                            In the
 United States Court of Appeals
              For the Seventh Circuit
                        ____________

No. 07-2118
U NITED S TATES OF A MERICA,
                                                Plaintiff-Appellee,
                               v.

C HARLES C. H OWELL,
                                            Defendant-Appellant.
                        ____________
           Appeal from the United States District Court
                for the Central District of Illinois.
           No. 05-CR-40113—Joe Billy McDade, Judge.
                        ____________
     A RGUED F EBRUARY 21, 2008—D ECIDED M AY 29, 2008
                        ____________


  Before F LAUM, R IPPLE, and R OVNER, Circuit Judges.
  F LAUM, Circuit Judge. Charles Howell lived in Seattle,
Washington and mailed drugs to the Midwest. He re-
ceived assistance in this process from at least two indi-
viduals. Eventually, he was caught, and charged with
possession with intent to distribute marijuana and ecstasy
and conspiring to do the same. The district court in-
creased his sentence for serving as a manager or super-
visor in the context of the criminal activity, and we affirm.
2                                               No. 07-2118

                       Background
  Early in 2003, Howell obtained a post office box at a
mail service business called Mail Services and More. He
used that service to mail packages of marijuana to Tennes-
see. Howell established a relationship with the sole Mail
Services employee, Ben Guevarra. Every time Howell
shipped a package from that location (and he did so over
100 times during the course of the conspiracy), he paid
Guevarra $50 to $200 in cash on the side. Usually, Howell
would bring the packages to the center himself. On
some occasions, Howell would bring the package, give
Guevarra the money, and ask him to fill out the packing
slip and send it for him. The money for the drugs would
often be sent back to the same location, so Howell would
go to the center to pick up the cash. Guevarra would
usually call Howell whenever a package arrived for him;
this was not done for other customers. A few times,
Guevarra kept the business open after closing at Howell’s
request.
   At some point in 2002, Howell met Chad Scott, who
also lived in Seattle. Scott started buying marijuana from
Howell, and the two also appeared to become good
friends. Scott learned that Howell shipped marijuana to
Tennessee, and that he was about to take a trip there. He
asked Howell if he could accompany him on this trip. At
first, Howell refused, but then he changed his mind. He
did not specify why he wanted Scott to come along, but
Scott’s understanding was that he was to serve as “the
muscle to keep an eye on things.” Scott was a signifi-
cantly bigger and more intimidating figure than Howell.
Howell paid all of Scott’s expenses (e.g., plane ticket,
meals) for the trip, which lasted a little over a week. They
stayed in an apartment that Howell rented. Scott went
No. 07-2118                                                  3

along when Howell was conducting drug business, but
he was never in the room when money was being counted
or drugs were exchanged. At the end of the trip, Howell
gave Scott $400 to $500.
  In December 2002, Scott communicated to Howell that
he needed money. It just so happened that Howell had
given an individual in Memphis, Tennessee two pounds
of marijuana in exchange for a Honda Prelude. Howell
asked Scott and an unknown Asian male to travel to
Memphis via plane and drive the vehicle from Memphis to
Seattle. The two were to be given cash for their efforts.
While in Memphis, Howell also wanted Scott and the
unidentified male to pick up a dog that belonged to his
half-brother, John Goode, and $4,000 from a female that
owed him the money as part of a marijuana deal. Scott
and his partner assented, and they eventually returned
with the vehicle, the drug proceeds, and the dog.
  Scott went down to Tennessee on a third occasion, this
time with Howell, and stayed at a hotel. As was the case
in their previous visit, Howell paid all expenses and did
not explain why he wanted Scott to accompany him. Scott,
again, assumed it was to protect Howell. 1 Significantly,
when the two were flying back, Howell gave Scott a
stack of cash (presumably drug proceeds) held together
with a rubber band and asked him to carry it through



1
  In their two trips to Tennessee together where Scott was
ostensibly providing bodyguard-like services, he never actu-
ally actively protected Howell by striking anyone. Once, Howell
and another individual started raising their voices, and Scott
told the latter that they did not want any trouble. The man
then backed off.
4                                                    No. 07-2118

airport security.2 Agreeing to the task, Scott made his
way through security without any problems. Once Howell
cleared security, Scott gave him the money, and he then
gave Scott a few hundred dollars. They parted ways at
the airport, as Howell returned to Seattle and Scott flew
to San Diego to visit his child and the child’s mother.
  At the end of 2003, Scott moved to Arizona, but he and
Howell kept their relationship going. He would give
Howell money, and Howell would then send him mari-
juana. During this period of time, Scott came into a sub-
stantial sum of money through a robbery. He subse-
quently sent several thousand dollars to Howell so that
he would send three pounds of marijuana to Scott’s uncle
in the Quad Cities. 3 The thought was that the drugs could
be sold at a higher price there as opposed to Arizona.
This arrangement—where Scott would send money to
Howell, and Howell would send drugs to Scott’s uncle
in the Quad Cities—continued for some time. Later,
Howell introduced Scott to Guevarra, and told him to
let Scott ship a package. Howell instructed Scott to pay
Guevarra $100 to $150 extra per package. At this point,
the nature of the arrangement changed, and Scott would
obtain drugs from Howell and would then ship them
himself to the Quad Cities through Mail Services and
More. This continued for eight months, and during this
time, Howell also started selling MDMA (“ecstasy”) to


