United States v. Simpson, Robert ( 2007 )

In the
United States Court of Appeals
For the Seventh Circuit
____________
No. 05-2993
UNITED STATES OF AMERICA,
Plaintiff-Appellee,
v.
ROBERT SIMPSON,
Defendant-Appellant.
____________
Appeal from the United States District Court
for the Northern District of Illinois, Eastern Division.
No. 04 CR 260—Ronald A. Guzman, Judge.
____________
ARGUED JUNE 5, 2006—DECIDED MARCH 13, 2007
____________
Before BAUER, ROVNER, and WILLIAMS, Circuit Judges.
WILLIAMS, Circuit Judge. After his first trial ended in a
hung jury, the government retried Robert Simpson for a
single delivery of crack cocaine. Although on trial only
for a single sale, the jury heard evidence concerning
Simpson’s involvement in prior unrelated crack cocaine
transactions. The prosecution repeated this evidence
during its closing argument and also said Simpson had
told a law enforcement agent he was a crack dealer and
could have done the delivery at issue, but that he did not
remember whether he had. Over defense counsel’s ob-
jection, the prosecution then told the jury that the infer-
ence to be drawn from these statements was that Simp-
son had done so many crack cocaine deals that he could not
2 No. 05-2993
remember the deal for which he was on trial. This argu-
ment, and the evidence on which it was based, improperly
appealed to Simpson’s propensity to deal in crack cocaine.
Because we are not assured that Simpson received a fair
trial, we vacate Simpson’s conviction and remand his case
for a new trial.
I. BACKGROUND
A federal grand jury returned a single-count indict-
ment against Robert Simpson. This indictment charged
Simpson with distributing over 50 grams of a mixture
containing cocaine base on March 6, 2003, in Joliet,
Illinois. Before his first trial, Simpson filed a motion in
limine to bar evidence of his other bad acts, arguing that
such evidence is not admissible to prove a defendant’s
propensity to commit a crime. As the government repre-
sented that it had no intention of eliciting testimony
regarding Simpson’s prior bad acts, the district court did
not enter a ruling on the motion. The first trial ended in
a mistrial after the jury was unable to reach a verdict.
The case was subsequently retried before a second jury.
During the second trial, the government introduced
evidence that on March 6, 2003, law enforcement officials
met with confidential informant Emmanuel Bradley and
directed him to buy 2 and 1/4 ounces of crack cocaine
that day. Around 3:20 that afternoon, a white minivan,
later determined to be registered to Simpson’s wife, pulled
into a small parking area behind 402 North Center
Street in Joliet, Illinois where Simpson’s sister lived. FBI
Agent Mike Brown testified that he saw the minivan
driver get into Bradley’s car. However, Agent Brown could
not identify the minivan driver as Simpson. Agent Brown
subsequently recovered from Bradley a digital tape
recorder, a plastic bag containing 61.5 grams of cocaine
base, and $100 of the $1600 in buy money provided to
No. 05-2993 3
Bradley. Agent Brown also testified that he saw Bradley
make a number of telephone calls that day, including
one to a telephone number belonging to Simpson; he also
saw Bradley receive a phone call from that same number
a short time later.
Although Bradley had testified at the first trial and
identified Simpson as the person from whom he bought
crack cocaine on March 6, Bradley did not testify during
the second trial. Agent Brown also did not identify
Simpson as the minivan driver. Instead, the government
presented Deputy Jim Stadt of the Will County Sheriff ’s
Office as the only eyewitness to identify Simpson. Deputy
Stadt testified that while using binoculars from about 75-
100 yards away, he saw a person arrive in a minivan,
enter Bradley’s car for a minute or two, and then leave
the car. While conducting this surveillance, Deputy Stadt
did not know the name of the person he saw leave the
minivan. After he returned to his office, he viewed a
photograph of a person identified to him as Robert
Simpson and concluded that Simpson was the person he
had observed leaving the minivan.
Law enforcement officials waited over a year before
arresting Simpson. FBI Agent Christopher Hendon
effected the arrest and told the jury that on March 9, 2004,
he went to Simpson’s sister’s home looking for Simpson.
Simpson was not present, and Agent Hendon left his
business card with contact information. About forty-five
minutes later, Simpson called, and, after Agent Hendon
informed Simpson there was a warrant for his arrest,
Simpson agreed to meet him. Simpson was placed under
arrest and received Miranda warnings. Agent Hendon
testified that during the subsequent interview, after
Simpson had been informed of the charge against him,
“Simpson told us . . . although he didn’t specifically,
according to what he told us, remember delivering this
2 1/4 ounce of crack cocaine amount, that it was possible
4 No. 05-2993
because he had done similar type[s] of transactions and
delivered for an individual that he primarily dealt with
by the name of Michael Hatton.”
Agent Hendon also testified that Simpson told him he
had been a crack cocaine dealer for three to four years and
purchased half an ounce of crack cocaine from Hatton
approximately every two or three weeks. He would then
break it up into smaller quantities to sell. When asked
what Simpson said about 2 and 1/4 ounce quantities of
crack cocaine, Hendon testified that Simpson “stated he
had made similar types of deliveries on behalf of Mr.
