United States v. Anthony Pemberton

In the
United States Court of Appeals
For the Seventh Circuit
____________________
No. 21-3224
UNITED STATES OF AMERICA,
Plaintiff-Appellee,
v.
ANTHONY PEMBERTON,
Defendant-Appellant.
____________________
Appeal from the United States District Court for the
Southern District of Indiana, Indianapolis Division.
No. 1:19-CR-00268-001 — Tanya Walton Pratt, Chief Judge.
____________________
ARGUED OCTOBER 3, 2023 — DECIDED NOVEMBER 1, 2023
____________________
Before BRENNAN, SCUDDER, and ST. EVE, Circuit Judges.
PER CURIAM. Anthony Pemberton sold methamphetamine
to an undercover informant and pleaded guilty to distrib-
uting drugs, 21 U.S.C. § 841(a)(1). The district court then ruled
that his 2003 conviction for conspiracy to commit robbery un-
der Indiana law was a “serious violent felony” under
18 U.S.C. § 3559(c)(2)(F), thereby subjecting him to a 15-year
mandatory minimum sentence. On appeal he argues that In-
diana’s crime of conspiracy is not a categorical match to the
2 No. 21-3224
federal conspiracy counterpart of § 3559(c)(2)(F) and thus the
state crime is not a “serious violent felony” meriting the en-
hanced minimum. But Pemberton raised this argument for
the first time on appeal and therefore forfeited it. Because he
has not demonstrated that the district court plainly erred
when it determined his prior conviction was a serious violent
felony, we affirm.
I. Background
Pemberton was sentenced after he pleaded guilty to two
counts of possessing and distributing at least 50 grams of
methamphetamine in 2019, 21 U.S.C. § 841(a)(1). At sentenc-
ing, the parties disputed which statutory minimum sentence
applied. Ordinarily, distributing the quantity of drugs Pem-
berton admitted to distributing carries a 10-year minimum
sentence under § 841(b)(1)(A)(viii). But if the defendant was
previously convicted of a “serious violent felony," a 15-year
minimum applies. Id. The phrase “serious violent felony” is
defined in 21 U.S.C. § 802(58), which cross-references the def-
inition in 18 U.S.C. § 3559(c)(2)(F). The government identified
a prior conviction that might satisfy that definition: Pember-
ton’s 2003 conviction under Indiana law for conspiracy to
commit robbery, Ind. Code 35-41-5-2.
Pemberton objected to the application of the enhanced
mandatory minimum on two grounds related to the circum-
stances of his offense. First, he argued that the facts underly-
ing his 2003 conviction fell under an exception to the defini-
tion of “serious violent felony” where no dangerous weapon
was used. See 18 U.S.C. § 3559(c)(3)(A). On appeal, he aban-
dons this argument. Second, he contended that his particular
conduct did not qualify as a conspiracy under federal law. In
his view, a conspiracy under federal law required an
No. 21-3224 3
agreement between two people to commit an unlawful act.
But in his case, only his coparticipant carried a weapon, Pem-
berton had not agreed that his coparticipant would carry a
weapon, and his coparticipant was never convicted. There-
fore, Pemberton argued, he was not guilty of conspiracy un-
der federal law.
The district court overruled the objections, found that
Pemberton’s 2003 conviction was a “serious violent felony,”
and sentenced Pemberton to 15 years’ imprisonment and
10 years’ supervised release. It reasoned that the facts of his
2003 crime included a dangerous weapon that caused serious
harm (his coconspirator had fired a gun during the robbery,
hitting a bystander), and his plea of guilty to conspiracy to
commit armed robbery precluded him from denying his in-
volvement in a conspiracy. After that ruling, both Pemberton
and the government argued for the 15-year minimum sen-
tence, and the court adopted that recommendation after con-
sidering the parties’ arguments and 18 U.S.C. § 3553(a) fac-
tors.
II. Analysis
On appeal, Pemberton has reframed his objection to the
enhancement. Rather than focus on the facts of his crime, he
now argues that his Indiana conviction for conspiracy to com-
mit robbery is not a categorical match to the generic federal
offense of conspiracy, and therefore falls outside the defini-
tion of “serious violent felony” in 18 U.S.C. § 3559(c)(2)(F) and
21 U.S.C. § 802(58). He contends (and the government agrees)
that Indiana conspiracy covers both “bilateral” and “unilat-
eral” conspiracies; the latter involves a person who agrees to
commit a crime with, for example, an undercover agent who
does not sincerely conspire to break the law. See Tidwell v.
4 No. 21-3224
State, 644 N.E.2d 557, 559 (Ind. 1994). Pemberton contends
that the generic federal definition of conspiracy is narrower.
