John Worman v. Frederick Entzel ( 2020 )

In the
United States Court of Appeals
For the Seventh Circuit
____________________
No. 19‐2048
JOHN WORMAN,
Petitioner‐Appellant,
v.
FREDERICK ENTZEL, Warden,
Respondent‐Appellee.
____________________
Appeal from the United States District Court for the
Central District of Illinois.
No. 1:18‐cv‐1144 — James E. Shadid, Judge.
____________________
ARGUED FEBRUARY 27, 2020 — DECIDED MARCH 26, 2020
____________________
Before BRENNAN, SCUDDER, and ST. EVE, Circuit Judges.
SCUDDER, Circuit Judge. John Worman reacted to losing his
job and a business opportunity by mailing a pipe bomb to his
former supervisor. Federal charges ensued, and a jury con‐
victed Worman on all counts, leading to a sentence of 44
years’ imprisonment. Worman was unsuccessful in challeng‐
ing his sentence on direct appeal and in a motion to vacate his
sentence. The Supreme Court then decided Dean v. United
States, 137 S. Ct. 1170 (2017), which Worman was right to
2 No. 19‐2048
recognize as calling into question the length of his sentence.
But Congress has limited prisoners to one pursuit of habeas
corpus relief, subject to very narrow exceptions. So Worman’s
challenge became finding a viable path to file a second request
for habeas relief, and he ultimately invoked 28 U.S.C. § 2241.
The district court concluded that, even though Dean provided
Worman a surefire basis for a meaningful sentencing reduc‐
tion (from 44 to 30 years), he did not meet the exacting and
narrow requirements for being able to use § 2241 to pursue a
new sentence. We agree and affirm, with today’s decision ex‐
emplifying the stark reality that the limitations on habeas cor‐
pus relief can have very real and lasting consequences for
prisoners laboring to navigate its complexities.
I
John Worman used to work at Winnebago Industries, an
Iowa company that manufactures and sells recreational vehi‐
cles. His supervisor, Paulette Torkelson, repeatedly noted his
poor performance and in time the company terminated him.
Worman then started his own company and landed a contract
to provide parts to Winnebago, but the agreement fell
through. Worman blamed Torkelson for the misfortune and
sought revenge by mailing her a pipe bomb. The U.S. Postal
Service intercepted the package, and a criminal investigation
commenced in short order.
A federal grand jury sitting in the Northern District of
Iowa charged Worman with mailing an explosive device (18
U.S.C. § 1716), possessing an unregistered destructive device
(26 U.S.C. §§ 5861(d), 5845(f)), transporting an explosive de‐
vice (18 U.S.C. § 844(d)), and possessing and using a destruc‐
tive device in furtherance of a crime of violence (18 U.S.C.
§ 924(c)(1)(A), (B)(ii)). Worman’s mailing of a pipe bomb
No. 19‐2048 3
constituted the predicate crime of violence for purposes of the
§ 924(c) charge. See, e.g., United States v. Strickland, 261 F.3d
1271, 1274 (11th Cir. 2001) (concluding that the offense of
transporting an explosive, 18 U.S.C. § 844(d), constitutes a
predicate offense under § 924(c)); United States v. Collins, 109
F.3d 1413, 1419 (9th Cir. 1997) (reaching same conclusion for
crime of mailing a destructive device, 18 U.S.C. § 1716).
On the alleged facts—and owing to the gravity of
Worman’s conduct—the § 924(c) charge brought with it a
mandatory minimum sentence of 30 years’ imprisonment. See
18 U.S.C. § 924(c)(1)(B)(ii). Congress further required that the
30‐year mandatory sentence be served consecutive to (as op‐
posed to concurrently with) any other sentence imposed on
any other count of conviction. See id. § 924(c)(1)(D)(ii); see
also U.S.S.G. § 5G1.2(a) (explaining consecutive and concur‐
rent sentences).