Hatton in exchange for being paid in crack cocaine but that
he did not specifically remember this transaction he was
being asked about during the interview.” Agent Hendon
did not ask Simpson to read or verify the notes he took of
their conversation, stating that the FBI did not take
written statements from suspects if an agent believed the
subject had been less than candid.
About two days later, Agent Hendon was asked to listen
to a tape recording of the March 6, 2003 controlled pur-
chase made using the digital recorder worn by Bradley.
Agent Hendon concluded that the voice on the recording
“seemed” to be that of Simpson. He acknowledged at trial
that he was not an expert in voice identification, and the
prosecution did not tender him as such. The jury heard
the tape recording and received a transcript of the re-
cording. No physical evidence tying Simpson to the trans-
action was introduced.
After the jurors had heard all the evidence, the prosecu-
tion argued to the jury in its closing argument, “And you
know what the defendant told him: Yes, I’m a crack dealer.
I’ve been a crack dealer for three to four years, and I could
have done this transaction, 2 1/4 ounces, on behalf of
Michael Hatton, but I don’t remember, because my view of
the inference, the inference being - -”. At this point,
No. 05-2993 5
defense counsel objected. The objection was overruled, and
the prosecutor continued: “The inference being he’s done
so many that he couldn’t remember this one.”
The jurors submitted to the judge several questions
about the evidence presented. In particular, the jurors
asked why Bradley (the confidential informant) had not
testified, whether any fingerprints had been lifted from
the bag of cocaine, whether any voice recognition tech-
niques had been conducted on the tape recording, and
whether transcripts of Deputy Stadt’s testimony and an
FBI report were available to them. At the close of their
deliberations, the jurors returned a guilty verdict on the
sole count in the indictment. Simpson received a sentence
of 188 months’ imprisonment and five years’ supervised
release, and he now appeals.
II. ANALYSIS
Simpson was tried only for making a single delivery of
cocaine base on March 6, 2003. He was not charged with
participation in a conspiracy to distribute illegal drugs.
And he was not charged with distribution of cocaine
base on any occasion other than March 6, 2003. With that
backdrop in mind, we turn to Simpson’s argument that
the admission of evidence that Simpson had engaged in
prior unrelated crack cocaine deals, as well as the infer-
ence the prosecutor drew in his closing argument, improp-
erly suggested to the jury that Simpson had a propensity
to act as a drug dealer and thereby denied him a fair trial.
It should be clear by now that evidence that a defendant
had engaged in other drug transactions is not always
admissible in a subsequent drug prosecution. See, e.g.,
United States v. James, 464 F.3d 699, 711 (7th Cir. 2006);
United States v. Wright, 901 F.2d 68, 70 (7th Cir. 1990);
United States v. Beasley, 809 F.2d 1273, 1278 (7th Cir.
6 No. 05-2993
1987). Introducing only prior drug convictions or bad acts,
with nothing more, proves nothing but propensity. United
States v. Jones, 389 F.3d 753, 757 (7th Cir. 2004), vacated,
545 U.S. 1125 (2005) (remanding for further considera-
tion in light of United States v. Booker, 543 U.S. 220
(2005)); see James, 464 F.3d at 711. As one of our col-
leagues observed recently, “Allowing a prosecutor rou-
tinely to introduce drug convictions in the case in chief
without demonstrating relevance to some concrete dis-
pute between the litigants creates needless risk that a
conviction will rest on the forbidden propensity inference.”
United States v. Jones, 455 F.3d 800, 812 (7th Cir. 2006)
(Easterbrook, J., concurring). In that risk lies Simpson’s
concern, and ours.
A. Admission of Evidence Concerning Prior Unre-
lated Drug Sales
Simpson argues on appeal that Agent Hendon’s testi-
mony concerning Simpson’s involvement in unrelated drug
deals was admitted in violation of Federal Rule of Evi-
dence 404(b). Evidence that he had sold crack cocaine in
the past, Simpson argues, could show only his propensity
to sell crack cocaine, not that he was the person responsi-
ble for selling crack cocaine to a confidential informant on
March 6, 2003. The government, however, contends that
this evidence was admissible either under the “identity”
exception to Rule 404(b) or pursuant to the “intricately
related evidence” doctrine.
1. Standard of Review
When a defendant fails to object to the admission of
evidence during trial, as here, our review of a challenge to
the evidence’s admission is for plain error. United States
v. Olano, 507 U.S. 725, 731-35 (1993); James, 464 F.3d at
No. 05-2993 7
709; cf. United States v. Chavis, 429 F.3d 662, 667 (7th Cir.
2005) (reviewing decision to admit evidence for abuse of
discretion where timely objection made). Our review for
plain error asks whether (1) error occurred; (2) the error
was “plain”; (3) and the error affected the defendant’s
substantial rights. James, 464 F.3d at 709; see also United
States v. Meadows, 91 F.3d 851, 855 (7th Cir. 1996)
(defining “error” as a “deviation from a legal rule” and an
error that is “plain” as one that is “clear or obvious”)
(citations omitted). If these three conditions have been
met, we may exercise our discretion to correct the error
if it seriously affects the fairness, integrity, or public
reputation of judicial proceedings. James, 464 F.3d at 709.
