In the

United States Court of Appeals 

For the Seventh Circuit ____________________ 

No. 20-2413 

UNITED STATES OF AMERICA, 

Plaintiff-Appellee, 

v.

DAVID A. BRIDGEWATER, 

Defendant-Appellant. 

____________________ 

Appeal from the United States District Court for the

Southern District of Illinois. 

No. 4:19-cr-40012-SMY-1 — Staci M. Yandle, Judge. 

____________________ 

ARGUED JANUARY 15, 2021 — DECIDED APRIL 28, 2021 

____________________ 

Before SYKES, Chief Judge, and WOOD and HAMILTON, Circuit Judges. 

HAMILTON, Circuit Judge. In his plea agreement, defendant 

David Bridgewater waived the right to seek any modification 

of his sentence. Nonetheless, in light of the current pandemic, 

Bridgewater filed in the district court a motion for compassionate release under the First Step Act of 2018, as codified in 

18 U.S.C. § 3582(c)(1)(A). He seeks release based on medical 

conditions that he says make him vulnerable to serious illness
2 No. 20-2413 

or death from the spread of COVID-19 in prison. Bridgewater 

argues that his plea waiver does not bar this motion because 

the waiver does not cover compassionate release, was not voluntary, and, in any event, should be unenforceable under contract-law principles of public policy and unconscionability. 

The district court rejected these arguments. We dismiss the 

appeal. Bridgewater’s knowing and voluntary waiver of the 

right to seek compassionate release under the First Step Act is 

enforceable.

I. Factual and Procedural Background

On January 30, 2019, Bridgewater was charged with one 

count of attempted enticement of a minor in violation of 18 

U.S.C. § 2422(b) (Count One) and one count of soliciting an 

obscene visual depiction of a minor in violation of 18 U.S.C. 

§ 2252A(a)(3)(B) (Count Two). On March 19, 2019, he pleaded 

guilty to Count Two pursuant to a plea agreement. The government agreed to dismiss Count One, which would have carried a mandatory minimum ten-year sentence, and to recommend a minimum five-year sentence for Count Two. The district court approved the plea agreement on March 19, 2019. 

Most relevant to this appeal, Bridgewater’s plea agreement included the following waiver of his rights to appeal or otherwise challenge his conviction and sentence:

[I]n exchange for the recommendations and 

concessions made by the United States in this 

Plea Agreement, Defendant knowingly and voluntarily waives the right to seek modification of or contest any aspect of the conviction or sentence in any 

type of proceeding, including the manner in 

which the sentence was determined or imposed, 

that could be contested under Title 18 or 28, or 
No. 20-2413 3

under any other provision of federal law, except 

that if the sentence imposed is in excess of the 

Sentencing Guidelines as determined by the 

Court (or any applicable statutory minimum, 

whichever is greater), Defendant reserves the 

right to appeal the substantive unreasonableness of the term of imprisonment. 

Dkt. 32, at 7–8 (emphasis in original). 

At sentencing, the district court chose to impose an aboveguideline sentence of 78 months, plus seven years of supervised release. Bridgewater appealed his sentence, relying on 

the appellate waiver’s exception for an above-guideline sentence. We affirmed his sentence. United States v. Bridgewater, 

950 F.3d 928, 929 (7th Cir. 2020). Bridgewater is currently imprisoned at the Forrest City Federal Correctional Institution 

in Arkansas.

On April 30, 2020, Bridgewater filed a motion for compassionate release under 18 U.S.C. § 3582(c)(1)(A)(i), which allows a district court to reduce a defendant’s sentence for “extraordinary and compelling reasons.” Bridgewater asked the 

district court to release him for time served due to his medical 

conditions, which he says present “extraordinary and compelling” reasons for release because they make him especially 

susceptible to serious illness or death from the COVID-19 outbreak at Forrest City.

