United States v. James Harding

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[PUBLISH]

In the

United States Court of Appeals

For the Eleventh Circuit

____________________

No. 23-10479

____________________

UNITED STATES OF AMERICA,

Plaintiff-Appellee,

versus

JAMES HARDING,

a.k.a. Old School,

a.k.a. Shakey,

Defendant-Appellant.

____________________

Appeal from the United States District Court

for the Southern District of Alabama

D.C. Docket No. 1:21-cr-00165-TFM-MU-1

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2 Opinion of the Court 23-10479

____________________

Before WILLIAM PRYOR, Chief Judge, and JORDAN and BRASHER, Cir-

cuit Judges.

WILLIAM PRYOR, Chief Judge:

This appeal requires us to decide whether the district court

abused its discretion by admitting evidence of drug trafficking as

intrinsic evidence of a charged conspiracy that allegedly ended

years earlier in a different federal district. A grand jury in the South-

ern District of Alabama charged James Harding with conspiracy to

possess with intent to distribute heroin and possession with intent

to distribute heroin. At trial, the United States introduced evidence

that agents, in a separate investigation, found multiple firearms and

almost two kilograms of heroin at Harding’s home in the Northern

District of Alabama over two years after the alleged end of the

charged conspiracy. The United States offered no evidence linking

the seized evidence to other members of the charged conspiracy.

The district court admitted the evidence as intrinsic evidence and

ruled, in the alternative, that the evidence was admissible as extrin-

sic evidence under Federal Rule of Evidence 404(b). But the district

court rejected Harding’s several requests for a limiting instruction.

The jury found Harding guilty of both charges. Because the district

court abused its discretion by admitting the evidence as intrinsic

and because its alternative ruling that the evidence was admissible

under Rule 404(b) cannot be affirmed in the absence of a limiting

instruction, we vacate Harding’s convictions and sentence and re-

mand for a new trial.

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23-10479 Opinion of the Court 3

I. BACKGROUND

A federal grand jury returned an indictment that charged James

Harding and four codefendants with drug offenses. The indictment

alleged that Harding participated in a conspiracy to distribute her-

oin in the Southern District of Alabama that began in early 2018

and ended on or about April 23, 2019. The indictment charged Har-

ding with two counts: conspiracy to possess with intent to distrib-

ute heroin, see 21 U.S.C. § 846, and possession with intent to dis-

tribute heroin, see id. § 841(a)(1).

Before trial, Harding moved to exclude all evidence obtained

from a search of his home. While executing a search warrant at

Harding’s home on September 15, 2021, officers recovered multi-

ple firearms and almost two kilograms of heroin. Prosecutors

sought to introduce this evidence under Federal Rule of Evi-

dence 404(b) to establish Harding’s intent to participate in the con-

spiracy. Harding argued that the evidence failed to satisfy

Rule 404(b) because it was offered to establish his bad character for

drug trafficking.

At a pretrial hearing, the United States argued that the evidence

was extrinsic evidence admissible under Rule 404(b), but the district

court asked whether the evidence could also be intrinsic evidence

of the charged conspiracy. The United States responded that the

evidence could be “admissible as intrinsic evidence” because the

indictment identified Harding “as a source of supply for heroin in

the charged conspiracy.” The district court ruled that the evidence

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4 Opinion of the Court 23-10479

was intrinsic to the conspiracy. Alternatively, the district court

ruled that the evidence was admissible under Rule 404(b).

At trial, the United States called Matthew McCrary, a special

agent with the Federal Bureau of Investigation, to explain how

agents first learned about Harding, at least under his street name,

“Ol’ School.” McCrary explained that he had received a tip that a

person named Kendrick Patrick was trafficking a large quantity of

narcotics. After confirming the tip and investigating, McCrary de-

termined that the supplier was Jeremy Snowden. McCrary ex-

plained that wiretaps revealed that Snowden and another person,

Quantis Clark, were purchasing heroin from someone in Birming-

ham called Ol’ School. But the wiretaps never revealed Ol’ School’s

real name. McCrary also testified that he arrested Harding at 2700

Ensley Five Points West Avenue in Birmingham.