2. Admission of Evidence of Prior Unrelated Drug
Sales Constitutes Error That Was Plain
Federal Rule of Evidence 404(b) provides:
Evidence of other crimes, wrongs, or acts is not
admissible to prove the character of a person in
order to show action in conformity therewith. It
may, however, be admissible for other purposes,
such as proof of motive, opportunity, intent, prepa-
ration, plan, knowledge, identity, or absence of
mistake or accident . . . .
The first sentence in Rule 404(b) plainly prohibits the
government from introducing evidence of prior bad acts
to show that the defendant’s character is consistent with
a propensity to commit the charged crime. United States v.
Holt, 460 F.3d 934, 937 (7th Cir. 2006); United States v.
Macedo, 406 F.3d 778, 792-93 (7th Cir. 2005). As then-
Judge Breyer put it, “Although . . . ‘propensity evidence’
is relevant, the risk that a jury will convict for crimes
other than those charged—or that, uncertain of guilt, it
will convict anyway because a bad person deserves
8 No. 05-2993
punishment—creates a prejudicial effect that outweighs
ordinary relevance.” United States v. Moccia, 681 F.2d 61,
63 (1st Cir. 1982); see also Michelson v. United States, 335
U.S. 469, 475-76 (1948); United States v. Seals, 419 F.3d
600, 610-11 (7th Cir. 2005) (Posner, J., concurring).
a. Identity Exception to Rule 404(b)
The government maintains that the evidence of
Simpson’s prior unrelated drug sales is admissible to
show “identity” under Rule 404(b). Rule 404(b) is first a
rule of prohibition: “[e]vidence of other crimes, wrongs, or
acts is not admissible to prove the character of a person
in order to show action in conformity therewith” (emphasis
added), subject only to limited exceptions. The presump-
tion set forth in the Rule is against admissibility. And, we
emphasize, simply because the evidence in question tends
to show intent, motive, identity, or the like does not mean
the evidence is automatically admissible. Rather, the
second sentence of the rule makes explicitly clear that
such evidence “may” be admissible, not that admission is
automatic. See Jones, 455 F.3d at 810 (Easterbrook, J.,
concurring).
With these principles in hand, we turn to the four-part
test this circuit has adopted for determining whether
evidence should be admitted under Rule 404(b). We have
said that evidence of a defendant’s prior bad acts is
admissible only if four requirements are met:
(1) the evidence is directed toward establishing a
matter in issue other than the defendant’s propen-
sity to commit the crime charged; (2) the evidence
shows that the other act is similar enough and
close enough in time to be relevant to the matter
in issue; (3) the evidence is sufficient to support a
jury finding that the defendant committed the
No. 05-2993 9
similar act; and (4) the evidence has probative
value that is not substantially outweighed by the
danger of unfair prejudice.
Jones, 455 F.3d at 806; United States v. Owens, 424 F.3d
649, 653 (7th Cir. 2005). Simpson maintains that in this
case, neither the first nor the fourth requirement has
been satisfied.
First, and most importantly, we must determine whether
the statements in question are directed toward establish-
ing a matter other than Simpson’s propensity to sell crack
cocaine. Although Simpson maintains the testimony
showed only his propensity to sell drugs, the government
argues the statements were directed toward establishing
Simpson’s identity as the person responsible for the
March 6, 2003 drug delivery.
One way we have allowed admission of a defendant’s
prior bad acts is to prove identity through evidence of a
defendant’s distinctive manner of operation, or modus
operandi. See, e.g., United States v. Anifowoshe, 307 F.3d
643, 647 (7th Cir. 2002); United States v. Rollins, 301 F.3d
511, 519 (7th Cir. 2002). We only allow evidence to be
admitted under the modus operandi theory when the
evidence bears “a singular strong resemblance to the
pattern of the offense charged” with the similarities
between the two crimes “sufficiently idiosyncratic to
permit an inference of pattern for purposes of proof.”
United States v. Thomas, 321 F.3d 627, 634-35 (7th Cir.
2003). The reason we allow the use of other acts to show
modus operandi is that the same person probably com-
mitted both the other acts and the charged crime due to
their sufficiently idiosyncratic similarities. See United
States v. Robinson, 161 F.3d 463, 468 (7th Cir. 1998). This
reasoning does not require an inference concerning the
defendant’s character. But we have cautioned that “[i]f
defined broadly enough, modus operandi evidence can
10 No. 05-2993
easily become nothing more than the character evidence
that Rule 404(b) prohibits.” United States v. Smith, 103
F.3d 600, 603 (7th Cir. 1996); see also Thomas, 321 F.3d
at 635 (“If a pattern so generic can establish modus
operandi, this fairly limited exception to Rule 404(b) would
gut the Rule, rendering it useless as a check on character
evidence that would otherwise be inadmissible.”).
