                              In the

United States Court of Appeals
               For the Seventh Circuit

Nos. 11-2532 & 11-2877

U NITED STATES OF A MERICA,
                                                    Plaintiff-Appellee,
                                  v.

O SCAR B UENO and
JOSE G ONZALEZ-Z AVALA ,
                                             Defendants-Appellants.


            Appeals from the United States District Court
        for the Northern District of Illinois, Eastern Division.
         Nos. 1:09-cr-00546-6, -3—William J. Hibbler, Judge.



   A RGUED S EPTEMBER 24, 2012—D ECIDED JANUARY 7, 2013




  Before B AUER, FLAUM, and H AMILTON, Circuit Judges.
   B AUER, Circuit Judge. Oscar Bueno and Jose Gonzalez-
Zavala belonged to a drug trafficking organization in-
vestigated by the Drug Enforcement Administration
(“DEA“). Both pleaded guilty to conspiracy to possess
with intent to distribute five kilograms or more of cocaine,
21 U.S.C. § 846. Prior to entering his guilty plea, Bueno
filed a motion to suppress evidence obtained following a
2                                   Nos. 11-2532 & 11-2877

traffic stop, the denial of which he now appeals. Gonzalez-
Zavala appeals his sentence, contending that the district
court relied on clearly erroneous facts in determining
his sentence and that the evidence was insufficient
to sustain the application of enhancements under
§§ 2D1.1(b)(12) and 2D1.1(b)(14)(E) of the United States
Sentencing Guidelines. For the reasons that follow, we
affirm the judgments of the district court.


                   I. BACKGROUND
  Bueno and Gonzalez-Zavala were members of a Chicago-
based distribution cell of the La Familia Michoacana
drug trafficking organization (the “Organization”) based
in Mexico. The DEA conducted an investigation of the
Organization from 2007 to 2009.
  Gonzalez-Zavala worked for the Chicago cell from
at least 2007 through 2009. From December 2008 through
June 2009, Gonzalez-Zavala was a leader and supervisor
of the cell and was responsible for overseeing the dis-
tribution of cocaine and the collection of drug proceeds
in the Chicago area. This was not a small endeavor; the
cell’s drug trafficking activity generated proceeds ex-
ceeding $20 million for the Organization. Gonzalez-
Zavala personally supervised the distribution of 420
kilograms of cocaine and the collection of over $5.7 million
in drug proceeds. In order to facilitate the distribution
of drugs and the collection of drug proceeds, Gonzalez-
Zavala maintained several stash houses, including a
house in Joliet, Illinois, where 54 kilograms of cocaine
Nos. 11-2532 & 11-2877                                  3

were found on the day of his arrest, and a house in
Plainfield, Illinois, where $1.3 million in cash drug pro-
ceeds were discovered.
  The proceeds generated by the Chicago cell’s cocaine
distribution were returned to Mexico by the Organiza-
tion’s couriers, including Bueno and Ismael Flores. Ap-
proximately every two weeks, from November 2008 to
April 2009, Bueno and Flores collected money from
different wholesale cocaine distributors in the Chicago
area, including Gonzalez-Zavala and his associates, and
drove it to Texas. Between January and April 2009,
Bueno and Flores picked up cash five times in amounts
ranging from $450,000 to $900,000 from Gonzalez-
Zavala’s couriers. In total, Bueno was involved in trans-
porting approximately $3 million in cash drug proceeds.
  As part of the DEA’s investigation into the Organiza-
tion, agents intercepted conversations between Gonzalez-
Zavala and Flores on April 14 and 15, 2009, and learned
of plans to transport narcotics proceeds from Chicago to
Mexico. Based on these calls, DEA agents conducted
surveillance of one of Gonzalez-Zavala’s stash houses,
and subsequently observed the delivery of what they
believed to be cash to Flores on April 15.
   On April 16, agents observed Flores and Bueno
loading boxes into a blue Chevrolet van owned by
Flores. Later that night, Bueno and Flores were driving
southbound on Interstate 57 in Douglas County, Illinois,
in the blue Chevrolet van. Bueno was driving the van
and Flores sat in the front passenger seat. At 9:56 p.m.,
Illinois State Trooper Chris Owen stopped the van after
4                                 Nos. 11-2532 & 11-2877

observing it traveling 69 miles per hour in a 65 miles
per hour zone.1
   After curbing the van, Trooper Owen approached the
passenger side of the van and spoke with Bueno and
Flores. He informed them that the van had been
speeding and asked for their identification and registra-
tion documents. Bueno provided a valid Texas driver’s
license, and Flores provided the van’s registration and
a Texas license. According to Trooper Owen, both Bueno
and Flores appeared nervous during this exchange:
their hands were trembling, and Flores appeared
flustered as he searched the glove box of the van for
the registration.
  Trooper Owen noticed that the back of the van was
full of boxes and commented that they were “loaded
down.” Flores responded that they were headed to
Dallas. Trooper Owen inquired further, and Flores told
Trooper Owen that he and Bueno lived in Dallas and
that he owned a transportation company. He said that
they were currently transporting packages to Mexico
and gave Trooper Owen a business card bearing the
name “Transportes Ocampo” and a Chicago address.
Trooper Owen asked Flores if he had motor carrier or
Department of Transportation authority, and Flores
said that his accountant told him he did not need
such authority for his business.


1
  What happened during the stop is largely undisputed as
Trooper Owen’s squad car camera recorded audio and video
of the stop.
Nos. 11-2532 & 11-2877                                  5

  Trooper Owen next asked Bueno to exit the van, patted
him down, and directed him to the front seat of his
squad car. A dog was caged in the rear seating area of the
car. As Trooper Owen ran Bueno’s license for active
warrants, he asked Bueno questions regarding the con-
tents, loading, shipping bills, and transportation of the
packages. Bueno said that he had been working for
Flores for about twelve months, and that he was paid
for transporting packages from Chicago to Dallas. He
said that they were paid by the individuals who sent
the packages, and agreed that the company was similar
to FedEx. Bueno said that they were taking the packages
to Texas, and that someone else would then transport
them to Mexico. After confirming that Bueno had no
outstanding warrants, Trooper Owen told him that he
would issue him a written warning for speeding, and
began preparing the written warning.
  During this time, Trooper Owen continued to question
Bueno about the transportation business. Bueno
confirmed again that the business did not operate under
any sort of authority similar to those under which many
shipping companies operate. Trooper Owen also asked
about the origins and contents of packages. Bueno said
that they usually contained clothing and personal items
like DVD players, and that “different people” dropped
the boxes off, such as people sending items to family
members in Mexico. He said that there were shipping
bills or receipts for each box, which Flores maintained.
Bueno said that he helped load the boxes in Chicago
about every two weeks, and that he was only a driver
for the company.
6                                  Nos. 11-2532 & 11-2877

