United States of America v. Nathaniel J. Jacobs , Sr .

In the
United States Court of Appeals
For the Seventh Circuit
____________________
No. 22-2615
U NITED STATES OF A MERICA ,
Plaintiff-Appellee,
v.
NATHANIEL J. J ACOBS , SR .,
Defendant-Appellant.
____________________
Appeal from the United States District Court for the
Southern District of Indiana, Evansville Division.
No. 3:20-cr-9 — Richard L. Young, Judge.
____________________
A RGUED D ECEMBER 4, 2023 — D ECIDED A PRIL 18, 2025
____________________
Before R OVNER , SCUDDER , and P RYOR , Circuit Judges.
P RYOR , Circuit Judge. A jury found Nathaniel Jacobs guilty
of several drug and gun possession offenses, as well as wit-
ness tampering. Jacobs raises two issues for review. First, he
argues the district court violated his rights under the Sixth
Amendment by not allowing him to confront his ex-girlfriend
about possible bias arising from state criminal charges pend-
ing against her. Second, he argues the district court erred by

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2 No. 22-2615
admitting into evidence drugs found in Jacobs’s home. We af-
firm.
I. BACKGROUND
A. Factual Background
On the morning of January 31, 2020, Jacobs appeared at
the Deaconess Midtown Hospital in Evansville, Indiana, with
a gunshot wound to his hand. The hospital contacted local po-
lice to investigate. Detective Michael Evans was assigned to
the case, and, at the hospital, asked Jacobs how he was shot.
Jacobs responded that he was taking out the trash when two
juveniles playing in a field nearby shot him.
Skeptical about Jacobs’s story, Detective Evans asked
whether Jacobs had shot himself. Jacobs confessed he had. He
told Detective Evans that he inherited three guns from his late
father-in-law, which he kept in a safe in his bedroom. That
morning, he was attempting to retrieve money from the safe
when a Derringer fell to the ground and fired, striking him in
the hand. Jacobs admitted that he was not allowed to possess
firearms as a convicted felon.
Law enforcement obtained a warrant to search Jacobs’s
home. The warrant allowed police to search for “firearms,”
“ammunition,” “firearm accessories,” “cell phones and other
electronic devices used to store information or communica-
tions,” a “safe,” “video surveillance equipment,” and proof of
residency. In executing the warrant, officers discovered blood
spatter and debris on the floor and a safe beside the bed in the
primary bedroom. In front of the safe, officers found the
loaded Derringer firearm that Jacobs had shot himself with.
Officers also found ammunition boxes and two Smith & Wes-
son firearms.

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No. 22-2615 3
The search uncovered drug-related evidence, as well. A
nightstand next to the bed held tobacco cans labeled “ball”
and “G.” The cans contained baggies with a powdery sub-
stance that later tested positive for methamphetamine. Within
an ammunition box and in the nightstand, there were note
cards detailing quantities of methamphetamine, prices, and
customers. In the kitchen and dining area, officers found ad-
ditional drug paraphernalia, including a digital scale with
methamphetamine residue, more baggies, and a plate with
white powder. They also discovered four cell phones, which
contained evidence of drug dealing such as text messages
from customers telling Jacobs his prices were too high and a
response from Jacobs that he only had “a ball” of metham-
phetamine to sell.
B. Procedural Background
A grand jury indicted Jacobs with three counts of illegal
possession of a firearm by a convicted felon, 18 U.S.C.
§ 922(g)(1); possession with intent to distribute methamphet-
amine, 21 U.S.C. § 841(a)(1) and (b)(1)(B)(viii); possession of a
firearm in furtherance of a drug trafficking crime, 18 U.S.C.
§ 924(c)(1)(A); and witness tampering, 18 U.S.C. § 1512(b)(1).
After a change in defense counsel and several continuances,
the district court scheduled the jury trial for May 31, 2022.
During pretrial proceedings, the government filed mo-
tions in limine. One of the motions in limine focused on Ja-
cobs’s girlfriend, Lisa Barton, who the government antici-
pated calling as a witness. The government maintained that
evidence of Barton’s misdemeanor convictions and pending
felony criminal charges was inadmissible under Federal Rule
of Evidence 609 to impeach her. See FED. R. EVID. 609(a). While
Jacobs agreed concerning the misdemeanors, he maintained

