United States v. Theodore Richards

In the

United States Court of Appeals
For the Seventh Circuit

No. 12-2790

U NITED S TATES OF A MERICA,
Plaintiff-Appellee,
v.

T HEODORE R ICHARDS,
Defendant-Appellant.

Appeal from the United States District Court
for the Northern District of Illinois, Eastern Division.
No. 10 CR 993—Milton I. Shadur, Judge.

A RGUED A PRIL 5, 2013—D ECIDED JUNE 14, 2013

Before E ASTERBROOK, Chief Judge, and F LAUM and
W OOD , Circuit Judges.
F LAUM, Circuit Judge. As Theodore Richards tells it,
he was the unwitting stooge of California drug dealers
who flew him from California to Chicago on a mission
to pick up and transport money but, unbeknownst to
him, sent him home with ten kilograms of cocaine in-
stead. Unfortunately for him, a joint federal-state
task force had his pick-up site under surveillance in
2 No. 12-2790

coordination with a controlled buy scheduled to occur
there that day. Officers stopped Richards, too, and dis-
covered the cocaine. A jury convicted him of possession
with intent to distribute after he took the stand in his
own defense and after the government introduced
taped phone calls in which Richards talked about
unrelated drug activity. Richards appealed, challenging
the district court’s denial of his motion to suppress, its
denial of his motion to exclude the phone calls under
Rule 404(b), and the government’s use of the phone call
evidence during closing arguments. Because the gov-
ernment improperly relied on the phone calls to
argue propensity, we now vacate Richards’s conviction
and remand for a new trial.

I. Background
A. Factual Background
On November 21, 2010, federal and state police took
up surveillance around the house located at 109 South
Pinecrest in Bolingbrook, Illinois. In their sights was
Juan Regalado, a suspected high-level drug dealer.
Police had converged on the Pinecrest house that day
because an undercover police officer was scheduled
to purchase a large amount of cocaine there.
The operation required some advance work. First, the
undercover officer met with Regalado at his ranch in
Frankfort, Illinois. The day of the transaction, Novem-
ber 21, the officer rendezvoused with a lead car at an
offsite location and then followed that lead car to the
No. 12-2790 3

Pinecrest house. Upon arrival, the lead car left, and the
officer pulled his car into the driveway. He backed into
the garage, where the plan called for Regalado’s men
to load cocaine into a trap compartment accessed
through the trunk of the officer’s car. Opening the trunk,
however, prevented the officer from pulling his car com-
pletely into the garage; this protrusion in turn pre-
vented the garage door from closing. Regalado’s men
loaded bags into the trunk, and the officer left. Officers
later confirmed that the bags contained ten kilograms
of cocaine. Officers continued surveillance of the
Pinecrest house because the undercover officer sus-
pected additional drugs remained on the property.1
About twenty minutes later, a silver pick-up truck
arrived. The driver exited the car, entered the home, and
returned to the truck after a short conversation with
an occupant of the house. Officer Kenneth Mok, one of

1
Richards heavily attacked the government’s reliance on
the undercover officer’s statements that additional drugs
remained but the district court ultimately disagreed:
[Y]ou criticize the Government’s assertion that Officer Mok
later learned that the undercover officer stated that there
appeared to be more drugs in the garage. Now, you have
read “appeared” as literally, that is, something viewed.
But that usage I think carries the concept of taking all the
circumstances into account inadequate—“appeared”
I think is not used there literally but rather it is in the
terms of—seemed likely is I think a fair reading of the
use of that word. So an attempt to make sort of a mountain
out of a nonexistant molehill doesn’t help us a great deal.
4 No. 12-2790

the surveillance officers, followed the pick-up after it
departed the Pinecrest property. The truck ultimately
met another car in a mall parking lot, a gray Lexus. The
truck drove slowly past the Lexus and, as far as
Officer Mok could tell, neither driver communicated
with the other. The pick-up led the Lexus back to the
Pinecrest house and then left. The Lexus, meanwhile,
backed into the garage. The garage door closed. When it
reopened ten minutes later, the Lexus emerged and drove
away from the property with Officer Mok following
behind.
While tailing the Lexus, Officer Mok received confirma-
tion that the substance loaded into the undercover
officer’s car had tested positive for cocaine. After an
hour of surveillance during which the Lexus violated no
traffic laws, Officer Mok stopped the car. The defendant,
Theodore Richards, was driving the car, and Nickelle
Rodgers sat in the passenger seat. Officers questioned
the pair.
Richards presented a California driver’s license and,
when asked who owned the car, admitted several times
that it was not his. He never named the owner, however,
until Officer Mok asked if the name “Jason Cook”—which
Officer Mok had obtained from the vehicle registra-
tion—sounded familiar. According to Richards, Cook
was his cousin. Richards told Mok he had flown in
from Bakersfield, California, and had picked up Rodgers
from Indianapolis to go on a date. The two were on
their way to get something to eat, Richards explained.
For her part, Rodgers told the police that she and
Richards had been playing video games at another
No. 12-2790 5

house and were on their way to grab a bite to eat. Neither
mentioned their stop at the Pinecrest house.
Without consent, police searched the car and found
a backpack in the trunk. It contained about ten
kilograms of cocaine. Both Richards and Rodgers
denied ownership of the bag and both were arrested.
None of the officers involved in the operation had—before
the gray Lexus arrived at the Pinecrest property—any
information connecting either Richards or Rodgers
with Regalado nor did the officers have any specific
information (aside from the undercover officer’s sug-
gestion that more drugs may have been at the Pinecrest
house) suggesting another drug deal would occur that day.

B. Procedural History
The government charged Richards with one count of
possession of more than five kilograms of cocaine with
intent to distribute. Richards moved to suppress the
cocaine, arguing that the government lacked probable
cause to stop and search the gray Lexus. The district
court disagreed, concluding that Richards “tr[ied] to
separate the strands of the information on which the
officers acted as though they somehow ought to be
looked at separately rather than together.” And viewing
all the information together—the undercover officer’s
drug buy, the similarities between the undercover
officer’s approach and Richards’s approach in the gray
Lexus, and the undercover officer’s suggestion that
the Pinecrest property may have housed more drugs—the
6 No. 12-2790

district court found probable cause. It denied the
motion, and the case proceeded to trial.
At trial, Richards’s primary defense rested on the
assertion that he thought the backpack contained money,
not drugs. He took the stand in furtherance of that de-
fense. According to Richards’s testimony, he had borrowed
$50,000 from some Latinos that he knew collectively only
as the Pelon brothers. He needed the money to start a
trucking company with his cousin, but the company
faltered when his cousin—the driver—became ill.
Unable to repay his loan, the Pelons enlisted Richards’s
assistance transporting packages, telling him that his help
would repay the debt. According to Richards, he trans-
ported several packages for the Pelons, all of which he
opened (against orders from the Pelons) and all of which
contained money. Usually, Richards would communicate
with the Pelons and obtain his instructions by meeting
them at a ranch. Each time he visited the ranch, he testi-
fied, about thirty people were present “doing work and
doing things.” Moreover, Richards explained that at the
ranch, “[e]verybody called each other Pelon. That
was the term that they used amongst each other.”
Richards also told the jury why he thought the Pelons
wanted his trips transporting money to remain secret:
Well, I knew [the Pelons] were over here illegally. And
they ran a lot of different businesses and stuff. And
I also knew about strip clubs and prostitution. And
I was being told about things about people sneaking
over through the border, or whatever. That is
what they said. There was also like—people that
No. 12-2790 7