2
  Howell’s half-brother previously had nearly $25,000 in cash
seized at the same airport by law enforcement agents.
3
  The term is actually a bit of a misnomer, as it refers to a group
of five cities in Iowa and Illinois that border the Mississippi
River. See Quad Cities, W IKIPEDIA , May 1, 2008, http://
en.wikipedia.org/wiki/Quad_Cities.
No. 07-2118                                             5

Scott. Quantities ranged from 200 to 1000 pills per ship-
ment. Scott then stopped buying ecstasy from Howell
and instead bought directly from Howell’s dealer.
  In almost all instances, Scott would pay Howell up front
before Howell would send him drugs. And the two never
shared profits as a part of the Quad Cities operation. In
total, about 25 to 30 of these packages were sent to the
Quad Cities. Eventually, authorities intercepted one of
these packages, and the arrangement fell apart.
  On May 17, 2006, the grand jury returned a super-
seding indictment charging Howell with conspiracy to
distribute both ecstasy and 100 kilograms or more of
marijuana, and possession with intent to distribute the
same substances. Howell pled guilty to the charges. The
pre-sentence report recommended adding a four point
enhancement to Howell’s sentence for serving as an
organizer or leader of the criminal activity. The district
court stated that it was not convinced that Howell as an
organizer or leader, but thought instead that his role
was that of a manager or supervisor. As a result, Howell
was given a three level enhancement under § 3B1.1(b) of
the U.S. Sentencing Guidelines. This resulted in an advi-
sory imprisonment range of 235 to 293 months, which
was about 80 more months than would have been the
case absent the enhancement. The district court subse-
quently sentenced Howell to 235 months’ imprisonment.
This appeal followed.


                       Discussion
  The sole issue on appeal is whether the district court
committed error in concluding that Howell managed or
supervised at least one other participant in the drug
6                                                  No. 07-2118

distribution conspiracy. We review a district court’s
determination as to whether a defendant exercised a
managerial role in the charged offense for clear error.
United States v. Hall, 101 F.3d 1174, 1176 (7th Cir. 1996). The
sentencing guidelines provide a three level increase for
a defendant who was a manager or supervisor of the
charged activity. U.S.S.G. § 3B1.1(b).4 While the guidelines
do not define the terms “manager” or “supervisor,”
the application note to this section suggests that the
following seven factors be considered when deciding
whether to enhance a defendant’s offense level: (1) the
exercise of decision-making authority; (2) the nature of
participation in the commission of the offense; (3) the
recruitment of accomplices; (4) the claimed right to a
larger share of the fruits of the crime; (5) the degree of
participation in planning and organizing the offense;
(6) the nature and scope of the illegal activity; (7) the
degree of control and authority exercised over others. Id.,
comment. (n.4). We have noted that these factors are to
be used to distinguish leadership from management, but
have found that they are still relevant in ascertaining
whether an individual had a supervisory role at all. United
States v. Brown, 944 F.2d 1377, 1380 n.1 (7th Cir. 1991).



4
    Section 3B1.1 specifically states:
      (a) If the defendant was an organizer or leader of a crim-
      inal activity that involved five or more participants or
      was otherwise extensive, increase by 4 levels.
      (b) If the defendant was a manager or supervisor (but not
      an organizer or leader) and the criminal activity involved
      five or more participants or was otherwise extensive,
      increase by 3 levels.
No. 07-2118                                                  7

   Our case law indicates that certain of the seven factors
listed in the application note to § 3B1.1 are more signif-
icant than others. Howell places great weight on our
decision in United States v. Brown, where we held that the
defendant’s status as a middleman or distributor of
marijuana did not, by itself, support a finding that he
was a “supervisor” or “leader” subject to the increase in
his base offense level. 944 F.2d at 1381. The rationale for
this conclusion, according to Howell, is that a distributor
or middleman does not truly exercise control over an-
other individual. But we later clarified our holding in
Brown in United States v. Skinner, 986 F.2d 1091 (7th Cir.
1993), where we stated that
    The holding in Brown focused on one of the [applica-
    tion note] factors—control and authority. Our focus
    on this one factor, however, was not meant to obscure
    that the “central concern” of section 3B1.1, is relative
    responsibility for the offense. While we referred to
    the element of control as “an important and recurring
    factor,” . . . we hardly established it as the sine qua non
    of liability for enhancement under [the section].
Id. at 1097.
And in Brown itself, we explicitly noted that “[m]iddlemen
are not, of course, immune from application of § 3B1.1.”
944 F.2d at 1381. So while we examine all of the factors, we
emphasize both relative responsibility and control over
other participants, and recognize that middleman status
is not necessarily inconsistent with being a manager or
supervisor.
  Howell contends that he did not have a manager or
supervisor relationship with Scott: he was his supplier, and
his friend. When Scott bought drugs, he almost always
8                                              No. 07-2118