In his view, federal conspiracy generally requires a bilateral
agreement between two or more people who intend to com-
mit a crime. See United States v. Corson, 579 F.3d 804, 811 (7th
Cir. 2009). The government responds that Pemberton for-
feited this categorical-mismatch argument. Therefore, it con-
cludes, our review is limited to whether the district court
plainly erred. It also contends that on the merits the generic
federal definition of conspiracy includes unilateral conspira-
cies. Thus, it insists, the district court properly applied the en-
hanced mandatory minimum.
Before we address the issue of forfeiture, we clarify further
the legal background and where the parties agree. A “serious
violent felony” is “a Federal or State offense … consisting of
… robbery (as described in [18 U.S.C.] section 2111, 2113, or
2118) … or attempt, conspiracy, or solicitation to commit any
of the above offenses.” 18 U.S.C. § 3559(c)(2)(F)(i). Pemberton
does not dispute that Indiana’s offense of robbery qualifies as
“robbery” under § 3559. The parties dispute only whether a
conspiracy offense under Indiana law qualifies as a state “con-
spiracy” offense for purposes of § 3559. In squaring off, the
parties also agree that the answer requires resort to the famil-
iar categorical approach, under which this court must com-
pare the least-culpable conduct of the state offense with the
generic federal offense. Mathis v. United States, 579 U.S. 500,
509 (2016). If the state offense sweeps more broadly than the
generic federal offense, then the defendant does not qualify
for the enhancement. Id.; see also United States v. Elder, 900 F.3d
491, 499 (7th Cir. 2018) (applying the categorical approach to
a separate 21 U.S.C. § 841 enhancement for “felony drug of-
fense”); accord United States v. Leaverton, 895 F.3d 1251, 1254
No. 21-3224 5
(10th Cir. 2018) (applying categorical approach to “serious vi-
olent felony” definition).
That brings us to the issue of forfeiture. If Pemberton
raised his argument about a categorial mismatch for the first
time on appeal, then our review of the district court’s appli-
cation of the enhancement is deferential: We review the appli-
cation only for plain error—an error that is obvious and af-
fects the defendant’s substantial rights as well as the fairness
and integrity of the judicial proceeding. See FED R. CRIM.
P. 52(b); Puckett v. United States, 556 U.S. 129, 135 (2009).
Pemberton contends that his argument on appeal about a
categorical mismatch is consistent with his fact-based objec-
tion to the enhancement in the district court. We disagree.
Nothing about Pemberton’s fact-based arguments in the dis-
trict court alerted the judge and the government to the cate-
gorical-mismatch argument he now raises. As mentioned ear-
lier, Pemberton raised two fact-based arguments about the se-
rious violent felony enhancement in the district court: (1) the
exception at § 3559(c)(3) applied to the facts underlying his
conviction, and (2) the facts of his Indiana conviction showed
he did not conspire to commit robbery. But these two case-
specific inquiries are incompatible with the purely legal, cat-
egorical-approach argument he now raises. For under the cat-
egorical approach, judges cannot even consider the “underly-
ing brute facts” of the conviction. Mathis, 579 U.S. at 509 (in-
ternal quotation marks omitted). Because Pemberton’s objec-
tion did not challenge the enhancement on categorical
grounds, he forfeited the objection. See United States v. Thomas,
845 F.3d 824, 831 (7th Cir. 2017).
We thus must limit our review to whether the district
court plainly erred in applying the enhancement for a
6 No. 21-3224
“serious violent felony.” Under that standard, “the district
court commits plain error when there is ‘(1) an error or defect,
(2) that is clear or obvious (3) affecting the defendant’s sub-
stantial rights (4) and seriously impugning the fairness, integ-
rity, or public reputation of judicial proceedings.’” United
States v. Hammond, 996 F.3d 374, 400 (7th Cir. 2021) (quoting
United States v. Goodwin, 717 F.3d 511, 518 (7th Cir. 2013)).
Here, we must decide whether it is “obvious,” Puckett,
556 U.S. at 135, that conspiracy under Indiana law in 2003 was
broader than the federal definition of conspiracy. As we now
explain, that is not obvious.
In determining whether the federal definition of conspir-
acy matches Indiana’s broad, “unilateral” approach, we ex-
amine the generic definition of conspiracy in 1994, when Con-
gress enacted the sentencing enhancement for a “serious vio-
lent felony.” The government urges us to examine generic
trends in the criminal law of conspiracy that occurred after
Congress enacted the enhancement. But we think the categor-
ical approach requires us to consider the generic offense of
conspiracy as defined at the time of passage in 1994. Accord
Pugin v. Garland, 599 U.S. 600, 604 (2023) (relying on diction-
aries from time of enactment to determine generic offense);
Esquivel-Quintana v. Sessions, 581 U.S. 385, 391 (2017) (same).
