United States v. Trenkler

United States Court of Appeals
For the First Circuit

No. 21-1441

UNITED STATES,

Appellant,

v.

ALFRED W. TRENKLER,

Defendant, Appellee.

APPEAL FROM THE UNITED STATES DISTRICT COURT
FOR THE DISTRICT OF MASSACHUSETTS

[Hon. William E. Smith, U.S. District Judge*]

Before

Thompson, Selya, and Gelpí,
Circuit Judges.

Donald C. Lockhart, Assistant United States Attorney, with
whom Nathaniel R. Mendell, Acting United States Attorney, was on
brief, for appellant.

Amy Barsky, with whom Fick & Marx LLP was on brief, for
appellee.

Mary Price, Shanna Rifkin, Rebecca F. Izzo, Andrew M. Debbins,
and Connors LLP on brief for amicus curiae Families Against
Mandatory Minimums.

Jamesa J. Drake, Drake Law LLC, Michael L. Waldman, Courtney
L. Millian, Roy T. Englert, Jr., and Kramer Levin Robbins Russell

* Of the District of Rhode Island, sitting by designation.
on brief for amicus curiae National Association of Criminal Defense
Lawyers.

August 29, 2022
 THOMPSON, Circuit Judge. Before us is the government's

appeal from the district court's grant of a motion for

compassionate release filed by appellee, Alfred W. Trenkler

("Trenkler"), a federal inmate serving a life sentence for

convictions stemming from his role in a 1991 car bombing.

Trenkler's is a familiar face: By our count, this appeal marks

his ninth visit to this court after he was convicted and received

his life sentence nearly thirty years ago.1 Consequently, there

is a dense factual and procedural background here.2 For today,

though, we primarily assume the parties' familiarity with the

extensive history of Trenkler's case, the various issues

presented, and the bevy of arguments advanced, providing only the

information and context necessary to explain our reasoning and the

path forward. As we will explain, we remand this matter to the

district court for further review consistent with this opinion.

BACKGROUND

The latest chapter in Trenkler's litigation story began

on January 15, 2021, when Trenkler filed a motion for compassionate

1 The published collection of Trenkler cases consists of:
Trenkler v. United States, 536 F.3d 85 (1st Cir. 2008); Trenkler
v. United States, 268 F.3d 16 (1st Cir. 2001); and United States
v. Trenkler, 61 F.3d 45 (1st Cir. 1995). His other appeals to
this court resulted in unpublished writings.

2 The curious reader can consult the district court's
compassionate release Opinion and Order, which comprehensively
recaps this history. United States v. Trenkler, 537 F. Supp. 3d
91, 95-96 (D. Mass. 2021).

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release pursuant to 18 U.S.C. § 3582 (the statute governing

sentence reductions, colloquially known as the compassionate

release statute) based on his serious health risks related to the

ongoing COVID-19 pandemic as well as the unique circumstances of

his case. According to Trenkler, those unique circumstances

include: questions surrounding his guilt; the fundamental

unfairness of his conviction; the fact that his co-defendant

received a lesser sentence; and an error that occurred at his

sentencing in 1994, resulting in an unlawfully imposed life

sentence.

That the sentencing error was, in fact, error is

undisputed. The jury, in convicting Trenkler, found only intent

to destroy property,3 but the trial judge inferred from the

evidence an intent to kill, and thus handed down a life sentence.4

Unbeknownst at the time to the trial judge, prosecution, and

3Trenkler was convicted of illegal receipt and usage of
explosive material with the intent to destroy property, which
conduct had caused death and serious personal injury, in violation
of 18 U.S.C. § 844(d) and (i), and of knowingly conspiring to
commit the foregoing acts in violation of 18 U.S.C. § 371. The
trial judge sentenced Trenkler to concurrent life terms on the two
substantive counts, and to a concurrent sixty-month term for
conspiracy.

We refer to the district court judge who reviewed and granted
4

Trenkler's compassionate release motion, U.S. District Judge
William E. Smith, as "the district court," and refer to the judge
who presided over the trial and sentencing, U.S. District Judge
Rya W. Zobel, as "the trial judge."

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defense counsel, this sentence was imposed in violation of 18

U.S.C. § 34 (1988), as incorporated by 18 U.S.C. § 844 (1988),

which required life sentences to be assigned by the jury. Six

months after Trenkler's sentencing, Congress amended 18 U.S.C.