were also out at the ranch, they were also involved in
drugs. But they never told me so I don’t know.
Finally, Richards explained how the trip that led to
his arrest came about. He received instructions from
“Pelon” and was told he would travel to Chicago to
transport money. As instructed, he waited until a
gray truck drove by and then proceeded to the Pinecrest
property where individuals loaded a dark backpack into
his trunk. According to Richards, he was “shocked, con-
fused” when officers removed the cocaine from his
trunk because “[i]t wasn’t supposed to be in [his] car.”
Richards also testified that he had never been told he
would pick up drugs in any of his “conversations with
the Pelon brothers or with their associates.”
In cross-examining the defendant, the government
asked Richards if he had ever talked on the phone with
a man named Juan Beltran, which the defendant denied.
The government also accused Richards of conversing
with Beltran or another person regarding the need to
obtain drugs. Richards admitted that he used marijuana
but specifically denied discussing cocaine with anyone.
On re-direct, Richards told the jury that he would talk
with his brothers Lou and Chuckie about marijuana.
Lou, he explained, was at the Pelon brothers’ ranch “all
the time.” And while Lou was at the ranch, Richards
continued, he went by the name “Pelon.” Lou, however,
was not involved in Richards’s trip to Chicago that ulti-
mately culminated in Richards’s arrest.
Given this testimony, the government offered a brief
rebuttal case involving taped phone conversations
8 No. 12-2790

between Richards and a Bakersfield man named Juan
Beltran. According to Drug Enforcement Administration
Agent Shawn Riley, who monitored the wiretap on
Beltran’s phone during an unrelated investigation,
Beltran also went by the alias “Pelon.” The conversations
all occurred in the days leading up to Richards’s arrest.
In them, Beltran and Richards discussed drug quantity
and drug quality. Although Beltran and Richards never
specifically mentioned any drugs by name, Riley testi-
fied that, based on his prior experience investigating
drug transactions and listening to wiretaps, the language
Beltran and Richards used indicated that the two
were discussing cocaine.
Richards moved to exclude the phone calls as improper
prior bad acts evidence. See Fed. R. Evid. 404(b). In the
two months that Riley listened to the wiretap on
Beltran’s phone, Beltran never talked about transporting
money or drugs in Bolingbrook. According to Richards,
these tapes were improper evidence because the gov-
ernment could not show that Beltran (also known as
Pelon) was the same Pelon who sent Richards to Chi-
cago. Richards also challenged introduction of the evi-
dence on grounds that the government did not
comply with Rule 404(b)’s notice requirement. For its
part, the government acknowledged no definitive con-
nection between Beltran and the Pelon brothers. Never-
theless, the government argued that nexus to the criminal
trafficking in this case was unnecessary: Richards had
professed complete ignorance as to how the drug trade
worked and these phone conversations undermined
that assertion by showing Richards’s familiarity with the
drug trade more generally, thus proving probative of
No. 12-2790 9

Richards’s knowledge that the bag contained cocaine.
See Fed. R. Evid. 404(b)(2) (permitting use of prior bad
act to show defendant’s knowledge). The district court
agreed and, after a voir dire of Agent Riley and review
of the tapes, permitted Agent Riley to testify regarding
some but not all of the conversations between Beltran
and Richards.
This evidence of the phone calls between Beltran and
Richards became the centerpiece of the government’s
closing argument. Shortly into the argument, the pros-
ecutor began referring to Richards as a “cocaine dealer.”
With little delay, the government explained how it
reached this conclusion: the California calls required it.
In particular, the prosecutor identified one call between
Beltran and Richards in which Richards complained of
poor quality drugs. “[T]he defendant knew this cocaine
was terrible quality based on the packaging and just by
looking at it,” the prosecutor told the jury. “How does
he know that?” she asked. “Because he is a drug traf-
ficker.” At this point, defense counsel objected, sug-
gesting that the California calls were being used for
propensity in violation of Rule 404. The district court
admonished defense counsel for interjecting during
closing arguments but did provide a mid-argument
instruction that cautioned the jury against inferring
guilt solely from evidence of Richards’s prior bad acts.
The government pressed on, continuing to characterize
Richards as a “cocaine dealer” and a “drug trafficker” and
arguing that such status required the inference that
Richards knew the backpack contained drugs, not
money. For example, immediately after quoting defen-
10 No. 12-2790

dant’s words in the phone calls, the prosecutor told the
jury: “Now, based upon the defendant’s own conduct
on November 21st, 2010 and his own statements, when
you use your common sense, there can be only one con-
clusion, the defendant, a cocaine dealer, knew exactly
what he was transporting on November 21st of 2010.”
The theme continued in rebuttal:
• The only thing that is disputed is whether the
defendant knew he had just picked up ten kilo-
grams of cocaine. And in answering that question
think about what is reasonable and what makes
sense. And there is [sic] two things in particular
that will help you answer that question. The de-
fendant is a cocaine dealer and the defendant is
a liar.
• But if we have met our burden on the instruction
that will be given, then the California calls are
absolutely relevant to knowledge and intent on
November 21st. And the Judge will instruct you
as much. To think that that is not relevant is ab-
surd. He is a cocaine dealer.
• The problem is you have heard what the defendant
sounds like when he doesn’t think anyone is
listening, when he doesn’t think anyone is watch-
ing. You heard the calls. You reviewed the tran-
scripts. When he doesn’t think anyone is listening,
he is a cocaine dealer. When he thinks people
are watching and listening, he is back to poor me,
I was just delivering money to pay back the
loan. That is absurd.
No. 12-2790 11

• And we are not saying the ten kilos of cocaine
were connected to the intercepted call from Cali-
fornia. We are not arguing that. We are not saying
that. Clearly the defendant’s drug dealing is not
limited to California. It happens here too.
• These layers of concealment are used to give
drug dealers plausible deniability. But that
doesn’t work for the defendant because we
already know he is a cocaine dealer.
The government relied solely on the California calls as
evidence to support its characterization of Richards as
a drug dealer. And it did not connect drug dealing in
the abstract with the specific patterns in this case.
For example, nothing in closing remarks suggested
that drug couriers (as opposed to money couriers) use
the lead-car approach or that a drug dealer would
know that a pick-up conducted as occurred in this case
would involve drugs, not money.
At the end of closing arguments, defense counsel re-
quested a sidebar and again complained that the gov-
ernment had used the California calls to argue propen-
sity. The district court again disagreed, stating “I don’t
think that is fair. I think that the ‘don’t believe him’ was
contrasting his statements with what they say the evidence
reflects. And that is perfectly permissible.”
Richards now appeals the district court’s denial of
his motion to suppress. He also challenges the district
court’s decision to admit the California calls and
its approval of the government’s use of those calls
in closing.
12 No. 12-2790

II. Discussion
A. The Undercover Officer’s Controlled Buy Generated
Probable Cause to Search the Gray Lexus
The Fourth Amendment protects citizens against unrea-
sonable searches and seizures. Ordinarily, warrantless
searches are presumptively unreasonable. Cars, however,
are exempted from the warrant requirement provided
officers have probable cause to believe the car contains
contraband. United States v. Slone, 636 F.3d 845, 848 (7th
Cir. 2011); see also Florida v. White, 526 U.S. 559, 564-65
(1999); Carroll v. United States, 267 U.S. 132, 160-62 (1925).
When officers have such probable cause, the search may
extend to “all parts of the vehicle in which contraband
or evidence could be concealed, including closed com-
partments, containers, packages, and trunks.” 2 United
States v. Williams, 627 F.3d 247, 251 (7th Cir. 2010). We
review de novo a district court’s conclusion regarding
probable cause. Id.
Probable cause exists when “based on the known
facts and circumstances, a reasonably prudent person
would believe that contraband or evidence of a crime
will be found in the place to be searched.” Id. This
requires a “common-sense judgment” based upon the

