Case: 13-14253   Date Filed: 08/15/2014   Page: 1 of 20


                                                           [DO NOT PUBLISH]

               IN THE UNITED STATES COURT OF APPEALS

                       FOR THE ELEVENTH CIRCUIT
                         ________________________

                               No. 13-14253
                           Non-Argument Calendar
                         ________________________

                    D.C. Docket No. 1:12-cr-20914-WPD-11

UNITED STATES OF AMERICA,


                                                                 Plaintiff-Appellee,

                                    versus

RICHARD EUGENE YOUNG, JR.,


                                                            Defendant-Appellant.

                         ________________________

                  Appeal from the United States District Court
                      for the Southern District of Florida
                        ________________________

                               (August 15, 2014)

Before TJOFLAT, WILSON and JORDAN, Circuit Judges.

PER CURIAM:

      Richard Eugene Young appeals his convictions and total sentence of 327

months’ imprisonment, imposed after being convicted of one count of conspiracy
              Case: 13-14253     Date Filed: 08/15/2014   Page: 2 of 20


to possess with intent to distribute cocaine, in violation of 21 U.S.C. §§ 841(a)(1),

(b)(1)(C), and 846, and one count of possession with intent to distribute cocaine, in

violation of 21 U.S.C. §§ 841(a)(1) and (b)(1)(C). Young argues on appeal that the

district court abused its discretion by allowing the government to introduce a stale

conviction during cross-examination. We agree and further conclude that this error

was not harmless. Accordingly, we vacate Young’s convictions and sentence.

                                          I.

      At trial, Young conceded that he was guilty of the lesser-included offense of

possession of cocaine but maintained that he intended to use the drugs he

possessed, not distribute them. Because this strategy put Young’s intent in issue,

the government sought to introduce, under Federal Rule of Evidence 404(b)(2),

Young’s two prior Florida felony convictions for possession with intent to

distribute. See Fed. R. Evid. 404(b)(2). Given Young’s trial strategy, the court

found one of Young’s convictions, a 2008 conviction involving cocaine

distribution, admissible for purposes of proving his intent. See 

ruled

that the other conviction, a 2001 conviction involving cocaine distribution and

trafficking, was inadmissible given how old it was, but the court stated that it might

be admissible for impeachment purposes if Young testified. The government

presented the 2008 conviction as evidence of Young’s intent to distribute cocaine

in the present case.


                                          2
              Case: 13-14253     Date Filed: 08/15/2014    Page: 3 of 20


      Young then testified in his own defense. Consistent with his account that he

intended to use the cocaine in question, which was in powder form, Young testified

that he had been addicted to powder cocaine since the age of 16 and that, due to his

addiction, he never dealt powder cocaine because he would use his supply. Young

accounted for the 2008 distribution conviction by explaining that he sold crack

cocaine to support his drug habit. He stated that he had been arrested and spent

time in prison for selling crack and that he had been released in 2010, indicating

that he was referencing his 2008 conviction.

      On cross examination, the government again cited Young’s 2008 conviction

for possession with intent to distribute cocaine, this time in an effort to contradict

his testimony. Young insisted that his 2008 conviction was for dealing crack, but

the government countered again by reiterating that Young’s 2008 conviction was

for distribution of cocaine. Realizing the possibility for confusion, the court

excused the jury and explained to the government that Florida did not distinguish

between powder and crack cocaine and that Young’s 2008 conviction “probably”

involved crack, just as Young stated during his testimony. The jury then returned,

and the court explained to the jury what had just been explained to the government.

Then, the jury retired for the day.

      At this point, the government renewed its request to introduce the 2001

conviction for distribution of cocaine and cocaine trafficking. Young objected, but


                                           3
                Case: 13-14253       Date Filed: 08/15/2014       Page: 4 of 20


the district court overruled the objection, holding that the government would be

allowed to introduce the 2001 conviction for impeachment purposes. Young

appeals on this issue, claiming the court committed reversible error by admitting

the stale conviction.

                                                A.

       “The decision of a defendant with prior convictions to testify has always

raised a problem . . . . [O]n the one hand, a jury cannot properly infer from

evidence of prior criminal convictions that the accused is a bad man, who, with a

proven propensity to commit crimes, probably committed the crime in question.”