§§ 34 and 844(d) and (i), removing the requirement of a jury

recommendation for a life sentence.5 It seems likely this change

aided in obscuring the error, as it was not until almost ten years

later that finally Trenkler discovered this sentencing error

himself.6 In the matter now before us, Trenkler points to this

institutional failure in support of his motion for compassionate

release.

Based on the legal landscape as it then appeared,7 the

district court tackled Trenkler's motion by reasoning through the

statutory construction of the compassionate release statute and

5 After the statute was amended, section 844(d) and (i)
provided for life imprisonment with no reference to section 34,
and section 34 authorized the imposition of a life sentence without
any requirement for a jury trial on the issue. See Violent Crime
Control and Law Enforcement Act of 1994, Pub. L. No. 103-322,
§ 60003(a)(1), (a)(3)(A), (a)(3)(C), 108 Stat. 1796, 1968-69.

6 Prompted by his discovery, Trenkler specifically (albeit
unsuccessfully) challenged this error several times.

7 In the months after the district court issued its decision
here, a panel of this court published a case involving first-
impression issues regarding prisoner-initiated compassionate
release motions. See United States v. Ruvalcaba, 26 F.4th 14 (1st
Cir. 2022). That case, which we'll discuss in much more detail
shortly, explained in depth, for the first time, the framework for
reviewing prisoner-initiated motions for compassionate release.

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applying persuasive sister-circuit precedent. United States v.

Trenkler, 537 F. Supp. 3d 91, 107 (D. Mass. 2021). While the

district court was not sufficiently persuaded by some of the

circumstances Trenkler proffered to support his motion (questions

surrounding his guilt, fundamental unfairness, co-defendant

sentence disparity), taken individually, it concluded that the

sentencing error constituted an "extraordinary and compelling"

reason to grant compassionate release. Id. at 108. Specifically,

the life sentence was handed down by a judge when the controlling

statute provided that a life sentence could be imposed only by a

jury, and there was no other available avenue for relief from this

error. Id. Accordingly, the district court reduced Trenkler's

sentence from a term of life imprisonment to forty-one years,

crediting time served. Id. at 114.

The government timely appealed, disputing the district

court's conclusion that the sentencing error was an extraordinary

and compelling reason warranting compassionate release. It argues

that the district court's ruling "circumvents the [Antiterrorism

and Effective Death Penalty Act of 1996 ("AEDPA"), as codified in

28 U.S.C. § 2255(h)]'s limitations on successive habeas petitions,

supplants habeas law generally, and conflicts with this Court's

conclusion that compassionate release represents a 'narrow

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exception' to the statutory ban on altering prison terms once they

have been imposed."8

DISCUSSION

We review a district court's denial or grant of a

compassionate release motion for abuse of discretion. See United

States v. Ruvalcaba, 26 F.4th 14, 19 (1st Cir. 2022). Questions

of law are reviewed de novo and findings of fact are reviewed for

clear error. Id.

Before we proceed, a brief primer will provide important

additional context.

Compassionate release, codified under 18 U.S.C. § 3582

and amended by the First Step Act of 2018, Pub. L. No. 115-391,

sec. 603(b), § 3582, 132 Stat. 5194, 5239 [hereinafter "FSA"],

governs sentence reductions generally. The passage of the FSA in

2018 represented "a paradigm shift" for compassionate release

"[b]y empowering district courts to grant compassionate release"

on prisoner-initiated motions.9 Ruvalcaba, 26 F.4th at 22. This

8 It does not appear that the government challenges that this
is a valid prisoner-initiated motion, nor does it challenge the
district court's conclusion that Trenkler exhausted all other
administrative remedies as required by 18 U.S.C. § 3582.

9 "Section 603(b) of the FSA fundamentally changed the
compassionate-release mechanism. The amendment, entitled
'Increasing the Use and Transparency of Compassionate Release,'
created a new regime in which -- for the first time -- prisoners
may seek compassionate release even when the [Bureau of Prisons]
does not deign to act on their behalf." Ruvalcaba, 26 F.4th at 22
(citing FSA sec. 603(b), 132 Stat. at 5239).

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resulted in a swirl of litigation around the scope of compassionate

release, with other circuits weighing in to interpret the statute

to mean that the existing policy statement on compassionate release

promulgated by the Sentencing Commission does not constrain a

district court when adjudicating prisoner-initiated motions. See

id. at 21 (collecting cases from our sister circuits).

