not void an appellate waiver)
United States v. Nunez, 546 F.3d 450 (7th Cir. 2008) (waivers stay intact notwithstanding related rulings about the plea)
United States v. Wenger, 58 F.3d 280 (7th Cir. 1995) (considerations of prosecutorial discretion and plea bargains)
United States v. Quintero, 618 F.3d 746 (7th Cir. 2010) (challenge to government breaches and remedies within pleas)
Wade v. United States, 504 U.S. 181 (1992) (limits on review of decisions denying substantial-assistance motions)
Mabry v. Johnson, 467 U.S. 504 (1984) (plea challenges under Due Process when not fairly apprised of consequences)
Puckett v. United States, 556 U.S. 129 (2009) (limited ability to challenge plea promises post-Puckett)