United States v. Tumblin, 

, 1004 (5th Cir. 1977). 1 We have

recognized that even with limiting instructions the jury is likely to make just this

type of impermissible inference. See United States v. Pritchard, 

, 908

(11th Cir. 1992). Nevertheless, “the credibility of a defendant, like that of any

other witness, is subject to impeachment through evidence of his prior

convictions.” 

. In light of these competing concerns,

the Federal Rules of Evidence have created a presumption against admissibility in

cases like this, where the prior conviction is more than ten years old, 2 and “such



       1
          This court adopted as binding precedent all decisions made by the Fifth Circuit issued
on or before October 1, 1981. See Bonner v. City of Pritchard, 

, 1209 (11th Cir.
1981).
        2
          See Fed. R. Evid. 609(b) (“This subdivision applies if more than ten years have passed
since the witness’s conviction or release from confinement . . . .”). It is undisputed that Young
                                                4
               Case: 13-14253      Date Filed: 08/15/2014     Page: 5 of 20


convictions will be admitted very rarely and only in exceptional circumstances.”

(emphasis added) (internal quotation marks omitted);

see also Fed. R. Evid. 609(b) (“Evidence of the [stale] conviction is admissible

only if . . . its probative value . . . substantially outweighs its prejudicial

effect . . . .” (emphasis added)). Further, even when prior convictions are

admissible, the scope of cross examination regarding those prior convictions is

narrowly circumscribed. See 

.

       Both parties and the district court analyzed the admissibility of the 2001

conviction under these familiar rules, but we believe they were mistaken in doing

so. Rule 609 applies when a party uses a prior conviction to attack “a witness’s

character for truthfulness,” Fed. R. Evid. 609(a) (emphasis added), and it

accordingly applies “in those cases where the conviction is offered only on the

theory that people who do certain bad things are not to be trusted to tell the truth.”

United States v. Johnson, 

, 235 (5th Cir. 1976) (emphasis added).

This was not the purpose for which the 2001 conviction was introduced, as the

government instead sought to directly respond to Young’s testimony about his

intent. As we said in Johnson, “[w]e do not believe Rule 609 was meant to cover

this particular species of impeachment use of a prior conviction.” 

was released from confinement following his 2001 conviction in November of 2002, which
makes the 2001 conviction more than ten years old for purposes of Rule 609(b).
                                             5
               Case: 13-14253        Date Filed: 08/15/2014      Page: 6 of 20


evidence had a different, surer value in that it directly contradicted the position

taken by the witness.” 

we find that by testifying as he did, Young did more than open the

door to impeachment by prior convictions under Rule 609, circumscribed by

Tumblin’s strict limitations on the scope of permissible cross examination. Young

testified about his criminal history, opening the door further, allowing additional

convictions into evidence and expanding the scope of permissible cross

examination about those convictions. See also United States v. Vigliatura, 

, 1351 (11th Cir. 1989) (per curiam) (recognizing that counsel “opened

the door” to broader cross examination by questioning the defendant about prior

charges and convictions which were otherwise clearly inadmissible under Rule

609).

        Where a defendant testifies about his criminal history or where he puts facts

that might be contradicted by a prior conviction in issue, we are comfortable

concluding that Rule 609’s standard does not apply for two primary reasons. First,

when a prior conviction contradicts (or more fully explains) a defendant’s

        3
          Were we to analyze Young’s claim under Rule 609(b) as he and the government suggest
we should, we would have little difficulty concluding that the district court erred. For reasons
discussed more fully below, the prejudicial effect of the 2001 conviction substantially outweighs
its probative value. Under Rule 609(b), the conviction would only be admissible if the exact
opposite were true. Thus, the district court clearly erred to the extent that it allowed the
government to rely on the 2001 conviction for general impeachment purposes under Rule 609(b).
We continue our analysis from here only because, under Johnson, there appears to be a stronger
basis for affirming the district court’s decision than the reasons presented by the government or
considered by the district court below.
                                               6
                Case: 13-14253       Date Filed: 08/15/2014       Page: 7 of 20


testimony, instead of drawing a circuitous connection between a ten year old

felony and a general lack of trustworthiness, “the evidence ha[s] a different, surer

value.” 