Snowden testified as the United States’s key witness against

Harding. Snowden explained that he asked Clark to help him find

a heroin supplier. Clark referred Snowden to someone named Ol’

School, who also went by “Shaky.” Snowden identified Harding as

Ol’ School and explained that he met with Harding and Clark in

Birmingham to discuss entering the heroin business together. Dur-

ing that meeting, Harding provided Snowden with two ounces of

heroin and directed him to obtain future shipments through Clark.

Snowden explained that after the initial meeting, he received regu-

lar heroin shipments from Harding and that Harding also supplied

heroin on consignment. Snowden testified that Harding taught

Clark, who then taught Snowden, how to cut the heroin to make

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23-10479 Opinion of the Court 5

more of it. When shown a picture of a house located at 2700 Ensley

Five Points West Avenue in Birmingham, Snowden identified the

house as Harding’s residence. Snowden explained that he knew

where Harding lived because Clark had pointed out Harding’s

home while driving by it one day. Snowden admitted that he was

arrested in 2019 and was in custody for drug crimes, that he had

entered into a plea agreement with the United States, and that he

hoped to receive a lesser sentence for his cooperation.

Keith Kidd also testified for the United States. He explained

that for several years he had purchased cocaine from Snowden.

During one transaction, Snowden told Kidd that the heroin was

coming from “[s]omebody from Birmingham named Ol’ School.”

But according to Kidd, Snowden never identified Ol’ School. Kidd

testified that, like Snowden, he was in custody at the time of his

testimony and had entered into an agreement with the United

States in exchange for his cooperation.

The United States also called agents to testify about the Sep-

tember 2021 search of Harding’s home as part of a separate federal

investigation in the Northern District of Alabama. Agents testified

that on September 15, 2021, they arrived at Harding’s home in Bir-

mingham to execute a drug search warrant. They explained that

during the search, they recovered multiple firearms and large quan-

tities of drugs, including two bricks of compressed powder. A

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forensic drug analyst testified that the two bricks amounted to

nearly two kilograms of heroin.

Harding objected to this evidence. But the district court ruled

again that the evidence was admissible “evidence of [the] conspir-

acy itself” and, in the alternative, that the evidence would have

“come in as 404(b) evidence.” Before and during each day of trial,

Harding requested that the district court give the jury a limiting

instruction under Rule 404(b) about the evidence from the Septem-

ber 2021 search of his home, but the district court declined to do so

because it ruled the evidence to be “part and parcel” of the charged

conspiracy.

The jury found Harding guilty of both charges. The district

court sentenced Harding to 960 months of imprisonment, by im-

posing consecutive sentences of the statutory maximum punish-

ment. Harding appealed.

II. STANDARD OF REVIEW

We review for abuse of discretion the admission of evidence.

United States v. Troya, 733 F.3d 1125, 1131 (11th Cir. 2013). A district

court abuses its discretion when its ruling “rests upon a clearly er-

roneous finding of fact, an errant conclusion of law, or an improper

application of law to fact.” United States v. Smith, 459 F.3d 1276,

1295 (11th Cir. 2006) (citation and internal quotation marks omit-

ted). The district court enjoys broad discretion to admit relevant

evidence. United States v. Watkins, 42 F.4th 1278, 1287 (11th Cir.

2022). We also review for abuse of discretion a refusal to give a

proposed jury instruction. United States v. Gonzalez, 975 F.2d 1514,

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1516 (11th Cir. 1992). A district court abuses its discretion by deny-

ing a requested jury instruction when the instruction is substan-

tively correct, it was not substantially covered in the charge given

to the jury, and the failure to give it seriously impaired the defend-

ant’s ability to present an effective defense. Id.

III. DISCUSSION

We divide our discussion into two parts. First, we explain that

the district court abused its discretion by admitting the September

2021 search evidence as intrinsic evidence of the charged conspir-

acy and that the error was not harmless. Second, we explain that

although the search evidence was admissible under Rule 404(b),

the district court abused its discretion by failing to provide a limit-

ing instruction and that the error was not harmless.

