Stegemann v. United States

23-7712
Stegemann v. United States
In the
United States Court of Appeals
FOR THE SECOND CIRCUIT
A UGUST TERM 2024
No. 23-7712
JOSHUA G. S TEGEMANN ,
Petitioner-Appellant,
v.
U NITED STATES OF A MERICA,
Appellee.*
On Appeal from the United States District Court
for the Northern District of New York
A RGUED: NOVEMBER 21, 2024
D ECIDED: MARCH 20, 2025
Before: L IVINGSTON, Chief Judge, and JACOBS and MENASHI,
Circuit Judges.
Petitioner-Appellant Joshua G. Stegemann appeals from a
judgment of the district court denying his sixth motion to amend his
§ 2255 petition. Stegemann sought to amend his petition to add a
* The Clerk of Court is directed to amend the caption as set forth above.

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claim that his counsel was ineffective for failing to argue that his prior
conviction under Massachusetts General Laws ch. 94C, § 32E(b), did
not qualify as a “controlled substance offense” under the sentencing
guidelines because the “bringing in” provision of the state statute
criminalizes conduct that federal law does not. The district court
denied leave to amend because the proposed amendment repeated an
argument that the Second Circuit had already rejected in Stegemann’s
prior appeal. We agree with the district court that Stegemann’s
motion to amend was properly denied as futile because he has not
provided a sufficient justification to depart from the law of the case.
We affirm the judgment of the district court.
Z ACHARY S. S EGAL (Richard W. Levitt, on the brief), Levitt
& Kaizer, New York, NY, for Petitioner-Appellant.
RAJIT S. D OSANJH , Assistant United States Attorney
(Richard D. Belliss, Assistant United States Attorney, on
the brief), for Carla B. Freedman, United States Attorney
for the Northern District of New York, Syracuse, NY, for
Appellee.
MENASHI, Circuit Judge:
Petitioner-Appellant Joshua G. Stegemann appeals from an
order of the U.S. District Court for the Northern District of New York,
entered on October 18, 2023, denying Stegemann’s sixth motion for
leave to amend his § 2255 petition. Stegemann challenges the
determinations of the district court that (1) his motion for leave to
amend was dilatory or otherwise abusive and (2) the amendment
would be futile. We agree with the district court that Stegemann’s

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motion for leave to amend was properly denied as futile, so we need
not decide whether the motion was also dilatory or otherwise
abusive. We affirm the judgment of the district court.
BACKGROUND
In August 2015, Stegemann was convicted following a jury trial
of (1) possession of cocaine, heroin, and oxycodone with intent to
distribute in violation of 21 U.S.C. § 841(a)(1) and (b)(1)(B);
(2) possession of firearms in furtherance of a drug trafficking crime in
violation of 18 U.S.C. § 924(c)(1)(A); and (3) possession of firearms
and ammunition by a convicted felon in violation of 18 U.S.C.
§ 922(g)(1). The Presentence Investigation Report identified
Stegemann as a “career offender” based on (1) his 1999 conviction in
Massachusetts for trafficking cocaine in violation of Massachusetts
General Laws ch. 94C, § 32E(b), and (2) his 2003 conviction in
Massachusetts for distribution of cocaine. Stegemann was sentenced
to an aggregate term of imprisonment of 360 months. The district
court entered judgment on July 20, 2016, and this court affirmed the
judgment on direct appeal. See United States v. Stegemann, 701
F. App’x 35, 36 (2d Cir. 2017).
On June 28, 2018, Stegemann moved to vacate his conviction
and sentence pursuant to 28 U.S.C. § 2255, raising multiple claims of
ineffective assistance of counsel. The district court permitted
Stegemann to amend his petition five times to add additional claims,
including the claim that his sentencing attorney was ineffective for
failing to argue that neither his 1999 nor his 2003 Massachusetts
conviction qualified as a “controlled substance offense” for the
purpose of the career offender guideline. On June 30, 2020, the district
court denied Stegemann’s § 2255 petition in its entirety and declined
to issue a certificate of appealability. This court granted a motion for

