United States v. David Bridgewater

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, Cir-
cuit 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 compas-
sionate 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 vol-
untary, and, in any event, should be unenforceable under con-
tract-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 gov-
ernment agreed to dismiss Count One, which would have car-
ried a mandatory minimum ten-year sentence, and to recom-
mend a minimum five-year sentence for Count Two. The dis-
trict court approved the plea agreement on March 19, 2019.
Most relevant to this appeal, Bridgewater’s plea agreement in-
cluded the following waiver of his rights to appeal or other-
wise 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 volun-
tarily waives the right to seek modification of or con-
test 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 unreasonable-
ness of the term of imprisonment.
Dkt. 32, at 7–8 (emphasis in original).
At sentencing, the district court chose to impose an above-
guideline sentence of 78 months, plus seven years of super-
vised release. Bridgewater appealed his sentence, relying on
the appellate waiver’s exception for an above-guideline sen-
tence. We affirmed his sentence. United States v. Bridgewater,
950 F.3d 928, 929 (7th Cir. 2020). Bridgewater is currently im-
prisoned at the Forrest City Federal Correctional Institution
in Arkansas.
On April 30, 2020, Bridgewater filed a motion for compas-
sionate release under 18 U.S.C. § 3582(c)(1)(A)(i), which al-
lows a district court to reduce a defendant’s sentence for “ex-
traordinary 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 com-
pelling” reasons for release because they make him especially
susceptible to serious illness or death from the COVID-19 out-
break at Forrest City.
Before 2018, only the Bureau of Prisons itself could have
filed such a motion on Bridgewater’s behalf. In 2018, in re-
sponse 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 de-
fendants to file such motions directly with a district court so
long as they first give the Bureau 30 days to act on their re-
quests. 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 com-
passionate release program, resulting in inmates who may be
eligible candidates for release not being considered”). Bridge-
water invoked this new process to seek compassionate re-
lease.
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 ex-
plained that reducing Bridgewater’s term of imprisonment
from six and a half years to less than one year would not re-
flect the seriousness of his offense, promote respect for law,
foster specific deterrence, or protect the public from his po-
tential 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 re-
viewed denials of many motions seeking compassionate re-
lease 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 modifica-
tion 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 Bridge-
water’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 ad-
dresses Bridgewater’s unenforceability arguments. After set-
ting the legal landscape in Parts IV-A and IV-B, we explain in
Part IV-C why Bridgewater’s public policy and unconsciona-
bility 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 dismis-
sal 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 unneces-
sarily limit review and “‘discredit’ the legitimacy of the sen-
tencing 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 Bridge-
water’s waiver confirms that it extends to compassionate re-
lease. Bridgewater waived “the right to seek modification of
… any aspect of the … sentence.” Compassionate release un-
der 18 U.S.C. § 3582(c)(1)(A) is clearly a form of sentence mod-
ification. 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 subsec-
tion.
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 Ti-
tle 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 rea-
sons unrelated to the legality of the original sentence. Bridge-
water 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 proceed-
ing 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] … sen-
tence,” applies to his right to seek compassionate release un-
der 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 no-
tice 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 Agree-
ment. Did you specifically have a chance to dis-
cuss those waivers with your attorney … so that
you understand what rights to appeal you are
actually waiving in exchange for the agree-
ment?
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) (“Vol-
untariness 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 some-
thing 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 volun-
tarily 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 ul-
timately 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 con-
vinced 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, stat-
utory 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, compassion-
ate 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 doc-
trine of force majeure or so-called Acts of God. See generally Restatement
(Second) of Contracts 11 Intro. Note (Am. L. Inst. 1981). In contracts, par-
ties 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 ex-
plicitly. Those doctrines, however, clearly do not apply here to relieve
Bridgewater of his obligations under the waiver term of his plea agree-
ment, and he does not rely on them.
10 No. 20-2413
and unconscionability challenges than § 1983 release-dismis-
sal agreements, which the Supreme Court has held are gener-
ally 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 prin-
ciple that statutory rights are waivable in plea agreements, at
least where Congress has not signaled otherwise. The Su-
preme Court clarified this presumption in Mezzanatto, where
it enforced a defendant’s voluntary waiver of a protection un-
der Federal Rule of Evidence 410, which normally bars the
government from impeaching defendants with statements
made during plea negotiations. Mezzanatto had agreed to en-
ter plea negotiations on the condition that—despite Rule
410—anything he said during the negotiation would be admis-
sible to impeach him if his case went to trial. The plea discus-
sions 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 ex-
pressly allow waiver.
The Supreme Court reversed, emphasizing that the cir-
cuit’s analysis was “directly contrary to the approach we have
taken in the context of a broad array of constitutional and stat-
utory provisions. Rather than deeming waiver presumptively
unavailable absent some sort of express enabling clause, we
instead have adhered to the opposite presumption.” Mezza-
natto, 513 U.S. at 200–01. The Court emphasized that defend-
ants 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-incrim-
ination, right to jury trial, and right to confront one’s accus-
ers); Johnson v. Zerbst, 304 U.S. 458, 465 (1938) (Sixth Amend-
ment 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 in-
dication of Congress’ intent to preclude waiver, we have pre-
sumed that statutory provisions are subject to waiver by vol-
untary 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 de-
fendant “is voluntarily absent after the trial has com-
menced”); 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 rea-
soned, 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 compas-
sionate 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 Su-
preme 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 prob-
ably 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 princi-
ples 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 dur-
ing the plea negotiation process are not enforceable because in-
effective 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.”), quot-
ing 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 “exculpa-
tory 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 impeach-
ment 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 maxi-
mums, Feichtinger, 105 F.3d at 1190, may be challenged de-
spite an otherwise valid appellate waiver.