Before 2018, only the Bureau of Prisons itself could have 

filed such a motion on Bridgewater’s behalf. In 2018, in response to longstanding criticism over the Bureau’s minimal 

use of compassionate release, Congress enacted § 603(b)(1) of 
4 No. 20-2413 

the First Step Act of 2018 to expand the process to allow defendants to file such motions directly with a district court so 

long as they first give the Bureau 30 days to act on their requests. See Pub. L. 115-391, 132 Stat. 5194, 5239 (Dec. 21, 2018), 

codified at 18 U.S.C. § 3582(c)(1)(A); see also Dep’t of Justice, 

Office of the Inspector General, The Federal Bureau of Prisons’ 

Compassionate Release Program (Apr. 2013), at 11 (concluding 

in 2013 that the Bureau “does not properly manage the compassionate release program, resulting in inmates who may be 

eligible candidates for release not being considered”). Bridgewater invoked this new process to seek compassionate release. 

The district court denied Bridgewater’s motion on two 

separate grounds. The court first concluded that, in his plea 

agreement, Bridgewater voluntarily waived his right to seek 

compassionate release under the First Step Act and that his 

waiver is enforceable. The court then concluded that, even if 

Bridgewater had not waived his right to seek compassionate 

release, his motion would fail on the merits. The court found 

that the sentencing factors under 18 U.S.C. § 3553(a) weighed 

against Bridgewater’s release, even assuming that he faced 

heightened health risks from COVID-19. Judge Yandle explained that reducing Bridgewater’s term of imprisonment 

from six and a half years to less than one year would not reflect the seriousness of his offense, promote respect for law, 

foster specific deterrence, or protect the public from his potential future crimes. Bridgewater appeals the denial of his 

compassionate release motion. We have jurisdiction under 18 

U.S.C. § 3742(a)(1) and 28 U.S.C. § 1291. 
No. 20-2413 5

We dismiss the appeal based on the district court’s first 

reason—waiver. Due to the pandemic, we have recently reviewed denials of many motions seeking compassionate release under the First Step Act.1 We have not yet addressed the 

waiver issue presented in this case. In his plea agreement, 

Bridgewater voluntarily waived “the right to seek modification of or contest any aspect of the conviction or sentence in 

any type of proceeding.” We hold that this waiver included 

Bridgewater’s right to seek compassionate release under the 

First Step Act and that his knowing and voluntary waiver of 

that right in an approved plea agreement is enforceable. We 

dismiss this appeal without reaching the merits of Bridgewater’s motion.

Part II explains why Bridgewater’s waiver included his 

right to seek compassionate release. Part III briefly explains 

why his waiver was knowing and voluntary. Part IV addresses Bridgewater’s unenforceability arguments. After setting the legal landscape in Parts IV-A and IV-B, we explain in 

Part IV-C why Bridgewater’s public policy and unconscionability arguments are not persuasive.

II. Scope of the Waiver 

We review de novo the enforceability of an appellate waiver 

in a plea agreement. United States v. Chapa, 602 F.3d 865, 868 

1 For cases reviewing pandemic-related compassionate release motions 

under the First Step Act, see, e.g., United States v. Sanders, 992 F.3d 583 (7th 

Cir. 2021); United States v. Joiner, 988 F.3d 993 (7th Cir. 2021); United States

v. Williams, 987 F.3d 700 (7th Cir. 2021); United States v. Saunders, 986 F.3d

1076 (7th Cir. 2021); United States v. Sanford, 986 F.3d 779 (7th Cir. 2021);

United States v. Gunn, 980 F.3d 1178 (7th Cir. 2020). We have also recently 

issued numerous non-precedential orders affirming the denial or dismissal of such motions.
6 No. 20-2413 

(7th Cir. 2010). We generally enforce an appellate waiver if its 

terms are express and unambiguous and the record shows 

that it was knowing and voluntary. Id. In determining the 

scope of a waiver, we “interpret the terms of the agreement 

according to the parties’ reasonable expectations and construe 

any ambiguities against the drafter—the government—and in 

favor of the defendant.” United States v. Woods, 581 F.3d 531, 

534 (7th Cir. 2009), overruled on other grounds, United States 

v. Taylor, 778 F.3d 667 (7th Cir. 2015). This approach ensures 

that waivers are not applied loosely in ways that unnecessarily limit review and “‘discredit’ the legitimacy of the sentencing process.” United States v. Ready, 82 F.3d 551, 556 (2d 

Cir. 1996), quoting United States v. Mezzanatto, 513 U.S. 196, 

204 (1995). 