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4 No. 22-2615
that the facts surrounding the pending charges for dealing
methamphetamine and carrying a handgun without a license
in Vanderburgh County, Indiana, against Barton were “very
relevant” to his case, as both Barton and Jacobs lived in the
same home at the time of his arrest. At the final pretrial con-
ference, the district court granted the government’s motion.
Trial began on May 31, 2022. The government called
twelve witnesses, including police officers, neighbors, and
customers of Jacobs’s drug operation. Officers testified about
Jacobs’s admission that he shot himself following his initial
contention that a teenager had fired the shot. They also testi-
fied about evidence uncovered during their search of Jacobs’s
home. A neighbor recounted giving Jacobs empty tobacco
cans in which methamphetamine was found and described
observing Jacobs using a digital scale and selling drugs to cus-
tomers at his home. Two customers also testified to buying
drugs from Jacobs.
The jury also heard from Barton. On direct, Barton ex-
pressed discomfort about keeping guns in the home she
shared with Jacobs and denied that the drug evidence and
guns in the home belonged to her. When asked whether she
suspected Jacobs was selling drugs from the home, she an-
swered “yes” and said that Jacobs told her it was “none of
[her] business.” She also testified that while Jacobs was de-
tained and awaiting trial, he suggested they get married to
avoid testifying against each other. On cross-examination,
however, Barton admitted that she and Jacobs had discussed
getting married several times prior to Jacobs shooting himself.
Following her cross-examination, defense counsel re-
quested permission to elicit testimony from Barton concern-
ing her pending case in Vanderburgh County, Indiana.

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No. 22-2615 5
Counsel acknowledged the court had previously ruled those
topics off-limits, but represented that he believed he could
still ask Barton whether she “had contact with law enforce-
ment” and whether she was “in a vehicle” in which drugs and
a handgun were found within a purse a few months after Ja-
cobs’s arrest. Counsel assured the court he would do so with-
out asking Barton whether she had been convicted or
charged. The judge told counsel that he would be allowed to
make the offer of proof later.
Defense counsel renewed the request after the close of the
government’s case in chief. He reiterated that he did not in-
tend to ask Barton about her pending charges, but urged that
he should “be allowed to ask her about the facts of the traffic
stop without asking her about any of the conditions that are
going on with her case.” Invoking the Sixth Amendment, he
asserted that he believed the facts of the traffic stop and items
uncovered in the vehicle search indicated Barton was “more
involved than her testimony [suggested].” The court rejected
this argument, allowing the prior ruling to stand.
The jury convicted Jacobs on all counts.
II. DISCUSSION
On appeal, Jacobs argues the district court violated the
Confrontation Clause of the Sixth Amendment by prohibiting
him from confronting Barton about any potential bias or mo-
tive she had to testify favorably for the federal government in
return for leniency in her state proceeding. He also argues the
district court should have suppressed evidence of the drugs
seized from his home on the basis that the drugs fell outside
the scope of the search warrant, in contravention of the Fourth
Amendment.