. That is, the prior conviction is more probative

in this context. Second, the prejudicial effect of a prior conviction is likely to be

much lower in this context, where a defendant has already testified about prior

convictions or events that can be contradicted by those prior convictions. In these

situations, the impeaching cross-examination is likely not the first time the jury

learns of the defendant’s criminality. We are therefore confident that Rule

609(b)’s presumption need not apply here. See 

opened the door further than the ordinary testifying defendant

does not give the government carte blanche to introduce all prior convictions and

to discuss them for any purpose, however. 4 Particularly here, where it is clear that

the 2001 conviction was not admissible for Rule 609(b) general impeachment

purposes, we must consider the perhaps more appropriate purposes for which the

2001 conviction might have been admissible. Two purposes are apparent: first, the

       4
          The Supreme Court has held that if a defendant is notified in advance by the court and
the government that a prior conviction will be introduced under Rule 609 for impeachment
purposes if he chooses to testify, and the defendant opts to do so but attempts to “remove the
sting” of the conviction by bringing the conviction up himself, he waives his right to challenge
the admissibility of the conviction under Rule 609 on appeal. See Ohler v. United States, 

, 755, 758 

, 1852–54 (2000). Ohler does not bar Young’s appeal
because Young testified only about his 2008 conviction and thus did not waive his right to
challenge the admissibility of the 2001 conviction. Moreover, he was not the first to introduce
his convictions because the government introduced his 2008 conviction in its case in chief for
Rule 404(b)(2) purposes. Thus, Young retains the right to challenge the district court’s decision
to admit the 2001 conviction.
                                                7
              Case: 13-14253      Date Filed: 08/15/2014     Page: 8 of 20


government sought to introduce the 2001 conviction to directly contradict

statements made by Young; second, the government sought to introduce the 2001

conviction to reestablish intent. Accordingly, Rules 403 applies. See United States

v. Leavis, 

, 220 (4th Cir. 1988) (explaining, after citing our opinion in

Johnson, that convictions “introduced to contradict specific statements made by

[the defendant] on direct examination [are] analyzed under Fed. R. Evid. 403”).

Additionally, because the prior conviction was arguably offered to prove Young’s

intent, Rule 404(b) applies. See Fed. R. Evid. 404(b) (“(1) Evidence of a crime . . .

is not admissible to prove a person’s character in order to show that on a particular

occasion the person acted in accordance with the character. (2) This evidence may

be admissible for another purpose, such as proving . . . intent . . . .”).

      We have explained that admissibility under Rule 404(b) is analyzed in two

steps. United States v. Dothard, 

, 501 (11th Cir. 1982). The first step

is a Rule 401 analysis for relevance to an issue other than the defendant’s

character. 

Here, it is clear that the 2001 conviction has at least

some relevance for purposes of establishing Young’s intent to deal drugs. The

second step is a Rule 403 analysis under which the court must “balance the

probative value of the [prior conviction] against its potential for undue prejudice.

This determination lies within the sound discretion of the trial court and calls for a

commonsense assessment of all the circumstances surrounding the [prior] offense,


                                            8
                Case: 13-14253       Date Filed: 08/15/2014       Page: 9 of 20


including prosecutorial need, the overall similarity between the extrinsic act and

the charged offense, and the temporal proximity of the two.” 

(internal quotation marks omitted); see also Fed. R. Evid. 403 (“The court may

exclude relevant evidence if its probative value is substantially outweighed by a

danger of . . . prejudice . . . or misleading the jury . . . .” (emphasis added).5

Ultimately, then, we should vacate Young’s conviction only if the district court

erred in admitting the 2001 conviction under Rule 404(b), which includes a Rule

403 analysis.

                                               B.

       Even under a pro-admissibility standard and a deferential standard of review,

we ultimately conclude that the 2001 conviction was admitted in error because the

prejudicial effect of the evidence was substantial and the probative value was

exceedingly low. Accordingly, we find an abuse of discretion and vacate Young’s

convictions and sentence.