Here, the “express and unambiguous” text of Bridgewater’s waiver confirms that it extends to compassionate release. Bridgewater waived “the right to seek modification of 

... any aspect of the ... sentence.” Compassionate release under 18 U.S.C. § 3582(c)(1)(A) is clearly a form of sentence modification. The heading to § 3582(c) reads “Modification of an 

imposed term of imprisonment,” and compassionate release 

is just one of several modifications authorized in that subsection.

Bridgewater’s waiver was written broadly to reach his 

rights to appeal and to bring a habeas corpus petition under 

28 U.S.C. § 2255, as well as his right “to seek modification of 

or contest any aspect of the conviction or sentence in any type 

of proceeding.” The waiver applies to proceedings “under Title 18 or 28, or under any other provision of federal law ... .” 

The waiver’s broad language and reference to “modify” 

make clear that the waiver was not limited to direct appeals 
No. 20-2413 7

and § 2255 petitions. Motions to modify sentences exhibit “a 

fundamentally different character than an appeal or collateral 

attack.” United States v. Monroe, 580 F.3d 552, 557 (7th Cir. 

2009). Sentence modification motions do not “seek to impugn 

the district court's rationale, nor ... claim that the district court

erred in any way by imposing” the defendant’s sentence. Id. 

They instead ask the court to impose a new sentence for reasons unrelated to the legality of the original sentence. Bridgewater waived his right to seek modification of his sentence in 

2019, after the First Step Act gave incarcerated people the 

right to seek modification without the support of the Bureau 

of Prisons. In other words, this type of modification proceeding was known and available when Bridgewater agreed not 

to use it.2 Accordingly, Bridgewater’s waiver, barring him 

from “seek[ing] modification of ... any aspect of [his] ... sentence,” applies to his right to seek compassionate release under 18 U.S.C. § 3582(c)(1)(A). 

III. Knowing and Voluntary Waiver

The record establishes that Bridgewater knowingly and 

voluntarily entered into this plea agreement with this broad 

waiver. As noted, Bridgewater and his attorney were on notice of the rights he might be waiving under the First Step Act. 

His Rule 11 plea colloquy confirmed that he understood his 

waiver: 

2 This case is therefore distinguishable from United States v. Glasper, 

No. 3:11-CR-30053, 2020 WL 6363703 (S.D. Ill. Oct. 29, 2020), where the 

district court found that an appellate waiver did not foreclose the right to 

seek compassionate release because it was entered into before the First Step 

Act was enacted. We express no view on the issue in Glasper, where an 

appeal is pending. Bridgewater signed his plea agreement in 2019, after 

the First Step Act took effect.
8 No. 20-2413 

Q: All right. And in terms of, finally, waiving 

your appeal rights. [The prosecutor] mentioned 

certain waivers that are part of the Plea Agreement. Did you specifically have a chance to discuss those waivers with your attorney ... so that 

you understand what rights to appeal you are 

actually waiving in exchange for the agreement? 

A: Yes ma’am. 

The entire Rule 11 colloquy, including that exchange about 

the waiver itself, was enough to confirm that Bridgewater’s 

plea, including the waiver, was knowing and voluntary. See 

United States v. Jones, 381 F.3d 615, 619 (7th Cir. 2004) (“Voluntariness of a guilty plea is ensured by a court's compliance 

with Federal Rule of Criminal Procedure 11.”).

The change of circumstances brought on by the pandemic 

does not render Bridgewater’s earlier waiver unknowing or 

involuntary. “At worst, he did not fully appreciate that he 

might wish to change his mind later ... . Yet, such is the risk 

with plea-bargaining and waiver.” United States v. Alcala, 678 

F.3d 574, 580 (7th Cir. 2012) (affirming waiver of defendant’s 

right to withdraw his plea agreement); see also United States 

v. McGraw, 571 F.3d 624, 630–31, quoting United States v. 

