United States District Court, E.D. Kentucky, Southern Division, Pikeville
MEMORANDUM OPINION AND ORDER
R. THAPAR UNITED STATES DISTRICT JUDGE.
habeas law is rather basic. A prisoner challenging the
legality of his sentence must do so under 28 U.S.C.
§ 2255; a prisoner challenging the legality of his
detention must do so under 28 U.S.C. § 2241.
But from these roots a tangled forest has grown. Part of the
confusion stems from the back door that Congress created
between Sections 2255 and 2241: When Section 2255 “is
inadequate or ineffective to test the legality of his
detention, ” the prisoner may bring his challenge under
Section 2241. 28 U.S.C. § 2255(e). The circuits are
split on when Section 2255 is “inadequate or
ineffective.” Many require a petitioner to prove his
“actual innocence” before invoking the savings
clause and attacking his sentence under Section 2241. In this
case, the Sixth Circuit went a different way.
point, however, the debate has largely overlooked the
practical problems a district court faces when it
must provide Section 2255 relief via Section 2241.
Logistically, how can a court that never sentenced a prisoner
resentence him? What power does it have to do so?
Does Congress want it to use that power in that way? Those
are some of the questions here.
Dave Hill challenges the sentencing enhancement he received
for qualifying as a career offender. The Court has been
directed to hear that sentencing challenge under Section 2241
through the savings clause. Before proceeding further, the
Court would like to hear what the parties think the Court
can-and should-do. The issues are laid out below.
2001, shortly after his trial began in the District of South
Carolina, Hill pled guilty to conspiring to distribute
heroin. See Hill v. Masters, 836 F.3d 591, 592-94
(6th Cir. 2016) (recounting the facts). The sentencing judge
then needed to calculate Hill's guidelines range. The
sentencing guidelines provide longer sentences for career
offenders. U.S. Sentencing Guidelines Manual (U.S.S.G.)
§ 4B1.1. Hill qualified: His most recent crime, “a
controlled substance offense, ” followed “at
least two prior felony convictions of either a crime of
violence or a controlled substance offense.” U.S.S.G.
§ 4B1.1(a). Hill, who was on the Maryland books with a
drug offense and a second-degree assault, had one of each.
With the enhancement, Hill had a criminal history category of
VI and an offense level of thirty-five. Id. §
4B1.1(b). These coordinates landed him in a guidelines range
of 292 to 365 months. And back then, the guidelines were
mandatory, meaning the court was required to sentence him
somewhere within this range. See United States v.
Booker, 543 U.S. 220, 245 (2005) (holding, later, that
the guidelines are advisory). The court gave him 300 months.
decade later, the law on the career-offender enhancement
changed. In Descamps v. United States, 133 S.Ct.
2276 (2013), the Supreme Court clarified when a prior felony
is a “violent” felony under the Armed Career
Criminal Act (ACCA). The ACCA, like the career-offender
guideline, imposes stiffer penalties on defendants with prior
violent offenses or serious drug crimes. See Id. at
2283-86. Later that year, the Fourth Circuit held in light of
Descamps that Maryland's second-degree-assault
statute-the one Hill had once violated- did not describe a
“violent felony” under the ACCA. See United
States v. Royal, 731 F.3d 333, 342 (4th Cir. 2013).
filed a habeas petition, arguing that Descamps and
Royal entitle him to a lower sentence. R. 1. The
career-offender guidelines define “crime of
violence” the same way that the ACCA defines
“violent felony.” Compare 18 U.S.C.
§ 924(e)(2)(B)(i), with U.S.S.G. §
4B1.2(a)(1). Knowing what we know now about Maryland's
second-degree-assault law, Hill argues, he should not have
been classified as a career offender-and if so, his mandatory
range should have dropped to 235 to 292 months. See
Hill, 836 F.3d at 593. Not only that: He might also have
qualified for certain guideline amendments that could have
moved his range as low as 188 to 235 months. Id.
a federal habeas petitioner wishing to challenge his sentence
must do so in his sentencing court through a motion under 28
U.S.C. § 2255. But as discussed below-and because of the
quirks that have grown from the habeas laws-Hill brought his
petition under 28 U.S.C. § 2241 and in the district
where he was confined.