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6 No. 22-2615
A. Confrontation Clause Challenge
The Sixth Amendment guarantees criminal defendants an
opportunity to effectively cross-examine witnesses at trial.
United States v. Martin, 618 F.3d 705, 727 (7th Cir. 2010). Effec-
tive cross-examination occurs when a jury has enough infor-
mation to assess the motive and bias of a witness. United States
v. Kaufmann, 985 F.2d 884, 897 (7th Cir. 1993).
Jacobs argues the district court erred by failing to afford
him an opportunity under the Sixth Amendment to explore
Barton’s potential bias in favor of the government. Specifi-
cally, Jacobs asserts he should have been permitted to probe
whether Barton agreed to testify favorably for the govern-
ment in return for leniency in her pending criminal case; or
whether, more generally, she felt that testifying against Jacobs
would have afforded her leniency even without a formal co-
operation agreement.
The parties dispute the appropriate standard of review in
assessing Jacobs’s Sixth Amendment challenge. The govern-
ment asks us to review for plain error on the basis that Ja-
cobs’s argument was forfeited. See United States v. Harris, 102
F.4th 847, 851 (7th Cir. 2024). As the government reasons, Ja-
cobs articulated his Sixth Amendment challenge before the
district court differently than he does on appeal. In the district
court, Jacobs sought to use the traffic stop to establish that
Barton was more involved in the criminal activity than her
testimony suggested—in other words, to impeach Barton by
contradiction. In contrast, the government argues, Jacobs now
on appeal maintains that he was entitled to cross-examine
Barton not to show her potential involvement in the criminal
activity, but to show that she had a reason to testify favorably
to the government.

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No. 22-2615 7
Jacobs asks us to avoid finding forfeiture, and therefore
avoid plain error review, because he invoked the Sixth
Amendment below and because his bias argument is a per-
missible “twist” on his impeachment argument. Accordingly,
Jacobs believes de novo review is appropriate. See Martin, 618
F.3d at 727.
We need not resolve whether Jacobs’s Sixth Amendment
challenge was adequately preserved, or whether the district
court erred in rejecting that challenge. The resolution of those
questions does not decide this case, because regardless of the
standard applied or the presence of error, any error was
harmless. See United States v. Parker, 11 F.4th 593, 596 (7th Cir.
2021) (declining to decide whether Confrontation Clause chal-
lenge was preserved when any error would have been harm-
less).
Even assuming a violation of the Sixth Amendment oc-
curred, we will not set aside Jacobs’s conviction if the Con-
frontation Clause violation was harmless beyond a reasonable
doubt. United States v. Turner, 709 F.3d 1187, 1194 (7th Cir.
2013). “Whether an error is harmless beyond a reasonable
doubt depends upon factors such as the importance of the
witness’s testimony in the prosecution’s case, whether the tes-
timony was cumulative, the presence or absence of corrobo-
rating or contradictory evidence and the overall strength of
the prosecution’s case.” Id. at 1194–95 (quoting United States
v. Walker, 673 F.3d 649, 658 (7th Cir. 2012) (internal quotations
omitted)). We have found an error harmless, for instance,
where the evidence of a defendant’s guilt was “overwhelm-
ing.” Parker, 11 F.4th at 596; Martin, 618 F.3d at 731.
Jacobs’s conviction did not hinge on Barton’s testimony
nor credibility. Even had Jacobs shown Barton was more

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8 No. 22-2615
involved in the criminal activity than she had let on, or that
her testimony was the product of an effort to receive leniency
in her criminal case, the evidence against Jacobs would have
remained overwhelming. Barton’s testimony was cumulative
of, but not necessary to, the government’s case.
Ample evidence, apart from Barton’s testimony, sup-
ported the firearm charges. The jury saw photos of Jacobs
standing near the safe in his bedroom with a Smith & Wesson
on his left hip. Two of Jacobs’s neighbors testified about Ja-
cobs offering to sell them firearms, including a different Smith
& Wesson, which Jacobs had allowed one of those neighbors
to examine in his living room. Detective Evans testified that
Jacobs admitted to inheriting three firearms from his late fa-
ther-in-law and confessed to accidentally shooting himself in
his bedroom with a loaded Derringer, which Jacobs’s son tes-
tified that he had seen Jacobs possess. And customers of Ja-
cobs testified to seeing Jacobs in possession of firearms when
purchasing drugs from him.
There was also extensive evidence to support the drug
charges. This included customers’ testimony about purchas-
ing methamphetamine from Jacobs; a neighbor’s testimony
about seeing Jacobs put the drug inside tobacco cans, weigh
it on digital scales in Jacobs’s home, and sell it to customers;
and a detective’s testimony as to evidence found in Jacobs’s
home, including note cards in Jacobs’s handwriting that in-
cluded drug amounts and customers.
Finally, the obstruction charge did not depend on Barton’s
credibility. The jury heard for itself recorded phone calls be-
tween Jacobs and Barton in which Jacobs stated that he did
not want them to testify against each other; that “[t]he only
way out of here is if we get married”; and that after he “get[s]