Worman proceeded to trial in the Northern District of
Iowa, and the jury convicted him on all counts. The district
court then sentenced Worman to 361 months’ imprison‐
ment—360 months (30 years) for the § 924(c) offense and one
month for each, to run concurrently, of the other offenses of
conviction. The latter sentence—the one month for mailing
and possessing and transporting a pipe bomb—was 167
months below the low end of the advisory guidelines range
of 168 to 201 months for those predicate offenses. The sentenc‐
ing judge explained that a total sentence of 361 months was
sufficient, especially given that Worman would not be re‐
leased until he was 84. The sentencing court likewise pointed
to Worman’s lack of any prior criminal history in justifying
the 167‐month downward variance.
4 No. 19‐2048
As sensible as it may sound, the sentence reflected a legal
error. The reason is because, at the time of Worman’s sentenc‐
ing, the Eighth Circuit prohibited district judges from consid‐
ering a mandatory consecutive sentence (like Worman’s 30‐
year § 924(c) sentence) when granting a downward variance
on another count. See United States v. Hatcher, 501 F.3d 931,
934 (8th Cir. 2007) (ordering resentencing because district
court impermissibly considered the severity of a firearm sen‐
tence with a mandatory and consecutive minimum when im‐
posing a reduced sentence on other counts). On appeal, there‐
fore, the Eighth Circuit followed its precedent, vacated
Worman’s sentence, and ordered resentencing. See United
States v. Worman, 622 F.3d 969, 978 (8th Cir. 2010). The Su‐
preme Court declined Worman’s request to review the case.
On remand the district court adhered to the Eighth Cir‐
cuit’s direction and resentenced Worman to 528 months’ (44
years’) imprisonment—168 months (14 years) for the pipe‐
bomb offenses and 360 mandatory and consecutive months
(30 years) for the § 924(c) offense. In doing so, the district
judge made plain that this outcome—which added 14 years
to the original sentence—worked an injustice for Worman.
In 2016, Worman turned to pursuing post‐conviction re‐
lief, filing a pro se motion for a new sentence under 28 U.S.C.
§ 2255. He sought relief based on the Supreme Court’s deci‐
sion in Johnson v. United States, 135 S. Ct. 2251 (2015), which
invalidated the residual clause of the Armed Career Criminal
Act, 18 U.S.C. § 924(e)(2)(B). The motion had no merit,
though, because Johnson’s holding did not extend to any as‐
pect of Worman’s conviction under § 924(c). Worman did not
pursue an appeal.
No. 19‐2048 5
Two years later the Supreme Court decided Dean v. United
States, 137 S. Ct. 1170 (2017). Dean overruled the Eighth Cir‐
cuit’s case law prohibiting sentencing courts from consider‐
ing § 924(c)’s mandatory minimum when determining the ap‐
propriate sentence for the other counts of conviction. See id.
at 1176–78. By extension, then, Dean established that the dis‐
trict court committed no legal error in initially sentencing
Worman to 361 months.
Worman recognized the importance of Dean and turned
his attention to securing a sentencing reduction through a sec‐
ond pursuit of habeas relief. In doing so, though, he had to
overcome a substantial procedural obstacle—he had already
filed a motion to vacate his sentence, the one seeking relief
based on Johnson. Even though it went nowhere, Worman’s
first filing had consequences: subject to narrow exceptions,
Congress has limited federal inmates to one motion for ha‐
beas relief. See 28 U.S.C. § 2255(h). To file a second § 2255 mo‐
tion, inmates like Worman must receive express authorization
from a circuit court and that requires showing the claim in
question relies on either newly discovered evidence showing
that a reasonable jury could not have found the inmate guilty
of the offense of conviction or a new rule of constitutional law
previously unavailable that applies retroactively to cases on
collateral review. See id. § 2255(h)(1), (2). These requirements
are demanding. See, e.g., Suggs v. United States, 705 F.3d 279,
281 (7th Cir. 2013) (explaining that the statute “sharply re‐
strict[s] a second or successive motion to narrow circum‐
stances”).
Worman realized this firsthand when the circuit court de‐
nied his request to file a second § 2255 motion. He went ahead
anyway and filed the motion, but the district court denied it
6 No. 19‐2048
as untimely. See 28 U.S.C. § 2255(f) (establishing a one‐year
limitation period absent certain circumstances). What
Worman tried next provides the basis for this appeal.