The structure of Sections 2241 and 2255
are generally two paths federal habeas petitioners can go by.
The first path is Section 2241, which lets them challenge the
legality of their detention. 28 U.S.C. § 2241. If a
prisoner wants to contest “the execution or manner in
which [his] sentence is served”-i.e., if the
jail is withholding good-time credits-Section 2241 is his
remedy. Terell v. United States, 564 F.3d 442, 447
(6th Cir. 2009). When the Great Writ issues under this
section, it gets served on the petitioner's jailer; after
all, he is the one who executes the sentence. Id.
The petitioner must therefore file his 2241 motion in a court
with jurisdiction over the jailer: the court for the district
where the petitioner is confined.
second path runs through Section 2255, which allows federal
prisoners to challenge the validity of their convictions and
sentences. See 28 U.S.C. § 2255. The remedy
that they can obtain is “exactly commensurate”
with what, before the days of Section 2255, they could have
obtained through a habeas petition in the district of their
confinement. Hill v. United States, 368 U.S. 424,
471 (1962). Why use Section 2255 instead of Section 2241?
Section 2255 explicitly enables a petitioner to challenge the
legality of the proceedings that led to his sentence, and it
is in fact the only way to collaterally attack
sentences. 28 U.S.C. § 2255(e). Petitioners may file
such challenges from anywhere in the country, but
in one court only: “the court which imposed
the sentence.” Id. § 2255(a). This
jurisdiction is not only the one Congress happened to choose,
but the one that makes the most sense. The jailer simply
executes the sentence handed down by a judge. If the judge
got that sentence wrong, he or she should fix it. And for
reasons that are obvious to any judge who has sentenced
before, the best judge to fix the sentence is the one
intimately familiar with the defendant, the case, and local
federal prisoner gets one free chance to file a 2255 motion.
If, after filing his first, he discovers some new evidence,
or if the Supreme Court creates a new constitutional rule
that applies retroactively to his case, he may bring a
“second or successive” 2255 motion. Id.
§ 2255(h). But when Section 2255 is “inadequate or
ineffective to test the legality of his detention, ” a
prisoner may bring his challenge under Section 2241 instead.
Id. § 2255(e). Although courts disagree about
what this “savings clause” means, they generally
agree that Section 2255 is not “inadequate or
ineffective” just because a prisoner is procedurally
barred from invoking it-the statute is not
“self-cancelling.” Brown v. Caraway, 719
F.3d 583, 600 (7th Cir. 2013) (Easterbrook, J., statement
concerning Circuit Rule 40(e) circulation); see United
States v. Peterman, 249 F.3d 458, 461 (6th Cir. 2001)
(“The unavailability of § 2255 relief does not
alone establish inadequacy or ineffectiveness under the
savings clause. The court has clearly stated ‘the
§ 2255 remedy is not considered inadequate or
ineffective simply because . . . the petitioner is
procedurally barred from pursuing relief under §
2255[.]'” (quoting Charles v. Chandler,
180 F.3d 753, 758 (6th Cir. 1999))).
courts have held that a prisoner may access the savings
clause when he has been convicted under a law that later
changes in a way that makes him “actually
innocent” of the offense. See Wooten v.