The same caution holds true for identity evidence that
is not evidence of a defendant’s modus operandi. “Cer-
tainly, the need to prove identity should not be, in itself, a
ticket to admission.” 1 McCormick on Evidence § 190 (6th
ed. 2006). Simply because the identity of the person who
sold crack cocaine to Emmanuel Bradley on March 6, 2003
was disputed does not give the government free reign to
introduce evidence about any prior crack cocaine deal in
which Simpson took part. Yet that seems to be the govern-
ment’s argument. It maintains that because Simpson
denied that he was the person who delivered the drugs
in question, it could introduce evidence that he had sold
crack cocaine in the past, in transactions unrelated to the
one at issue—evidence that we would otherwise deem
improper propensity evidence—simply because it needed
to prove that Simpson sold the drugs on March 6, 2003.
Our decision in United States v. Wright, 901 F.2d 68 (7th
Cir. 1990), is instructive. There, the government con-
tended that a wiretapped telephone call containing the
defendant’s admission that he participated in other drug
deals had been properly admitted to show that the defen-
dant committed the drug sale in question. 901 F.2d at 68-
69. In particular, the government maintained that Rule
404(b) did not prohibit the introduction of the evidence, as
it contended the evidence was admissible to show identity.
Id. at 69. Soundly rejecting this argument, we wrote that
the telephone conversation in question in Wright “may well
show that [the defendant] is more likely to be guilty of the
No. 05-2993 11
crime with which he is charged than the average man on
the street, who is not a drug dealer, but it does not in the
least show that the man who had sold the plainclothes
officers four bags of crack [in the transaction at issue] was
correctly identified” as the defendant. Id. Those words
hold true here. That Simpson allegedly admitted to prior
crack cocaine deals may well show that he was more likely
than an average person who had never before dealt in
drugs to have sold the drugs in question. But it does not
show that the identity of the person who sold drugs to
Emmanuel Bradley on March 6, 2003 was Robert Simpson.
We recognized in Wright that evidence of prior drug
crimes might tend to show the identity of the defendant
if, for example, “the conversation had indicated that [the
defendant] was at that time selling drugs on streets near
where the transactions occurred, or if he had said some-
thing that only a party to those transactions would know.”
901 F.2d at 69. Neither scenario exists here. Simpson’s
acknowledgment that he sold crack cocaine during the
same general time period (he admitted he had sold drugs
for several years prior to his arrest), and in similar
quantities, is nowhere near the similarity we contemplated
in Wright. The unfortunate reality is that Simpson was
far from the only person selling crack cocaine during
March of 2003 in the greater Joliet, Illinois area, and
Simpson’s acknowledgment that he was one of those
persons does not help clear up the identity of the person
responsible for the charged crime. Similarly, that Simpson
named Hatton as his supplier does not tend to show that
Simpson was guilty of this crime. Although there was
testimony that Hatton was one of many persons who were
part of law enforcement’s “large scale” investigation into
drug activity in the area, the government has never
contended that Hatton was involved in the March 6
transaction, that Hatton had any relationship with
Bradley, or that Hatton had supplied the drugs at issue.
12 No. 05-2993
Cf. United States v. Joseph, 310 F.3d 975, 978 (7th Cir.
2002) (defendant’s prior mail theft helped to establish
identity in instant case because it linked defendant with
one of the aliases used by the perpetrator). This evidence,
then, did not help establish a matter in issue other than
his propensity to sell crack cocaine.1
Furthermore, the admission of the evidence carried a
significant danger of unfair prejudice. Evidence is unfairly
prejudicial if it will cause the jury to decide the case on
“improper grounds.” Chavis, 429 F.3d at 668. Here, the
jurors were invited to conclude that Simpson’s prior drug
deals proved his guilt for the transaction charged in the
indictment. Significantly, too, the government’s evidence
did not stop at Simpson’s statement that it was “possible”
1
In United States v. Gibson, 170 F.3d 673 (7th Cir. 1999), to
which the government points, the defendant pursued the
specific defense that his brother had sold the drugs in question.
Id. at 679. There, the defendant’s history of drug dealing
distinguished him from the only other person he contended had
committed the crime. Here, in contrast, Simpson put forth no
defense except to deny that he was responsible for the charged
crime and to maintain the government had not proven its case
beyond a reasonable doubt. Wright, not Gibson, governs this
case. And as in Wright, evidence of Simpson’s prior drug activity
was not admissible to show identity, unless “[b]y ‘identity’ the
[government] must have meant ‘guilt,’ ” 901 F.2d at 69, which, of
course, is not proper. We explained in Wright that the “logic of
the district court’s ruling [to allow evidence of the defendant’s
unrelated drug deals] is that a drug defendant’s prior drug
convictions are admissible per se, even if they do not help to
clear up a question of identification or establish a modus
operandi or otherwise illuminate the particular conduct of which
the defendant is accused, and even if he does not take the
stand . . . .” Id. at 70. But “[t]his use of other crimes to establish
a propensity to commit the type of crime charged is the use of
such evidence that Rule 404(b) forbids.” Id.
No. 05-2993 13
he had delivered the crack cocaine at issue. Instead,
additional details regarding Simpson’s prior crack
cocaine deals were revealed. Agent Hendon testified that
Simpson thought his involvement was possible “because
he had done similar type[s] of transactions” and he had
“delivered for an individual that he primarily dealt with
by the name of Michael Hatton.” Agent Hendon then
continued to provide details about Simpson’s drug-dealing
past: he told the jurors that Simpson said he had been a
dealer of crack cocaine, that he had been a dealer for three
to four years, and that he purchased a half ounce of crack
cocaine from his supplier about every two or three weeks,
which he would then break up and sell.