Bownes, 405 F.3d 634, 636 (7th Cir. 2005) (“In a contract (and 

equally in a plea agreement) one binds oneself to do something that someone else wants, in exchange for some benefit 

to oneself. By binding oneself one assumes the risk of future 

changes in circumstances in light of which one’s bargain may 
No. 20-2413 9

prove to have been a bad one. That is the risk inherent in all 

contracts.”).3

IV. Compassionate Release Waivers in Approved Plea Agreements 

Are Enforceable

We now turn to Bridgewater’s most substantial attacks on 

his waiver. He argues that even if he knowingly and voluntarily waived his right to seek compassionate release under 

the First Step Act, the waiver should not be enforced because 

it is contrary to public policy and unconscionable. While we 

respect the concerns that give rise to these arguments, we ultimately disagree. As an initial matter, it is unclear whether 

contract law’s public policy and unconscionability doctrines 

fully extend to plea agreements. Even if they do, we are convinced that an approved plea agreement that waives the right 

to file compassionate release motions under the First Step Act 

is not unenforceable on public policy or unconscionability 

grounds.

We base this conclusion on two major premises. First, statutory rights are presumed to be waivable in plea agreements, 

just as most constitutional rights are waivable. See United 

States v. Mezzanatto, 513 U.S. 196 (1995). Second, compassionate release waivers are more defensible against public policy 

3 It is true that contract law allows for some unusual and unpredictable 

events to relieve a party of agreed obligations, such as through the doctrine of force majeure or so-called Acts of God. See generally Restatement 

(Second) of Contracts 11 Intro. Note (Am. L. Inst. 1981). In contracts, parties may and often do bargain over the scope of such terms, and the more 

general doctrine fills in the blanks when parties do not address them explicitly. Those doctrines, however, clearly do not apply here to relieve 

Bridgewater of his obligations under the waiver term of his plea agreement, and he does not rely on them.
10 No. 20-2413 

and unconscionability challenges than § 1983 release-dismissal agreements, which the Supreme Court has held are generally enforceable. See Town of Newton v. Rumery, 480 U.S. 386 

(1987). 

A. Rights Presumed Waivable in Plea Agreements

Bridgewater’s argument runs up against the general principle that statutory rights are waivable in plea agreements, at 

least where Congress has not signaled otherwise. The Supreme Court clarified this presumption in Mezzanatto, where 

it enforced a defendant’s voluntary waiver of a protection under Federal Rule of Evidence 410, which normally bars the 

government from impeaching defendants with statements 

made during plea negotiations. Mezzanatto had agreed to enter plea negotiations on the condition that—despite Rule 

410—anything he said during the negotiation would be admissible to impeach him if his case went to trial. The plea discussions eventually broke down, and at trial the prosecution was 

allowed to cross-examine Mezzanatto with statements he had 

made during negotiations. The Ninth Circuit reversed, ruling 

that Rule 410 is not waivable because its text does not expressly allow waiver. 

The Supreme Court reversed, emphasizing that the circuit’s analysis was “directly contrary to the approach we have 

taken in the context of a broad array of constitutional and statutory provisions. Rather than deeming waiver presumptively 

unavailable absent some sort of express enabling clause, we 

instead have adhered to the opposite presumption.” Mezzanatto, 513 U.S. at 200–01. The Court emphasized that defendants may waive even fundamental constitutional rights. Id. at 

201, citing Ricketts v. Adamson, 483 U.S. 1, 10 (1987) (double 

jeopardy defense); Boykin v. Alabama, 395 U.S. 238, 243 (1969) 
No. 20-2413 11

(guilty plea waives privilege against compulsory self-incrimination, right to jury trial, and right to confront one’s accusers); Johnson v. Zerbst, 304 U.S. 458, 465 (1938) (Sixth Amendment right to counsel may be waived). The Court concluded 

that the same presumption should apply to statutory rights 

unless Congress says otherwise: “absent some affirmative indication of Congress’ intent to preclude waiver, we have presumed that statutory provisions are subject to waiver by voluntary agreement of the parties.” Mezzanatto, 513 U.S. at 201. 

The Court bolstered this conclusion by reference to Crosby 

v. United States, 506 U.S. 255 (1993), and Smith v. United States, 

360 U.S. 1 (1959), which showed that Congress knows how to 

create non-waivable rights for the accused when it wishes. 

Both cases addressed protections in the Federal Rules of 

Criminal Procedure that limit when they can be waived. See 

Crosby, 506 U.S. at 258–60 (text of Rule 43 provides that right 

to be present at one’s own trial is waivable only when the defendant “is voluntarily absent after the trial has commenced”); Smith, 360 U.S. at 9 (text of Rule 7(a) provides that 

indictment requirement “may be waived, but only in those 

proceedings which are noncapital”). Mezzanatto explained 

that the explicit limits on waivers in Rules 7(a) and 43 and the 

history of the pertinent rights indicated an intent to preclude 

waiver in other, unstated circumstances. 513 U.S. at 201. By 

contrast, a rule’s complete silence as to waiver, Mezzanatto reasoned, should leave in place the general presumption that 

statutory or rules-based rights are waivable. Id. at 201–02. 