A. The District Court Abused Its Discretion by Admitting the

Evidence from the Search as Intrinsic Evidence of the Charged

Conspiracy, and the Error Was Not Harmless.

Harding argues that the district court abused its discretion by

admitting the evidence seized in the September 2021 search as in-

trinsic evidence of the charged conspiracy. He contends that the

evidence is too temporally remote and is otherwise unrelated to

the charged conspiracy. The September 2021 search occurred al-

most 29 months after the alleged end of the charged conspiracy,

and no trial evidence connects the evidence seized during that

search to the charged conspiracy.

Evidence of criminal activity other than the charged offense

may be admissible if it is “intrinsic evidence” of the charged offense.

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8 Opinion of the Court 23-10479

United States v. Joseph, 978 F.3d 1251, 1263 (11th Cir. 2020) (citation

and internal quotation marks omitted). Evidence is intrinsic if it

arises out of the same transaction or series of transactions as the

charged offense, is necessary to complete the story of the crime, or

is inextricably intertwined with the evidence regarding the charged

offense. Id. Our precedents explain each kind of intrinsic evidence.

Evidence arises from the same transaction or series of transac-

tions if it is “linked in time and circumstances” with the charged

crime. United States v. US Infrastructure, Inc., 576 F.3d 1195, 1210

(11th Cir. 2009). Although our precedents impose no firm temporal

proximity requirement, the uncharged act must be “connected

with the offenses charged.” See United States v. Muscatell, 42 F.3d

627, 630–31 (11th Cir. 1995) (citation and internal quotation marks

omitted). Evidence of uncharged criminal conduct can be linked

with the charged crime “whether the conduct occurs before or af-

ter” the charged offense. See United States v. Zapata, 139 F.3d 1355,

1357 (11th Cir. 1998).

We have ruled that uncharged acts arise from the same trans-

action or series of transactions when the uncharged acts involve

the same people and criminal scheme. For example, in United States

v. Horner, we held that evidence of fraudulent tax returns from 2005

and 2006 was intrinsic evidence of a scheme concerning 2007 and

2008 tax returns because the defendants had an “ongoing plan” to

divert business cash into their personal accounts and the older evi-

dence was “part of the same plan” and “used the same modus op-

erandi as the charged offenses—diverted cash receipts.” 853 F.3d

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1201, 1204, 1214–15 (11th Cir. 2017). The evidence of uncharged

conduct involved the same people and pattern of conduct. See id.

at 1215.

Similarly, in Muscatell, two defendants were charged with con-

spiracy, fraud, and money-laundering in connection with a land-flip

scheme. 42 F.3d at 628, 631. The scheme was accomplished with

inflated appraisals, buyer-rebate schemes, and fraudulent loan ap-

plications. Id. at 631. Co-conspirators testified about inflated ap-

praisals, buyer-rebate schemes, and fraudulent loan applications

that occurred in the months before and after the crimes charged in

the indictment. Id. at 628–30. We upheld the admission of that tes-

timony as intrinsic evidence because the uncharged acts concerned

the same series of transactions. Id. at 630. The charged offenses

“were not isolated acts,” but were instead “part of a series of trans-

actions involving the same principal actors, in the same roles, em-

ploying the same modus operandi.” Id. We explained that other

transactions connected with charged offenses “have long been used

to show a general pattern, the necessary criminal intent, or the

guilty knowledge of the defendant.” Id. at 631 (quoting United

States v. Dula, 989 F.2d 772, 777 (5th Cir. 1993)).

Evidence is necessary to complete the story of a crime when

the evidence explains the “context, motive, and set-up of the

crime” or reveals important details about the criminal scheme. See

United States v. Holt, 777 F.3d 1234, 1261–62 (11th Cir. 2015) (cita-

tion and internal quotation marks omitted). In Holt, we held that

evidence of drug transactions from 1995 was necessary “to

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10 Opinion of the Court 23-10479

complete the story” of the charged crime—a conspiracy that began

in 2000 and ended in 2010. Id. The 1995 evidence was necessary

because it helped the jury understand “how [the defendant] came

to know and participate in narcotics distribution” with his co-con-

spirators. Id. at 1262.