In addition, the jurors did not receive a relevant limiting
instruction, which can minimize prejudice from the
introduction of Rule 404(b) evidence. See Jones, 455 F.3d
at 809; Chavis, 429 F.3d at 668-69; United States v.
Kreiser, 15 F.3d 635, 640 (7th Cir. 1994) (upholding evi-
dence’s admission for purposes of knowledge, intent, and
motive where the “district court carefully explained to the
jury that Kreiser was not on trial for anything that
happened in 1984, but only for the events of 1991”); see
also Jones, 455 F.3d at 811 (Easterbrook, J., concurring).
The jury did receive the following instruction: “If you find
that the defendant did make the statement, then you must
decide what weight, if any, you feel the statement de-
serves. In making this decision, you should consider all
matters in evidence having to do with the statement . . . .”
This instruction drew attention to Simpson’s purported
statements to Agent Hendon, but the jurors did not re-
ceive any instruction limiting how they could or should
use the statements. We conclude that the identity excep-
tion to Rule 404(b) does not support the admission of
evidence pertaining to Simpson’s prior unrelated drug
sales.
14 No. 05-2993
b. “Intricately Related Evidence” Doctrine
Nor is this evidence admissible under the “intricately
related evidence” doctrine, the only other theory the
government suggests to supports its admission. By its
terms, Rule 404(b) only applies to “other” crimes and
conduct; it does not apply to acts that provide proof of the
charged conduct. See United States v. Lane, 323 F.3d 568,
579 (7th Cir. 2003). As a result, “[e]vidence of uncharged
criminal activity does not implicate the character/pro-
pensity prohibition of Rule 404(b) if the evidence is ‘intri-
cately related’ to the facts and circumstances of the
charged offense.” United States v. McLee, 436 F.3d 751,
760 (7th Cir. 2006). Admission is, of course, still contingent
on successfully passing the balancing test set forth in
Federal Rule of Evidence 403. James, 464 F.3d at 709;
Holt, 460 F.3d at 937-38.
The government argues that Agent Hendon’s testi-
mony was admissible as evidence that was intricately
related (or “inextricably intertwined”) with that of the
charge that Simpson delivered crack cocaine on March 6,
2003. According to the government, the details Simpson
provided about his involvement in uncharged drug deals
were admissible because they arose out of “the same
transaction or series of transactions as the charged of-
fense.” See United States v. Lott, 442 F.3d 981, 985 (7th
Cir. 2006).
We have upheld the admission of evidence under the
intricately related evidence doctrine when the evidence
was necessary to complete the story of a crime on trial.
McLee, 436 F.3d at 760; United States v. Gibson, 170 F.3d
673, 682 (7th Cir. 1999); cf. 1 McCormick on Evidence
§ 190 (6th ed. 2006) (cautioning that “[t]his rationale
should be applied only when reference to the other crimes
is essential to a coherent and intelligible description of
the offense at bar”). We have also done so when the
No. 05-2993 15
evidence was needed to avoid a conceptual or chronological
void in the narrative of the crime on trial. United States v.
Andreas, 216 F.3d 645, 665 (7th Cir. 2000); United States
v. Hattaway, 740 F.2d 1419, 1425 (7th Cir. 1984). And we
have found evidence admissible under the intricately
related evidence doctrine when it is so blended or con-
nected that it incidentally involves, explains the circum-
stances surrounding, or tends to prove any element of the
charged crime. United States v. Heath, 447 F.3d 535, 539
(7th Cir. 2006); United States v. Spaeni, 60 F.3d 313, 316
(7th Cir. 1995).
These rationales do not apply here. Simpson was not
charged with conspiracy to distribute crack cocaine. He
was not charged with responsibility for a series of drug
transactions. He was not charged with selling drugs on
Hatton’s behalf. Instead, he was on trial for only one
delivery, on one day, to one person. Evidence of any
prior unrelated drug sales was simply not necessary to
complete the story of the single delivery on trial. Nor was
it needed to avoid a conceptual or chronological void in the
story of the March 6, 2003 delivery. And it was not neces-
sary to explain the circumstances of the single crack
cocaine delivery on March 6, 2003.
The case to which the government pointed us when we
asked for an analogous case, United States v. Lott, 442
F.3d 981, is inapposite. First, Lott did not involve admis-
sion of unrelated, uncharged drug activity in a case where
only a single drug delivery was at issue. Cf. James, 464
F.3d at 710 (finding evidence of drugs seized one month
after drug offense for which defendant was indicted not
intricately related to charged conduct). In Lott, officers
recovered from a vehicle driven by the defendant a loaded
pistol on top of a bag containing a white powder that
turned out to be a crushed prescription drug. 442 F.3d at
985. The defendant was charged with being a felon in
16 No. 05-2993
possession of a firearm, and we upheld the admission of
evidence that he possessed the bag of white powder and
that he had previously dealt in “dummy drugs” under the
intricately related evidence doctrine. Id. We did so be-
cause the evidence explained the motive for the defen-
dant’s possession of a firearm, the crime with which he
was charged—to defend himself from angry customers. Id.