That description fits the new statutory right to seek compassionate release.

Accordingly, we have enforced waivers of a broad array 

of statutory rights by plea agreement, including appellate 
12 No. 20-2413 

rights. See, e.g., United States v. Hare, 269 F.3d 859, 863 (7th 

Cir. 2001); United States v. Feichtinger, 105 F.3d 1188, 1190 (7th 

Cir. 1997) (“The right to appeal is a statutory right, and like 

other rights—even constitutional rights—which a defendant 

may waive, it can be waived in a plea agreement.”). We have 

also enforced waivers of appeals “based on intervening Supreme Court decisions,” McGraw, 571 F.3d at 631, and “based 

on the ineffectiveness of [] counsel at sentencing,” United 

States v. Smith, 759 F.3d 702, 707 (7th Cir. 2014) (collecting 

cases). The waivers enforced in McGraw and Smith, like the 

waiver here, extended to circumstances that defendants probably could not foresee when signing their agreements.

B. Narrow Due Process Limits

The Due Process Clause of the Fifth Amendment places 

some limits on waivers of rights in plea agreements. “A plea 

agreement is a type of contract subject to contract law principles tempered by limits that the Constitution places on the 

criminal process.” Chapa, 602 F.3d at 868, citing Bownes, 405 

F.3d at 636. These constitutional limits do not invalidate the 

waiver here.

For instance, waivers of the right to effective counsel during the plea negotiation process are not enforceable because ineffective counsel undermines the voluntariness of the plea. 

Hurlow v. United States, 726 F.3d 958, 965 (7th Cir. 2013) (“[A] 

valid appellate waiver contained in a plea agreement does not 

preclude a defendant’s claim that the plea agreement itself 

was the product of ineffective assistance of counsel.”), quoting United States v. Hodges, 259 F.3d 655, 659 n.3 (7th Cir. 2001). 

We have also suggested, but not held, that a plea agreement 

might not be voluntary if the defendant waived the right un-
No. 20-2413 13

der Brady v. Maryland, 373 U.S. 83 (1963), to receive “exculpatory evidence of actual innocence” before pleading guilty. See 

McCann v. Mangialardi, 337 F.3d 782, 787–88 (7th Cir. 2003) 

(distinguishing evidence of actual innocence from impeachment evidence, which, under United States v. Ruiz, 536 U.S. 

622 (2002), need not be disclosed during plea-bargaining to 

ensure that guilty plea is knowing and voluntary). Similarly, 

sentences that are based on race, United States v. Hicks, 129 

F.3d 376, 377 (7th Cir. 1997), or that exceed statutory maximums, Feichtinger, 105 F.3d at 1190, may be challenged despite an otherwise valid appellate waiver. 

None of these due process limits apply, however, to a 

waiver of compassionate release under the First Step Act. Enforcing that waiver does not fundamentally infect the voluntariness of the plea because the extraordinary circumstances 

that invoke compassionate release occur after sentencing. 

They have nothing to do with misconduct during the plea negotiation process. 

Moreover, unlike a waiver of appeal for a sentence based 

on race or in excess of a statutory maximum, compassionate 

release waivers serve legitimate finality and resource interests. See below, Part IV-C. Such waivers stop defendants only 

from petitioning the district court directly, without approval 

of the Bureau of Prisons. Defendants can still seek compassionate release through the original Bureau process, which 

was the only available route for decades. It would thus be odd 

if a defendant’s decision to revert back to his pre-2018 rights 

violated the bare “minimum of civilized procedure.” See 

United States v. Josefik, 753 F.2d 585, 588 (7th Cir. 1985). That 

would imply that the law governing the compassionate re-
14 No. 20-2413 

lease process until 2018 was and always had been unconstitutional. No one suggests that. Nor does the Constitution grant 

or imply a right to seek or obtain from a court compassionate 

release from an otherwise lawful sentence, outside of executive pardons and clemency.

