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 mustreceive 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.