United States v. Richard Eugene Young, Jr. , 574 F. App'x 896 ( 2014 )


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  •              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    [DO NOT PUBLISH]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 
    id. The court
    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.
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    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
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    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, 
    551 F.2d 1001
    , 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, 
    973 F.2d 905
    , 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.” 
    Tumblin, 551 F.2d at 1004
    . 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, 
    661 F.2d 1206
    , 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
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    convictions will be admitted very rarely and only in exceptional circumstances.”
    
    Pritchard, 973 F.2d at 908
    (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 
    Tumblin, 551 F.2d at 1004
    .
    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, 
    542 F.2d 230
    , 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.” 
    Id. “Here the
    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
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    evidence had a different, surer value in that it directly contradicted the position
    taken by the witness.” 
    Id. 3 Thus,
    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, 
    878 F.2d 1346
    , 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
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    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.” 
    Johnson, 542 F.2d at 235
    . 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 
    id. That Young
    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, 
    529 U.S. 753
    , 755, 758 
    120 S. Ct. 1851
    , 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
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    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, 
    853 F.2d 215
    , 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, 
    666 F.2d 498
    , 501 (11th Cir. 1982). The first step
    is a Rule 401 analysis for relevance to an issue other than the defendant’s
    character. 
    Id. at 501–02.
    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,
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    including prosecutorial need, the overall similarity between the extrinsic act and
    the charged offense, and the temporal proximity of the two.” 
    Id. at 502–03
    (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 
    charged.” 973 F.2d at 908
    (internal quotation marks omitted); see also 
    Tumblin, 551 F.2d at 1004
    (“[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
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    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
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    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 
    hand.” 666 F.2d at 502
    (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.
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    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., 
    Tumblin, 551 F.2d at 1004
    (reversing a conviction where the “obvious significance of . . . questioning [a
    defendant about prior convictions] was not to damage [the] defendant’s credibility
    12
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    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 
    Dothard, 666 F.2d at 504
    (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
    
    discussed supra
    in note 5, the concerns underlying Rule 404(b)(1) and Rule 609(b) are the same.
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    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 
    Pritchard, 973 F.2d at 909
    (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 
    id., but here,
    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
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    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, 
    591 F.2d 268
    , 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.
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    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
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    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. 
    Pritchard, 973 F.2d at 908
    . 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
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    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, 
    975 F.2d 1035
    , 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.
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    [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.
    
    Id. (emphasis added).
    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 
    Dothard, 666 F.2d at 504
    (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
    
    Pritchard, 973 F.2d at 908
    (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, 
    112 F.3d 1089
    , 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 
    Dothard, 666 F.2d at 505
    .
    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, 
    159 F.3d 1328
    , 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