2
This probable cause also justifies the initial, warrantless stop
of the car that, as a seizure under the Fourth Amendment,
requires its own justification—be it the reasonable suspicion
needed for a Terry stop or the probable cause necessary for
a full stop. E.g., United States v. Bueno, 703 F.3d 1053, 1059
(7th Cir. 2013).
No. 12-2790 13

totality of the circumstances. Officers may “draw rea-
sonable inferences based on their training and experi-
ence in making that determination.” Id. Probable cause
does not require information sufficient to support con-
viction or even enough to show a preponderance of
the evidence. Id. at 252. A “fair probability of discovering
contraband” is enough. Id. Richards presents a close
case. Nevertheless, we believe that the facts and circum-
stances known to officers at the time of the stop pro-
vided probable cause to believe the Lexus had picked
up drugs during its brief stop at the Pinecrest residence.
As a result, officers had a “fair probability of discovering
contraband” in the gray Lexus, justifying the stop and
search under the Fourth Amendment.
First, officers knew their inside man had purchased
ten kilograms of cocaine at the Pinecrest residence less
than an hour before the gray Lexus arrived.3 The white
substance loaded into the trunk of the undercover
officer’s car had been confirmed as cocaine through a
field chemical test before Officer Mok stopped the
Lexus. Second, officers knew that the approach of the
gray Lexus mirrored that of their undercover officer:
At a different location, both cars met another vehicle

3
Our reliance on the timing of the undercover officer’s high-
volume drug purchase relative to Richards’s arrival does
not establish any rigid, temporal requirements for finding
probable cause. Instead, we simply note that, on these facts
and circumstances, the relative timing of the undercover
officer’s buy and Richards’s arrival at the Pinecrest house
supports officers’ probable cause determination.
14 No. 12-2790

that led them to the Pinecrest residence. After arrival,
the lead car left as both Richards and the undercover
officer backed into the garage where both remained for
less than ten minutes. And after that short period had
elapsed, both cars left the Pinecrest house. Given all
this information, a reasonable officer could say with a
fair probability that the gray Lexus had picked up
drugs from the Pinecrest house.
Unsurprisingly, Richards emphasizes what remained
unknown to the police. According to him, the police had
no evidence linking him to Juan Regalado, the target of
their sting, and no information indicating a second,
scheduled drug purchase that day. But “[o]ne can
always point out informational gaps, [and] the probable
cause inquiry asks what a law enforcement officer knew
rather than what he did not.” Slone, 636 F.3d at 849. No
doubt, these facts would have solidified probable cause
but their absence does not lessen the probable cause
generated by the highly unusual approach the Lexus
took to arrive at the Pinecrest residence, when an under-
cover officer had used the exact same approach (albeit
with a different lead car) to arrive at the house in anti-
cipation of purchasing a large amount of drugs.
Indeed, officers need no advance notice that a drug
deal will occur to have probable cause that they have just
witnessed one. In United States v. Funches, for example,
officers knew none of the defendants was “the man for
whom they were looking and had no information that
[they] were involved in drug trafficking[.]” 327 F.3d 582,
584 (7th Cir. 2003). The officers followed defendants’ car
No. 12-2790 15

anyway. In doing so, they eventually witnessed defen-
dants’ car meet a Nissan Altima in a supermarket parking
lot. Id. After brief interaction among the occupants of
the cars, defendants’ car led the Altima to an alley and
then drove to a nearby apartment. A woman exited the
apartment with a gray bag and passed that bag through
the window of defendants’ car, which returned to the
alley. Id. At that point, the defendants in the two cars
exchanged the gray bag for a gold bag. Id. That sequence
of events, Funches concluded, provided officers with
probable cause to believe a drug deal occurred because
“agents would recognize such action as consistent with
common precautions taken by dealers in drug transac-
tions.” Id. at 586-87.
And in Williams, officers suspected drug activity at a
particular residence. They confirmed that activity
through wiretapped phone calls and the arrest of an
individual leaving the house with a package containing
two kilograms of cocaine. 627 F.3d at 251-52. Additional
phone calls suggested a meeting at the residence with a
“black guy.” Id. at 249. This prior drug activity combined
with the phone call describing the meeting provided
probable cause to search a car when the Williams defen-
dants had entered the residence with a shoebox, left
fifteen minutes later carrying the same shoebox, and
then drove away. Id. at 251-52.
The officers’ knowledge in this case combines the
suspicious vehicular relocation of Funches with the
prior confirmation of drug activity in Williams. The cir-
cuitous approach that Richards took to the Pinecrest
16 No. 12-2790

house—meeting another car at an offsite location that
led Richards to the house—is not unlike the sequence of
events in Funches and not the sort of travel that an
innocent acquaintance would employ when visiting a
friend.4 See also Slone, 636 F.3d at 850-51 (probable cause
to find involvement in drug transaction when one car
followed another car, known to contain drugs, for a
circuitous and extended route); United States v. Soto,
375 F.3d 1219, 1222-23 (10th Cir. 2004) (probable cause
to find involvement in drug transaction when vehicle
entered gas station parking lot near site of deal, slowly
circled, and parked without patronizing gas station).
Indeed, the vehicular maneuvering in this case—meeting
a lead car at a different location who would escort the
buyer to the Pinecrest residence—justifies even stronger
conclusions of suspicious activity because unlike in
Funches, an undercover officer had participated in
nearly identical maneuvers immediately prior to pur-
chasing drugs.
And just as in Williams, where officers confirmed
drug dealing activity through a prior arrest, 627 F.3d at
251-52, here, officers had prior confirmation of drug
dealing activity through the undercover officer’s recent

4
Richards suggests some ambiguity regarding whether both
cars backed into the garage. The district court did not make
explicit factual findings in this regard but, in denying the
motion to suppress, did appear to credit the government’s
testimony over that of the defendant. In any event, the out-
come of this case does not hinge on that fact.
No. 12-2790 17

purchase. 5 Indeed, Williams itself highlights the factual
similarity to this case: “[T]he totality of the facts and
circumstances—that [the defendants] met Hinojosa and
Barmbila (suspected drug dealers) at the Monitor
residence (a suspected stash house), where agents knew
Hinojosa and Barmbila had carried out a drug transac-
tion as recently as the day before, and that [the
defendants] left that meeting carrying a shoebox (in
which they could conceal drugs)—were sufficient to
create probable cause even absent such details in the
[wiretapped] calls.” Id. at 252. Officers’ knowledge in
this case presents nearly identical facts and circum-
stances. Richards met suspected drug dealers at a sus-
pected stash house and left the property in precisely
the same way a confirmed buyer had left not an hour

5
Richards finds Williams less analogous to this case because
in Williams, the police had intercepted phone conversations
suggesting a “meeting” with a “black guy” at the residence
where officers had previously observed the drug activity. 627
F.3d at 249. But as explained above, probable cause does not
require advance notice that a drug deal will occur. All it
requires is a “fair probability” based on all the facts that a
drug deal occurred. Nor does the fact that Richards’s lead car
differed from the escort provided to the undercover officer
distinguish Williams, as Richards suggests. Drug dealing
operations are not shielded from probable cause simply
by hiring different individuals to fill similar roles in the or-
ganization.
18 No. 12-2790

before.6 On top of all this stands Officer Mok’s extensive
experience investigating drug operations: a twenty-
year veteran of the Chicago Police Department, Mok
had spent four years on the DEA task force at the
time of the Richards arrest. Thus, the “totality of the
circumstances”—and the factual similarity to both
Funches and Williams—“when considered in light of
[Officer Mok’s] training and experience, gave [him]
sufficient reason to believe that there was a significant
probability that” Richards had committed a crime.
United States v. Parra, 402 F.3d 752, 765 (7th Cir. 2005).
Richards relies heavily on the well-settled proposition
that mere proximity to suspected criminal activity
does not, without more, generate probable cause.
Richards accurately states the law, see United States v.
Bohman, 683 F.3d 861, 864 (7th Cir. 2012); United States v.
Ingrao, 897 F.2d 860, 863 (7th Cir. 1990); see also Illinois v.
Wardlaw, 528 U.S. 119, 124 (2000); United States v. Ceballos,
654 F.2d 177, 185 (2d Cir. 1981), but this rule does not
apply to him: officers could reasonably conclude from
his actions and the undercover officer’s reports that
Richards was not simply proximate to criminal activity
but a participant in it. Neither Bohman nor Ingrao aids
Richards as much as he suggests. In Bohman, police
stopped a car exiting property that officers suspected of