Unlike the admitted evidence in Lott, which helped
complete the story of the crime on trial in that case,
evidence relating to Simpson’s prior drug involvement
would not help a jury form a more complete picture of the
March 6 drug deal for which he was on trial. Evidence
that Simpson had sold drugs over the last three or four
years does not explain why he, as compared to any other
person who had also sold drugs at that time, was re-
sponsible for the drug sale for which he was on trial.
The government argues otherwise, contending that
“details” Simpson gave after stating it was “possible” he
had sold the drugs in question corroborated his “confes-
sion” that it was possible he had sold the drugs on March
6. First, there was no confession. Certainly, if Simpson
had told Agent Hendon he sold crack cocaine to Bradley
on March 6, 2003 under circumstances matching the
government witnesses’ testimony, the government could
have argued to the jury that Simpson had admitted to the
crime for which he was charged. But Simpson did not do
that. His statement that it was “possible” he was responsi-
ble for the charged transaction, but that he did not re-
member, does not constitute a confession of responsibility
for the March 6, 2003 drug deal. “A confession is a sus-
pect’s oral . . . acknowledgment of guilt often including
details about the crime.” United States v. Gilbertson, 435
F.3d 790, 798 (7th Cir. 2006) (quoting Black’s Law Dictio-
nary 317 (8th ed. 2004)); see Opper v. United States, 348
U.S. 84, 91 n.7 (1954). Here, at best, Simpson stated he
did not remember the transaction. At no time did he
No. 05-2993 17
acknowledge he was guilty of selling illegal drugs to
Bradley on the date in question. He provided no details
whatsoever about the March 6, 2003 drug deal, as he
could not even remember if he was there. Admitting that
he had engaged in similar drug deals in the past, making
“possible” his responsibility for the drug deal at issue, falls
far short of an acknowledgment of responsibility for the
charged deal.
Next, the “details” to which the government points—that
he had sold crack cocaine before, for a number of years, at
times in the same quantity—were only details about prior
uncharged drug deals and did not shed any light on the
question of the person responsible for the March 6 sale.
These “details” about prior unrelated drug deals on
unknown dates with unknown persons did not arise out
of the same transaction or series of transactions as the
March 6 transaction for which he was on trial. Evidence
of prior unrelated drug deals is not “intricately related” to
the transaction on trial simply because knowledge of the
other deals was gained in the same interview.
The testimony about Simpson’s prior acts did nothing
more than cloak him before the jury in his prior crack
cocaine deals. In short, had the jurors heard nothing about
Simpson’s prior drug sales, “it would not have occurred
to them that they were missing anything or have made
any of the other evidence in the case unintelligible.” See
United States v. Paladino, 401 F.3d 471, 475 (7th Cir.
2005). Admission of the evidence of Simpson’s prior drug
sales cannot be justified under the intricately related
evidence doctrine, and the evidence’s admission con-
stitutes error that was plain.2
2
The dissent maintains that the agent’s testimony concerning
details Simpson gave about his involvement in past drug deals
constituted admissions against Simpson’s interest. Such state-
(continued...)
18 No. 05-2993
3. Whether the Erroneous Admission of Evidence
Warrants a New Trial
Testimony concerning Simpson’s past drug sales thus
cannot be justified under either the identity exception to
Rule 404(b) or under the intricately related evidence
doctrine. To succeed on a plain error challenge, a defen-
dant must also demonstrate that the error in admission
affected his substantial rights, meaning that the error
“affected the outcome of the district court proceedings.”
Olano, 507 U.S. at 734. If so, we may correct the error
if it seriously affects the “fairness, integrity, or public
reputation of judicial proceedings.” Id. at 736.
Simpson urges that we look not simply at the erroneous
admission of evidence about his past drug deals when we
consider whether he should receive a new trial. Rather, he
2
(...continued)
ments are not hearsay. Fed. R. Evid. 801(d)(2)(A). That a
statement is not hearsay, however, does not answer the sepa-
rate question of whether the statement is precluded as improper
propensity evidence, the question at issue in this case. See United
States v. Oberle, 136 F.3d 1414, 1418 (10th Cir. 1998) (“Although
the statements are party admissions under Rule 801(d) and
thus not hearsay, they must nevertheless also be analyzed for
admissibility under Rule 404(b) because they reveal or suggest
prior criminal conduct.”); United States v. Mickle, 859 F.2d 473,
478-79 (7th Cir. 1988) (recognizing that testimony recounting
defendant’s statement qualified as party admission and was not
hearsay, but stating that “does not end our inquiry” before
analyzing whether statement was admissible under Rule 404(b));
see also United States v. Godinez, 110 F.3d 448, 454-55 (7th Cir.
1997) (analyzing first whether statement constituted inadmissi-
ble hearsay, then whether Rule 404(b) precluded its admission).
The government offered us two theories in support of the
admissibility of this evidence, the intricately related evidence
doctrine and proof of identity under Rule 404(b), and we con-
clude that neither justifies its admission.