Then came Ruvalcaba with our court's take on

compassionate release as impacted by the FSA. See id. at 23-24.

Ruvalcaba rejected the notion that the habeas statutes provide an

extratextual limit on a district court's discretion to

categorically omit any challenges based on sentence length or

sentencing errors, see id. at 25-26, but explained that any

concerns about the potential misuse of compassionate release can

still be allayed through the substantive "extraordinary and

compelling" criteria and based on appellate review of a district

court's determinations, see generally id. at 26-28. Along the

way, the Ruvalcaba court agreed "with the overwhelming majority of

the courts of appeals that have decided the issue," concluding

that the existing policy guidelines do not apply to prisoner-

initiated motions. Id. at 21.10 Under this statutory regime,

10The district court's analysis relied on some of the same
out-of-circuit authority that Ruvalcaba later used in support of
its reasoning. Compare Trenkler, 537 F. Supp. 3d at 99-100, with
Ruvalcaba, 26 F.4th at 21, 23.

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Ruvalcaba explained, the only exception to what may constitute an

extraordinary and compelling reason, as made explicit by

Congress,11 is rehabilitation. Id. at 25. Ruvalcaba then reasoned

that when reviewing these motions, district courts enjoy broad

discretion, and may conduct a holistic review to determine whether

the individualized circumstances, taken in the aggregate, present

an "extraordinary and compelling" reason to grant compassionate

release. Id. at 27, 28. The takeaway is this:

a district court, reviewing a prisoner-initiated motion
for compassionate release in the absence of an
applicable policy statement, may consider any complex of
circumstances raised by a defendant as forming an
extraordinary and compelling reason warranting relief.
It follows that a district court adjudicating such a
motion may consider the FSA's non-retroactive amendments
to the scope of the mandatory minimum penalties under
section 841(b)(1)(A) on a case-by-case basis grounded in
a defendant's individualized circumstances to find an
extraordinary and compelling reason warranting
compassionate release.

Id. at 28.

The parties here disagree about what Ruvalcaba means for

Trenkler's case.

Taking issue with Ruvalcaba's holding and the role (if

any) it should play in the present appeal, the government takes

11 "Congress has stated plainly -- in a separate statute
authorizing the Sentencing Commission to issue general policy
statements -- that '[r]ehabilitation . . . alone shall not be
considered an extraordinary and compelling reason.'" Ruvalcaba,
26 F.4th at 25 (alteration in original) (quoting 28 U.S.C.
§ 994(t)).

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the absolutist position that this court cannot consider a

sentencing error when making determinations of what qualifies as

extraordinary and compelling. In doing so, the government

essentially argues as an initial matter that the question is

whether Trenkler's motion for compassionate release should have

been recategorized by the district court, at least in part, as a

habeas motion. The government contends as much and urges from

there that it should have been rejected as an unauthorized

successive petition for habeas relief under 28 U.S.C. § 2255(h).

The government then insists that the district court erred in

deeming a sentencing error an extraordinary and compelling reason,

and asserts that for us to sign off on this would effectively allow

compassionate release to swamp habeas.

Trenkler, for his part, maintains that Ruvalcaba

unequivocally sets the standard here; habeas and compassionate

release are distinct in purpose and scope, and the district court

correctly reviewed his motion under the compassionate release

standard as later set forth in Ruvalcaba.

Here's how we see it. The initial question of what may

be considered in an "extraordinary and compelling" determination

by the district court is separate from the secondary,

individualized question of what can actually qualify as

extraordinary and compelling. And while the government would like

it to be, the initial question is not at issue in this case. As

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noted above, Ruvalcaba clarified that until the Sentencing

Commission speaks, the only limitation on what can be considered

an extraordinary and compelling reason to grant a prisoner-

initiated motion is rehabilitation. 26 F.4th at 25, 26; see also

id. at 23-24 ("If and when the Sentencing Commission issues updated

guidance applicable to prisoner-initiated motions . . . district

courts . . . will be required to ensure that their determinations

. . . are consistent with that guidance.").12

Contrary to the government's statutory arguments

otherwise, this does not alter the fact that habeas and

compassionate release are distinct vehicles for relief. Section

2255 deals with the legality and validity of a conviction and

provides a method for automatic vacatur of sentences (when

warranted under the statute). In contrast, as Trenkler and the

amici argue,13 the compassionate release statute is addressed to

the court's discretion as to whether to exercise leniency based on

an individualized review of a defendant's circumstances (it is not

12"The simple fact of the matter is that the Sentencing
Commission has lacked a quorum for most of the time that has
elapsed since the FSA's passage," Ruvalcaba, 26 F.4th at 21
(citing Guerrant v. United States, 142 S. Ct. 640, 640-41 (2022)
(statement of Sotomayor, J., joined by Barrett, J.); United States
v. Saccoccia, 10 F.4th 1, 7 (1st Cir. 2021)), and thus "it has not
had any realistic opportunity to issue a post-FSA policy
statement," id. Now that the Sentencing Commission has a quorum,
it could provide policy guidance on compassionate release.