It is also important to remember that even if a federally 

incarcerated person cannot petition directly for compassionate release due to medical conditions, he may still directly 

challenge any inadequate medical care he receives, or any 

medically unsafe conditions of confinement. See, e.g., Helling 

v. McKinney, 509 U.S. 25, 33 (1993) (affirming courts’ ability 

under Eighth Amendment to enjoin unsafe conditions that 

will likely affect an incarcerated person’s health: “We have 

great difficulty agreeing that prison authorities may not be 

deliberately indifferent to an inmate’s current health problems but may ignore a condition of confinement that is sure 

or very likely to cause serious illness and needless suffering 

the next week or month or year.”); Fields v. Smith, 653 F.3d 550, 

559 (7th Cir. 2011) (affirming injunction against denial of therapy to certain incarcerated people); see also Carlson v. Green, 

446 U.S. 14 (1980) (Bivens action for damages available where 

federal officials violate Eighth Amendment through deliberate indifference to serious medical needs). Accordingly, 

waiver of a right to seek compassionate release under the First 

Step Act does not inherently violate any constitutional limits 

on plea agreements. 
No. 20-2413 15

C. Public Policy and Unconscionability

Bridgewater argues primarily that his compassionate release waiver is unenforceable as a matter of contract law because it contravenes public policy and is unconscionable.4 In 

support, Bridgewater cites United States v. Osorto, 445 F. Supp. 

3d 103, 105 (N.D. Cal. 2020), in which Judge Charles Breyer 

rejected a plea agreement that contained a compassionate release waiver. He wrote that such a waiver “undermines Congressional intent and is an unconscionable application of a 

federal prosecutor's enormous power to set the terms of a plea 

agreement.” Id. 

We respectfully disagree, but we note that the issue in 

Osorto arose in a different way, and the procedural difference 

is important. In this case, the district court had approved and 

implemented the plea agreement. Bridgewater had already 

received substantial benefits under that agreement. Judge 

Breyer rejected a proposed waiver in Osorto, relying on a district judge’s “broad discretion to accept or reject a proposed 

4 As an initial matter, it remains undecided in this circuit whether plea 

provisions are even subject to public policy and unconscionability challenges in the same way that other contracts are. The Second Circuit has 

said they are. See United States v. Ready, 82 F.3d 551, 559 (2d Cir. 1996), 

superseded on other grounds by United States v. Cook, 722 F.3d 477, 481 

(2d Cir. 2013). A divided panel of the D.C. Circuit recently joined this view 

in Price v. Dep’t of Justice, 865 F.3d 676 (D.C. Cir. 2017), where it held that 

plea provisions must serve legitimate criminal-justice interests that outweigh any public policy concerns in enforcing such provisions. See 865 

F.3d at 681, 683. We have not explicitly adopted such a rule. While plea 

agreements are “usefully viewed through the lens of contract law,” 

Bownes, 405 F.3d at 636, we have repeatedly said that they are enforceable 

so long as they are entered into “knowingly and voluntarily.” See, e.g.,

Smith, 759 F.3d at 706.
16 No. 20-2413 

plea agreement.” Id. at 104; see Fed. R. Crim. P. 11(c)(3). Here, 

Judge Yandle accepted Bridgewater’s plea agreement back in 

2019 and acted accordingly. Our issue is whether the waiver 

term of the agreement can now be enforced after Bridgewater 

has received the benefits of the agreement. So while we disagree with Osorto’s analysis of the public policy and unconscionability issues concerning compassionate release waivers, 

we do not address here the scope of a district judge’s discretion to reject the terms of a proposed plea agreement in the 

first instance.

Regarding public policy, Osorto concluded that a compassionate release waiver undermines congressional intent because it “neatly undoes Congress’s work” and “restores the 

very obstacles the First Step Act removed.” 445 F. Supp. 3d at 

108. As to unconscionability, Osorto said that compassionate 

release waivers are “appallingly cruel” because they permanently stifle defendants’ ability to seek relief in “tragically unforeseeable” circumstances in which continued imprisonment 

no longer serves any penological purpose. Id. at 109. This left 

Judge Breyer asking: “why? Why would federal prosecutors 

exercise the tremendous discretion entrusted to them with 

such a lack of compassion?” Id. at 110. 