Cauley, 677 F.3d 303, 307-08 (6th Cir. 2012). To prove
that, he must show that (1) a new interpretation of
a statute, (2) issued too late for him to have incorporated
it into his previous motion, (3) is retroactive, and (4) not
only applies to his case but also makes it “more likely
than not that no reasonable juror would have convicted”
him of the offense. Id. When all of that is true, he
may challenge his conviction-not under Section 2255, but
under Section 2241. Id.
until recently, prisoners could not use the savings clause to
challenge sentencing enhancements. As some courts
have written, “[t]o say ‘that a petitioner can be
“actually innocent” of a sentencing enhancement,
' rather than an element of the actual crime,
‘would require a great deal of both verbal and logical
gymnastics.'” United States v. Surratt,
797 F.3d 240, 249 (4th Cir. 2015) (quoting Turner v.
Warden Coleman FCI (Medium), 709 F.3d 1328, 1334 n.3
(11th Cir. 2013)). Whether or not that's true, until this
case the Sixth Circuit had consistently held-albeit in
unpublished cases-that the savings clause “does not
apply to sentencing claims.” Reminsky v. United
States, 523 F. App'x 327, 329 (6th Cir. 2013);
see also, e.g., Jones v. Castillo, 489 F.
App'x 864, 866 (6th Cir. 2012) (same); Hayes v.
Holland, 473 F. App'x 501, 502 (6th Cir. 2012)
years of litigation, Hill's habeas claim had stalled. He
had already filed his free Section 2255 motion-plus one
more-both of which were denied. See United States v.
Hill, 158 F. App'x 436, 437 (4th Cir. 2005) (denying
Hill's first 2255 petition); United States v.
Hill, 442 F. App'x 76, 77 (4th Cir. 2011) (denying
his second 2255 petition). No new rule of
constitutional law applied to him (Descamps
is statutory), nor did any new evidence prove his actual
innocence of the heroin conspiracy, so he could not file a
third Section 2255 claim. But after the Fourth Circuit
reinterpreted his predicate offense, he brought another
motion-this time under Section 2241. R. 1. Since he wanted to
challenge a sentence enhancement, however, he could not (yet)
pass through the savings clause. Without any contrary
published precedent in sight, this Court held that Hill's
sentencing claim “does not belong in a § 2241
proceeding” and dismissed his petition at the screening
stage. R. 7 at 4.
boat stranded, Hill appealed. At which point the Sixth
Circuit gave him a tow, holding that petitioners barred from
bringing successive motions under Section 2255 may sometimes
challenge their sentence enhancements under Section 2241 via
the savings clause. See Hill, 836 F.3d at 599-600.
The court did not require Hill to prove his actual innocence
under the old savings-clause test. Instead, it adopted a new
test for prisoners who challenge “the legality of
[their] detention” by attacking their mandatory
sentence enhancements. 28 U.S.C. § 2255(e). To pass
this test, the prisoner must show that (1) a new
interpretation of a statute, (2) is retroactive and was
issued too late to incorporate into an earlier 2255 motion,
and (3) his enhanced sentence under the old interpretation is
“an error sufficiently grave to be deemed a miscarriage
of justice or a fundamental defect.” Hill, 836
F.3d at 595.
to the Sixth Circuit, Hill passes this test. The government
conceded that, in the hindsight of Descamps and
Royal, Hill's second-degree assault conviction
is no longer a crime of violence under the career-offender
guideline. Id. It also conceded that this change
applies retroactively. Id. Those concessions brought
Hill within view of shoreline. But see infra Part
II.D. As for the defect in his sentence, the court reflected
that serving a too-high sentence under mandatory guidelines
“shares similarities” with serving a sentence
higher than the statutory maximum. Id. at 599.
“Both sentences, ” the court said, “are
beyond what is called for by law.” Id. If Hill
had not qualified as a career offender, he could have been
sentenced in a lower range. Id. Because his sentence
thus “raises a fundamental fairness issue, ” Hill
has passed the new test and may challenge his career-offender
enhancement under Section 2241. Id.
it created a new rule, the court also limited its reach. The
rule applies only to petitioners in Hill's particular
position: “prisoners who were sentenced under the
mandatory guidelines regime, ” “who are
foreclosed from filing a successive  petition, ”
and who received the career-offender enhancement because of a
predicate offense that “a subsequent, retroactive
change in statutory interpretation by the Supreme Court
reveals” is no longer a qualifying predicate offense.
Id. at 599-600.