United States of America v. Antonio Figueroa

In the
United States Court of Appeals
For the Seventh Circuit
No. 11-2594
UNITED STATES OF AMERICA,
Plaintiff-Appellee,
v.
ANTONIO FIGUEROA,
Defendant-Appellant.
Appeal from the United States District Court
for the Northern District of Illinois, Eastern Division.
No. 10 CR 469-1—Samuel Der-Yeghiayan, Judge.
ARGUED APRIL 25, 2012—DECIDED JUNE 11, 2012
Before POSNER, SYKES, and TINDER, Circuit Judges.
POSNER, Circuit Judge. Section 3B1.1 of the U.S. Sen-
tencing Guidelines provides for an increase in the guide-
line range for a defendant who is found to be an
organizer, leader, manager, or supervisor of criminal
activity. Application Note 4 states (italics added):
In distinguishing a leadership and organizational role
from one of mere management or supervision, titles such
as “kingpin” or “boss” are not controlling. Factors the

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2 No. 11-2594
court should consider include the exercise of decision
making authority, the nature of participation in
the commission of the offense, the recruitment of
accomplices, the claimed right to a larger share of
the fruits of the crime, the degree of participation
in planning or organizing the offense, the nature and
scope of the illegal activity, and the degree of control
and authority exercised over others. There can, of
course, be more than one person who qualifies as
a leader or organizer of a criminal association or con-
spiracy. This adjustment does not apply to a
defendant who merely suggests committing the of-
fense.
Even though, as is obvious from its language, the Ap-
plication Note concerns only the meaning of the terms
“organizer” and “leader,” courts including our own
have on occasion suggested that the seven factors that
the Note says a sentencing judge should consider in
determining whether a defendant is an “organizer” or
“leader” are also helpful in determining whether he is a
“manager” or “supervisor.” E.g., United States v. Howell,
527 F.3d 646, 649 (7th Cir. 2008); United States v. Mustread,
42 F.3d 1097, 1104 (7th Cir. 1994); United States v. Jackson,
639 F.3d 479, 483 (8th Cir. 2011). Other opinions flat out
apply the seven factors to managers and supervisors, in
the teeth of the language that we’ve italicized. See, e.g.,
United States v. Payton, 636 F.3d 1027, 1048 (8th Cir. 2011);
United States v. McDonald, 521 F.3d 975, 978 (8th Cir. 2008);
United States v. Gonzalez Edeza, 359 F.3d 1246, 1248-49 (10th
Cir. 2004); United States v. Taylor, 248 F.3d 506, 515 (6th
Cir. 2001). But United States v. Cali, 87 F.3d 571, 578 (1st

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No. 11-2594 3
Cir. 1996), rejects the applicability of the seven factors
to determining whether a drug dealer is a manager or a
supervisor.
It is odd that the same factors should be thought to
identify a leader and a supervisor—the CEO of a super-
market chain, who is certainly a “leader,” but in addition
to him the head of the produce department at one of the
chain’s supermarkets, who is merely a “supervisor.” A
low-level supervisor does not “exercise . . . decision
making authority,” though virtually any employee has
to make some decisions (for example, whom to wait on
first, if he is a store clerk). The low-level supervisor has
no claim to a share in the “fruits” of the enterprise and
probably no hiring authority (“recruitment”) either. And
he does little in the way of “planning” or “organizing.”
Economy of words is not a defining characteristic
of lawyers, including the lawyers who drafted the sen-
tencing guidelines and application notes and the
lawyers and judges who have drawn on the seven
factors in Application Note 4 to help determine who is
a “supervisor.” The best that can be said for applying
the seven factors to supervisors is that section 3B1.1(c)
provides the same sentencing bonus whether the de-
fendant was an organizer, leader, manager, or supervisor,
if the criminal activity in which he occupied one of
those four roles had fewer than five participants and
was not “otherwise extensive.”
The quoted term is essential to sentence determination
in many cases (of which this case should probably have
been thought one) but is not defined, except that Ap-