We acknowledge and thank the amici and their attorneys for
13

their helpful submissions.

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a demand of a district court to recognize and correct what a

defendant says is an illegal conviction or sentence). Id. at 26

("To serve as a safety valve, section 3582(c)(1)(A) must encompass

an individualized review of a defendant's circumstances and permit

a sentence reduction -- in the district court's sound discretion

-- based on any combination of factors.").

We would add that, in addition to the fact that habeas

and compassionate release exist under two distinct statutory

schemes, correct application of the "extraordinary and compelling"

standard for compassionate release naturally precludes classic

post-conviction arguments, without more, from carrying such

motions to success. Compassionate release is a narrow exception

to the general rule of finality in sentencing. See United States

v. Saccoccia, 10 F.4th 1, 3 (1st Cir. 2021).14 It is the

This is as good a moment as any for us to dispatch the
14

government's argument that Ruvalcaba is inconsistent with
Saccoccia -- so much so, it says, that Saccoccia, not Ruvalcaba,
should govern here. The government's argument is untenable.
First, Ruvalcaba's take -- that a district court has broad
discretion, unbound by the current policy statement, to review
prisoner-initiated motions, 26 F.4th at 23-24 -- does not
constitute a retreat from Saccoccia's remarks about compassionate
release being a narrow exception and having difficult statutory
criteria to satisfy, 10 F.4th at 4. Rather, the inherently narrow
(and stringent) "extraordinary and compelling" standard still must
be met to grant relief. Ruvalcaba, 26 F.4th at 23, 29. These
views are compatible and not, as the government argues,
irreconcilable.
Second, despite the government's contention otherwise,
Saccoccia did not suggest that the FSA did not substantively alter
the compassionate release process. The government reads too far

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"extraordinary and compelling" criteria for compassionate release

that promises this general rule will not be superseded by the

exception. See Ruvalcaba, 26 F.4th at 23. Accordingly, the

government's contention that Trenkler's motion for compassionate

release fails at the threshold question of whether it is a habeas

petition in disguise is not persuasive and, in any event, it is

now foreclosed by Ruvalcaba.15

The question really at issue here is the secondary,

individualized question. That is, did Trenkler propose reasons

into Saccoccia's reference to United States v. Havener, 905 F.2d
3, 6 (1st Cir. 1990) (Breyer, J.); that reference suggested simply
that "extraordinary and compelling" must be read in light of the
statute's purpose to address cases of extreme hardship. Saccoccia,
10 F.4th at 4. This is not inconsistent with Ruvalcaba's
acknowledgment that the FSA expanded the use of compassionate
release by allowing prisoners the opportunity to file motions after
exhausting administrative remedies. 26 F.4th at 22-23.

15 Another quick aside, this time to acknowledge that the
government offers a separate, but related, threshold argument:
that this court's 2005 and 2008 Trenkler decisions preclude
compassionate release, which cannot be used to make an end-run
around AEDPA. See Trenkler, 536 F.3d at 85; In re Trenkler, No.
04-2147 (1st Cir. Feb. 16, 2005). The government appears to
contend that because this court dealt with the sentencing error
previously, finding that Trenkler's 2005 petition for writ of
mandamus and 2008 petition for writ of coram nobis were essentially
invalid habeas petitions, this prevents Trenkler from using the
error as a reason to support his compassionate release motion, and
thus that the motion itself should be discarded as another invalid
habeas petition. We are not persuaded. The government does not
point to any binding authority to support this notion, and the
argument is similarly overpowered by Ruvalcaba, which instructs
district courts to review (emphasis ours) "any complex of
circumstances raised by a defendant" and says nothing about the
type of exclusion the government offers up. 26 F.4th at 28.

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for compassionate release that are extraordinary and compelling,

under the plain meaning of those terms? See id. (noting that the

terms "extraordinary" and "compelling" are afforded their plain

meaning).