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a certificate of appealability for issues including the claim of
ineffective assistance.
On appeal, Stegemann abandoned his argument regarding his
2003 conviction and argued instead that his counsel was ineffective
for failing to assert at sentencing that his 1999 Massachusetts
conviction under § 32E(b) did not qualify as a “controlled substance
offense” under U.S.S.G. § 4B1.2. The sentencing guidelines define
“controlled substance offense” to include a prohibition on the
“import” of a controlled substance. According to Stegemann, the
word “import” must be understood to refer to the importation into
the United States from abroad. Because the Massachusetts statute
prohibits the “bringing in” of a controlled substance from anywhere
out of state—even from another state—the scope of the state statute
exceeds the guidelines definition. Our court rejected the “bringing in”
theory and affirmed the decision of the district court. We reasoned as
follows:
Stegemann cites to no authority to support his claim that,
at the time of his sentencing, his 1999 conviction under
Mass. Gen. Laws ch. 94C, § 32E(b) did not qualify as a
predicate under the career offender enhancement. To the
contrary, while Stegemann’s conviction was on direct
appeal, the First Circuit expressly held that this statute
was “unarguably a conviction for a controlled substance
offense and, thus, a proper predicate offense under the
career offender guideline.” United States v. Montoya, 844
F.3d 63, 72 (1st Cir. 2016). On that basis alone, counsel’s
decision to forego such a legal argument cannot be said
to fall below prevailing professional norms. Nor can it be
argued that Stegemann was prejudiced by that decision,
since it is not reasonably probable that the district court
would have credited the argument and reached a

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conclusion at odds with the First Circuit’s subsequent
holding on the same issue.
Stegemann v. United States, No. 20-3772, 2022 WL 17072983, at *3 (2d
Cir. Nov. 18, 2022) (citation omitted). Stegemann moved for
reconsideration and for rehearing en banc, which this court denied.
Shortly before filing the motion for reconsideration and for rehearing,
Stegemann also filed a “Motion for Resentencing under 28 U.S.C.
§ 2255” in the district court, again reiterating the claim that his 1999
Massachusetts conviction did not qualify as a controlled substance
offense because of the “bringing in” theory. The district court treated
this filing as a motion for leave to amend Stegemann’s § 2255 petition
yet again and denied the motion—as well as a certificate of
appealability—because “the gist of the argument raised in the filing
… was previously raised and rejected by this court and the Second
Circuit on appeal.” App’x 31. We granted a motion for a certificate of
appealability to challenge the denial of leave to amend. This appeal
followed.
STANDARD OF REVIEW
We review the denial of a motion for leave to amend for abuse
of discretion. See Littlejohn v. Artuz, 271 F.3d 360, 362 (2d Cir. 2001). If
the denial of leave to amend was based on a legal interpretation,
however, we consider the legal question de novo. Id. Federal Rule of
Civil Procedure 15(a) provides the standard for addressing a motion
for leave to amend a habeas petition. See id. at 363. Under Rule 15(a),
“a party may amend its pleading only with the opposing party’s
written consent or the court’s leave. The court should freely give leave
when justice so requires.” Fed. R. Civ. P. 15(a)(2). “[A]lthough Rule
15 requires that leave to amend be ‘freely given,’ district courts
nonetheless retain the discretion to deny that leave in order to thwart
tactics that are dilatory, unfairly prejudicial or otherwise abusive.”

