995 F.3d 591
7th Cir.2021Background:
- Bridgewater pleaded guilty in March 2019 to one count of soliciting an obscene visual depiction of a minor pursuant to a plea agreement that included a broad waiver: he waived the right to "seek modification of or contest any aspect of the conviction or sentence" in any type of proceeding under federal law.
- The plea agreement was entered after the First Step Act (2018) created a statutory right for prisoners to petition courts directly for compassionate release under 18 U.S.C. § 3582(c)(1)(A) (after giving BOP 30 days to act).
- At sentencing the district court imposed an above-guideline 78-month term; the sentence was later affirmed on direct appeal.
- In April 2020 Bridgewater moved for compassionate release (time served) based on medical vulnerability to COVID-19; the district court denied the motion first because of the plea-waiver and alternatively on the merits under § 3553(a).
- The Seventh Circuit dismissed Bridgewater’s appeal, holding the waiver encompassed compassionate-release motions, was knowing and voluntary, and was not unenforceable on public-policy or unconscionability grounds.
Issues:
| Issue | Plaintiff's Argument | Defendant's Argument | Held |
|---|---|---|---|
| Whether a plea waiver barring challenges to the conviction or sentence covers compassionate-release motions under § 3582(c)(1)(A) | Bridgewater: the waiver does not cover compassionate release (or is ambiguous) | Government: waiver expressly covers "modification" of the sentence in any proceeding, so it includes § 3582(c) motions | Waiver includes compassionate-release motions because those are sentence modifications and the waiver language is broad and unambiguous |
| Whether the waiver was knowing and voluntary given COVID-19 and changed circumstances | Bridgewater: pandemic makes waiver involuntary or uninformed | Government: waiver was entered after Rule 11 colloquy and after First Step Act existed; plea colloquy shows understanding | Waiver was knowing and voluntary; Rule 11 compliance and counsel discussion suffice; later changed circumstances do not invalidate plea bargains |
| Whether public policy or unconscionability make compassionate-release waivers unenforceable | Bridgewater: waivers undermine Congress’s intent in the First Step Act and are unconscionable because they bar relief in unforeseeable, humane circumstances | Government: statutory rights are presumptively waivable; waivers advance legitimate interests in finality and prosecutorial efficiency; BOP route remains available | Waivers are not per se unenforceable; public-policy and unconscionability arguments fail where waiver is knowing, voluntary, and was part of an approved plea that yielded substantial benefits |
| Whether constitutional/due-process limits bar enforcement of such waivers | Bridgewater: due process may limit waiving newly salient post-sentencing rights | Government: constitutional limits apply only in narrower scenarios (ineffective counsel, racial sentence, exceeding statutory max) not present here | Due-process constraints do not prevent enforcement; waiver does not undermine plea voluntariness or implicate the listed constitutional exceptions |
Key Cases Cited:
- Mezzanatto, 513 U.S. 196 (1995) (statutory rights are presumptively waivable in plea agreements absent Congressional intent to the contrary)
- Town of Newton v. Rumery, 480 U.S. 386 (1987) (release-dismissal agreements generally enforceable; public-interest/finality and efficiency weigh in favor of enforcement)
- Pepper v. United States, 562 U.S. 476 (2011) (resentencing may permit broad inquiry into post-sentencing changes for § 3553(a) purposes)
- Helling v. McKinney, 509 U.S. 25 (1993) (courts can enjoin prison conditions that pose a substantial risk to inmate health)
- United States v. McGraw, 571 F.3d 624 (7th Cir. 2009) (appellate waivers can cover unforeseen future developments and remain enforceable)
- United States v. Woods, 581 F.3d 531 (7th Cir. 2009) (waiver interpretation governed by parties’ reasonable expectations and ambiguities construed against government)
- United States v. Jones, 381 F.3d 615 (7th Cir. 2004) (Rule 11 plea colloquy ensures voluntariness of plea and attendant waivers)