6
Richards disputes the government’s characterization of the
Pinecrest property as a stash house. Regardless of how one
defines “stash house,” no one disputes that an undercover
officer had purchased ten kilograms of cocaine there.
No. 12-2790 19

housing a methamphetamine lab. 683 F.3d at 863-64.
That suspicion resulted from a tip they had received,
but when police stopped the car, they had not yet cor-
roborated the tip in any way. Id. at 864-65. Bohman
found no reasonable suspicion for the stop because the
only information pointing to criminal activity was the
defendant’s emergence from property that an uncorrobo-
rated tip accused of housing a meth lab. Id. That alone
was insufficient.
Ingrao involved similar facts. Officers in that case ar-
rested the defendant after he emerged from a gangway
between two houses while carrying a black, opaque
bag. 897 F.2d at 861. Officers could not, however, connect
the Ingrao defendant to the house on either side of the
gangway. Id. at 863-64. That fact proved significant, for
one of the houses belonged to an individual whom
police had been investigating. Id. at 861. Police had,
however, observed suspicious activity by other indi-
viduals emerging from the gangway. Id. Ultimately,
police lacked probable cause to arrest the Ingrao
defendant because his only connection to the previously
observed suspicious activity was his presence in the
gangway between the two homes. Id. at 863-64.
Richards is unlike the defendants in Bohman and
Ingrao. For one thing, officers did not act merely on uncor-
roborated information. The Pinecrest house was a con-
firmed drug den—an undercover officer had just pur-
chased ten kilos of cocaine there and suspected still
more product remained. Thus, officers had far more
incriminatory information regarding activity at the
20 No. 12-2790

Pinecrest house than the Bohman officers did in their
uncorroborated tip. For another, Richards did not
simply emerge from the location of criminal activity as
both the Bohman and Ingrao defendants did. Perhaps
Bohman and Ingrao would require reversal if officers’
first glimpsed Richards as he pulled out of the
Pinecrest garage. But they saw much more: They saw a
lead car leave the Pinecrest property and meet him in a
parking lot. They saw him follow that car back to the
Pinecrest property. And they saw him back into the
garage, and then leave. Each of these actions directly
mirrored the approach of the undercover officer in his
drug buy, thereby permitting the reasonable inference
that, like the officer, Richards arrived to pick up drugs.
Thus, there is “far more in this case . . . than . . . mere
physical proximity” to the criminal activity. United
States v. Burrell, 963 F.2d 976, 987 (7th Cir. 1992).
In short, the facts known to officers created a fair proba-
bility that Richards’s car contained drugs, even though
officers had never before seen Richards and had no
prior indication that Richards planned to pick up large
amounts of cocaine from the Pinecrest residence. An
undercover officer had previously purchased large
amounts of cocaine from the property and believed
more drug product remained onsite. Less than an hour
after the undercover officer left, Richards arrived under
the same travel protocol that the undercover officer
used when purchasing the drugs. These facts and cir-
cumstances generate a fair probability that Richards
had picked up drugs just as the undercover officer had.
No. 12-2790 21

We emphasize again that Richards presents a close
case. Were it not for the undercover officer’s drug
purchase within the hour and the strong similarity
between the actions of the undercover officer and the
gray Lexus, the police would surely have lacked prob-
able cause to stop Richards. As such, that the Lexus
followed another car to the Pinecrest residence would
not, standing alone, provide probable cause. Likewise,
neither would the Lexus’s association with the Pinecrest
property solely provide probable cause. But the com-
bination of Richards’s behavior and the undercover offi-
cer’s high-volume drug buy less than an hour before is
enough. For that reason, we affirm the district court’s
denial of Richards’s motion to suppress.

B. The District Court Did Not Abuse Its Discretion in
Admitting the California Calls as Probative of
Knowledge
We also find no error in the district court’s admission
of the California calls. Evidence of a defendant’s prior
bad acts is inadmissible to show propensity to commit
a crime. Fed. R. Evid. 404(b)(1). Such evidence is admissi-
ble, however, if the evidence is relevant to an issue in
question other than the defendant’s propensity to
commit the charged crime. Fed. R. Evid. 404(b)(2); e.g.,
United States v. Baker, 655 F.3d 677, 681 (7th Cir. 2011).
Additionally, we also consider whether the prior acts
are similar enough and close enough in time to be
relevant and whether the evidence is sufficient to
support a jury finding that the defendant committed the
22 No. 12-2790

act. E.g., Baker, 655 F.3d at 681. Finally, as with all
evidence, the danger of unfair prejudice must not sub-
stantially outweigh its probative value. Fed. R. Evid.
403; see also Baker, 655 F.3d at 681-82.
We review the district court’s admission of evidence
under Rule 404(b) for an abuse of discretion. Even when
an abuse of discretion occurs, however, reversal fol-
lows only if admission of the evidence affected the de-
fendant’s “substantial rights.” Fed. R. Crim. P. 52(a);
United States v. Hicks, 635 F.3d 1063, 1069 (7th Cir. 2011).
In making that evaluation, we “gauge what effect the
error had or reasonably may be taken to have had upon
the jury’s decision.” Hicks, 635 F.3d at 1069 (citing United
States v. Zapata, 871 F.2d 616, 622 (7th Cir. 1989)). Impor-
tantly, nothing “suggest[s] that after-the-fact remarks
during closing argument have any bearing on the
district court’s original Rule 404(b) determination.” United
States v. Kieffer, 68 F. App’x 726, 730 (7th Cir. 2003)
(non-precedential). Thus, the prosecutor’s use of
Rule 404(b) evidence during closing presents a question
separate from whether the court properly admitted
the evidence in the first place.
Richards wages three attacks on the district court’s
admission of the California calls. First, he argues that the
tapes are not relevant to knowledge, the non-propensity
issue proffered to justify their admission. Second, he
argues that the cocaine transactions discussed on the
tapes are not similar enough or temporally proximate
enough to be relevant. And third, Richards argues that
the potential for unfair prejudice outweighs the proba-
tive value of the evidence.
No. 12-2790 23