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Littlejohn, 271 F.3d at 363. Moreover, “a district court may properly
deny leave when amendment would be futile.” Jones v. N.Y. State Div.
of Mil. & Naval Affs., 166 F.3d 45, 50 (2d Cir. 1999).
DISCUSSION
In Stegemann’s prior appeal, this court considered and rejected
the argument that his sentencing counsel was ineffective for not
challenging the use of his 1999 Massachusetts conviction as a
predicate for designating him a career offender. The district court was
bound to follow that decision by the mandate rule, an aspect of the
law-of-the-case doctrine “that ‘rigidly binds the district court,’
barring it from considering issues ‘explicitly or implicitly decided on
appeal,’” United States v. Aquart, 92 F.4th 77, 87 (2d Cir. 2024) (quoting
Burrell v. United States, 467 F.3d 160, 165 (2d Cir. 2006)), and even from
considering “issues that were ripe for review at the time of an initial
appeal but nonetheless foregone by a party,” id. (internal quotation
marks and alteration omitted). For that reason, the district court was
correct to recognize that the proposed amendment—which repeated
the argument our court had already considered—was futile.
To be sure, “the law-of-the-case doctrine does not bind this
court with the same rigidity that the mandate rule binds the district
court,” but “we have consistently recognized it to reflect a sound
policy that we should depart from sparingly and only when
presented with cogent and compelling reasons.” Id. (internal
quotation marks and citation omitted). The “major grounds”
justifying such a departure are “an intervening change of controlling
law, the availability of new evidence, or the need to correct a clear
error or prevent manifest injustice.” United States v. Tenzer, 213 F.3d
34, 39 (2d Cir. 2000) (quoting Doe v. N.Y.C. Dep’t of Soc. Servs., 709 F.2d
782, 789 (2d Cir. 1983)). Stegemann argues that these grounds are

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present here because (1) the prior panel erred by relying on Montoya,
considering the purported ambiguity of the statute of conviction in
that case, (2) the subsequent decision in United States v. Bain, No. 14-
CR-10115, 2022 WL 4494036 (D. Mass. Jan. 14, 2022), provides new
support for the “bringing in” theory, and (3) the use of his 1999
Massachusetts conviction as a career offender predicate represents a
clear error that produced a manifest injustice. We consider each
argument in turn.
I
First, Stegemann argues that the First Circuit misidentified the
statute of conviction in Montoya and therefore the prior panel erred in
relying on that decision for the proposition that § 32E qualifies as a
controlled substance offense under the guidelines. In support of his
argument, Stegemann produces a letter from the Massachusetts
Supreme Judicial Court identifying § 32A(d) as the statute under
which Montoya was convicted.
We are not persuaded. The Montoya opinion expressly
identifies and discusses § 32E, see Montoya, 844 F.3d at 72 (“First, the
defendant has a prior state conviction for cocaine distribution. See
Mass. Gen. Laws ch. 94C, § 32E.”), and the prior panel cited Montoya
only for the proposition that such case law existed shortly after
Stegemann’s sentencing. The prior panel was not bound by Montoya
and did not purport to be so bound. Rather, in assessing Stegemann’s
argument that his counsel was ineffective, the prior panel evaluated
whether the failure to advance an argument based on the “bringing
in” theory “fell below an objective standard of reasonableness under
‘prevailing professional norms’” and could have affected the outcome
of the proceeding. Stegemann, 2022 WL 17072983, at *1 (quoting
Strickland v. Washington, 466 U.S. 668, 688 (1984)).

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That analysis depended on the legal landscape at the time of
the sentencing. The prior panel noted that Stegemann “cites to no
authority to support his claim that, at the time of his sentencing, his
1999 conviction under … § 32E(b) did not qualify as a predicate under
the career offender enhancement.” Id. at *3. It remains true that, at the
time of his sentencing, no authority supported the proposition that a
conviction under § 32E(b) did not qualify as a career offender
predicate—whether or not Montoya eventually pointed in the other
direction—and no change in controlling law has called into question
the conclusions of the prior panel that “counsel’s decision to forego
such a legal argument cannot be said to fall below prevailing
professional norms” and that “it is not reasonably probable that the
district court would have credited the argument.” Id.
II
Second, Stegemann suggests that the district court opinion in
Bain justifies a departure from the law of the case. In Bain, the U.S.
District Court for the District of Massachusetts concluded that a
defendant’s counsel engaged in deficient performance by failing to
argue that § 32E(b) did not qualify as a “serious drug offense” under
the Armed Career Criminal Act (“ACCA”). See 18 U.S.C. § 924(e)
(defining “serious drug offense” as “an offense under State law,
involving manufacturing, distributing, or possessing with intent to
manufacture or distribute, a controlled substance”). The district court
further held that if the counsel “had objected to the use of the
trafficking statute as an ACCA predicate at trial, there is a reasonable
probability the court would have found that ‘bringing into the
commonwealth’ was not a serious drug crime” because “[b]ringing
into the commonwealth lacks a connection to manufacturing or
distributing, or possessing with the intent to do either.” Bain, 2022 WL
4494036, at *5.