Ruvalcaba convincingly set the standard for a district

court reviewing a prisoner's proposed reasons for compassionate

release, making it clear that district courts have the discretion

to review prisoner-initiated motions by taking the holistic, any-

complex-of-circumstances approach we discussed earlier. Id. at

27, 28. See generally id. at 29-32 (Barron, J., concurring)

(expounding, by way of example, on the "soundness" of the premise

"that there may be an 'extraordinary and compelling reason' to

reduce the sentence when a particular statutory change is

considered in the context of the defendant's individualized

circumstances"). Indeed, this approach makes sense. After all,

it is possible that the whole may be greater than the sum of its

parts, and reasons that might not do the trick on their own may

combine to constitute circumstances that warrant a finding that

the reasons proposed are, in the aggregate, extraordinary and

compelling. This is not to say that a district court must find a

certain number of extraordinary and compelling reasons. Rather,

in conducting their reviews, district courts should be mindful of

the holistic context of a defendant's individual case when deciding

whether the defendant's circumstances satisfy the "extraordinary

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and compelling" standard -- "any complex of circumstances"

contemplates that any number of reasons may suffice on a case-by-

case basis, whether it's one, two, or ten. See id. at 28. Granted,

Ruvalcaba did not address the merits of whether any particular

reason or complex of circumstances actually met the "extraordinary

and compelling" standard's substantive criteria (nor do we do so

now, as we'll explain). And the Ruvalcaba court's instruction to

district courts to generally consider "any complex of

circumstances" does not foreclose a conclusion that certain

reasons, standing alone, may be insufficient as a matter of law

when measured against the "extraordinary and compelling" standard.

We identified in Ruvalcaba, for example, that a change in

sentencing law, standing alone, cannot suffice.

Against this backdrop, consider again the district

court's reasoning in granting Trenkler's compassionate release

motion. It is clear the district court found the sentencing error

constituted an extraordinary and compelling reason warranting a

sentence reduction. But its analytical path is susceptible to

multiple interpretations when it comes to how it navigated the

list of reasons Trenkler offered. On one hand, we can appreciate

the possibility that the district court discarded Trenkler's other

proposed reasons one by one but, with the holistic context of those

reasons in mind, deemed the circumstances surrounding the

sentencing error alone to meet the "extraordinary and compelling"

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criteria. But we can also see how discarding all proposed reasons

except one could represent a singular reason-by-reason analysis,

not a review of the individual circumstances overall. In the end,

our careful review of the district court's thorough (but pre-

Ruvalcaba) decision leaves us uncertain as to whether it took a

holistic approach when reviewing Trenkler's proposed reasons and

ultimately concluding that the sentencing error constituted a

sufficiently extraordinary and compelling reason to grant relief.

In the normal course, this is where we would come in,

applying abuse-of-discretion review to assess the district court's

work on the compassionate release motion, holding it up against

our precedent to assess the accuracy of the analysis offered. But,

at this juncture, the circumstances of this case prompt us to take

a different tack. We decline to weigh in on the district court's

analysis at this time. Instead, because the standard-setting

Ruvalcaba was decided on the heels of the district court's ruling,

and given the importance of the issues and the gravitas of abuse-

of-discretion review, we conclude that the prudent approach is to

remand to afford the district court the opportunity to reassess

the motion with the benefit of Ruvalcaba's any-complex-of-

circumstances guidance. See, e.g., Gastronomical Workers Union

Loc. 610 v. Dorado Beach Hotel Corp., 617 F.3d 54, 66 (1st Cir.

2010) (vacating and remanding when intervening precedent clarified

a mode of analysis, meaning the district court, without the benefit

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of that new case, "did not engage in the requisite analysis").

This prudential approach is especially apt here because the

district court's proposed sentence reduction, even if affirmed,

would have no practical effect until sometime in the future.

On remand, the district court is permitted to consider

any factual developments that have transpired since its May 2021

opinion issued, such as shifts in Trenkler's health status or the

ever-evolving COVID-19 pandemic.

We close with this: Today's opinion should not be read

as a rejection or endorsement of the district court's outcome or

any of its analysis of Trenkler's proposed reasons for granting

compassionate release. We express no view as to what should happen

on remand.

CONCLUSION

For the reasons just explained, we vacate the district

court's Opinion and Order and remand to the district court for

further proceedings consistent with this opinion.

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