1. The California Calls Are Relevant to Richards’s
Knowledge That the Bag Contained Cocaine
We have recently cautioned that district courts have
too readily admitted prior bad acts evidence in drug
cases. United States v. Miller, 673 F.3d 688, 696 (7th Cir.
2012) (“[A]dmission of prior drug crimes to prove
intent to commit present drug crimes has become too
routine.”); see also United States v. Jones, 389 F.3d 753, 756-58
(7th Cir. 2004), vacated on other grounds by 545 U.S. 1125
(2005). Rule 404, however, does not present an insur-
mountable barrier to admission of prior bad acts evi-
dence. To begin, “[i]dentification of an at-issue,
non-propensity Rule 404(b) exception is a necessary
condition for admitting the evidence[.]” Miller, 673 F.3d
at 697. Thus, district courts must consider “specifically
how the prior conviction tend[s] to” serve the non-pro-
pensity exception. Id. at 699 (emphasis added). Addition-
ally, not only must the evidence be relevant to a valid non-
propensity issue, the a defendant must also “meaning-
fully dispute” that non-propensity issue. Miller, 673
F.3d at 697.
We find both requirements satisfied in Richards’s case
and thus see no error in the district court finding the
California calls probative of a non-propensity purpose.
First, knowledge is a valid non-propensity purpose,
and Richards placed his knowledge of the bag’s contents
directly at issue when he took the stand and testified
that he believed the bag contained money, not drugs.
Second, a “specific” link exists between the calls and
Richards’s testimony, making the calls relevant to his
knowledge of the bag’s contents.
24 No. 12-2790

a. Richards’s Defense Put His Knowledge of the
Bag’s Contents Directly in Issue
A defendant must “meaningfully dispute” the non-
propensity issue justifying admission of the Rule 404(b)
evidence. Miller, 673 F.3d at 697. Thus, if the defendant
simply asserts his innocence in a more general way or
argues his conduct failed to satisfy some other element of
the crime besides intent or knowledge, prior bad acts
evidence is inadmissible. Id. Miller illustrates the more
general defense assertions that would not meaningfully
dispute a Rule 404(b) exception. In that case, the defen-
dant—on trial for possession with intent to distribute—
did not dispute intent. (That police found the large quan-
tity of drugs at issue packaged into smaller bags with
price tags attached made that a tough sell.) Nor did he
suggest he failed to recognize the substance as cocaine.
Instead, he argued simply that the drugs belonged to
his girlfriend. Id. at 699. His defense did not meaning-
fully dispute intent or knowledge so introduction of his
prior convictions for drug offenses proved intent only
to the extent that intent collapsed into propensity:
“He intended to do it before . . . so he must have
intended to do it again.” Id.; cf. Jones, 389 F.3d at 757
(“Propensity and intent are two different things, how-
ever, even if only a fine line sometimes distinguishes
them.”).
Richards directly and specifically disputed his knowl-
edge of the bag’s contents. On the stand, Richards de-
scribed traveling to a ranch with at least thirty indi-
viduals on the property, all known as “Pelon.” He
No. 12-2790 25

also admitted his awareness of criminal activity
originating from the ranch:
And [the Pelon brothers] ran a lot of businesses and
stuff. And I also knew about strip clubs and prostitu-
tion. And I was being told about things about people
sneaking over through the border, or whatever. That
is what they said. There was also like—people that
were also out at the ranch, they were also involved
in drugs. But they never told me that, so I don’t know.
(Emphasis added.) He acknowledged that his own
brother purchased drugs, marijuana, at the ranch and
that, while there, his brother went by “Pelon” just like
everyone else. And Richards also explained how his trip
to Bolingbrook originated at the Pelon ranch—a trio of
brothers, all known as Pelon, brought him to the ranch
where he received instructions about picking up and
transporting money to pay back a debt. Thus, Richards
told the jury, when he picked up the bag from the
Pinecrest house, he believed it contained money and
not drugs.7

7
We pause to note that trafficking drug money is, under
most circumstances, no less a federal crime than trafficking
the drugs themselves. See 21 U.S.C. § 846 (criminalizing con-
spiracy to violate the drug laws); cf. United States v. Saenz, 623
F.3d 461 (7th Cir. 2010) (affirming conviction under § 846
when defendant transported drug money). The government
did not charge Richards with conspiracy, however, allowing
him to argue that the Pelon brothers limited his involve-
ment in their illicit business endeavors only to that of a
money courier.
26 No. 12-2790

This testimony places his knowledge squarely in issue
and raises essentially the same circumstances as United
States v. Moore. In that case, officers arrested the
defendant after he tossed a bag of drugs out his car win-
dow. 531 F.3d 496, 500 (7th Cir. 2008). At trial, he
argued that “the driver of the stolen vehicle, in which
he was a passenger, gave Mr. Moore the bag and told
him to toss it, without telling him what was in it.” Id.
That defense, Moore concluded, put knowledge directly
at issue. Id. Richards raises nearly the identical
defense here—that someone gave him a bag filled
with drugs but he thought it contained something
else. Thus, Richards, like the Moore defendant, put knowl-
edge squarely at issue and opened the door to any
prior bad acts evidence relevant to knowledge. See
Hicks, 635 F.3d at 1069-70.

b. The California Calls Are Relevant to Richards’s
Knowledge of Drug Trafficking at the Pelon
Ranch
Relevant evidence has a tendency to make a fact of
consequence more or less probable. Fed. R. Evid. 401;
see also United States v. Gomez, No. 12-1104, 2013 WL
1352540, at *6 (7th Cir. Apr. 5, 2013). Thus, admission of
the California tapes requires a “persuasive and specific”
reason why the tapes make it more or less probable
that Richards knew the bag contained cocaine rather
than money. See Miller, 673 F.3d at 699. A specific and
persuasive reason exists here: Beltran’s Pelon alias links
him to the ranch so tapes of Richards discussing drugs
No. 12-2790 27

with Beltran suggest Richards knew of drug trafficking
that originated from the ranch.
Richards disagrees, suggesting that Miller controls
because, as in Miller, the prior bad acts evidence proves
knowledge only to the extent that knowledge collapsed
into propensity. See id. at 697-99. That would be true
and Richards would be right if the California calls
captured some generic conversation about drugs wholly
unconnected to the drug operation that brought
Richards to Bolingbrook. But the content of the
California calls—Richards speaking about cocaine with
a man known as “Pelon”—does relate to the Boling-
brook operation: Richards took his marching orders
from a group of individuals who, like all others present
at the ranch, shared that pseudonym.8 That common
monicker links Beltran to the ranch and directly
undercuts Richards’s testimony that he had no specific
knowledge of drug dealing there because “they never
told me that.” From Richards’s drug conversations with
Beltran, the jury could infer Richards’s awareness of
the Pelon brothers’ involvement in the drug trade
through a known drug supplier’s (Beltran) use of an
alias linked both to the ranch and to the individuals
that sent Richards to Chicago. And if Richards knew of

8
We note also the possibility that Richards knew Beltran only
by his Pelon pseudonym. Richards testified he did not know
anyone named Juan Beltran and stated that he never spoke
with anyone by that name. Thus, a jury could infer that, like
his association with the Latino Pelon brothers, Richards
knew Beltran only as Pelon.
28 No. 12-2790

the Pelon brothers’ involvement with drug trafficking,
it would “tend to make the existence of any fact that is
of consequence to the determination of the action”—such
as Richards’s knowledge that the bag contained cocaine
rather than money—“more probable[.]” Hicks, 635 F.3d
at 1069-70 (quoting Fed. R. Evid. 401); see also Gomez,
2013 WL 1352540, at *3 (“[T]he Rule 404(b) evidence
must respond to what is said to trigger admissibility.”).
Richards, however, ignores this connection and argues
Beltran was completely uninvolved in the Chicago trans-
action. Maybe so. The conversation suggests that
Beltran had no idea Richards had plans to travel to Chi-
cago. But the fact remains that Beltran went by an alias
associated with those who sent Richards to Bolingbrook.
From that, a jury could infer that Richards knew more
about drug trafficking by the Pelon brothers than he
testified to. At bottom, a prior bad act’s relevance in
proving knowledge does not require the exact same cast
of characters nor does it require a definitive link
between the prior bad act and the current one. Thus,
Beltran need not be directly involved in the Bolingbrook
transaction to make the California calls relevant to Rich-
ards’s knowledge. In Moore, the defendant’s prior bad
act of throwing a bag of cocaine from a car window
proved relevant to his knowledge of another bag’s con-
tents. 531 F.3d at 500. This was so despite no connec-
tion between the prior incident and the conduct under
prosecution—nothing suggested the Moore defendant
had received both bags from the same individual or
that one transaction related to the other. Id. at 498-500.
No. 12-2790 29