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No. 22-2615 9
out of here,” they could “get divorced.” These statements
were more than enough to sustain a conviction.
Because any error was harmless beyond a reasonable
doubt, we do not reach the merits of Jacobs’s Confrontation
Clause challenge.
B. Fourth Amendment Challenge
Jacobs also argues the district court should have sup-
pressed the drug evidence seized in his home because that ev-
idence was outside the scope of the search warrant in viola-
tion of the Fourth Amendment. Because Jacobs failed to file a
suppression motion in the district court, we must first deter-
mine whether Jacobs’s failure was the result of a calculated
strategic decision or neglect. The government asserts this ar-
gument is waived because Jacobs failed to file a motion to
suppress before trial and no good cause justified that failure.
Federal Rule of Criminal Procedure 12(b)(3)(C) requires
motions to suppress to be made before trial if the basis for the
motion is reasonably available at that time. If a defendant, out
of neglect, fails to move to suppress the evidence in the dis-
trict court, we attribute his omission to forfeiture. United
States v. Kelly, 772 F.3d 1072, 1079 (7th Cir. 2014). However,
before conducting plain error review of the forfeited argu-
ment, we first examine whether the defendant “has shown
good cause for his failure to make a timely motion to sup-
press” in the district court. United States v. Johnson, 415 F.3d
728, 730 (7th Cir. 2005). Therefore, without good cause, we are
foreclosed by Rule 12(c)(3) from reviewing Jacobs’s suppres-
sion argument. United States v. Hopper, 934 F.3d 740, 761–62
(7th Cir. 2019); see FED. R. CRIM. P. 12(c)(3).

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10 No. 22-2615
Jacobs asks us to find good cause based on instability with
his trial counsel and a change in the law relating to sentenc-
ing, which he asserts caused turmoil and confusion preclud-
ing him from timely moving to suppress. The record does not
support this assertion.
The district court appointed Jacobs new counsel approxi-
mately two weeks after his original lawyer withdrew from the
case. It extended the pretrial period on multiple occasions,
such that there were roughly ten months between the ap-
pointment of Jacobs’s new counsel and the jury trial. This
gave counsel ample time to assess any suppression claims and
determine whether to file a motion. And in fact, the record
indicates defense counsel represented to the district court that
he did not think he had valid legal grounds on which to file a
suppression motion. Consequently, the record does not show
that instability with defense counsel or a change in the law
precluded the timely filing of a motion to suppress. Rather, it
shows counsel, after considering the matter, chose not to pur-
sue a motion to suppress.
Even if Jacobs could demonstrate good cause, he is unable
to satisfy the requirements of plain error review. See United
States v. Page, 123 F.4th 851, 864 (7th Cir. 2024). In Jacobs’s
view, officers exceeded the scope of the search warrant by
looking inside tobacco cans, which are too small to fit fire-
arms. However, the warrant permitted officers to search Ja-
cobs’s residence for “ammunition” and “electronic devices
used to store information or communications”—both of
which may fit inside a tobacco can. When executing a war-
rant, officers may search “anywhere the items to be seized
might likely be discovered, so long as that is within the place
authorized to be searched.” Archer v. Chisholm, 870 F.3d 603,

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No. 22-2615 11
617 (7th Cir. 2017). As such, it would not be error to conclude
that the officers were permitted under the Fourth Amend-
ment to search the tobacco cans at issue.
III. CONCLUSION
For these reasons, we AFFIRM the judgment of the district
court.

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