No. 05-2993 19
contends that the inference the prosecutor drew in his
closing argument from the evidence regarding Simpson’s
prior crack cocaine sales, along with the erroneous ad-
mission of this evidence, deprived him of a fair trial.
B. The Prosecution’s Closing Argument
In this case, the reason the government had introduced
testimony of Simpson’s numerous prior crack cocaine
transactions became clear during the prosecution’s closing
argument. Throughout the first and second trials, until
its closing argument in the second trial, the government
suggested that Simpson’s statements to Agent Hendon
constituted a confession. During the prosecution’s closing
argument, it sought to use Simpson’s statements to
show propensity, explicitly stating: “The inference being
he’s done so many that he couldn’t remember this one.”
Simpson argues that the inference the prosecutor
explicitly drew for the jury during closing argument, one
that asked the jury to decide Simpson’s fate based on an
inference that he had done “so many” drug deals that he
could not remember the one for which he stood trial,
constituted prosecutorial misconduct. The government
argues that our standard of review on appeal on this
claim should be for plain error, the standard appropriate
when a criminal defendant challenges statements in the
prosecution’s closing argument for the first time on ap-
peal. See United States v. Bowman, 353 F.3d 546, 550 (7th
Cir. 2003). But Simpson’s counsel objected to the portion
of the closing argument he now challenges, and he did so
immediately after the prosecutor uttered the words, “the
inference being - -” in his closing argument. Because
Simpson’s counsel objected at the time the remarks
were made, our review of the district court’s decision to
overrule the objection is for an abuse of discretion. See
20 No. 05-2993
United States v. Sandoval, 347 F.3d 627, 631 (7th Cir.
2003).
We have evaluated claims that a prosecutor’s closing
argument constituted an improper appeal to a defen-
dant’s propensity to engage in certain conduct under the
framework of “prosecutorial misconduct.” See Bowman,
353 F.3d at 550. When evaluating claims that a prosecu-
tor’s comments to a jury rise to the level of prosecutorial
misconduct, we first determine whether the prosecutor’s
conduct was improper. United States v. Hale, 448 F.3d 971,
986 (7th Cir. 2006); see also United States v. Wesley, 422
F.3d 509, 515 (7th Cir. 2005). If so, we next assess whether
the conduct prejudiced the defendant. Hale, 448 F.3d
at 986; United States v. Washington, 417 F.3d 780, 786
(7th Cir. 2005).
1. Impropriety of the Closing Argument
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 com-
mit a crime. See Bowman, 353 F.3d at 551. Simpson
maintains that the prosecutor’s inference that Simpson
had done so many drug transactions in the past that he
could not remember the one for which he stood trial
amounts to nothing more than a prohibited “once a drug
dealer, always a drug dealer” argument. We agree.
This argument said nothing about which person arrived
in the minivan on March 6, 2003. It said nothing about
which person entered the car with Emmanuel Bradley on
that day. And it said nothing about which person sold
the crack cocaine to Bradley. The prosecution’s closing
argument simply, and improperly, asked the jury to
conclude that his admission to prior drug deals demon-
strated his guilt for the March 6, 2003 transaction. Cf.
No. 05-2993 21
Bowman, 353 F.3d at 551 (finding no prosecutorial mis-
conduct where prosecutor used facts adduced at trial “for
permissible purposes” and did not “ask[ ] the jury to draw
the inference that because Bowman had admitted prob-
lems abiding by the law, he must be guilty of the crime
in question”). Because the inference made by the prosecu-
tor instructed the jurors to convict Simpson based on his
prior uncharged drug deals, the inference was improper.3
2. Prejudice
We turn next to the question of prejudice. Our assess-
ment of whether a prosecutor’s improper conduct preju-
diced a defendant includes an examination of six fac-
tors: (1) whether the prosecutor misstated the evidence;
(2) whether the remarks implicated the specific rights of
the accused; (3) whether the defense invited the response;
(4) the trial court’s instructions; (5) the weight of the
evidence against the defendant; and (6) the defendant’s
opportunity to rebut. Hale, 448 F.3d at 986; Washington,
417 F.3d at 786. Simpson does not contend that the
comments implicated a specific right, such as the Fifth
Amendment right against self-incrimination. Cf. United
States v. Mietus, 237 F.3d 866, 870 (7th Cir. 2001). There-
fore, we “consider the remarks in light of the entire
record to determine if the defendant was deprived of a fair
trial.” United States v. Wesley, 422 F.3d at 515.
Our examination of the record as a whole leads us to
conclude that the prejudicial impact of the prosecution’s
closing argument, which the dissent does not even men-
3
In finding this way, although our precedent labels this claim
“prosecutorial misconduct,” we do not mean to suggest that the
prosecutor’s remarks in this case were made with the intent to
suggest an improper propensity inference to the jury.
22 No. 05-2993
tion, was significant. 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 powerful argument. Telling a jury to conclude that
a defendant cannot remember the drug sale for which he
is on trial because he had done “so many” in the past is no
insignificant matter.
Moreover, the jurors did not receive an instruction
limiting the conclusion that they could permissibly make
from the prosecutor’s improper comments, an instruc-
tion that might have limited the impact of the statement.