Nevertheless, we do not suggest, as the government
did at trial, that wholly unrelated prior bad acts may
show knowledge. The government could not therefore
introduce conversations depicting completely unrelated
drug activity under the rationale that the defendant’s
general familiarity with the drug trade proves relevant to
his knowledge. The admissibility of these phone calls
thus turns on Beltran’s Pelon alias: It connected Beltran
to the Pelon brothers via the Pelon ranch even if
Beltran himself did not direct the Bolingbrook operation.
Without it, the California calls would prove relevant
to knowledge only through the propensity inference—
precisely the result forbidden by Miller. In short, Richards
told the jury that he thought the bag contained money
and that he had no knowledge of drug trafficking orig-
inating at the Pelon ranch. Beltran’s alias linked him to
the ranch so any conversations between Richards and
Beltran suggesting knowledge of the drug trade permit
the jury to infer that Richards had greater knowledge
of drug trafficking at the ranch than he let on. This con-
nection makes the California calls relevant to Richards’s
knowledge of the bag’s contents.

2. The California Calls Are Similar Enough and
Close Enough in Time to be Relevant
Prior bad acts too dissimilar from the charged conduct
or too remote in time can render evidence inadmissible
under Rule 404(b). See Hicks, 635 F.3d at 1070; United
States v. Conner, 583 F.3d 1011, 1023 (7th Cir. 2009). Accord-
ing to Richards, the calls are too dissimilar from the
Bolingbrook operation because the calls discussed at
30 No. 12-2790

most a few ounces of cocaine, whereas the charges in-
volved transportation of ten kilograms of the drug. Rich-
ards, however, ignores the key similarity: in this case,
Richards took his marching orders from the Pelon
brothers and in the phone calls he discussed drugs with
a man known as Pelon. This similarity—not the amount
of drugs—provides the central link between the
California calls and the charged conduct. It makes the
calls relevant to Richards’s knowledge of drug trafficking
at the Pelon ranch and the contents of the gym bag.
Although nothing suggested the phone calls involved the
exact same characters running the Pinecrest operation, see
Conner, 583 F.3d at 1023 (prior bad acts admissible when it
involved “same characters and similar activities”); United
States v. Wilson, 31 F.3d 510, 515 (7th Cir. 1994) (prior bad
acts admissible when it involved the “same parties at the
same location”); see also Baker, 655 F.3d at 682 (prior
conviction substantially similar when it involved same
activity but different people), neither were the California
calls totally unrelated (or, at least, so a jury could con-
clude). Thus, the California calls are unlike the prior
drug convictions in Hicks, which had no relationship to
the drug deal resulting in the prosecution. 635 F.3d at
1070. As Hicks explained, nothing suggested the “prior
convictions for cocaine possession and distribution
make it more likely that [Hicks] was a ‘knowing partici-
pant’ in this drug deal[.]” Id. In contrast, the Pelon alias
of both Beltran and Richards’s handlers provides the
nexus between the two crimes that was absent in Hicks.
We thus conclude that the conduct described in the
California calls is sufficiently similar and close enough
in time to the Bolingbrook operation.
No. 12-2790 31

3. The Potential for Unfair Prejudice Did Not Sub-
stantially Outweigh the Probative Value of the
Calls
Rule 403 balancing applies with full force when con-
sidering the admission of prior bad acts evidence. Miller,
673 F.3d at 696. As an initial matter, nearly all govern-
ment evidence prejudices the defendant—if it did not, the
government would not introduce it. The inquiry turns on
whether the evidence prejudices the defendant in some
unfair way that substantially outweighs the value of the
evidence in determining the truth. See United States v.
Perkins, 548 F.3d 510, 515 (7th Cir. 2008). “Evidence is
unfairly prejudicial only to the extent that it will cause
the jury to decide the case on improper grounds.” United
States v. Chavis, 429 F.3d 662, 668 (7th Cir. 2005). In cases
involving Rule 404(b) evidence, that improper ground
is the propensity inference.
We have previously recognized, though, that properly
administered limiting jury instructions cure the danger of
unfair prejudice unless “the jury could not follow the
court’s limiting instruction.” Perkins, 548 F.3d at 515
(quoting United States v. James, 487 F.3d 518, 525 (7th Cir.
2007)); see, e.g., Baker, 655 F.3d at 682; United States v.
Denberg, 212 F.3d 987, 994 (7th Cir. 2000). The district
court here instructed the jury on several occasions to
consider the calls only in relation to Richards’s knowl-
edge of the bag’s contents. Richards ultimately makes no
showing that the district court’s instructions did not
resonate with the jury or were misunderstood. Moreover,
the district court engaged in a careful voir dire of Agent
32 No. 12-2790

Riley and reviewed transcripts of the calls before ruling
on their admissibility. See United States v. Beasley, 809
F.2d 1273, 1279 (7th Cir. 1987) (criticizing “perfunctory”
pretrial hearing on Rule 404(b) evidence). To further
mitigate the potential for prejudice, the calls themselves
do not directly reference drug activity and the jury, if
it chose, could have disbelieved the testimony of Agent
Riley. Defense counsel also had ample opportunity to—
and actually did—vigorously cross-examine Agent Riley.
Admittedly, the California calls are not as probative of
Richards’s knowledge as other evidence could have
been—such as evidence that Richards discussed drugs with
the Pelon who sent him to Chicago or evidence more
closely linking Beltran with those brothers. But the calls
were not wholly irrelevant—as we have explained, their
content supported an inference that, contrary to his
testimony, Richards knew of drug activity at the Pelon
ranch. And though not as probative of Richards’s knowl-
edge as other evidence would have been, neither were
the calls as prejudicial as other types of Rule 404(b) evi-
dence, such as an actual conviction for drug trafficking,
which would definitively establish Richards’s involve-
ment in the drug trade (and would be particularly tough
to attack on cross-examination). Evidence of such con-
victions involves a far greater risk that the jury will
“decide the case on improper grounds,” such as the
propensity inference, than on the evidence related to
the conduct charged. Yet we have previously declined
to find unfair prejudice in evidence as prejudicial as a
prior conviction when coupled with a limiting instruc-
tion. E.g., Moore, 531 F.3d at 500.
No. 12-2790 33

Ultimately, the district court took the proper prophylac-
tic steps to insure the jury drew no improper inference
from the California calls. Mountains of authority
confirm that, when introduced for a valid non-propensity
purpose, such limiting instructions and voir dire exam-
inations cure any unfair prejudice that results from in-
troduction of prior bad acts evidence. Baker, 655 F.3d
at 682; Perkins, 548 F.3d at 515 (quoting James, 487 F.3d at
525); Denberg, 212 F.3d at 994. Because no such unfair
prejudice arose from admission of the California calls,
and because those calls prove relevant to Richards’s
knowledge of the bag’s contents after he disavowed
knowing that drug trafficking originated at the Pelon
ranch, we affirm the district court’s admission of the
California calls under Rule 404(b).