       The government asserts that the evidence was properly admitted for four

primary reasons. (1) The 2001 conviction was useful to disprove Young’s account

       5
          The concern underlying the second step of a Rule 404(b) analysis (essentially, a Rule
403 analysis) is the same concern articulated in Pritchard: “The jury, despite limiting
instructions, can hardly avoid drawing the inference that the past conviction suggests some
probability that the defendant committed the similar offense for which he is currently 

(internal quotation marks omitted); see also 

(“[A]
jury cannot properly infer from evidence of prior criminal convictions that the accused is a bad
man, who, with a proven propensity to commit crimes, probably committed the crime in
question.”). Young’s appeal, at bottom, centers on this concern. We note that Young raised a
Rule 403 challenge in his brief.
                                                9
              Case: 13-14253     Date Filed: 08/15/2014     Page: 10 of 20


of his lack of intent to distribute cocaine in this case; this serves two related

purposes of rehabilitating the government’s own theory of intent and discrediting

Young’s theory. (2) The 2001 conviction, which involved trafficking as well as

distribution, “directly contradict[s] Young’s claim that he was nothing more than a

drug addict . . . and . . . low-level drug dealer.” Relatedly, the district court

explained that the trafficking conviction would be more probative than a mere

possession conviction. (3) As the district court and the government also noted, the

fact that the conviction was only stale (for Rule 609 purposes) by six months and

the fact that Young’s conduct since that conviction has not changed cut in favor of

admissibility. (4) Credibility was critical to this case, increasing the government’s

need to use all available evidence to impeach Young.

      These arguments are unpersuasive. As to the first argument—that the

evidence reestablished Young’s intent—the 2001 conviction was entirely

cumulative and thus minimally probative on this point. Young admitted to dealing

drugs in the past, and the 2008 conviction for possession with intent to distribute

had already been presented. There was no doubt whatsoever that Young had in the

past formed the intent to deal drugs. For this reason, the 2001 conviction was also

entirely unnecessary to directly contradict Young’s testimony about his prior drug-

dealing conviction. Young admitted to having dealt crack cocaine but denied ever

having dealt powder cocaine. The 2001 conviction did not contradict that


                                           10
              Case: 13-14253    Date Filed: 08/15/2014    Page: 11 of 20


statement. The only dispute regarding Young’s criminal history was whether he

had ever dealt powder cocaine, and like the 2008 conviction, the 2001 conviction

involved Florida statutes that do not distinguish between crack and powder

cocaine. Even after reviewing the details of that conviction, the district court

determined that the 2001 conviction was ambiguous as to the type of cocaine

involved. Thus, the 2001 conviction did not in fact contradict Young’s testimony

about his intent.

       Not only does this cut against admissibility under Rule 403 because it shows

that the probative value of the conviction is low, it also cuts against admissibility

under step one of the Rule 404(b) analysis. In Dothard, we explained that the prior

bad act “must have more than a mere characteristic in common [with the charged

offense]; the common characteristic must be the significant one for the purpose of

the inquiry at 

(emphasis added) (internal quotation marks

omitted). The significant characteristic in this case was not whether Young ever

intended to deal cocaine-type drugs; he admitted that he had that intent. Instead,

the significant characteristic is whether Young ever intended to deal powder

cocaine in the past, and the 2001 conviction does not shed light on that question.

In fact, as explained below, the 2001 conviction is potentially misleading on that

critical issue.




                                          11
             Case: 13-14253     Date Filed: 08/15/2014    Page: 12 of 20


      The second reason offered in favor of admitting the 2001 conviction—the

fact that it involved cocaine trafficking, a more serious drug offense than mere

distribution—actually leads to an entirely inappropriate inference, rather than

adding legitimate probative value. In admitting the conviction, the district court

noted that the trafficking offense has more probative value for purposes of

establishing a defendant’s intent to distribute than a mere possession conviction,

which is of course true, but does not advance the analysis. Because the key issue is

Young’s intent to distribute, a mere possession conviction would be less probative

than a trafficking offense, but a conviction for possession with intent to distribute,

like the already-admitted 2008 conviction, is most probative of his intent.