Recognizing that any further motions under § 2255 were a
dead end, Worman turned to 28 U.S.C. § 2241, a provision em‐
bodying and authorizing what is often referred to as tradi‐
tional habeas relief. Worman filed his § 2241 petition in the
Northern District of Iowa, but that court rightly transferred
the matter to the Central District of Illinois, the district in
which Worman is now incarcerated. See Chazen v. Marske, 938
F.3d 851, 856 (7th Cir. 2019) (explaining that whereas § 2255
motions must proceed in the jurisdiction of conviction, a
§ 2241 petition can be brought only in the district of incarcer‐
ation).
The district court dismissed the petition, concluding that,
even though the Supreme Court’s recent decision in Dean pro‐
vided Worman a strong challenge to his 44‐year sentence, he
could not satisfy the exacting requirements for pursuing relief
under § 2241. Worman now appeals.
II
A
Worman’s appeal implicates an area of law riddled with
complexity—the savings clause of 28 U.S.C. § 2255(e) and the
narrow and limited instances under which a prisoner can pur‐
sue relief under § 2241. Other cases have required us to spill
substantial ink traversing this complexity. See, e.g., Chazen,
938 F.3d at 856. Perhaps a future appeal will require, or pro‐
vide an opportunity for, our full court to sort out confusion in
our case law in this area. See id. at 864, 866 (Barrett, J., concur‐
ring) (explaining that our case law contains differing
No. 19‐2048 7
interpretations of key limiting language in § 2255(e) and has
been interpreted in ways that may undermine the limits Con‐
gress has imposed on second and successive pursuits of ha‐
beas relief in § 2255(h)). Worman’s appeal can be resolved on
much narrower grounds, however.
Section 2255(h) limits second and successive federal ha‐
beas motions. All agree that Worman does not meet either of
the two exceptions authorizing a second § 2255 motion. The
focus of the appeal is instead on § 2255(e)—the so‐called sav‐
ings clause. The provision affords prisoners the opportunity
to request traditional habeas relief under § 2241 if § 2255 is
“inadequate or ineffective to test the legality of [his] deten‐
tion.” 28 U.S.C. § 2255(e). It is referred to as the “savings
clause” because it may save § 2255 from constitutional infir‐
mity under the Suspension Clause. See Webster v. Daniels, 784
F.3d 1123, 1152 (7th Cir. 2015) (en banc) (Easterbrook, J., dis‐
senting) (noting that the Supreme Court treats § 2255(e)’s lan‐
guage as a safety valve (citing United States v. Hayman, 342
U.S. 205 (1952))).
We analyzed the savings clause in In re Davenport and de‐
termined that it allows petitioners “a reasonable opportunity”
to obtain a judicial determination of “the fundamental legal‐
ity” of their convictions and sentences. 147 F.3d 605, 609 (7th
Cir. 1998); see also Webster, 784 F.3d at 1136 (articulating the
same point and interpreting Davenport the same way). Since
then we have developed a three‐part test for determining
whether § 2255 is “inadequate or ineffective”:
 Step #1: the federal prisoner must seek relief
based on a decision of statutory interpretation
(as opposed to a decision of constitutional
8 No. 19‐2048
interpretation, which the inmate could raise in a
second or successive § 2255 motion);
 Step #2: the statutory rule of law in question
must apply retroactively to cases on collateral
review and could not have been invoked in a
first § 2255 motion; and
 Step #3: a failure to afford the prisoner collateral
relief would amount to an error “grave enough”
to constitute “a miscarriage of justice.”
Montana v. Cross, 829 F.3d 775, 783 (7th Cir. 2016); see also
Beason v. Marske, 926 F.3d 932, 935 (7th Cir. 2019) (articulating
and applying the same test).
We move quickly beyond step #1 because everyone agrees
that the Supreme Court’s decision in Dean was a decision of
statutory law—an interpretation of a district court’s sentenc‐
ing discretion under 18 U.S.C. § 3553(a). No aspect of Dean in‐
terpreted the Constitution.