paid first. And when he bought the drugs to send else-
where (e.g., Quad Cities), he decided when and where
they should be shipped, and how much should be
shipped. Beyond supplying the drugs to Scott, Howell
was not involved in the Quad Cities operation. Other than
Scott, he did not know any of the other participants. Plus,
there was no profit-sharing whatsoever. Further, Scott
did not purchase exclusively from Howell—he eventu-
ally went to Howell’s supplier for ecstasy, for instance.
In regards to the various trips to Tennessee, Scott insists
that he was merely going along as a friend, nothing more.
Howell also asserts that he had no authority over
Guevarra, who shipped packages as a part of his role as
an employee of a mail company. With respect to the
payments, he claims that Guevarra was a friend, and that
he was simply “tipping” him.
  The government paints a very different picture. In its
view, Howell was superior to Scott and Guevarra—and
therefore served as a manager or supervisor—in that he
controlled the supply, delivery, and money. Scott, for
example, provided muscle to Howell on at least two
trips to Tennessee. And he not only paid Scott’s expenses,
which would be consistent with his “we were just
friends” theory, but he also gave him additional cash at
the end of their trips, which connotes more of an
employer/employee relationship. Even more striking is
the airport incident, where Scott risked getting caught
by airport security with drug proceeds all in an effort
to protect Howell. Was this simply an act of friendship,
or devotion? Perhaps in part. But, again, Scott was paid
for taking this risk. Additionally, in a fourth instance,
Scott was paid in excess of his expenses for flying to
Tennessee to pick up Howell’s car, dog, and drug money.
No. 07-2118                                               9

In regards to Guevarra, it is true that he was simply doing
his job by shipping packages, but he took a big risk
in helping to ship packages that he knew or suspected to
contain illegal drugs. He was compensated for this risk,
and for staying quiet. There is nothing in the record that
reflects that other Mail Services and More customers
who were “friendly” with Guevarra were leaving him
“tips” for sending packages. Nor is there any indica-
tion that Guevarra was leaving the store open beyond
regular hours, or packaging and filling out mailing labels,
for other friendly but non-tipping customers. The gov-
ernment also submits that Howell exerted his influence
over the two men by waiting for quite some time before
introducing them to each other. Once he did make the
introduction, he instructed Scott on how much to pay
Guevarra. Overall, apart from his influence over Scott and
Guevarra, Howell played the biggest role in this scheme:
he acquired the drugs, arranged for their sale to Scott and
its shipment to Tennessee, paid Guevarra, and planned
trips to Tennessee with others.
  For purposes of ascertaining whether the enhance-
ment should apply to Howell’s sentence, it is useful to
segment the criminal activity into two parts: the Tennessee
operation, and the Quad Cities operation. With respect
to the latter, there is little reason to believe that Howell
played a managerial role. Simply put, he was acting as a
dealer—he took money from Scott and gave him drugs
in return. It was Scott who would then set the price and
work out who he would sell to, how he would sell it, and
when he would do it. In fact, he even decided who he
would buy from: he went over Howell’s head and went
straight to his dealer for ecstasy. But when we turn our
attention to the Tennessee operation, Howell and the
10                                              No. 07-2118

others do not appear to be co-equal. Guevarra was di-
rected to take risks with his job, and he got paid to do it.
More importantly, Scott openly admitted to serving as a
de facto bodyguard, currency courier, and errand boy,
and he too was compensated—above and beyond his
expenses—for his efforts. The Tennessee drug transac-
tions were all structured by Howell, indicating greater
culpability, and Scott played an accompanying role.
Howell can continue to assert that he and Scott, and he
and Guevarra, were just friends, but the fact of the mat-
ter is that you can supervise and manage individuals
even if they happen to be your friends. The nature of their
interaction vis-a-vis the Tennessee operation, including
the payments, evinces a managerial element layered
onto, and not inconsistent with, what may have been a
sincere friendship.


                       Conclusion
  For the foregoing reasons, we A FFIRM Howell’s sentence.




                   USCA-02-C-0072—5-29-08