C. Although Admissible, the Government Improperly
Used the California Calls to Argue Propensity
During Closing
Admission of Rule 404(b) evidence, however, does not
grant the government free rein to use that evidence how-
ever it wishes. Having obtained admission of the evi-
dence for a specific, non-propensity purpose, the gov-
ernment cannot then deploy the Rule 404(b) evidence in
support of some other argument or inference. Rather, it
must limit its use of the evidence to the purpose
proffered when admitting the evidence. See Gomez, 2013
WL 1352540, at *3 (“[T]he Rule 404(b) evidence must
respond to what is said to trigger admissibility.”). It
cannot ever rely upon that evidence to argue propen-
34 No. 12-2790

sity. The government did so in this case so we vacate
the conviction and remand for retrial.
Improper prosecutorial comments during closing
arguments are reviewed under a prosecutorial mis-
conduct framework. See, e.g., United States v. Bell, 624
F.3d 803, 811 (7th Cir. 2010). This analysis requires, first
a determination that prosecutors acted improperly, and
second a conclusion that the improper conduct prejudiced
the defendant. E.g., United States v. Simpson, 479 F.3d
492, 503 (7th Cir. 2007), abrogated on other grounds by
United States v. Boone, 628 F.3d 927, 933 (7th Cir. 2010).
Because Richards objected to the government’s closing,
we review the district court’s decision to permit the gov-
ernment’s argument for abuse of discretion. Id.

1. The Government’s Closing Argument Invited
the Jury to Draw the Prohibited Propensity Infer-
ence from the California Calls
“Just as introducing evidence to show propensity is
improper, so too is arguing to a jury that it should
convict a defendant based on the defendant’s propensity
to commit a crime.” Simpson, 479 F.3d at 503; accord
United States v. Klebig, 600 F.3d 700, 719 (7th Cir. 2010).
This prohibition remains even when the court has ad-
mitted the Rule 404(b) evidence for some permissible
non-propensity purpose—the government cannot
later argue that the evidence shows the defendant’s
propensity to engage in criminal behavior. Yet that is
precisely the inference the government invited in this
case. Indeed, during closing arguments, prosecutors
No. 12-2790 35

routinely called the defendant a “drug dealer” and a
“drug trafficker.” As support for these labels, the gov-
ernment relied exclusively on the California calls:
“You heard the calls. . . . When he doesn’t think anyone
is listening, he is a cocaine dealer.” 9 Jones, in fact, found
a propensity inference in nearly the same con-
duct—repeated prosecutorial characterizations of the
defendant as a drug dealer: “The Assistant U.S.
Attorney then repeatedly told the jury that Jones’s
prior convictions showed that he was a drug dealer,
and that they should therefore, find that he intended to
deal drugs in this case. This looks, walks, and sounds
like the argument ‘once a drug dealer, always a drug
dealer.’ ” Jones, 389 F.3d at 757; see also Simpson, 479 F.3d
at 503-04 (impermissible propensity argument in defen-
dant’s statement that he had participated in so many
drug deals he could not remember the specific deal
with which he was charged). No material differences
separate Jones from this case.
The government’s oft-repeated refrain naming the
defendant a “drug dealer” and “drug trafficker” is not
even the most glaring example of its propensity argu-
ment. On rebuttal, the prosecutor told the jury, “Clearly
the defendant’s drug dealing is not limited to California.

9
The government relied on the California calls to prove Rich-
ards’s status as a drug dealer at other times, too. “[T]he defen-
dant knew this cocaine was terrible quality based on the
packaging and just by looking at it,” the prosecutor told the
jury. “How does he know that?” she continued. “Because he
is a drug trafficker.”
36 No. 12-2790

It happens here too.” The prosecutor has all but linked
these two sentences with “because.” No matter that he
did not—the meaning is the same: Richards dealt drugs
in California so he must have done so here, too. And
later on, the prosecutor told the jury “These layers of
concealment are used to give drug dealers plausible
deniability. But that doesn’t work for the defendant
because we already know he is a cocaine dealer.” How,
precisely, does the government already know Richards is
a cocaine dealer? From the California calls, of course.
Again, the inference is the same. Richards dealt in Cali-
fornia so he must have dealt in Bolingbrook.
The government instead insists that the district court
properly admitted the evidence and, as a result, it was
free to “weave the statement into its theory of the case.”
Bell, 624 F.3d at 812; see also United States v. Bowman,
353 F.3d 546, 551 (7th Cir. 2003). Fair enough, but
Rule 404(b) prohibits the government’s theory of the
case from resting on the propensity inference. Here, the
government did precisely that, placing the propensity
inference at the center of its closing argument.
Prosecutors never explained to the jury specifically
how Richards’s conversations with a man known as
Pelon showed his knowledge of drug dealing at the
Pelon ranch. For example, the government could have
explained that Richards’s drug conversations with a
man known as Pelon suggested Richards knew of drug
trafficking originating from the Pelon ranch, thereby
showing Richards knew the bags contained drugs. It
did not. Instead, the government simply used the Cali-
fornia calls to label Richards a cocaine trafficker and
No. 12-2790 37

rested its case there. That is the propensity inference
that Miller, Jones, and Simpson prohibit. See Miller, 673
F.3d at 699 (“[T]he government must affirmatively
show why a particular prior conviction tends to show
the more forward-looking fact of purpose, design, or
volition to commit the new crime.” (quoting Jones, 389
F.3d at 757-58)). Neither Bowman nor Bell suggests other-
wise. Both cases found the challenged statements
devoid of “propensity aspects” or submitted for a
non-propensity purpose, such as challenging the defen-
dant’s credibility after he had testified. Bell, 624 F.3d
at 811-12; Bowman, 353 F.3d at 551 (noting prosecutor
never “asked the jury to draw the inference that because
Bowman had admitted problems abiding by the law,
he must be guilty”).
Reduced to its core, the government’s closing argument
revolved around the propensity inference with the Cali-
fornia calls as its centerpiece. The government paid
scant attention to the knowledge rationale that justified
admitting the tapes and instead deployed the tapes
as evidence of Richards’s propensity for drug trafficking.
That argument was improper, and we conclude that
the district court abused its discretion in concluding
otherwise.

2. The Government’s Propensity Arguments at
Closing Prejudiced Richards and Entitle Him
to a New Trial
Prejudice does not require an ironclad guarantee
that, absent the prosecutorial misconduct, the outcome
38 No. 12-2790

of trial would have differed. See Simpson, 479 F.3d at
505 (“[I]t is not enough to say that the outcome
probably would have been the same without the pros-
ecutor’s improper propensity inference and the evi-
dence of [the defendant’s] past unrelated drug deals.”).
“Doubts—a lack of ‘fair assurance’—call for a new
trial.” Miller, 673 F.3d at 701.1 0 Thus, Richards need not
show that, on remand, a jury would not convict him a
second time.
When gauging prejudice, we “consider the remarks
in light of the entire record to determine if the defendant
was deprived of a fair trial.” Simpson, 479 F.3d at 504
(quoting United States v. Wesley, 422 F.3d 509, 515
(7th Cir. 2005)). Six factors influence this determina-
tion: (1) whether the prosecutor misstated evidence;
(2) whether the statements implicate a specific right of
the defendant; (3) whether the defense invited the pros-
ecutor’s remarks; (4) the trial court’s instructions; (5) the
weight of the evidence against the defendant; and (6) the
defendant’s opportunity to rebut. Id.
At the outset, several factors clearly favor the absence
of prejudice. The statements did not implicate a

10
We note that the prejudice bar stands higher when the
defendant does not object to prosecutorial misconduct.
Bowman, 353 F.3d at 550. In that situation, prejudice requires
that the “outcome of the proceedings would have been dif-
ferent absent” the misconduct. Id. Richards preserved his
objections with the district court, though, so he need not
satisfy this high bar.
No. 12-2790 39

specific right, and the district court did give a limiting
instruction.11 Even that limiting instruction did little to
mitigate the prejudice arising from the government’s
propensity arguments. Limiting instructions mitigate
prejudice associated with Rule 404(b) evidence when the
government offers the evidence for some permissible
purpose and actually argues that permissible purpose
at closing. E.g., Moore, 531 F.3d at 500. When the gov-
ernment explicitly argues propensity, however, the cura-
tive value of a limiting instruction diminishes dramatically.
Other factors, however, weigh in favor of prejudice.
Although the prosecution did not misstate the
evidence, it “invited the jury to make an improper in-
ference from the evidence, an action with a similar ef-
fect.” Simpson, 479 F.3d at 504. Also, Richards had
no opportunity to address the statements because the
government made most inflammatory statements
during its rebuttal argument. See United States v.
McMath, 559 F.3d 657, 668 (7th Cir. 2009). And neither
did Richards invite the prosecutor’s statements with
anything presented in his defense. True, Richards put
knowledge at issue. That defense, however, simply
allows the government to introduce the calls and