      Any further inference drawn from the fact that Young also trafficked cocaine

is prejudicial and not legitimately probative. The government admitted that the

trafficking conviction tended to show that Young was a higher-level drug dealer

than his 2008 conviction alone might suggest. This type of character evidence,

which paints Young as a big-time drug dealer and a bad man, is exactly what Rule

404(b)(1) is designed to keep from the jury. See, e.g., 

(reversing a conviction where the “obvious significance of . . . questioning [a

defendant about prior convictions] was not to damage [the] defendant’s credibility




                                          12
               Case: 13-14253      Date Filed: 08/15/2014       Page: 13 of 20


as a witness . . . but instead to suggest, quite improperly, that defendant was a man

who had spent most of his young life committing and serving time for crimes”). 6

       So why would this conviction be admitted? As just discussed, it was not

necessary to establish Young’s intent. The government asserts that this evidence

was necessary to rebut Young’s assertion that he was a low-level drug dealer, but

the problem is, neither Young nor his attorney asserted that he was a low-level

drug dealer. He distinguished his drug dealing by type (crack versus powder

cocaine), not by quantity. It appears, then, that the government itself identified a

highly prejudicial inference that the jury was supposed to draw from this evidence

that did not serve a legitimately probative purpose. See 

(finding reversible error under Rule 404(b) where “the prosecutor, by his own

admission, undertook to try [Defendant’s] propensity for crime rather than his state

of mind at the time of the charged offense”). Because the evidence is cumulative

on the only issue for which it could be properly used, the evidence’s probative

value is minimal.

       Next, the government asserted that the 2001 conviction was only ten years

and six months old and that Young’s subsequent behavior showed that the 2001

conviction, though old, paints a fairly accurate picture of who Young was at the

time of his trial. That is certainly true, but again, Young painted that picture for

       6
         Tumblin dealt with the admissibility of a prior conviction under Rule 609, but as

in note 5, the concerns underlying Rule 404(b)(1) and Rule 609(b) are the same.
                                              13
               Case: 13-14253       Date Filed: 08/15/2014      Page: 14 of 20


the jury himself: he admitted to being a drug addict and a drug dealer, so the 2001

conviction was entirely unnecessary to complete that picture. Moreover, in

Dothard, we explained that under the second step of a Rule 404(b) analysis,

“temporal remoteness of the [prior conviction] depleted this evidence of any force

of probity whatsoever.” Id.; see also 

(noting that, as

time passes, the probative value of a prior conviction into a defendant’s character

for truthfulness fades). Stale convictions are sometimes admissible, however,

when they are the only conviction available, see 

other newer

convictions were available.7

       This same response weakens the government’s fourth argument in favor of

the 2001 conviction’s probative value, as well. It is certainly true that credibility

was central to this case, and that entitled the government to thoroughly impeach

Young’s credibility by use of prior convictions. But to the extent that the

conviction was offered for general impeachment purposes, Rule 609(b)’s anti-

admissibility standard applies. For Rule 609 purposes, the probative value of the

2001 conviction was relatively low. To the extent that evidence of Young’s

criminality was going to persuade the jury that he lacked credibility, the jury

already had more and better information upon which to make this determination.

       7
         Pritchard analyzed the admissibility of a prior conviction under Rule 609. As
discussed, to the extent that the government offered the 2001 conviction for Rule 609 general
impeachment purposes, it was clearly inadmissible. We cite Pritchard here merely to support
the common sense proposition that a prior conviction’s probative value diminishes with time.
                                               14
             Case: 13-14253      Date Filed: 08/15/2014    Page: 15 of 20


Young admitted to having a criminal drug conviction, and the government had

already impeached him with the 2008 conviction.

      Further, when considering prejudice under a Rule 609 analysis, the more

similar a prior conviction is to the present offense, the more prejudicial it is,

militating against admissibility. See United States v. Cathey, 

, 275–

76 (5th Cir. 1979) (“[I]f the prior conviction is similar to the new charges, the jury

may misuse the prior conviction as evidence of guilt . . . .” (citation omitted)).