Evidence is inextricably intertwined with a charged crime if it

“forms an integral and natural part of” an account of a crime, United

States v. Edouard, 485 F.3d 1324, 1344 (11th Cir. 2007), or is “vital to

an understanding of the context of the government’s case,” United

States v. McLean, 138 F.3d 1398, 1404 (11th Cir. 1998). In McLean, a

defendant was charged with drug and firearm offenses stemming

from controlled sales by confidential informants. Id. at 1401. We

held that evidence of the defendant’s involvement in a drug-sale

organization was intrinsic evidence of the charged offenses because

the evidence established how the defendant became a target for

controlled buys. Id. at 1404. The evidence also explained the rela-

tionship between the defendant and the confidential informant and

was “vital” to establishing the confidential informant’s credibility.

Id.

The district court abused its discretion by ruling that the evi-

dence seized during the September 2021 search was intrinsic evi-

dence of the charged conspiracy. The evidence did not arise from

the same transactions. It was not necessary to complete the story

of the charged crime. And it was not inextricably intertwined.

The seized evidence did not arise from the same transaction or

series of transactions because it was not “linked in time and

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circumstances” with the charged crime. See US Infrastructure, 576

F.3d at 1210. Harding was charged with a conspiracy in the South-

ern District of Alabama beginning in early 2018 and ending on or

about April 23, 2019. The search evidence was seized in the North-

ern District of Alabama in September 2021—almost 29 months af-

ter the alleged end of the conspiracy. The United States failed to

prove any link between the search evidence and the charged con-

spiracy. Harding was not distributing heroin to Snowden in Sep-

tember 2021 because Snowden was arrested in 2019 and remained

in custody afterward. See United States v. Postal, 589 F.2d 862, 888

(5th Cir. 1979) (stating that “[a] coconspirator’s participation in a

conspiracy ends with his arrest”). The United States provided no

evidence of how Harding acquired the heroin and firearms in his

home or where they were headed. In contrast, when we have ruled

that uncharged acts were “linked in time and circumstances” with

a charged crime, the uncharged acts involved the same parties and

the same agreement. See, e.g., Horner, 853 F.3d at 1213–15 (holding

that tax returns from 2005 and 2006 were intrinsic evidence of a

later conspiracy because the evidence proved that the defendants

“had an ongoing plan” to divert business cash into their personal

accounts and the older evidence was “part of the same plan” and

“used the same modus operandi as the charged offenses—diverted

cash receipts”).

Nor was the search evidence necessary to complete the story

of the charged crime. See Holt, 777 F.3d at 1262. We have held that

evidence of drug transactions from five years before a conspiracy

began was necessary to complete the story of a crime because it

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“explained how [the defendant] came to know and participate in

narcotics distribution[s]” with his co-conspirators. See id. But the

evidence seized in Harding’s home tells us nothing about how Har-

ding conspired to distribute heroin in 2018 and 2019, and the evi-

dence does not implicate any of Harding’s co-conspirators.

The search evidence also was not inextricably intertwined with

the charged crime. Without some link between the search evi-

dence and the charged conspiracy, we cannot say that the search

evidence “form[ed] an integral and natural part of” the account of

the charged crime, Edouard, 485 F.3d at 1344, or that it is “vital to

an understanding” of the case, McLean, 138 F.3d at 1404. The

United States tried to prove the charged conspiracy by establishing

that Harding formed an agreement with Snowden. The search ev-

idence does not enhance one’s understanding of that theory be-

cause Snowden was arrested in 2019.