In doing so, we consider contemporaneous federal and state
laws, dictionary definitions, and the Model Penal Code. Pu-
gin, 600 U.S. at 604.
When we examine the state of the law in 1994, we see sig-
nals that point in opposite directions for the generic meaning
of conspiracy. On the one hand, as Pemberton contends, fed-
eral conspiracy law has historically followed the bilateral-
only approach. The Supreme Court has observed that federal
No. 21-3224 7
law has followed the bilateral approach to conspiracies be-
cause a genuine agreement among two or more people to
commit a crime increases the reach of the crime, the chance
that it will succeed, and the threat to the public. See Callanan
v. United States, 364 U.S. 587, 593–94 (1961); see also Salinas v.
United States, 522 U.S. 52, 65 (1997). Federal drug coconspira-
tors, for example, must “actually intend to carry out the
agreed-upon criminal plan.” Corson, 579 F.3d at 811. Likewise,
“[a] defendant is not liable for conspiring solely with an un-
dercover government agent or a government informant.” Id.(citing United States v. Mahkimetas, 991 F.2d 379, 383 (7th Cir.
1993)). This historical evidence points toward a categorical
mismatch between the federal definition of conspiracy and In-
diana’s.
On the other hand, when § 3559 was enacted in 1994,
many states, including Indiana, had adopted the unilateral
approach, which the Model Penal Code endorsed. The Code
requires only that a coconspirator “agree (or believe he is
agreeing) with another” to commit a crime. Model Penal Code
§ 5.03(1)(a) & n.1. The adoption was not universal, and even
some states that adopted the Model Penal Code still rejected
the unilateral theory of conspiracy. See, e.g., People v. Foster,
457 N.E.2d 405, 408 (Ill. 1983). Nonetheless, by 1994, a signifi-
cant minority of jurisdictions—20 states and territories, ac-
cording to Pemberton—had adopted the unilateral theory of
conspiracy. See 1 Wharton’s Crim. L. § 8.4 (rev. Sept. 2023).
This widening acceptance suggests that the generic federal
definition of conspiracy may similarly include the unilateral
theory.
Against this backdrop, we conclude that the answer to
whether Indiana’s definition of conspiracy is a categorical
8 No. 21-3224
mismatch to the federal counterpart is unclear. Because state
and federal authorities point in different directions, it is not
obvious that the generic definition of conspiracy in 1994 either
included or excluded the unilateral theory of conspiracy. And
because it is not obvious, the district court did not plainly err
in applying the enhancement for a “serious violent felony”
based on the 2003 Indiana conspiracy conviction. See United
States v. Thomas, 835 F.3d 730, 734 (7th Cir. 2016) (“While there
are good arguments on each side of the debate, the fact that
the law is unsettled itself prevents any discovery violation
from being plain error.”); United States v. Dominguez Benitez,
542 U.S. 74, 82 (2004) (the plain-error burden “should not be
too easy”). The answer to the question of the generic meaning
of conspiracy must wait for a case in which it has been pre-
served.
Pemberton cautions that this result creates a circuit split
because the Ninth Circuit has held that the generic federal
conspiracy offense includes only bilateral conspiracies.
See United States v. Brown, 879 F.3d 1043, 1048 (9th Cir. 2018).
But that overlooks the difference in the standard of review.
The defendant in Brown preserved the objection, and so the
court reached the issue on a fresh slate. See id. As we have
previously said, the standard of review can make a difference
in the outcome of a case. See United States v. Haas, 37 F.4th
1256, 1265 (7th Cir. 2022) (reviewing an issue for plain error
does not require this court to “choose sides” of a circuit split).
The Tenth Circuit, for example, when applying plain-error re-
view to a district court’s decision defining generic conspiracy
under the Sentencing Guidelines, affirmed the district court’s
use of the unilateral approach. See United States v. Maloid,
71 F.4th 795, 816 (10th Cir. 2023).
No. 21-3224 9
Finally, in his reply brief, Pemberton asks us to delay our
decision in this case. He notes that he might be eligible for re-
lief from the 15-year minimum through the “safety valve” of
18 U.S.C. § 3553(f) if the Supreme Court overturns our prece-
dent in United States v. Pace, 48 F.4th 741, 756 (7th Cir. 2020),
when the Court decides Pulsifer v. United States, No. 22-340
(argued Oct. 2, 2023). Because Pemberton has sought to pre-
serve his argument for Supreme Court review, we deny his
request to stay the case until the Court decides Pulsifer.
Thus, we AFFIRM the judgment of the district court.