Here, as the government and the court admitted, the nature of the 2001

conviction—a trafficking offense—was perhaps even more prejudicial than an

identical distribution conviction would have been, as it could, in addition to

supporting an inference that Young had a propensity to deal drugs, also support an

inference that Young had a propensity to deal drugs in large quantities. All of

these factors cut against admissibility here: there were other less similar (and

therefore less prejudicial), newer (and therefore more probative into character for

truthfulness) prior convictions readily available for use to impeach Young,

including a non-stale simple possession conviction. Yet the government did not

seek to introduce these convictions; it only sought to introduce the one with the

most potential for inappropriate prejudice. Given Rule 609(b)’s anti-admissibility

standard, the district court erred to the extent that it allowed the government to rely

on the 2001 conviction for general impeachment purposes.


                                           15
             Case: 13-14253     Date Filed: 08/15/2014    Page: 16 of 20


      Taken as a whole, the government’s assertions about the 2001 conviction’s

probative value are weak. At the same time, it appears that the only information

the 2001 conviction conveyed to the jury that the jury did not already know created

the possibility of an impermissible inference. However, given the extent to which

the jury already knew about Young’s criminal history, the prejudicial effect of the

2001 conviction was partially blunted. If the jury was inclined to ignore the

court’s limiting instructions and draw an improper propensity inference, it already

had the information necessary to do so. In two ways, however, the 2001

conviction created the potential for additional prejudice beyond that created by the

2008 conviction and other evidence properly before the jury.

      First, the government conceded that the 2001 conviction for cocaine

trafficking created the potential for an inappropriate inference that was more severe

than the similar potential created by the 2008 conviction. The trafficking

conviction showed that Young was “more than a drug addict and, at most, low-

level drug dealer.” As noted, however, Young did not state differently, so this use

of the 2001 conviction was highly prejudicial and, contrary to the government’s

position, had no impeaching value. Again, persuading the jury that Young is a big-

time drug dealer creates precisely the type of inference that Rules 403, and, more

specifically, 404(b)(1), are designed to prevent: “Evidence of a crime . . . is not

admissible to prove a person’s character in order to show that on a particular


                                          16
             Case: 13-14253     Date Filed: 08/15/2014    Page: 17 of 20


occasion the person acted in accordance with the character.” See Fed. R. Evid.

404(b)(1). As we explained in Pritchard, even with a limiting instruction, and

even without explicit argument on the point, a jury is likely to draw improper

propensity inferences. 

. The introduction of the 2001

conviction substantially increased this possibility.

      Second, after the 2001 conviction for cocaine trafficking was introduced, the

jury was not informed that Florida’s cocaine trafficking statute did not differentiate

between powder and crack cocaine. After the 2008 conviction for possession with

intent to distribute cocaine was introduced to the jury, the court recognized that the

jury was under the mistaken impression that Young’s conviction involved powder

cocaine when, in fact, it probably did not. The court clarified any confusion by

explaining the Florida statute to the jury. When the court determined that the 2001

conviction was admissible, it stated that “the same understanding has to be given to

the jury that the trafficking in cocaine could have been crack cocaine.” This never

happened, however.

      Moreover, the 2001 conviction was not introduced until the day after the

court’s clarification that the 2008 conviction did not necessarily involve powder

cocaine, decreasing the odds that the jury would recall that clarification. And even

if the jury recalled the clarification, the 2001 conviction involved a new statute, so

the jury may have assumed—both because a new statute was at issue and because


                                          17
               Case: 13-14253       Date Filed: 08/15/2014       Page: 18 of 20


the court reacted differently than before—that the trafficking conviction did indeed

involve powder cocaine. To the extent that the jury reached this conclusion, the

prejudice to Young was extreme, as this conclusion would erroneously convey that

his testimony was directly contradicted by a prior conviction and that he lied. In

reality, the 2001 conviction neither confirmed nor contradicted his testimony. 8

Given the court’s different treatment of the 2001 conviction and the fact that it

involved a different statute, the 2001 conviction was uniquely prejudicial.

Weighed against the conviction’s minimal probative value, prejudice

predominates.