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“[T]he standard for showing a change in law sufficient to avoid
the mandate rule or law-of-the-case doctrine” demands “that more
than ‘mere doubt’ is necessary to reconsider prior decisions.” Aquart,
92 F.4th at 92 (quoting Fogel v. Chestnutt, 668 F.2d 100, 109 (2d Cir.
1981)). Instead, “[t]he law of the case will be disregarded only when
the court has ‘a clear conviction of error’ with respect to a point of law
on which its previous decision was predicated.” Fogel, 668 F.2d at 109
(quoting Zdanok v. Glidden Co., 327 F.2d 944, 953 (2d Cir. 1964)).
The district court in Bain concluded that “bringing in” under
§ 32E(b) could not qualify as a “serious drug offense” as the ACCA
defines that term because the act of bringing a drug into the state does
not involve “manufacturing, distributing, or possessing with intent to
manufacture or distribute” the drug. 18 U.S.C. § 924(e). The
sentencing guidelines, however, do not define “controlled substance
offense” by reference to the same activities. Under the guidelines, a
“controlled substance offense” is an offense “under federal or state
law … that prohibits the manufacture, import, export, distribution, or
dispensing of a controlled substance.” U.S.S.G. § 4B1.2(b)(1). Bain
does not answer the question of whether “bringing in” a drug violates
a law that prohibits its “import.” That is because such a law qualifies
as a “controlled substance offense” under the guidelines but not as a
“serious drug offense” under the ACCA. Given that distinction, Bain
cannot create “a clear conviction of error” with respect to the legal
conclusion on which the prior panel relied. Fogel, 668 F.2d at 109
(quoting Zdanok, 327 F.2d at 953).
Moreover, it is undisputed that Bain was (1) decided after
Stegemann’s sentence was final (2) by a district court in another
circuit. For those reasons, it represents neither an intervening change
in controlling law nor new evidence that would justify a departure

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from the decision of the prior panel regarding the legal landscape at
the time of sentencing.
III
Third, Stegemann argues that the prior panel’s rejection of the
“bringing in” theory reflects a clear error such that reconsideration is
necessary to avoid a manifest injustice. We again disagree.
The sentencing guidelines define “controlled substance
offense” to include the violation of a “state or federal law” that
prohibits the “import” of a controlled substance. U.S.S.G.
§ 4B1.2(b)(1). The word “import” means “to bring from a foreign or
external source.” Import, Merriam-Webster’s Third New International
Dictionary 1135 (1981). The plain meaning of “import” therefore
includes “bringing in” a controlled substance from out of state—
which means that a conviction under § 32E(b) qualifies as a controlled
substance offense under the guidelines.
Stegemann invokes the Jerome presumption, according to
which “we must generally assume, in the absence of a plain indication
to the contrary, that Congress when it enacts a statute is not making
the application of the federal act dependent on state law.” Jerome v.
United States, 318 U.S. 101, 104 (1943). He observes that we have
applied the Jerome presumption to the term “controlled substance” in
order to conclude that it “must refer exclusively to those drugs listed
under federal law” because otherwise the guidelines enhancement
would turn on a state decision to control a substance that federal law
leaves uncontrolled. United States v. Townsend, 897 F.3d 66, 71 (2d Cir.
2018). In Stegemann’s view, the term “import” must also refer
exclusively to the concept of importation under federal law—which
would mean that it refers only to importation from abroad. See