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4 No. 11-2594
plication Note 3 to section 3B1.1 states that “in assessing
whether an organization is ‘otherwise extensive,’ all
persons involved during the course of the entire offense
are to be considered. Thus, a fraud that involved only
three participants but used the unknowing services
of many outsiders could be considered extensive.”
Some circuits hold that for an organization to be “other-
wise extensive” the number of participants plus out-
siders must be five or more (for example, three par-
ticipants and two outsiders), United States v. Skys, 637
F.3d 146, 156-58 (2d Cir. 2011); United States v. Anthony, 280
F.3d 694, 699-701 (6th Cir. 2002); United States v. Wilson, 240
F.3d 39, 47-51 (D.C. Cir. 2001); United States v. Helbling,
209 F.3d 226, 244-46 (3d Cir. 2000). Others—the majority,
including our court—hold that the term “otherwise
extensive” can refer to geographical extent and to the
quantity and value of drugs sold, even if participants
plus outsiders don’t add up to five or more. United States
v. Pabey, 664 F.3d 1084, 1096-97 (7th Cir. 2011); United
States v. Diekemper, 604 F.3d 345, 353-54 (7th Cir. 2010);
United States v. Thiongo, 344 F.3d 55, 62-63 (1st Cir. 2003);
United States v. Vasquez-Rubio, 296 F.3d 726, 729 and n. 3
(8th Cir. 2002); United States v. Yarnell, 129 F.3d 1127, 1138-
39 (10th Cir. 1997); cf. United States v. Booth, 309 F.3d 566,
576-77 (9th Cir. 2002).
In a tiny enterprise, neither extensive nor “otherwise
extensive,” the four roles—organizer, leader, manager,
supervisor—are unlikely to be differentiated. There is
likely to be one boss, and it doesn’t matter what one
calls him. But in a substantial enterprise, organized as

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No. 11-2594 5
substantial enterprises legal or criminal usually are—that
is, hierarchically—there will be organizer-leaders
(the guidelines do not distinguish between those two
designations) and manager-supervisors (again not distin-
guished, and in fact not distinguishable on any ground
that we can relate to sentencing policy) intermediate
between the organizer-leaders and the rank and file.
Application Note 4 relates only to the organizer-
leaders; we cannot see what guidance it provides to
determining whether a participant who is neither a boss
nor a grunt is a manager or (the same thing, just a dif-
ferent word) a supervisor.
On the recommendation of the probation service, the
judge in this case gave the defendant the two-level en-
hancement provided for in section 3B1.1(c). That, recall, is
the enhancement for organizers, leaders, managers, and
supervisors in an organization with fewer than five
participants and not “otherwise extensive”—an organiza-
tion in which the four terms are apt to be synonymous,
although it’s conceivable that a four-person organiza-
tion could have a boss, an underboss, and two workers
supervised directly by the underboss (the manager or
supervisor) and indirectly by the boss (the organizer
or leader). The defendant argues that however many
participants there were in the conspiracy of which he
was a member, he was just a communication channel;
his lawyer calls him a “conduit,” a “messenger,” between
“people in an organization” in which he served “a
middle function,” being directed by a man named Primo
who was one of “the people that are actually running
this drug operation.”

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6 No. 11-2594
The defendant supervised a man named Cruz, who
obtained heroin in Texas and transported it to the defen-
dant in Chicago for further distribution. The defendant
was thus a middle manager in a drug enterprise. The
enterprise had only four confirmed participants—the
defendant, Cruz, Primo, and an assistant to the defendant,
identified only as “Individual A.” Nevertheless the en-
terprise was “otherwise extensive.” Figueroa paid for
Cruz and his family to fly from Chicago to Texas, and
doubtless the purpose of having Cruz drive with his
family rather than alone was, by making his trip seem
innocent, to reduce the likelihood of his being appre-
hended en route. The family members thus were out-
siders involved in the drug enterprise. In addition, Cruz
made a number of heroin-bearing trips to Chicago, and
in the one that led to the defendant’s arrest was carrying
37 kilograms of heroin, which would have a wholesale
value of up to $2.5 million. A drug operation that
handles such large quantities is likely, though not
certain, to have at least five participants, even if they
can’t all be identified, which further supports an infer-
ence, drawn from the geographical extent and amount
of drugs, that the conditions for the sentencing enhance-
ment were satisfied in this case. United States v. Brown,
944 F.2d 1377, 1381-82 (7th Cir. 1991); United States v.
Herrera, 878 F.2d 997, 1001-02 (7th Cir. 1989); United
States v. Childress, 58 F.3d 693, 714 (D.C. Cir. 1995) (per
curiam); United States v. Meyers, 847 F.2d 1408, 1414
(9th Cir. 1988).
So the defendant lucked out to get only a 2-level en-
hancement; as a manager or supervisor in an “otherwise