The United States counters that a conspiracy is a “series of

transactions” and that the search evidence was intrinsic evidence

because it “show[s] that Harding engaged in the same types of

transactions” after Snowden’s arrest. But that argument proves too

much. The September 2021 search evidence proves that Harding

engaged in drug-related crimes on a different occasion and in a dif-

ferent district than the charged conspiracy. And evidence that a per-

son engaged in “the same types of transactions” on a different oc-

casion 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.” FED. R. EVID. 404(b)(1) (emphasis added).

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We review evidentiary errors for harmlessness. United States v.

Green, 873 F.3d 846, 866–67 (11th Cir. 2017). A non-constitutional

error warrants reversal only if “there is a reasonable likelihood that

the error affected the defendant’s substantial rights.” Id. at 867.

When conducting a harmless-error analysis, we ask “whether the

error had substantial influence and whether enough evidence sup-

ports the result apart from the error.” Id. We have held that the

erroneous admission of prior-act evidence was harmless when five

witnesses gave consistent accounts about a defendant’s involve-

ment in a drug-distribution conspiracy. See United States v. Hubert,

138 F.3d 912, 914 (11th Cir. 1998). By contrast, we held in United

States v. Hands that an evidentiary error was not harmless when the

United States relied on eight “highly questionable” witnesses who

“each testified in the hope of receiving a reduced sentence” and

whose testimony the United States was “unable to bolster” with

“independent corroborating evidence.” 184 F.3d 1322, 1330–31

(11th Cir. 1999).

We cannot say that “enough evidence supports the result apart

from the error,” so the admission of the September 2021 search ev-

idence was not harmless. See Green, 873 F.3d at 867. As the United

States concedes, Snowden was the “central witness” against Har-

ding. Several witnesses testified that someone named Ol’ School

was involved in drug activity, but Snowden was the only witness

who identified Harding as Ol’ School. And like the “highly ques-

tionable” witnesses in Hands, Snowden testified that he had been

involved in drug transactions and that he had entered into an agree-

ment with the United States and cooperated with the hope of

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receiving a lesser sentence. See 184 F.3d at 1330–31. If testimony

from eight “highly questionable” witnesses was insufficient to ren-

der an evidentiary error harmless, see id., then testimony from one

highly questionable witness is certainly not enough. Snowden’s tes-

timony supports the verdict, but the quantity and strength of that

untainted evidence is far less substantial than the erroneously ad-

mitted evidence.

The United States contends that other evidence corroborated

Snowden’s testimony: wiretaps established that Snowden and

Clark received heroin from someone named Ol’ School; Snowden

identified Harding’s house in a photograph; an agent testified that

officers arrested Harding at that photographed home; and Kidd tes-

tified that Snowden suggested that he received heroin from a per-

son called Ol’ School. But that corroboration is weak. The wiretaps

and Kidd’s testimony corroborate Snowden’s assertion that he re-

ceived heroin from someone called Ol’ School. But that evidence

does not establish that Harding was Ol’ School. That Snowden

identified Harding’s home in a photograph and that Harding was

later arrested at that home does not strongly corroborate Snow-

den’s testimony about Harding’s involvement in the drug scheme.

Those facts instead corroborate Snowden’s testimony that Clark

told him where Harding lived.

The United States also encouraged the jury to rely on the erro-

neously admitted evidence for an improper purpose. During clos-

ing argument, the prosecutor asserted that “exhibits that came

from the search at Mr. Harding’s residence” were “relevant to the[]

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23-10479 Opinion of the Court 15