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21 U.S.C. § 952(a) (prohibiting the importation of a controlled
substance “into the United States from any place outside thereof”).
We do not agree that the term “import” in § 4B1.2 must be so
limited. In Townsend, we identified an “ambiguity in defining
‘controlled substance’” because that term of art must refer to those
drugs proscribed by a particular body of law. Townsend, 897 F.3d at
70. We see no similar ambiguity in the words describing the conduct
of an offender—that is, “the manufacture, import, export,
distribution, or dispensing” of the drugs. U.S.S.G. § 4B1.2(b)(1).
Accordingly, there is no obstacle to applying the normal principle that
an undefined term receives its ordinary meaning. See Asgrow Seed Co.
v. Winterboer, 513 U.S. 179, 187 (1995) (“When terms used in a statute
are undefined, we give them their ordinary meaning.”). 1 The
“import” of a drug may be prohibited under federal or state law, and
the term naturally refers to bringing the controlled substance into the
relevant jurisdiction. There is no indication that the Sentencing
Commission referred only to importation from abroad; to the
contrary, the Commission referred to a “federal or state law” that
“prohibits” the “import” of a controlled substance. U.S.S.G.
1 See also Smith v. United States, 508 U.S. 223, 242 (1993) (Scalia, J., dissenting)
(“In the search for statutory meaning, we give nontechnical words and
phrases their ordinary meaning.”); Chapman v. United States, 500 U.S. 453,
461-62 (1991) (“Neither the statute nor the Sentencing Guidelines define the
terms ‘mixture’ and ‘substance,’ nor do they have any established common-
law meaning. Those terms, therefore, must be given their ordinary
meaning.”); Moskal v. United States, 498 U.S. 103, 108 (1990) (“In determining
the scope of a statute, we look first to its language, giving the words used
their ordinary meaning.”) (internal quotation marks and citation omitted);
Perrin v. United States, 444 U.S. 37, 42 (1979) (“A fundamental canon of
statutory construction is that, unless otherwise defined, words will be
interpreted as taking their ordinary, contemporary, common meaning.”).

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§ 4B1.2(b)(1) (emphasis added). And there is no danger—as there was
in Townsend—that giving the term “import” its ordinary meaning
would allow the enhancement to turn on a state’s decision to
proscribe conduct that bears no resemblance to the federally
proscribed conduct. Unlike “controlled substance,” the term “import”
has an ordinary meaning independent of a particular body of law.2
In our view, therefore, the definition of “controlled substance
offense” under § 4B1.2 includes a state law offense such as that under
§ 32E(b) prohibiting the “bringing in” of drugs from out of state. For
that reason, we see no clear error in the prior panel’s decision and no
manifest injustice that warrants its reconsideration.
CONCLUSION
Because Stegemann identifies no circumstances that warrant a
departure from the law of the case, it would have been futile to amend
the petition to reassert the same “bringing in” theory that was
2 We recognize that in United States v. Martinez, the Ninth Circuit decided
that the term “import” in § 4B1.2(b) “must necessarily mean importing
across an international border.” 232 F.3d 728, 732 (9th Cir. 2000). It did so
after observing that “a federal sentencing enhancement provision such as
the career criminal guideline here at issue is interpreted according to a
uniform, national definition, not dependent upon the vagaries of state law.”
Id. (citing Taylor v. United States, 495 U.S. 575, 591-92 (1990)). In Taylor, the
Supreme Court said that an enhancement should turn on “the generally
accepted contemporary meaning of a term” in the federal statute rather
than “depend upon the label employed by the State of conviction.” Taylor,
495 U.S. at 596, 589; see id. at 603 (Scalia, J., concurring in part and concurring
in the judgment) (“The Court says, correctly, that the statutory term
‘burglary’ has a ‘generally accepted contemporary meaning’ which must be
given effect.”). Here, we conclude that the guidelines term “import” has an
accepted ordinary meaning that does not depend on vagaries of state law.
Accordingly, we diverge from the Ninth Circuit’s approach.

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considered and rejected in the prior appeal. The district court did not
abuse its discretion by denying leave to amend. We affirm the
judgment of the district court.

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