Nor did Simpson invite the prosecutor’s propensity infer-
ence. And, although Simpson’s counsel’s closing argument
followed the prosecution’s improper comments, Simpson
could not introduce any evidence of good character at
that point, and the damage from the prosecutor’s inference
was already done.
Next, although the government argues that the prosecu-
tion’s closing arguments did not misstate admitted evi-
dence, it invited the jury to make an improper inference
from the evidence, an action with a similar effect. As we
made clear, neither the identity exception to Rule 404(b)
nor the intricately related evidence doctrine support the
admission of Agent Hendon’s testimony concerning
Simpson’s prior drug deals, and the introduction of this
evidence was erroneous.
And with Simpson’s statements about his prior drug
deals omitted, the circumstantial evidence presented
by the government was far from overwhelming. Notably,
confidential informant Bradley did not testify at the
second trial. Even though the jurors at the first trial had
the benefit of Bradley’s testimony that he had purchased
crack cocaine from Simpson on March 6, 2003, that jury
No. 05-2993 23
did not convict Simpson. In addition, the jurors’ questions
during the second trial illustrate that like the jurors in
the first trial, they too had doubts about Simpson’s guilt.
The jurors asked whether any fingerprints had been lifted
from the bag of cocaine, whether any voice recognition
techniques had been conducted on the tape recording, and
why Bradley had not testified, all questions relating to
the amount of evidence that linked Simpson to the
charged crime in a case where no physical evidence had
been introduced connecting him to the deal. They also
asked to see transcripts of Deputy Stadt’s testimony and
an FBI report, but neither was produced.
Although the circumstantial evidence in this case would
be enough to uphold a jury’s guilty verdict under a chal-
lenge to the sufficiency of the evidence supporting such
a verdict, it is not enough to say that the outcome prob-
ably would have been the same without the prosecutor’s
improper propensity inference and the evidence of
Simpson’s past unrelated drug deals. In the second trial
at issue here, where the jurors did not have the benefit of
the confidential informant’s testimony, the introduction
of evidence that Simpson had been a crack cocaine dealer
for several years created the risk that Simpson’s convic-
tion would be the result of the “forbidden propensity
inference.” See Jones, 455 F.3d at 812 (Easterbrook, J.,
concurring). And when the prosecutor explicitly told the
jurors to draw the inference that Simpson had done so
many drug deals in the past that he could not remember
doing this one, the risk that the jury would convict
Simpson based on his history as a crack cocaine dealer
was only compounded. Thus, we are not assured that
Simpson received a fair trial, and we remand his case
for a new trial.
24 No. 05-2993
III. CONCLUSION
The judgment of the district court is VACATED, and this
matter is remanded to the district court with instruc-
tions to grant a new trial.
BAUER, Circuit Judge, dissenting. I respectfully dissent.
Stripped of all unnecessary verbiage, the majority
takes the position that it was plain error (because its
admission was not objected to at trial—in fact, not at
either trial) for the agent of the FBI to relate the state-
ment of the defendant, delivered voluntarily after he
received the Miranda warning. As the majority agree, the
statement was based on an exchange between the defen-
dant and the agent essentially as follows: The defendant
asked what the charge against him was. The agent told
him. The agent then testified that: The defendant “told
us . . . although he didn’t remember delivering this 2-1/4
ounce of crack . . . it was possible because he had done
similar types of transactions” around the time and place
of the charged crime. And, said the defendant, he had
been a crack cocaine dealer for three or four years.
Quibbling over this statement, obviously against inter-
est, penal and otherwise, as to whether it was a full
confession or not misses the point; the admission of the
statement was not only not plain error, it was admissible
even in the face of an objection. The defense trial tactic
was to deny that the statement was made, not that it
wasn’t admissible evidence.
No. 05-2993 25
In the beginning of the trial, the government agreed
that evidence of prior crimes—meaning, of course, the
convictions for armed robbery and aggravated battery
with a firearm—would not be referenced by the govern-
ment unless the defendant testified. The defendant’s
voluntary statement, which virtually amounted to a
confession in the true sense of the word, was not in
contention. It was discussed without objection in the
opening statement, referred to by the defense attorney
acknowledging the proposed testimony but pooh-poohing
its existence in his opening statements and was consid-
ered, together with the other evidence such as the tape
recording of the defendant negotiating a sale with a
confidential witness, and other evidence, by the jury. The
defendant’s statement that he “might have committed the
crime” was certainly relevant and his reason for the
memory fog was explained by the fact that the transac-
tion was just one of many similar transactions, all dis-
tributing crack, and saying that, a year later, an exact
recollection of every sale was more that he could muster.
I know of no reason why the defendant’s statement was
inadmissible, nor do I know how it could have been used
without using it entirely. The defendant not only did not
deny the crime, he acknowledged the possibility was
undeniable; he was in the business, in the area, and in the
time span. To rule the statement inadmissible is to
defy logic.
I would affirm.
26 No. 05-2993
A true Copy:
Teste:
________________________________
Clerk of the United States Court of
Appeals for the Seventh Circuit
USCA-02-C-0072—3-13-07