We believe there is an answer to Osorto’s “why?”—one 

that assures us that compassionate release waivers are at least 

not so indefensible as to be inherently unconscionable or 

against public policy. In short, the answer is that compassionate release waivers—like other appellate waivers—sacrifice 

an opportunity for review in order to advance the government’s legitimate interest in finality and the efficient use of 

prosecutorial resources, and in exchange for some other benefit that the defendant values more highly.
No. 20-2413 17

We disagree with Osorto’s assertion that Congress silently 

intended the First Step Act’s new compassionate release right 

to be non-waivable. The very nature of any waiver of a statutory right is that it “neatly undoes Congress’s work.” See id.

at 108. Nor is the First Step Act unusual in remedying a decades-long problem. New rights often address old problems. 

Mezzanatto held in 1995 that such statutory rights are presumptively waivable, and that has been the rule ever since. 

When Congress passed the First Step Act in 2018, it was certainly on notice of the legal effect of its silence as to waiver. 

Until Congress says otherwise, the better course is to allow 

defendants to waive this new right for something they value 

more in return. “Often a big part of the value of a right is what 

one can get in exchange for giving it up.” United States v. Barnett, 415 F.3d 690, 692 (7th Cir. 2005).

Beyond congressional intent, Osorto’s broader policy and 

unconscionability concerns do not persuade us to void compassionate release waivers in approved plea agreements. 

Those concerns are twofold. First, Osorto suggests that there 

is no legitimate prosecutorial reason for compassionate release waivers. Second, a defendant waives the right to seek 

compassionate release at a time when he cannot foresee it becoming salient. But if and when it later does, it becomes extremely salient, and he is then trapped in promises made by 

his earlier, less desperate self. 

We recognize the humane foundation for the second concern. But we enforce waivers in other scenarios presenting 

similar concerns, such as when defendants waive future appeals that may be based on unforeseen changes to Supreme 

Court precedent or the Sentencing Guidelines. See above, Part 

IV-A, discussing McGraw, 571 F.3d at 631, and Smith, 759 F.3d 
18 No. 20-2413 

at 707. Moreover, defendants who waive their First Step Act 

rights can still petition the Bureau of Prisons for compassionate release. That provides a safety valve, albeit one not in the 

control of the defendant.

As to the first concern about legitimate prosecutorial interests, Osorto presented the issue as if every motion for compassionate release were meritorious. If that were true, there 

might be no valid reason to keep defendants from filing such 

motions. But as with other appeals, not all are meritorious or 

even plausible. During the pandemic alone, we have affirmed 

many denials of compassionate release. So on the other side 

of the ledger there are legitimate prosecutorial interests in efficiency and finality that weigh against the interest in allowing defendants to petition directly for modification. 

Town of Newton v. Rumery, 480 U.S. 386 (1987), is instructive on this point. In that case, the Supreme Court assessed the 

enforceability of “release-dismissal agreements” in which an 

accused defendant releases his right to file a civil § 1983 action 

in return for the dismissal of criminal charges against him. 480 

U.S. at 389. Rumery argued that his release-dismissal agreement was contrary to public policy and unconscionable. The 

Court, however, rejected those arguments. It held that releasedismissal agreements are not per se unenforceable and instead 

should be assessed case by case. Critically, the Court generally upheld the enforceability of release-dismissal agreements 

based on the same efficiency and finality interests that we see 

here: 

[A] per se rule of invalidity fails to credit other 

relevant public interests ... . No one suggests 

that all such suits are meritorious. Many are 

marginal and some are frivolous. Yet even when 
No. 20-2413 19

the risk of ultimate liability is negligible, the 

burden of defending such lawsuits is substantial. ... This diversion of officials from their normal duties and the inevitable expense of defending even unjust claims is distinctly not in 

the public interest. To the extent release-dismissal agreements protect public officials from the 

burdens of defending such unjust claims, they 

further this important public interest.

Rumery, 480 U.S. at 395–96 (plurality opinion); id. at 399–400 

(O’Connor, J., concurring) (same).