  Trooper Owen then gave Bueno a copy of the written
warning. At this point, about eleven minutes had passed
since Trooper Owen initiated the stop. Trooper Owen
again questioned Bueno about the packages, and asked
Bueno if he was nervous. Trooper Owen told Bueno
that he could “hear [his] heart beating in [his] voice.”
Bueno denied that he was nervous or had any reason to
be nervous, but then agreed that being around police
officers made him nervous. Trooper Owen next told
Bueno that he was going to talk to Flores and “investigate
a little further” about the packages they were transport-
ing. He advised Bueno to remain in the vehicle, then
asked if he would mind doing so; Bueno said “that’s fine.”
  Trooper Owen returned to the van. He told Flores that
he had only issued Bueno a written warning, and that
they should be careful in the construction zone they
were approaching on the highway. Trooper Owen next
asked Flores for the “bills” for all the boxes and asked
what the boxes contained. Flores said that the bills were
in the back of the van, and that the boxes contained
items such as clothing and shoes destined for Mexico.
When Trooper Owen again requested the shipping
papers for the packages, Flores exited the van and re-
trieved a plastic bag from the cargo area that contained
small shipping papers and a large amount of cash. Flores
said that the cash, which was later determined to
total around $4,000, was the money they collected on
the trip. Trooper Owen reviewed the shipping papers,
but as they did not identify the contents of the packages,
he asked if Flores knew what the boxes contained.
Flores said that he checked the contents of some of
Nos. 11-2532 & 11-2877                                     7

the boxes, but that others were not checked because
they arrived as he and Bueno were leaving. He then
denied responsibility for the contents of the packages.
  Trooper Owen asked Flores for consent to search the
van, and Flores gave him verbal permission. He also
signed a written form confirming his consent. Trooper
Owen retrieved the dog from the squad car to conduct
a canine sniff of the van’s exterior, and in less than
a minute, the dog positively alerted for the odor of nar-
cotics. At this point, the stop had lasted nineteen
minutes, and about eight to nine minutes had passed
since Trooper Owen gave Bueno the written warning
and left him in the squad car. Following the dog’s
positive alert, Trooper Owen and other law enforcement
officers who had arrived at the scene of the stop
removed and opened boxes from the van. They found
a box containing a large number of brick-shaped objects
that were wrapped in plastic, and the dog gave another
positive alert.2 A subsequent search of the van recovered
$2,694,000 from the boxes. Bueno and Flores were
then handcuffed and brought to the police station,
where both made inculpatory statements admitting
that the currency they were transporting resulted from
the sale of narcotics and that its ultimate destination
was Mexico.
 On January 13, 2011, Bueno and Gonzalez-Zavala
were charged in a seventeen-count third superseding


2
  This is not evident in the video and is instead reported in
Trooper Owen’s report of the stop. Bueno, however, does not
dispute this fact.
8                                   Nos. 11-2532 & 11-2877

indictment along with several co-defendants. On Feb-
ruary 10, 2011, Bueno filed a motion to suppress the
physical evidence and statements the police obtained as
a result of the stop of the van. He argued that the
traffic stop conducted by Trooper Owen was unduly
prolonged beyond the time reasonably required to
conduct a traffic stop in violation of the Fourth Amend-
ment. The district court denied Bueno’s motion to sup-
press, finding that the stop was supported by probable
cause based on Trooper Owen’s observations during
the stop as well as the collective knowledge of agents of
the DEA. Bueno subsequently entered a conditional
guilty plea, reserving his right to appeal the denial of
his motion to suppress, to count one of the third super-
seding indictment, conspiracy to possess with intent
to distribute five kilograms or more of cocaine, 21
U.S.C. § 846. He was sentenced to sixty-three months’
imprisonment and three years of supervised release.
  On March 8, 2011, Gonzalez-Zavala pleaded guilty
to count one of the third superseding indictment
without the benefit of a plea agreement. The presen-
tence investigation report (“PSR”) recommended a base
offense level of 38 and three enhancements and one
reduction: a two-level enhancement under U.S.S.G.
§ 2D1.1(b)(12) for maintaining a premises to dis-
tribute a controlled substance; a two-level enhancement
under U.S.S.G. § 2D1.1(b)(14)(E) for committing the
offense as part of a pattern of criminal conduct engaged
in as a livelihood; a four-level enhancement under
U.S.S.G. § 3B1.1(a) for being a leader of a criminal activity
that involved five or more participants; and a three-level
Nos. 11-2532 & 11-2877                                  9

reduction for acceptance of responsibility pursuant to
U.S.S.G. § 3E1.1(a). Gonzalez-Zavala did not file any
objections to the PSR.
  At sentencing, after providing the parties an oppor-
tunity to correct or change the PSR—neither party opted
to do so—the district court adopted its findings and
recommended total base offense level of 43 and criminal
history category of III. This resulted in a Guidelines
range of life imprisonment. The Government requested
a life sentence, while Gonzalez-Zavala argued that a 262-
month sentence was appropriate. He contended that
a below-Guidelines sentence was warranted because
his legitimate employment opportunities were limited
due to his third-grade education, he had traveled to the
United States to assist his family in Mexico, and his fear
of reprisals against his family constrained his ability
to cooperate with the Government. In support, he sub-
mitted letters from his wife and daughter in Mexico. In
her letter, Gonzalez-Zavala’s wife described the family’s
dire financial situation and wrote, “We were doing
okay when [Gonzalez-Zavala] lived with us but unfortu-
nately he left my children and I.” Gonzalez-Zavala’s
daughter similarly described her family’s struggles and
need for her father’s financial support. The pictures of
his family in Mexico included a picture of his daughter
gathering wood for a fire used to heat the family home.
  The district court discussed Gonzalez-Zavala’s argu-
ments in favor of a lower sentence, and ultimately
rejected the Guidelines range of life imprisonment. Re-
garding the letters and pictures from Gonzalez-
10                                    Nos. 11-2532 & 11-2877

Zavala’s family, the district court acknowledged the
family’s circumstances, but expressed concern that the
letters indicated that his family still suffered despite
Gonzalez-Zavala’s access to funds while he was
directing the Chicago cell of the Organization. The
district court also acknowledged Gonzalez-Zavala’s
argument regarding his failure to cooperate with the
Government, but noted the central role Gonzalez-
Zavala played in the Chicago cell. Ultimately, the dis-
trict court sentenced Gonzalez-Zavala to 480 months’
imprisonment.