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No. 11-2594 7
extensive” enterprise he should have received the 3-level
enhancement in section 3B1.1(b). The record and parties
are silent on why he did not; someone dropped the
ball. But that is immaterial to the issue presented by
the appeal.
When the question is not whether the defendant is
a leader or organizer, but instead a manager or
supervisor in a hierarchical organization (hence a
“middle manager”), there is no need to sweat over the
terms “manager” or “supervisor”—to worry, for example
as we did recently in United States v. Robertson, 662
F.3d 871, 877 (7th Cir. 2011), quoting earlier cases, over
whether a defendant given an enhancement under one
of these rubrics “exercised some control over others”
or alternatively “played a coordinating or organizing
role.” If a judge, a probation officer, a lawyer, even
a defendant, doesn’t know what a “manager” or “super-
visor” is, Application Note 4 isn’t going to help
him—especially since it’s about organizers and leaders
and not middle managers and low-level supervisors, as
the cases, hungry for text to hang a decision on, are
reluctant to acknowledge. So we won’t try the reader’s
patience with a trip to the dictionary, where we would
find other unhelpful synonyms for “supervisor,” such
as one who “oversees,” or unhelpful periphrases such
as “to coordinate, direct, and inspect continuously and
at first hand [in order] to accomplish” some objective.
The defendant supervised Cruz. He told him where to
go to get the drugs and, when he returned with them,
where to meet him to deliver the drugs and get paid. Cruz

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8 No. 11-2594
was a “mule”; the defendant was the mule skinner. We
don’t call real mule skinners supervisors, because mules
are not people. But drug mules are people and the de-
fendant was a supervisor, or if one prefers a manager.
A supervisor, a manager, tells people what to do and
determines whether they’ve done it. That was the de-
fendant’s job.
But, he argues, he was merely transmitting orders
received from Primo. He had no discretion. He was like
a Western Union messenger, or indeed like a tele-
phone wire. But supervision often consists of trans-
mitting directives from above. Low-level supervisors
are themselves closely supervised and thus have little
discretion. The defendant argues that the only reason
Primo didn’t communicate directly with Cruz was to
reduce the probability of being apprehended, by having
a layer between himself and the mule, that layer being
the defendant (a “cutout”). But by the same token
the defendant obtained some protection against appre-
hension by having a mule to fetch the drugs, rather
than courting arrest by doing that himself—and indeed
it was Cruz who was arrested first and the defendant
only after Cruz agreed to cooperate with the authorities
and led the defendant into a trap.
Because to be a “manager” or “supervisor” is to occupy
a role—to have a status—cases distinguish between
ongoing supervision and merely asking a coconspirator
on one occasion to do something. United States v.
Mankiewicz, 122 F.3d 399, 405-06 and n. 4 (7th Cir. 1997);
United States v. Mitchell, 85 F.3d 800, 813-14 (1st Cir.

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No. 11-2594 9
1996); United States v. McGregor, 11 F.3d 1133, 1138-39 (2d
Cir. 1993). The defendant’s supervision of Cruz, how-
ever, was continuous.
The defendant was, as the district judge rightly
found, Cruz’s supervisor; that is all we know or need
to know.
AFFIRMED.
6-11-12

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