None of these due process limits apply, however, to a
waiver of compassionate release under the First Step Act. En-
forcing that waiver does not fundamentally infect the volun-
tariness of the plea because the extraordinary circumstances
that invoke compassionate release occur after sentencing.
They have nothing to do with misconduct during the plea ne-
gotiation 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 inter-
ests. 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 compas-
sionate 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 unconstitu-
tional. 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 execu-
tive pardons and clemency.
It is also important to remember that even if a federally
incarcerated person cannot petition directly for compassion-
ate 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 prob-
lems 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 ther-
apy 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 deliber-
ate 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 re-
lease waiver is unenforceable as a matter of contract law be-
cause 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 re-
lease waiver. He wrote that such a waiver “undermines Con-
gressional 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 dis-
trict 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 chal-
lenges 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 out-
weigh 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 disa-
gree with Osorto’s analysis of the public policy and uncon-
scionability issues concerning compassionate release waivers,
we do not address here the scope of a district judge’s discre-
tion to reject the terms of a proposed plea agreement in the
first instance.
Regarding public policy, Osorto concluded that a compas-
sionate release waiver undermines congressional intent be-
cause 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 perma-
nently stifle defendants’ ability to seek relief in “tragically un-
foreseeable” 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 compassion-
ate release waivers—like other appellate waivers—sacrifice
an opportunity for review in order to advance the govern-
ment’s legitimate interest in finality and the efficient use of
prosecutorial resources, and in exchange for some other ben-
efit 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 statu-
tory right is that it “neatly undoes Congress’s work.” See id.
at 108. Nor is the First Step Act unusual in remedying a dec-
ades-long problem. New rights often address old problems.
Mezzanatto held in 1995 that such statutory rights are pre-
sumptively waivable, and that has been the rule ever since.
When Congress passed the First Step Act in 2018, it was cer-
tainly 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. Bar-
nett, 415 F.3d 690, 692 (7th Cir. 2005).
Beyond congressional intent, Osorto’s broader policy and
unconscionability concerns do not persuade us to void com-
passionate release waivers in approved plea agreements.
Those concerns are twofold. First, Osorto suggests that there
is no legitimate prosecutorial reason for compassionate re-
lease waivers. Second, a defendant waives the right to seek
compassionate release at a time when he cannot foresee it be-
coming salient. But if and when it later does, it becomes ex-
tremely salient, and he is then trapped in promises made by
his earlier, less desperate self.
We recognize the humane foundation for the second con-
cern. But we enforce waivers in other scenarios presenting
similar concerns, such as when defendants waive future ap-
peals 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 compassion-
ate release. That provides a safety valve, albeit one not in the
control of the defendant.
As to the first concern about legitimate prosecutorial inter-
ests, Osorto presented the issue as if every motion for compas-
sionate 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 ef-
ficiency and finality that weigh against the interest in allow-
ing defendants to petition directly for modification.
Town of Newton v. Rumery, 480 U.S. 386 (1987), is instruc-
tive 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 agree-
ment was contrary to public policy and unconscionable. The
Court, however, rejected those arguments. It held that release-
dismissal agreements are not per se unenforceable and instead
should be assessed case by case. Critically, the Court gener-
ally 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 substan-
tial. … This diversion of officials from their nor-
mal duties and the inevitable expense of de-
fending even unjust claims is distinctly not in
the public interest. To the extent release-dismis-
sal 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 de-
fendant can file. The statutory standard, “extraordinary and
compelling reasons,” is flexible and can be interpreted expan-
sively 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 compassion-
ate 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 “tra-
ditional discretion of sentencing courts to ‘conduct an inquiry
broad in scope, largely unlimited either as to the kind of in-
formation [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, compassion-
ate 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 unethi-
cal and illegal conduct. First, a suspect’s ability to waive
§ 1983 claims reduces the legal incentives that discourage po-
lice officers from violating a suspect’s constitutional rights.
Second, once a constitutional violation occurs, the natural de-
sire to avoid liability “may tempt prosecutors to bring frivo-
lous 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 cov-
enant 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 cen-
tral problem with the release-dismissal agreement is that pub-
lic criminal justice interests are explicitly traded against the
private financial interest of the individuals involved in the ar-
rest and prosecution.” Id. at 401 (O’Connor, J., concurring).
These corrupting influences are not present with compas-
sionate release waivers. Prosecutors may be motivated to re-
duce 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 un-
foreseen 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 in-
effective 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-wai-
vable 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 conclu-
sion that it is not unconscionable to enforce his waiver. In re-
turn 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 prin-
cipal detriment.” United States v. Wenger, 58 F.3d 280, 283 (7th
Cir. 1995). “That is the one outcome that would be most de-
structive 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 de-
fendant’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