                     II. DISCUSSION
  As we have noted, Bueno challenges the denial of his
motion to suppress, whereas Gonzalez-Zavala challenges
his sentence. We consider each appeal in turn.


    A. Bueno
  Bueno contends that the district court erred in denying
his motion to suppress because he was detained beyond
the time reasonably required to conduct a traffic stop.
When reviewing the denial of a motion to suppress,
we review the district court’s conclusions of law de novo
and findings of fact for clear error. United States v. Smith,
668 F.3d 427, 430 (7th Cir. 2012).3



3
  We note, as an initial matter, that the Government challenges
Bueno’s “standing to challenge the search of Flores’ van”
                                                  (continued...)
Nos. 11-2532 & 11-2877                                            11

  The Fourth Amendment of the Constitution guarantees
the “right of people to be secure in their persons, houses,
papers, and effects, against unreasonable searches and
seizures.” U.S. C ONST. amend. IV. When police officers
stop an automobile and detain the occupants, even if


3
   (...continued)
because he failed to establish a subjective expectation of privacy
in the van as Flores was the owner of the van. This argument
misses the point: Bueno challenges the reasonableness of the
prolongation of the stop—and the resulting seizure—not the
search of the van. See Brendlin v. California, 551 U.S. 249, 253, 127
S.Ct. 2400, 2404, 168 L.Ed.2d 132 (2007) (“He did not assert that
his Fourth Amendment rights were violated by the search
of Simeroth’s vehicle, cf. Rakas v. Illinois, 439 U.S. 128, 99 S.Ct.
421, 58 L.Ed.2d 387 (1978), but claimed only that the traffic
stop was an unlawful seizure of his person.”). Regardless of
whether Bueno had a possessory interest in the vehicle, he
has standing to challenge the lawfulness of his detention. See
United States v. Green, 275 F.3d 694, 699 (8th Cir. 2001) (“Even
though Green lacked a possessory or property interest in the
motor vehicle that would enable him to directly challenge
the search, he may still contest the lawfulness of his own
detention and seek to suppress evidence as the fruit of his
illegal detention.” (citation omitted)); United States v. DeLuca,
269 F.3d 1128, 1132 (10th Cir. 2001) (“[A]lthough a defendant
may lack the requisite possessory or ownership interest in
a vehicle to directly challenge a search of that vehicle, the
defendant may nonetheless contest the lawfulness of his own
detention and seek to suppress evidence found in the vehicle
as the fruit of the [defendant’s] illegal detention.’ ” (quoting
United States v. Nava-Ramirez, 210 F.3d 1128, 1131 (10th
Cir. 2000)).
12                                  Nos. 11-2532 & 11-2877

only for a brief period, the stop amounts to a seizure
within the meaning of the Fourth Amendment. Whren v.
United States, 517 U.S. 806, 809-10, 116 S.Ct. 1769, 135
L.Ed.2d 89 (1996) (citations omitted). A traffic stop
must therefore satisfy the Fourth Amendment’s require-
ment of reasonableness. Id. at 810. As a general matter,
the decision to stop an automobile is reasonable when
the police have probable cause to believe that a person
has committed a traffic offense. United States v. Taylor, 596
F.3d 373, 376 (7th Cir. 2010). Here, Trooper Owen
stopped the van after observing it exceed the speed
limit, and Bueno does not dispute this fact. Accordingly,
the initial stop of the van and questioning of Bueno
were proper.
  Even a “seizure that is lawful at its inception,” however,
can “violate the Fourth Amendment if its manner of
execution unreasonably infringes interests protected by
the Constitution.” Illinois v. Caballes, 543 U.S. 405, 407,
125 S.Ct. 834, 160 L.Ed.2d 842 (2005) (citation omitted). In
the context of a traffic stop, this means that “[a] seizure
that is justified solely by the interest in issuing a
warning ticket to the driver can become unlawful if it is
prolonged beyond the time reasonably required to com-
plete that mission.” Id. Thus, while officers need not have
reasonable suspicion to ask questions unrelated to the
purpose of the traffic stop, “questions that prolong
custody may affect the reasonableness of the detention.”
United States v. Muriel, 418 F.3d 720, 725 (7th Cir. 2005).
  Relying on Caballes, Bueno argues that his continued
detention after Trooper Owen issued the written warning
ran afoul of the Fourth Amendment. As Bueno points
Nos. 11-2532 & 11-2877                               13

out, Trooper Owen gave Bueno the written warning
around eleven minutes into the stop, but he was
detained while Trooper Owen questioned Flores and
searched the van, and he was not placed in handcuffs
until thirty-nine minutes into the stop. Bueno argues
that his detention after Trooper Owen left him in the
squad car was unreasonable, and that all evidence
obtained as a result of this unlawful detention—namely,
the currency recovered from the van and Bueno’s
inculpatory statements—must be suppressed.
  Although Bueno challenges the entirety of the stop
after the issuance of the written warning, we view the
traffic stop as having three distinct phases. The first
phase began with Trooper Owen’s initiation of the stop
and lasted through the issuance of the written warning.
This phase lasted approximately eleven minutes, and
as mentioned above, was reasonable based on Trooper
Owen’s observation of the van exceeding the speed
limit. In the next phase of the stop, which lasted about
eight to nine minutes, Trooper Owen left Bueno in the
squad car, questioned Flores about the packages,
requested the shipping papers, and received Flores’
consent to search the van, resulting in the positive dog
alert. In the final phase of the stop, Trooper Owen and
other law enforcement agents searched the van,
recovered brick-shaped objects wrapped in plastic, to
which the dog again alerted for the presence of
narcotics, and handcuffed Bueno. This phase lasted
approximately twenty minutes.
  Based on this timeline, we agree with Bueno that the
record shows that Trooper Owen prolonged the stop
14                                  Nos. 11-2532 & 11-2877