11
The instruction read, in pertinent part: “Let me make plain
once again to the jurors that you are to consider for purposes
of this trial whether the Government has proved beyond
a reasonable doubt the event that is charged in the indictment
that occurred on November 21st. You are not to consider
for purposes of finding him guilty conduct at an earlier point
of the type that [the prosecutor] is referring to.”
40 No. 12-2790

explain to the jury how they show knowledge. It does
not invite the government to argue propensity.
The weight of the evidence factor also favors preju-
dice. Explaining away ten kilograms of cocaine is
difficult and certainly supports an inference that
Richards knew of its presence. But the govern-
ment offered no direct evidence of that fact. Neither
Officer Mok nor the other officers tailing Richards
testified to seeing him open the bag, and the garage
door to the Pinecrest house had closed after Richards
backed into it. But Richards mounted a vigorous defense
and told the jury he thought the bag contained money.
A Michigan state trooper even bolstered Richards’s
defense by testifying that on a previous occasion police
had found large amounts of money in a bag in the trunk
of Richards’s car. In short, Richards’s fate hung on his
credibility with the jury. The government’s improper
propensity argument shattered this credibility in unsal-
vageable ways. See Simpson, 479 F.3d at 504 (“In a case
where the circumstantial evidence against Simpson
was close, the prosecution’s explicit instruction to the
jury to draw the inference that Simpson had conducted
‘so many’ crack cocaine deals that he could not
remember the deal for which he stood trial was a power-
ful argument.”); see also Bell, 624 F.3d at 813 (finding
no prejudice in case that was not a “swearing contest”).
Only one factor counsels strongly toward finding
no prejudice. The others call into question the fairness
of Richards’s trial and raise doubts that the jury
would have convicted him absent the government’s
No. 12-2790 41

improper propensity argument at closing. As a result,
we conclude Richards deserves a new trial.

IV. Conclusion
The police possessed sufficient probable cause to
justify stopping and searching the gray Lexus so we
A FFIRM the district court’s denial of Richards’s motion
to suppress. Likewise, we agree with the district court
that Richards placed his knowledge squarely in issue
when he took the stand in his own defense. We also
find the California calls relevant to Richards’s knowl-
edge of drug dealing at the Pelon ranch and, therefore,
relevant to Richards’s knowledge of the bag’s contents.
We thus A FFIRM the district court’s admission of the
California calls under Rule 404(b). We cannot, however,
characterize the government’s statements in closing
arguments as anything other than an invitation to the
jury to infer Richards’s guilt in this case from his
previous conversations involving drug dealing. That the
government may not do. This improper suggestion
of propensity prejudiced Richards so we V ACATE Rich-
ards’s conviction and R EMAND for a new trial.
42 No. 12-2790

W OOD , Circuit Judge, concurring in the judgment.
Theodore Richards stands convicted of possession of
cocaine with intent to distribute, in violation of 21 U.S.C.
§ 841(a)(1). On appeal, he has raised three principal
issues: (1) whether the district court properly denied
Richards’s motion to suppress on the ground that there
was probable cause to stop his car and arrest him;
(2) whether the district court abused its discretion when
it admitted evidence of Richards’s telephone calls with
a person in California, over an objection under Federal
Rule of Evidence 404(b); and (3) whether the govern-
ment improperly used that evidence during its closing
argument. Like my colleagues, I find the first question
close, but in the end I conclude that the district court’s
decision not to suppress the evidence that resulted
from the stop of Richards’s car was supportable,
taking all the circumstances into account. And like my
colleagues, I find that the prosecutor’s closing argument
violated the limits that the court had placed on the evi-
dence of the California calls, by inviting the jurors to
convict Richards solely on propensity grounds. More-
over, this violation was prejudicial to Richards. Thus,
I join my colleagues in their judgment that Richards
has demonstrated that he must have a new trial. Where
I part company with them is on the second issue
Richards has raised: the admissibility of the California
calls under Rule 404(b). I write to explain my position
because this issue may arise in a retrial.
As the majority notes, ante at 25 n.7, this is an odd case:
normally it does not make any difference whether the
defendant is holding actual drugs or the proceeds from
No. 12-2790 43

the sale of drugs. But here, it does, because Richards was
charged only with possession of cocaine with intent to
distribute it. There was no conspiracy count, nor was
there a direct distribution count that would have
permitted a conviction based on the money. In my
opinion, this was a fatal misstep on the prosecution’s
part in this case. It allowed Richards to argue, without
fear of incriminating himself (at least with respect to
the charges in the present case), that he thought that the
backpack was filled with money, not drugs; this was
in keeping with the role that he had played in the
Michigan transaction. Nothing in the California calls
gave the slightest reason to think that Richards had
drugs rather than money, or money rather than drugs.
I thus find the California calls useless when it comes to
the particular question of knowledge that we have in
this case: did Richards know that the bag contained drugs?
My colleagues place great weight on the fact that Rich-
ards’s conversations in California were with a person
who went by the name “Pelon,” and that he was sent to
the Pinecrest residence by men from “the Ranch,” where
lots of people also went by that name. But “pelon” is just
a Spanish word that means “Bald Guy,” or “Baldy.”
I therefore cannot read anything into the fact that a
number of people adopted the “pelon” moniker, any
more than I would if people called themselves “Shorty”
or “Red-head” or “Curly.” The fact that several people
use the same nickname, with nothing more, does not
establish that those people work together in the same
enterprise or are in any way connected to each other.
And it certainly tells us nothing about anyone’s role
44 No. 12-2790

within the enterprise (supplier; distributor; courier;
lookout; money-handler) for any given transaction.
Other than the common nickname, there is no evidence
that the man with whom Richards discussed drug deals
in the wiretapped calls, Beltran (a.k.a. Pelon), had any
connection to the men from “the Ranch” who sent
Richards to the Pinecrest house. Ante at 26-28. Traveling
to Chicago was never mentioned during the phone calls
between Richards and Beltran. Id. at 7. The majority
recognizes that evidence of “completely unrelated drug
activity” would not be admissible to show that Richards
likely knew that drugs as opposed to currency were
inside the bag. Id. at 29. And it essentially admits
that Richards’s phone calls with Beltran would be com-
pletely unrelated aside from the fact that “Beltran went
by a common alias associated with those who sent Rich-
ards to Bolingbrook.” Id.
Richards contested the fact—essential to the govern-
ment’s theory—that he knew that the backpack in the
trunk of his car contained drugs. The California calls
shed no light on that issue; they show only that Richards
had discussed drugs with a man who goes by the same
nickname as the people who sent him on the trip to
the Pinecrest residence. These facts do not have a
tendency to make it more or less probable that Richards
knew that the particular bag had drugs, not money,
and thus they fail the test of relevance imposed by
Federal Rule of Evidence 401. I would find that this case
is governed by United States v. Miller, 673 F.3d 688 (7th
Cir. 2012): the contested evidence proved nothing but
Richards’s propensity to be involved in the drug
No. 12-2790 45

trade. It shed no light on the crucial question whether
the backpack contained drugs or money.
For these reasons, I respectfully concur in the judgment.

6-14-13