charges” against Harding. The prosecutor asked the jury to con-

sider “all the[] firearms” and the “[two] kilograms of heroin” found

in Harding’s home when deciding Harding’s guilt. And the prose-

cutor explained that if the jury found Harding guilty of conspiracy,

then it should consider “the [two] kilograms [of heroin] that were

seized from his house” when determining the quantity of heroin

for which Harding was accountable. These invitations to rely on

the erroneously admitted evidence as evidence of Harding’s guilt

likely had a “substantial influence” on the jury’s verdict. See Green,

873 F.3d at 867. So the error was not harmless.

The United States argues that any taint to the conspiracy of-

fense should not affect the distribution charge. But our precedents

make clear that evidence of multiple firearms and a large quantity

of drugs in a defendant’s home can lead to inferences about one’s

intent to distribute. See United States v. Madera-Madera, 333 F.3d

1228, 1233 (11th Cir. 2003) (explaining that federal law “permits an

inference of intent to distribute from a defendant’s possession of a

significantly large quantity of drugs”); United States v. Terzado-

Madruga, 897 F.2d 1099, 1120 (11th Cir. 1990) (“It is uniformly rec-

ognized that weapons are often as much ‘tools of the trade’ as the

most commonly recognized narcotics paraphernalia.” (citation

omitted)). The erroneously admitted evidence could have improp-

erly influenced the jury on both charges.

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B. Although the Evidence Was Admissible Under Rule 404(b), the

District Court Abused Its Discretion by Failing to Give a

Limiting Instruction, and the Error Was Not Harmless.

The district court admitted evidence from the September 2021

search of Harding’s home on the alternative ground that it qualified

as extrinsic evidence under Federal Rule of Evidence 404(b). Har-

ding argues that this ruling was an abuse of discretion, and he ar-

gues that the district court should have provided a limiting instruc-

tion. The United States responds that the evidence was plainly ad-

missible under Rule 404(b) and that Harding has abandoned any

challenge about the limiting instruction.

A threshold issue is whether Harding abandoned any challenge

to the denial of his request for a limiting instruction. A party aban-

dons an issue when he “makes only passing references to it or raises

it in a perfunctory manner without supporting arguments and au-

thority.” Sapuppo v. Allstate Floridian Ins., 739 F.3d 678, 681 (11th

Cir. 2014). Harding’s brief focuses primarily on whether the evi-

dence met the requirements for admissibility under Federal Rule

of Evidence 404(b). But in a paragraph of his opening brief, he ex-

plains that the district court denied his request for a limiting in-

struction. And he argues that “a limiting instruction could have re-

duced the risk of undue prejudice.” The United States argues that

Harding abandoned any challenge regarding the lack of a limiting

instruction.

Harding adequately presented a challenge to the denial of his

request for a Rule 404(b) limiting instruction. Harding frames his

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argument in terms of whether the evidence was admissible under

Rule 404(b), and our precedent too frames the limiting instruction

as a requirement for admissibility. See United States v. Costa, 947

F.2d 919, 925 (11th Cir. 1991) (“Extrinsic evidence of past bad acts

is admissible to establish intent, provided the judge offers a limiting

instruction to the jury to the effect that the evidence may not be

used to establish that the defendant acted in conformity with the

past behavior.” (emphasis added)). Harding explains that the dis-

trict court denied his request for a limiting instruction, and he ar-

gues, with a citation to supporting authority, that a limiting instruc-

tion would have reduced the risk of unfair prejudice.

Extrinsic evidence of uncharged bad acts is not admissible “to

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

casion the person acted in accordance with the character.” FED. R.

EVID. 404(b)(1). But the same evidence might be admissible for

other purposes, “such as proving motive, opportunity, intent, prep-

aration, plan, knowledge, identity, absence of mistake, or lack of

accident.” Id. R. 404(b)(2). To be admissible under Rule 404(b), the

evidence “must be introduced for a proper purpose, be supported

by sufficient evidence, and have probative value that is not substan-

tially outweighed by unfair prejudice.” Horner, 853 F.3d at 1215.

Rule 404(b) is a “rule of inclusion,” and Rule 404(b) evidence

“should not lightly be excluded when it is central to the prosecu-

tion’s case.” United States v. Jernigan, 341 F.3d 1273, 1280 (11th Cir.

2003) (citation and internal quotation marks omitted), abrogated in

part on other grounds by Rehaif v. United States, 139 S. Ct. 2191 (2019).

Nevertheless, when the district court admits extrinsic evidence

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18 Opinion of the Court 23-10479

under Rule 404(b), it “must provide a limiting instruction.” United

States v. Tokars, 95 F.3d 1520, 1537 (11th Cir. 1996).