beyond the time reasonably required to issue the
written warning. Nevertheless, that a traffic stop ex-
tends beyond the time necessary to effectuate its
purpose does not necessarily render it unreasonable.
Rather, we and other courts have recognized several
permissible grounds for prolonging a traffic stop after
the original mission of the stop has been completed.
First, continuation of the stop beyond its otherwise
lawful limits is justified where the encounter has become
consensual, thus terminating the seizure. See e.g., United
States v. Figueroa-Espana, 511 F.3d 696, 702 (7th Cir. 2007)
(“A consensual encounter between an individual and a
law enforcement official does not trigger Fourth Amend-
ment scrutiny.” (citation omitted)); United States v.
Munoz, 590 F.3d 916, 921 (8th Cir. 2010) (“If the
encounter becomes consensual, it is not a seizure, the
Fourth Amendment is not implicated, and the officer
is not prohibited from asking questions unrelated to
the traffic stop or seeking consent to search the vehi-
cle.” (internal quotation marks and citation omitted)).
Here, the Government contends in passing that Bueno
consented to remaining in the squad car after Trooper
Owen issued him the written warning. We find that the
record is less than clear on this issue, however, and given
the underdeveloped nature of the Government’s argu-
ment, we decline to find Bueno’s continued detention
permissible based on this ground.
  We have also recognized that the prolongation of a
traffic stop based on probable cause due to further ques-
tioning by a police officer is reasonable so long as the
officer asks “[q]uestions that hold potential for detecting
Nos. 11-2532 & 11-2877                                     15

crime, yet create little or no inconvenience.” United States
v. Childs, 277 F.3d 947, 954 (7th Cir. 2002) (en banc). In
reaching this conclusion, we distinguished stops based
on probable cause from those based on reasonable suspi-
cion, and reasoned that because a stop based on probable
cause will also justify a custodial arrest, traffic stops
based on probable cause are not subject to the time limita-
tions of Terry v. Ohio, 392 U.S. 1, 20, 88 S.Ct. 1868, 20
L.Ed.2d 889 (1968). Id. at 952-53; but see United States v.
Guijon-Ortiz, 660 F.3d 757, 768 n.9 (4th Cir. 2011) (rejecting
the Childs court’s discussion about “whether a stop sup-
ported by probable cause gives officers freer rein to ask
unrelated questions than do stops supported only by
reasonable suspicion” and affirming that the Terry two-
step framework applies to traffic stops based on
probable cause). Thus, as we explained in Childs, the
Fourth Amendment “does not require the release of a
person arrested on probable cause at the earliest
moment that can be accomplished. What the Constitution
requires is that the entire process remain reasonable.”
277 F.3d at 953-54; see also Arizona v. Johnson, 555 U.S.
323, 129 S.Ct. 781, 172 L.Ed.2d 694 (2009) (“An officer’s
inquiries into matters unrelated to the justification
for the traffic stop, this Court has made plain, do not
convert the encounter into something other than a lawful
seizure, so long as those inquiries do not measurably
extend the duration of the stop.” (citation omitted)).
Based on this reasoning, we have permitted additional
questioning by officers during a traffic stop that did not
increase the length of detention, or that extended it by
only a reasonable period of time. See Childs, 277 F.3d at 953;
United States v. McBride, 635 F.3d 879, 883 (7th Cir. 2011).
16                                  Nos. 11-2532 & 11-2877

  The Government argues that the additional in-
vestigatory actions undertaken by Trooper Owen after
he completed the written warning—phase two of the
stop—fell within the permissible grace period we recog-
nized in Childs because the conduct “[held] the potential
for detecting crime, yet create[ed] little or no inconve-
nience.” While we agree that Trooper Owen’s actions
clearly had the potential to uncover criminal activity,
we are less convinced that the duration and manner of
Bueno’s detention that resulted caused him little or
no inconvenience. This a fact-bound, context-specific
inquiry, but we note that the defendants in Childs,
McBride, and several of our unpublished decisions
allowing the “reasonable” prolongation of a traffic stop
were detained for, at most, a few minutes and not in-
convenienced in any appreciable way. See Childs, 277 F.3d
at 953 (“By asking one question about marijuana, officer
Chiola did not make the custody of Childs an ‘unreason-
able’ seizure.”); McBride, 635 F.3d at 883 (noting that “the
additional questions extended the stop by ‘roughly
two minutes’ at most”); United States v. Dixie, 382 Fed.
Appx. 517, 519 (7th Cir. 2010) (unpublished) (concluding
that the stop was not unreasonably prolonged where
the district court noted that it took “only seconds lon-
ger” for the officer to ask the defendant about any
weapons on his person and then to recover the de-
fendant’s knife and unlicensed gun when he answered
in the affirmative); United States v. Brown, 355 Fed. Appx.
36, 38-39 (7th Cir. 2009) (unpublished) (concluding that
the defendant’s detention was reasonable because the
trooper’s additional questioning “transpired in less
Nos. 11-2532 & 11-2877                                    17

than one minute after he issued the warning”); United
States v. Johnson, 331 Fed. Appx. 408, 409-10 (7th Cir. 2009)
(unpublished) (noting that only two minutes passed
between the time the defendant signed the written
warning and his admission that someone smoked mari-
juana in the car that day, which provided an additional
reason to prolong the stop); but see United States v.
Harrison, 606 F.3d 42, 45 (2d Cir. 2010) (per curiam)
(listing cases in which intervals longer than five or six
minutes have been deemed tolerable); United States v.
Robinson, 455 F.3d 832, 834 (8th Cir. 2006) (noting cases
in which seizures of less than ten minutes were upheld
as de minimis intrusions that did not amount to unrea-
sonable seizures). In United States v. Carpenter, we permit-
ted a delay in a traffic stop that lasted between zero
and five minutes because it was only a “modest incremen-
tal delay” in the stop. 406 F.3d 915, 916-17 (7th Cir. 2005).
Here, however, almost nine minutes passed—nearly
doubling the length of the stop—between the issuance
of the written warning and the dog alert that gave
Trooper Owen reason to detain Bueno further. Addition-
ally, although Trooper Owen had already issued Bueno
the written warning, he advised Bueno to wait in the
police squad car—with the police dog pacing at his
back—while he questioned Flores.
  Even if this amounted to an impermissible inconve-
nience, however, we conclude that the continuation of
Bueno’s detention beyond its otherwise lawful limits was
justified in light of the circumstances that developed
during the stop. We have recognized on numerous occa-
sions that information lawfully obtained during a traffic
18                                  Nos. 11-2532 & 11-2877