Step #2 presents the question on which Worman’s appeal
turns—whether Dean applies retroactively to cases on collat‐
eral review. Because we conclude that it does not, our analysis
ends there.
B
The north star precedent on the question of retroactivity
in the law of habeas corpus came in Teague v. Lane, 489 U.S.
288 (1989) (plurality opinion). The proper analysis follows the
model of a decisional tree, with each branch presenting se‐
quential questions of increasing levels of detail. See Chaidez v.
United States, 655 F.3d 684, 688 (7th Cir. 2011) (laying out
Teague’s multi‐step analysis).
No. 19‐2048 9
Worman begs to differ, urging us to refrain from applying
Teague’s retroactivity framework and instead to rely on Bous‐
ley v. United States, 523 U.S. 614 (1998), to conclude that all in‐
terpretations of criminal statutes apply retroactively to cases
on collateral review. We decline the invitation. Bousley ad‐
dressed the retroactivity of Bailey v. United States, 516 U.S. 137
(1999), and decided that Bailey announced a substantive (and
therefore retroactive) rule because it narrowed the scope of a
criminal statute, 18 U.S.C. § 924(c). No court has interpreted
Bousley to sideline or limit Teague’s application. Right to it,
Teague supplies the decisional framework for Worman’s ap‐
peal.
At the outset, Teague requires identification of the rule of
law in question and asks whether it embodies an “old” or
“new” rule. To be “new,” the rule at issue—here, the degree
of sentencing discretion the Supreme Court recognized in
Dean—must not have been dictated by precedent. See Teague,
489 U.S. at 301. If the rule is determined to be old (or, if you
prefer, “not new”), it cannot provide the basis of a claim un‐
der the savings clause because the petitioner could have
raised it earlier. See In re Davenport, 147 F.3d at 610 (explaining
that a § 2241 petition must be based on a claim that the peti‐
tioner “could at no time present in a motion under section
2255, nor earlier in his direct appeal”).
If the rule is new, however, Teague proceeds to require de‐
termining what type of rule the Court announced. See 489
U.S. at 311. So‐called “substantive” rules—which reduce or
enlarge the scope of a criminal statute—are always retroac‐
tive. See Schriro v. Summerlin, 542 U.S. 348, 351–52 (2004). Pro‐
cedural rules, which govern all other aspects of a criminal
proceeding, are retroactive only if they are “watershed.”
10 No. 19‐2048
Teague, 489 U.S. at 311; see also Schriro, 542 U.S. at 352 (ex‐
plaining that habeas petitioners need to make a more de‐
manding showing to rely retroactively on a new procedural
rule because changes to procedure have a “more speculative
connection to innocence” than substantive rules). To make
that determination, we must look closer at the content of the
rule and decide whether it goes to the fundamental fairness
and accuracy of the criminal proceeding. See Teague, 489 U.S.
at 313 (limiting retroactive effect to “those new procedures
without which the likelihood of an accurate conviction is se‐
riously diminished”).
Starting from the beginning—with the threshold old or
new rule question—the answer is easy: Dean is new because
the rule the Court announced, the sentencing discretion it rec‐
ognized, was not compelled by any prior precedent. Recall
that the Eighth Circuit’s precedent in place at the time of
Worman’s initial sentencing precluded the district court from
exercising the very discretion that led to the 361‐month sen‐
tence. See, e.g., United States v. Dean, 810 F.3d 521 (8th Cir.
2015); see also Chaidez, 655 F.3d at 689 (noting that a Supreme
Court rule is likely to be new “if the lower courts were split
on the issue”). Indeed, Dean itself made its way to the Su‐
preme Court from the Eighth Circuit. Put differently, it took
the Supreme Court deciding Dean to reveal the error in the
Eighth Circuit’s law, settle a circuit split, and announce a new
rule.
The next fork in the road comes with determining whether
Dean announced a new substantive or procedural rule. By its
terms, Dean is only about the proper and available scope of
discretion district judges can exercise in sentencing defend‐
ants like Worman, who find themselves facing a § 924(c)
No. 19‐2048 11
mandatory minimum and a separate sentence for one or more
§ 924(c) predicate offenses. That means the rule announced in
Dean is procedural, not substantive. Dean, in short, regulates
sentencing procedure, with the Court leaving untouched the
reach of any criminal statute. See Welch v. United States, 136 S.