       Relying on Rules 403 and 404(b)(1), the Fourth Circuit has vacated a

conviction in similar circumstances. See United States v. Hernandez, 

, 1041 (4th Cir. 1992). In Hernandez, the Fourth Circuit stated:



       8
          An example shows how misleading this would be to the jury. Most people, when they
hear someone refer to a beverage as Coke, assume the speaker is referring to Coca-Cola. But
some people mean soda in general when they use the word Coke. So if someone says, “I never
drank Coke,” but an official document of the state of Florida says the person drank Coke, most
people would assume the speaker was lying. But if the speaker admitted to drinking Sprite and if
it were further clarified that the Florida document was using Coke in the general sense that
simply means soda, most people would conclude that the speaker was in fact telling the truth,
and certainly people would no longer conclude that the speaker was necessarily lying.
        To prove just how misleading and confusing the Florida statute’s use of the generic word
cocaine would be to a jury, the prosecution in this case apparently believed that the 2008 and
2001 convictions for cocaine distribution and trafficking directly disproved the defendant’s
testimony, even after the defendant had already explained that his convictions were for crack. It
did not register with the prosecution that a conviction involving cocaine could include a
conviction involving crack until the judge explained Florida’s drug laws in some detail. Given
that Young’s credibility hinged largely on the substance involved in his prior convictions, the
potentially misleading presentation of the 2001 conviction was highly prejudicial.
                                               18
             Case: 13-14253     Date Filed: 08/15/2014    Page: 19 of 20


      [T]he probative value of the evidence is slight. [The defendnat’s] . . .
      sale of crack in New York at some indefinite time [was] in no way
      connected to the cocaine she is charged with conspiring to sell in this
      case. The evident effect, if not the purpose, of [the disputed]
      testimony [was to] depict[] [the defendant] as an experienced crack
      dealer. But this is precisely the effect Rules 403 and 404(b) seek to
      avoid. Upon consideration of all the circumstances, we think the
      balance so one-sided that admission of the evidence was error.

It seems that the government’s admitted purpose for

presenting the 2001 conviction was, at least in part, to create this exact same

prejudicial effect by persuading the jury that Young was a high-level drug dealer.

See also 

(explaining that a court erred under Rule 404(b)

in admitting evidence of a prior bad act where the evidence was used for

propensity purposes).

      The 2001 conviction is also similarly one-sided. Its prejudicial effect was

severe as it misleadingly undermined perhaps the most important portion of

Young’s testimony. Moreover, it cast Young as a “high-level” drug dealer, making

the prospect of an improper propensity inference all the more likely. See

(explaining that, despite a limiting instruction, it will be

very difficult for juries not to draw inappropriate propensity inferences when prior

convictions are admitted). But see United States v. Chirinos, 

, 1100

(11th Cir. 1997) (explaining that we presume a jury follows instructions).

      To offset this prejudice, there is almost no probative value. The only

legitimate purposes the conviction might have served were never in dispute and
                                          19
             Case: 13-14253      Date Filed: 08/15/2014   Page: 20 of 20


had already been proven conclusively. Contrary to the government’s assertion, the

2001 conviction did not actually contradict Young’s testimony and at least partially

confirmed it. Accordingly, we find that the district court abused its discretion in

admitting the 2001 conviction.

      Moreover, given the substantial prejudice injected into this trial on a critical

issue, we cannot say that this error was harmless. See 

.

Erroneously admitting evidence will not result in reversal if the error was harmless,

such that the defendant “has not shown prejudice to a substantial right.” United

States v. Burston, 

, 1336 (11th Cir. 1998). Here, however, admitting

the 2001 conviction prejudiced the jury against Young in multiple ways. Further,

the government’s case was far from overwhelming as evidenced by the fact that

nothing directly contradicted Young’s theory of the case and by the fact that the

first jury to consider this case, a jury that did not know of the 2001 conviction,

could not reach a verdict.

      Because the district court’s error in admitting the 2001 conviction was not

harmless, we vacate Young’s convictions and sentence.

                                          II.

      Our holding in Part I renders it unnecessary for us to consider the

substantive reasonableness of Young’s sentence.

      VACATED and REMANDED.


                                          20