stop may “provide the officer with reasonable suspicion
of criminal conduct that will justify prolonging the stop
to permit a reasonable investigation.” United States v.
Martin, 422 F.3d 597, 602 (7th Cir. 2005) (citations omit-
ted); see also Figueroa-Espana, 511 F.3d at 702 (holding
that even if the defendant was detained, “such a de-
tention was part of an extension of the initial traffic
stop entirely justified by reasonable suspicion of criminal
activity”); McBride, 635 F.3d at 882 (citing Estrada v.
Rhode Island, 594 F.3d 56, 64 (1st Cir. 2010) (recognizing
that information gathered during a stop may provide
reasonable suspicion of criminal conduct that will
justify extending the stop)). “Reasonable suspicion is
more than a hunch but less than probable cause and
‘considerably less than preponderance of the evidence.’ ”
Jewett v. Anders, 521 F.3d 818, 823 (7th Cir. 2008) (quoting
Illinois v. Wardlow, 528 U.S. 119, 123, 120 S.Ct. 673, 675,
145 L.Ed.2d 570 (2000)). Whether it was reasonable for
an officer to suspect that the defendant was engaged
in wrongdoing “calls for an objective inquiry into all of
the circumstances known to the officer at the time”
he detained the defendant. United States v. Snow, 656
F.3d 498, 500 (7th Cir. 2011). This “ ‘totality of the cir-
cumstances’ test necessarily includes the experience of
the law enforcement agent and the behavior and charac-
teristics of the subject.” United States v. Zambrana, 428
F.3d 670, 675 (7th Cir. 2005) (citing United States v.
Odum, 72 F.3d 1279, 1284 (7th Cir. 1995)).
  Here, the Government points to several facts and cir-
cumstances observed by Trooper Owen during the first
phase of the stop that justified his decision to investigate
Nos. 11-2532 & 11-2877                                  19

further. First, Trooper Owen noted that the van took
“an abnormally long amount of time” to pull to the side
of the road and that his experience taught him that this
could be indicative of two people forming a plan or
coordinating a story prior to police contact. The van was
traveling at a high speed, however, and the squad car’s
video recording shows the van slowing at a reasonable
rate, so we give this observation little weight. Trooper
Owen also observed that both Bueno and Flores
appeared “excessively” nervous during the stop: ac-
cording to Trooper Owen, Bueno’s hand trembled when
he handed Trooper Owen his license; Flores’ search for
the van’s registration was “hurried and exaggerated”;
Flores’ hand shook when he gave Trooper Owen the
registration card; and Bueno’s voice was shaky and weak
at times and his leg was shaking when he was ques-
tioned in the squad car. Some nervousness around
law enforcement officials is to be expected, however,
and we have expressed skepticism regarding the value
of such observations. See United States v. Broomfield,
417 F.3d 654, 655 (7th Cir. 2005). Nevertheless, while
“the appearance of anxiety may not by itself form an
objective basis for suspecting criminal activity,” McBride,
635 F.3d at 882 (citation omitted), we consider such be-
havior as a factor in the totality of circumstances,
United States v. Brown, 188 F.3d 860, 865 (7th Cir. 1999)
(citation omitted).
  Other observations and information obtained by
Trooper Owen before he finished giving Bueno the
written warning provide a stronger basis for suspecting
that he and Flores were engaged in illegal activity.
Almost immediately after Trooper Owen initiated the
20                                Nos. 11-2532 & 11-2877

stop, he saw that the van was “loaded down” with
boxes. Flores informed him that the boxes originated in
Chicago and were bound for Mexico, which Trooper Owen
knew from his experience was a common route for drug-
trafficking and other contraband. See United States v.
Funds in Amount of Thirty Thousand Six Hundred Seventy
Dollars, 403 F.3d 448, 467 (7th Cir. 2005) (giving weight
to fact that the claimant “was traveling to Phoenix, a
recognized source city for illegal narcotics,” in deter-
mining the existence of probable cause connecting the
seized property with illegal drug transactions in a for-
feiture case). Although Flores said that they were trans-
porting the packages under the auspices of a transporta-
tion company, the van was registered to Flores, not the
company, and bore no company markings as would
be typical of a transportation company. Flores also ad-
mitted that he did not have any motor carrier authority
to operate the business and transport the packages
across state lines (he said he did not believe he needed
any). Additionally, even though Flores said he was the
owner of the transportation company and that both
he and Bueno lived in Dallas, the business card he pro-
vided Trooper Owens listed a Chicago address. These
circumstances obviously raised red flags regarding the
legitimacy of Flores’ transportation company, and
when Trooper Owens questioned Bueno about the
business while issuing him the written warning, he was
unable to get specific answers regarding the origins and
contents of the packages. Instead, Bueno told him only
what the boxes typically contain and that “different
people” dropped them off. He said that he was only the
Nos. 11-2532 & 11-2877                                  21

driver, and that Flores maintained the shipping papers
for the packages. We find that these developments, taken
in combination, gave rise to a reasonable suspicion of
criminal activity, and that Trooper Owen was justified
in prolonging the stop for a few minutes to ask Flores
about his business and the packages he was transporting
in order to confirm or dispel his suspicions. See McBride,
635 F.3d at 882 (extended stop justified by nervous-
ness of vehicle’s occupants and their conflicting stories);
Figueroa-Espana, 511 F.3d at 703 (prolonged stop
supported by driver’s nervous demeanor, inconsistent
story, conflicting information, and failure to provide a
driver’s license or vehicle registration); Muriel, 418 F.3d
at 726 (“By the time Sgt. McDonald had completed his
work on the traffic stop, he had, by virtue of the incon-
sistent stories received from the occupants, reasonable
suspicion to inquire further.”).
  We acknowledge that each of these independent facts
has an innocent explanation. Money, clothing, and other
items are regularly sent from the United States to Mex-
ico. And almost every major city can be described as a
destination or source for contraband. Nevertheless, our
inquiry requires us to consider the totality of the circum-
stances, and “behavior which is susceptible to an
innocent explanation when isolated from its context
may still give rise to reasonable suspicion when
considered in light of all of the factors at play.” United
States v. Baskin, 401 F.3d 788, 793 (7th Cir. 2005). When
viewed in combination, the demeanors of Bueno and
Flores, the unknown contents and origins of the
packages, their destination, and the way in which they
22                                      Nos. 11-2532 & 11-2877

were being transported—by a transportation “business”
that lacked any trappings of a legitimate business—gave
rise to a reasonable suspicion of criminal activity that
justified Trooper Owen’s brief prolongation of the
stop to investigate.4 And we note that the additional
investigation was brief: Trooper Owen’s questions were