The September 2021 search evidence was admissible under

Rule 404(b) to establish Harding’s intent to distribute heroin. A de-

fendant who pleads not guilty to a drug conspiracy puts his intent

at issue and “opens the door to admission of prior drug-related of-

fenses as highly probative, and not overly prejudicial, evidence of

[his] intent.” United States v. Smith, 741 F.3d 1211, 1225 (11th Cir.

2013) (citation and internal quotation marks omitted). Officers

found a large quantity of heroin in Harding’s home. That fact sup-

ports an inference that Harding intended to distribute it. See

Madera-Madera, 333 F.3d at 1233 (explaining that federal law “per-

mits an inference of intent to distribute from a defendant’s posses-

sion of a significantly large quantity of drugs”). The firearms seized

in proximity to the heroin reinforce the inference that Harding in-

tended to distribute heroin. See Terzado-Madruga, 897 F.2d at 1120

(“It is uniformly recognized that weapons are often as much ‘tools

of the trade’ as the most commonly recognized narcotics parapher-

nalia.” (citation omitted)).

The probative value of the evidence was not substantially out-

weighed by a risk of unfair prejudice. We have repeatedly held that

evidence of prior drug-related offenses is “highly probative” of a

defendant’s intent and “not overly prejudicial.” See, e.g., United

States v. Perry, 14 F.4th 1253, 1275 (11th Cir. 2021) (citation and in-

ternal quotation marks omitted). And the evidence was not so tem-

porally remote that it lost its probative value. Evidence might

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23-10479 Opinion of the Court 19

become less probative as time passes, but we have allowed the in-

troduction of drug-related convictions to prove intent, even when

the prior conviction “is many years old.” Smith, 741 F.3d at 1225.

The extrinsic acts in Smith occurred six and ten years before the

charged crimes. Id. at 1226. And in United States v. Dickerson, this

Court affirmed the introduction of drug-distribution evidence that

occurred almost two years after the charged conspiracy. 248 F.3d

1036, 1046–47 (11th Cir. 2001). Here, the September 2021 search

occurred almost 29 months after the alleged end date of the con-

spiracy alleged in the indictment. The probative value was not sub-

stantially outweighed by a risk of unfair prejudice.

Nevertheless, the district court abused its discretion by denying

Harding’s request for a limiting instruction. Our precedent is clear:

when a district court admits extrinsic evidence under Rule 404(b),

the district court “must provide a limiting instruction.” Tokars, 95

F.3d at 1537 (emphasis added). The failure to provide a limiting in-

struction is an abuse of discretion if the omission “seriously im-

paired the defendant’s ability to present an effective defense.” Gon-

zalez, 975 F.2d at 1516. We have held that the absence of a limiting

instruction seriously impaired a defendant’s ability to present an

effective defense when it “opened the door for the jury to consider

th[e] evidence in an improper light.” Id. at 1517. Here, the jury was

permitted to consider the search evidence only for a limited pur-

pose. See FED. R. EVID. 404(b). The jury was not permitted to con-

sider the evidence as “evidence of [Harding’s] character” or as

proof “that on a particular occasion [Harding] acted in accordance

with [that] character.” See id. R. 404(a)(1). But the jury was never

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20 Opinion of the Court 23-10479

informed of this prohibition. So the absence of a limiting instruc-

tion “opened the door for the jury to consider this evidence in an

improper light.” Gonzalez, 975 F.2d at 1517. The district court

abused its discretion by declining Harding’s request for a limiting

instruction.

The error was not harmless because it “seriously impaired”

Harding’s ability to present an effective defense. See id. As we have

explained, the United States encouraged the jury to rely on errone-

ously admitted evidence from the search of Harding’s home for an

improper purpose. By allowing the jury to consider extrinsic evi-

dence as evidence of the charged crimes, the district court relieved

the United States “of its burden of persuasion beyond a reasonable

doubt of every essential element of the crime.” Id.

IV. CONCLUSION

We VACATE Harding’s convictions and sentence and

REMAND for a new trial.