Ct. 1257, 1264–65 (2016) (distinguishing between procedural
rules, which have “to do with the range of permissible meth‐
ods a court might use,” and substantive rules, such as the one
announced in Johnson, which invalidated the Armed Career
Criminal Act’s residual clause and thereby redefined the
range of conduct punishable by the Act).
The final branch in Teague’s decisional tree requires asking
whether the new procedural rule announced in Dean consti‐
tutes a so‐called “watershed rule”—a rule both necessary to
prevent “an impermissibly large risk” of an inaccurate con‐
viction and which changes our understanding of the “bedrock
procedural elements” essential to the fairness of a proceeding.
Teague, 489 U.S. at 311–13; see also Whorton v. Bockting, 549
U.S. 406, 418 (2007) (applying Teague and identifying the same
twofold inquiry at this step). If this dimension of the Teague
analysis sounds demanding, that is the right reaction. With
the exception of Gideon v. Wainwright, 372 U.S. 335 (1963), the
landmark decision recognizing an indigent criminal defend‐
ant’s right to counsel, the Supreme Court has not identified
any other procedural rules qualifying for watershed status.
See Whorton, 549 U.S. at 418 (emphasizing that “in the years
since Teague, [the Court] has rejected every claim that a new
rule satisfie[s] the requirements for watershed status”).
It is this final hurdle that Worman cannot clear. Dean did
not establish a watershed rule of criminal procedure, and we
reach that conclusion by heeding the Supreme Court’s
12 No. 19‐2048
emphasis in Teague itself that it is “unlikely that many such
components of basic due process have yet to emerge.” 489
U.S. at 313. No court has held otherwise.
Consider, too, the many other new procedural rules that
have fallen short of watershed status. A prime example came
in Crawford v. Washington, 541 U.S. 36 (2004). The Court in
Crawford held that the Sixth Amendment’s Confrontation
Clause prohibits the use of out‐of‐court testimonial state‐
ments at trial unless that witness is unavailable and the de‐
fendant had a prior opportunity for cross‐examination. Id. at
68. Crawford worked a sea change in criminal procedure—a
point many commentators recognized. See, e.g., Robert P.
Mosteller, Crawford v. Washington: Encouraging and Ensuring
the Confrontation of Witnesses, 39 U. RICH. L. REV. 511, 626
(2005) (“After Crawford, the world of confrontation law has
been radically altered.”). Yet three years later, in its 2007 deci‐
sion in Whorton, a unanimous Supreme Court concluded that
Crawford did not announce a new watershed rule of criminal
procedure. See 549 U.S. at 421. Crawford did not qualify, the
Court explained, because the confrontation right recognized
there was not a “profound and sweeping change” that rede‐
fined our understanding of what a fair proceeding requires.
Id. If a new Supreme Court case meaningfully expanding a
defendant’s right to confront witnesses does not sufficiently
implicate the fundamental fairness and accuracy of a proceed‐
ing to be a watershed rule, a rule governing what a judge may
consider at sentencing cannot either.
* * *
We are not blind to how difficult this opinion will be for
John Worman to read. Yes, he committed a horrific crime—
sending a pipe bomb to his former supervisor. And yes, the
No. 19‐2048 13
district court was right to conclude that Worman deserved a
substantial sentence. But so, too, is there no doubt that the dis‐
trict court believed that a 361‐month sentence was adequate,
leaving Worman in jail until he was 84. That exercise of sen‐
tencing discretion likely would have stood had the Supreme
Court decided Dean before Worman filed his first § 2255 mo‐
tion seeking resentencing. That timing, of course, is nothing
Worman had any control over, and it is hard to fault him for
choosing to file his first § 2255 motion. He did so pro se, with‐
out the benefit of counsel and surely in a good‐faith effort to
reduce his sentence. But it is the timing of Dean, when applied
to the very stringent demands imposed on second and succes‐
sive § 2255 motions as well as requests for traditional relief
under § 2241, that requires us to AFFIRM.