4
   The cases relied upon by Bueno, United States v. Perkins, 348
F.3d 965 (11th Cir. 2003), and United States v. Jones, 234 F.3d 234
(5th Cir. 2000), do not support a different result. In Perkins, a
highway patrol officer detained the defendant after giving him
a warning citation for a traffic offense “because of [the defen-
dant’s] nervousness,” “what he perceived as [the defendant’s]
evasiveness in response to” questions he asked while running
a check on the defendant’s driver’s license, and “his hunch
that [the defendant] was being untruthful about his destina-
tion.” 348 F.3d at 968. The Eleventh Circuit affirmed the
granting of the defendant’s motion to suppress, reasoning
that more was required to give rise to reasonable suspicion
than “the innocuous characteristics of nervousness, a habit
of repeating questions, and an out-of-state license[.]” Id. at 970-
71. Similarly, in Jones, the Fifth Circuit found no reasonable
suspicion based solely upon inconsistent answers to certain
employment questions and the defendant’s admission that
he had a prior arrest on drug charges. 234 F.3d at 241. Here,
unlike in Perkins and Jones, Trooper Owen had more than “a
hunch” based on the nervousness of Bueno and Flores when
he continued Bueno’s detention; he had a reasonable suspicion
of criminal activity based on—in addition to the nervousness
of Bueno and Flores—the unusual circumstances regarding
Flores’ purported transportation business, the origin and
ultimate destination of the packages in the van, and the un-
known contents of the packages.
Nos. 11-2532 & 11-2877                                  23

focused on obtaining information regarding the
shipping papers and contents of the packages, and Flores
consented to the search of the van within minutes,
leading to the positive dog alert.
  Bueno also challenges the third phase of the stop,
contending that it was unreasonable for him to be
detained during the search of the car and that his arrest
was not supported by probable cause. These arguments
are also unavailing. Once the dog alerted to the presence
of narcotics, Trooper Owen clearly had additional
grounds to search the van and detain Bueno further.
See Florida v. Royer, 460 U.S. 491, 506, 103 S.Ct. 1319, 75
L.Ed.2d 229 (1983) (positive dog alert would justify
turning investigative detention into arrest); United States
v. Ganser, 315 F.3d 839, 844 (7th Cir. 2003) (“Once the
canine alerted to the letter, reasonable suspicion was
elevated to probable cause.” (citations omitted)); United
States v. Thomas, 87 F.3d 909, 912 (7th Cir. 1996) (dog’s
positive reaction to narcotics establishes probable
cause). And his continued detention—we will assume it
was an arrest at this point—was supported by probable
cause. “Probable cause means that there are ‘facts and
circumstances within the officer’s knowledge that
are sufficient to warrant a prudent person, or one of
reasonable caution, in believing, in the circumstances
shown, that the suspect has committed, is committing, or
is about to commit an offense.’ ” United States v. Slone,
636 F.3d 845, 849 (7th Cir. 2011) (quoting Michigan v.
DeFillippo, 443 U.S. 31, 37, 99 S.Ct. 2627, 61 L.Ed.2d
343 (1979)).
24                                  Nos. 11-2532 & 11-2877

  By the time Bueno was placed in handcuffs, the search
of the van that Bueno had been driving had revealed a
box containing brick-shaped objects wrapped in plastic.
Trooper Owen stated that the wrapping had an ap-
pearance consistent with that of contraband. See United
States v. Reed, 443 F.3d 600, 604 (7th Cir. 2006) (“It is
common for [currency related to illegal drug transac-
tions] to be wrapped in cellophane so as to minimize
the ability for a drug-sniffing dog to detect the drug
residue often found on such currency[.]”). Additionally,
despite the plastic wrapping, the narcotics dog positively
alerted to the box for the presence of narcotics odors. When
viewed in combination with the circumstances dis-
cussed above, these developments were sufficient to
support a reasonable belief that Bueno was involved in
criminal activity. See id. at 603-04 (finding probable
cause to arrest based on inconsistent stories, evasiveness
in answering questions, prior drug arrests, and the dis-
covery of large amounts of currency “concealed in a
manner that is typical for currency related to illegal
drug transactions[]”). Contrary to Bueno’s arguments, we
do not believe that Trooper Owen needed to open the
plastic-wrapped objects to confirm the contents as he
was entitled to rely on his “common-sense judgment,” id.
at 603, and probable cause does not require law enforce-
ment officials to gather enough evidence to support a
conviction or even enough to demonstrate that it was
more likely than not that the suspect was engaged in
criminal activity. Wheeler v. Lawson, 539 F.3d 629, 634
(7th Cir. 2008) (citation omitted). As we have said
before, “[o]ne can always point out informational gaps,
Nos. 11-2532 & 11-2877                                   25

yet the probable cause inquiry asks what a law enforce-
ment officer knew rather than what he did not.” Slone,
636 F.3d at 849. “If an officer had in every case to
observe an illegal act before effecting an arrest, the test
would be called certain cause, or more-likely-than-not
cause, two formulations that have been rejected.” Id. at
850 (citations omitted).
  Seeking to avoid this result, Bueno attempts to dis-
tance himself from the events that occurred while he sat
in the squad car. He concedes that the dog’s positive
alert and Flores’ consent to search provided grounds to
detain the car and Flores—the owner of the car—but
contends that there was “no reason” to continue to
detain him at the scene. We disagree. Bueno’s arguments
allude to the notion that a person’s “mere propinquity”
to others independently suspected of criminal activity
is insufficient to support probable cause as to that
person as well. See Ybarra v. Illinois, 444 U.S. 85, 91, 100
S.Ct. 338, 62 L.Ed.2d 238 (1978) (holding that officers
executing a warrant on a tavern lacked probable cause
to search all patrons of that tavern at the time); see also
United States v. Ingrao, 897 F.2d 860, 863 (7th Cir. 1990)
(“[P]hysical proximity to a suspected crime, without
indicia of [the defendant’s] involvement, is insufficient
to support a finding of probable cause.” (citation omit-
ted)). But as the Supreme Court has noted, “a car
passenger . . . will often be engaged in a common enter-
prise with the driver[.]” Maryland v. Pringle, 540 U.S. 366,
373, 124 S.Ct. 795, 157 L.Ed.2d 769 (2003). In Pringle,
the Supreme Court held that it was reasonable for the
officer to infer a common enterprise among the three
26                                    Nos. 11-2532 & 11-2877