These interests in efficient resource allocation and finality 

apply to compassionate release motions under the First Step 

Act. There is no obvious limit on how many motions a defendant can file. The statutory standard, “extraordinary and 

compelling reasons,” is flexible and can be interpreted expansively by incarcerated people seeking modifications. Nor are 

there obvious limits on information that a district court may 

consider in deciding such a motion. A motion for compassionate release thus creates the prospect that all sentencing factors 

under § 3553(a) could be in play, updated from the original 

sentencing. Cf. Pepper v. United States, 562 U.S. 476, 489 (2011)

(in case of resentencing after appellate reversal, stressing “traditional discretion of sentencing courts to ‘conduct an inquiry 

broad in scope, largely unlimited either as to the kind of information [they] may consider, or the source from which it 

may come.’”), quoting United States v. Tucker, 404 U.S. 443, 446 

(1972). Accordingly, as with appellate waivers, compassionate release waivers can serve legitimate interests. There are 

certainly important and humane interests on the other side. 

But the competing interests persuade us that knowing and 
20 No. 20-2413 

voluntary compassionate release waivers are not so cruel or 

unreasonable as to render them unconscionable.

Compassionate release waivers also do not present the 

concerns that made Rumery a close case. Rumery recognized 

that release-dismissal agreements create conflicts of interest 

that can motivate prosecutors and police to engage in unethical and illegal conduct. First, a suspect’s ability to waive 

§ 1983 claims reduces the legal incentives that discourage police officers from violating a suspect’s constitutional rights. 

Second, once a constitutional violation occurs, the natural desire to avoid liability “may tempt prosecutors to bring frivolous charges, or to dismiss meritorious charges, to protect the 

interests of other officials.” Rumery, 480 U.S. at 395 (plurality 

opinion). In fact, “the prosecutor's interest in obtaining a covenant not to sue will be strongest in those cases in which he 

realizes that the defendant was innocent and was wrongfully 

accused.” Id. at 409 (Stevens, J., dissenting). Hence, “[t]he central problem with the release-dismissal agreement is that public criminal justice interests are explicitly traded against the 

private financial interest of the individuals involved in the arrest and prosecution.” Id. at 401 (O’Connor, J., concurring). 

These corrupting influences are not present with compassionate release waivers. Prosecutors may be motivated to reduce litigation but would have no reason to expect these 

waivers could shield their own abuses or those of police. 

Compassionate release waivers by their very nature affect unforeseen circumstances that arise long after the prosecution 

and police’s interactions with the defendant.

Compassionate release waivers are also more defensible 

than the plea waiver invalidated in Price v. Dep’t of Justice, 865 

F.3d 676 (D.C. Cir. 2017). In Price, the D.C. Circuit held that a 
No. 20-2413 21

defendant’s waiver of Freedom of Information Act rights in a 

plea agreement was unenforceable as against public policy. In 

reaching that conclusion, Price emphasized that FOIA waivers 

can prevent defendants from uncovering files that reveal ineffective assistance of counsel or prosecutorial misconduct in 

their cases. 865 F.3d at 682. So, unlike compassionate release 

waivers, FOIA waivers could undercut defendants’ non-waivable right to effective counsel during plea negotiations. Id. 

Moreover, like release-dismissal agreements, FOIA waivers 

raise concerns about shielding government abuse that simply 

do not apply to compassionate release waivers.

Finally, in this case, the fact that Bridgewater has already 

reaped the benefits of his plea agreement bolsters our conclusion that it is not unconscionable to enforce his waiver. In return for his waiver and other promises in his agreement, 

Bridgewater received a substantial benefit—dismissal of a 

charge that carried a ten-year mandatory minimum sentence. 

Now that the government has delivered on the substantial 

benefits it promised him, it is not unconscionable to hold 

Bridgewater to his end of the bargain. In the end, Bridgewater 

“wants the benefits of the existing agreement but not the principal detriment.” United States v. Wenger, 58 F.3d 280, 283 (7th 

Cir. 1995). “That is the one outcome that would be most destructive of the plea agreement process. Defendants must take 

the bitter with the sweet.” Id. 

Conclusion

A district court has discretion to approve and enforce a 

knowing and voluntary plea agreement that waives the defendant’s right to seek compassionate release under the First 

Step Act. Bridgewater’s waiver was knowing and voluntary, 
22 No. 20-2413 

and he has already received a substantial benefit under the 

agreement. His appeal is DISMISSED