occupants of a car because the drugs and cash found in
the car were accessible to all three men in the car, and
“[t]he quantity of drugs and cash in the car indicated
the likelihood of drug dealing, an enterprise to which a
dealer would be unlikely to admit an innocent person
with the potential to furnish evidence against him.” Id.
  We find that the totality of the circumstances in this
case similarly supports an inference of a common enter-
prise between Bueno and Flores. Bueno was not merely
a passenger, but rather the driver of the car to which
the dog positively alerted and where the box of plastic-
wrapped objects was found. He told Trooper Owen that
he had been working for Flores for a year, and was in-
volved in the loading of the boxes. Moreover, the trip
they were taking was long—Chicago to Dallas—and one
that he and Flores had made together on numerous
occasions. See Reed, 443 F.3d at 604-05 (“This was not a
quick trip to the grocery store in which Reed was an
unwitting passenger. This was a trip out of state. It is
less likely that an innocent person would be allowed to
accompany persons for such a trip.”). These circum-
stances provided Trooper Owen with particularized
reasons to believe that Bueno was involved in criminal
activity even though he was not the owner of the van.
Accordingly, the entirety of Bueno’s detention caused
by the traffic stop was justified, and the district court
correctly denied his motion to suppress.5



5
  Bueno also argues that the district court should have held an
evidentiary hearing on his motion to suppress. The only
                                                  (continued...)
Nos. 11-2532 & 11-2877                                         27

    B. Gonzalez-Zavala
  Gonzalez-Zavala appeals his sentence. He contends
that the evidence was insufficient to sustain the applica-
tion of the enhancements under U.S.S.G. §§ 2D1.1(b)(12)
and 2D1.1(b)(14)(E) and also challenges the district
court’s findings regarding his support of his family in
Mexico.6 We generally review factual findings for clear
error, and the interpretation and application of the Sen-
tencing Guidelines de novo. United States v. Rollins, 544
F.3d 820, 837 (7th Cir. 2008) (citations omitted). Here,
however, Gonzalez-Zavala did not raise these objections
before the district court, so our review is for plain error.
United States v. Anderson, 604 F.3d 997, 1001 (7th Cir. 2010)




5
  (...continued)
disputed issue of fact he identifies, however, is whether the
DEA agents communicated with Trooper Owen prior to his
stop. This disputed fact bears only on whether the district
court erred in relying on the collective knowledge doctrine in
denying Bueno’s motion to suppress without a hearing, see
United States v. Williams, 627 F.3d 247, 252 (7th Cir. 2010) , and
as we affirm on other grounds, we deny Bueno’s request for
a remand for an evidentiary hearing.
6
  Gonzalez-Zavala also argues that the application of the
enhancements, which became effective after the issuance of the
indictment charging him, violates the ex post facto clause of
the Constitution. As he concedes, however, our precedent
forecloses that claim. E.g., United States v. Robertson, 662 F.3d
871, 876 (7th Cir. 2011); United States v. Demaree, 459 F.3d 791,
795 (7th Cir. 2006).
28                                    Nos. 11-2532 & 11-2877

(citations omitted); see also Fed. R. Crim. P. 52(b).7 Ap-
plying this standard, we will reverse the determination
of the district court only if we find: “(1) an error or
defect (2) that is clear or obvious (3) affecting the defen-
dant’s substantial rights (4) and seriously impugning
the fairness, integrity, or public reputation of judicial
proceedings.” Anderson, 604 F.3d at 1002 (quoting
United States v. Olano, 507 U.S. 725, 736, 113 S.Ct. 1770,
123 L.Ed.2d 508 (1993)).
  Regarding Gonzalez-Zavala’s first argument, we find
no clear error in the district court’s application of
the enhancements under U.S.S.G. §§ 2D1.1(b)(12) and
2D1.1(b)(14)(E). Section 2D1.1(b)(12) calls for an enhance-
ment where a defendant “maintained a premises for the
purpose of manufacturing or distributing a controlled
substance.” At his change of plea hearing, Gonzalez-Zavala
admitted that he had been a leader of the Chicago cell
from December 2008 to June 2009, and that his “oversight
of the Chicago distribution cell included obtaining
and maintaining stash houses for the purpose of storing
cocaine and cash drug proceeds.” He also admitted to


7
  The Government contends in passing that Gonzalez-Zavala
waived these arguments, but offers no strategic reason for
the failure of Gonzalez-Zavala’s counsel to object. As “[w]aiver
principles must be construed liberally in favor of the defen-
dant,” Anderson, 604 F.3d at 1002 (citation omitted), and we
“assume forfeiture where the government fails to proffer a
strategic justification for a defendant’s decision to bypass
an argument,” United States v. Johnson, 668 F.3d 540, 542 (7th
Cir. 2012) (citation omitted), we will review for plain error.
Nos. 11-2532 & 11-2877                                   29

maintaining two specific stash houses in Plainfield and
Joliet where drugs and drug proceeds were found on
the day of his arrest. The PSR provided similar details
regarding Gonzalez-Zavala’s role in the Chicago cell
and the stash houses, and Gonzalez-Zavala did not
have any objections to the PSR and declined to suggest
any changes or corrections when offered the oppor-
tunity to do so at his sentencing hearing. Given these
admissions and his failure to object to the PSR’s
findings, the district court did not clearly err in finding
the evidence sufficient to support this enhancement.
Gonzalez-Zavala points out that the district court did not
specifically inquire into the factors listed in the commen-
tary to the Guidelines, see U.S.S.G. § 2D1.1, cmt. n.28, but
we do not believe that such a discussion was necessary
given Gonzalez-Zavala’s failure to object to the findings
in the PSR and his admission that as a leader of the Chi-
cago cell, a position he held for at least seven months,
he “obtained and maintained” several stash houses for
“the purpose of storing cocaine and cocaine proceeds.”
While we can easily envision closer cases in which
the defendant objects to the enhancement and a more
detailed examination of the factors set forth in the com-
mentary may be required, this was not a close case.
  Gonzalez-Zavala’s challenge to the application of the
U.S.S.G. § 2D1.1(b)(14)(E) enhancement also fails. Section
2D1.1(b)(14)(E) provides for a two-level enhancement to
a defendant’s offense level where (1) the defendant com-
mitted the offense as part of a pattern of criminal con-
duct, and (2) the defendant engaged in the criminal
conduct as a livelihood. See U.S.S.G. § 2D1.1(b)(14)(E).
30                                 Nos. 11-2532 & 11-2877

Gonzalez-Zavala argues that the district court erred
under both prongs.
  The commentary to the Guidelines states that “pattern
of criminal conduct” and “engaged in as a livelihood”
have the meaning given to those terms in U.S.S.G. § 4B1.3.
U.S.S.G. § 2D1.1, cmt. n.29. The commentary to U.S.S.G.
§ 4B1.3 defines “pattern of criminal conduct” as “planned
criminal acts occurring over a substantial period of time.”
U.S.S.G. § 4B1.3, cmt. n.1. Gonzalez-Zavala contends that
the evidence before the district court did not support a
finding that his conduct was of a sufficient duration to
support the enhancement. We disagree. Gonzalez-Zavala
admitted to participating in the conspiracy to distribute
drugs from at least 2007 through June 2009, and he was
a leader of the Chicago cell for at least seven months of
that period. Given this admission, it was not clear error
for the district court to find that Gonzalez-Zavala’s
conduct occurred over a “substantial period of time.”
  Gonzalez-Zavala also argues that the evidence was
insufficient to support a finding that he “engaged in” the
conspiracy to distribute drugs “as a livelihood.” Under
the commentary to U.S.S.G. § 4B1.3, “engaged in as a
livelihood” means:
     (1) that the defendant derived income from
     the pattern of criminal conduct that in any
     twelve-month period exceeded 2,000 times the
     then existing hourly minimum wage under
     federal law; and (2) the totality of the circum-
     stances shows that such criminal conduct was the
     defendant’s primary occupation in that twelve
Nos. 11-2532 & 11-2877                                         31

    month period (e.g., the defendant engaged in
    criminal conduct rather than regular, legitimate
    employment; or the defendant’s legitimate employ-
    ment was merely a front for his criminal conduct).
U.S.S.G. § 4B1.3, cmt. n.2. Gonzalez-Zavala points out
that neither the Government nor the PSR identified
exactly how much he earned while participating in the
conspiracy. Given the other undisputed facts before
the district court, however, we cannot conclude that it
clearly erred in finding that Gonzalez-Zavala earned
more than $13,100 during at least one twelve-month
period in which he was involved in the conspiracy.8
During at least seven months of that period, Gonzalez-
Zavala was a leader of the Chicago cell’s multimillion
dollar drug distribution operation and he admitted to
personally supervising the collection of over $5.7 million
in drug proceeds and the distribution of over 420 kilo-
grams of cocaine. In this role, he coordinated the
delivery of cocaine to wholesale distributors, the collec-
tion of payments, the return of the proceeds via couriers
to the Organization in Mexico, and the maintenance
of several stash houses. The PSR specifically lists ten
occasions on which Gonzalez-Zavala was involved in
collecting drug proceeds in quantities ranging from


8
  Although the dates do not line up precisely, we used $6.55, the
federal minimum wage effective from July 24, 2008, through
July 24, 2009, for this calculation. United States Dept. of Labor,
History of Federal Minimum Wage Rates Under the Fair Labor
Standards Act, 1938-2009, http://www.dol.gov/whd/minwage/
chart.pdf (last visited January 2, 2013).
32                                    Nos. 11-2532 & 11-2877

$28,000 to $165,000. These same facts regarding his role
in the Chicago cell and the scope of his duties
support the finding that Gonzalez-Zavala’s participation
in the drug distribution conspiracy was his primary
occupation, notwithstanding his unverified claim
that he worked as a self-employed landscaper during
this time.
  We likewise find no error in the district court’s findings
regarding Gonzalez-Zavala’s support of his family in
Mexico. In evaluating the factors under 18 U.S.C. § 3553(a),
the district court discussed the letters and pictures
from Gonzalez-Zavala’s family and concluded that:
     With all the access [Gonzalez-Zavala] had to funds
     as a result of this enterprise, his family still suffered,
     so that despite the fact that he is going to be away
     from his family for years, and maybe life, the family
     quite frankly is probably better off than to have a
     person who has access to means and they still
     suffer those kinds of circumstances.
   Gonzalez-Zavala contends that the district court com-
mitted procedural error by relying on clearly erroneous
facts in reaching this conclusion. “We will disturb the
district court’s findings as clearly erroneous only if our
review of the record leaves us with the definite and
firm conviction that a mistake has been committed.”
United States v. Selvie, 684 F.3d 679, 682 (7th Cir. 2012)
(internal quotation marks and citations omitted).
  Gonzalez-Zavala challenges two findings the district
court relied upon in determining his sentence: (1) that
Gonzalez-Zavala had access to substantial funds as a
result of his involvement in the Organization, and (2) that
Nos. 11-2532 & 11-2877                                  33

he did not provide “much, if any” support to his family
despite his access to those funds. The record here does
not convince us that the district court clearly erred re-
garding either finding. As to the first finding, as our
discussion above indicates, there was ample support
for the conclusion that Gonzalez-Zavala had access to
significant dollars as a leader of the Organization’s large
drug distribution cell in Chicago. The evidence before
the district court likewise supported the finding that
Gonzalez-Zavala’s family suffered economically while
he was in the United States. Specifically, in the letter
largely devoted to discussing her family’s economic
woes, Gonzalez-Zavala’s wife wrote, “We were doing
okay when [Gonzalez-Zavala] lived with us but unfortu-
nately, he left my children and I.” Gonzalez-Zavala con-
cedes that this statement “could be read to mean that
Gonzalez-Zavala abandoned his family to seek riches in
the United States,” but argues that the more accurate
inference from the letter is that Gonzalez-Zavala’s
family missed his emotional support when he left for
the United States. Given that even Gonzalez-Zavala
recognizes that the district court chose from one of two
permissible interpretations of the letter, we will not
disturb the district court’s finding as clearly erroneous.


                   III. CONCLUSION
 For the foregoing reasons, we A FFIRM the denial of
Bueno’s motion to suppress and A FFIRM Gonzalez-
Zavala’s sentence.

                           1-7-13
