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United States v. Larry Gildersleeve, III - Criminal Sentencing Appeal

Favicon for www.courtlistener.com 6th Circuit Court of Appeals
Filed March 20th, 2026
Detected March 21st, 2026
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Summary

The Sixth Circuit Court of Appeals affirmed the criminal sentence of Larry Keith Gildersleeve, III. Gildersleeve appealed the procedural and substantive reasonableness of his sentence related to his failure to pay federal employment taxes and the misappropriation of business funds for personal use.

What changed

The Sixth Circuit Court of Appeals has affirmed the criminal sentence of Larry Keith Gildersleeve, III, in case number 25-3351. The appeal concerned the procedural and substantive reasonableness of his sentence. Gildersleeve owned Progressive Alternatives, a company that failed to pay federal employment taxes from 2011 to 2019. Additionally, substantial funds were transferred from the business account to personal accounts, and personal purchases were made directly from the business account without filing personal income tax returns for these funds.

This appellate decision means Gildersleeve's sentence stands as imposed by the district court. For compliance officers, this case highlights the critical importance of accurate tax remittance for businesses, proper segregation of business and personal funds, and adherence to tax filing obligations. While this is an individual case, it underscores the potential severe consequences, including criminal sentencing, for non-compliance with federal employment tax laws and financial impropriety.

What to do next

  1. Review internal controls for tax remittance and fund segregation.
  2. Ensure accurate filing of all personal and business federal income tax returns.

Source document (simplified)

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March 20, 2026 Get Citation Alerts Download PDF Add Note

United States v. Larry Gildersleeve, III

Court of Appeals for the Sixth Circuit

Combined Opinion

NOT RECOMMENDED FOR PUBLICATION
File Name: 26a0148n.06

Case No. 25-3351

UNITED STATES COURT OF APPEALS
FOR THE SIXTH CIRCUIT FILED
Mar 20, 2026
KELLY L. STEPHENS, Clerk
)
UNITED STATES OF AMERICA,
)
Plaintiff-Appellee, ) ON APPEAL FROM THE UNITED
) STATES DISTRICT COURT FOR
v. ) THE NORTHERN DISTRICT OF
) OHIO AT CLEVELAND
LARRY KEITH GILDERSLEEVE, III, )
Defendant-Appellant. ) OPINION
)

Before: BOGGS, SILER, and KETHLEDGE, Circuit Judges.

SILER, Circuit Judge. Defendant Larry Keith Gildersleeve appeals the procedural and

substantive reasonableness of his criminal sentence. We AFFIRM.

I. Background

In 2011, Gildersleeve purchased Progressive Alternatives, a company providing care

services to the developmentally disabled. Following the purchase, Gildersleeve made the business

a sole proprietorship under his name. As with such businesses, Progressive Alternatives had to

pay federal employment taxes, both on its own behalf and by deducting and paying over its

employees’ taxes. But the company failed to pay such taxes from the beginning of Gildersleeve’s

ownership in 2011 until it closed in 2019.

Beyond failing to pay business taxes, money flowed freely from Progressive Alternatives’

operating account to personal accounts held by Gildersleeve and his husband. And the net transfers

were substantial: 2015: $188,000, 2016: $283,000, 2017: $284,000, 2018: $339,000, 2019:
No. 25-3351, United States v. Gildersleeve

$155,000. Notably, neither Gildersleeve nor his husband filed personal federal income-tax returns

for the money received from the business.

In addition, the couple made personal purchases using funds directly from the business

account. These personal expenditures included credit card payments ($91,385), cash withdrawals

($65,585), rent for their joint residence ($61,300), family trips ($21,982), and Sam’s Club

($19,231).

Between December 2017 and September 2019, Progressive Alternatives failed to pay a

total of $692,697.50 in quarterly taxes, in violation of 26 U.S.C. § 7202. The total tax loss,

reflecting both employee and employer portions from 2011 to 2019, was $2,616,354.

The government charged Gildersleeve by information on eight counts of failure to account

for and pay over taxes. Gildersleeve later pled guilty to the offenses.

At sentencing, the district court agreed with the parties’ calculation of Gildersleeve’s base

offense level and accepted the offense-level reductions recommended in his plea agreement. The

district court then accepted an additional four-level, downward departure based on Gildersleeve’s

substantial assistance in a government investigation, resulting in a total offense level of 13 and a

sentence range of 12 to 18 months.

After the parties’ arguments and Gildersleeve’s allocution, the district court began its

sentencing determination by stating that it had “carefully considered the matter, [and] reviewed

the nature and circumstances of the offense.” On this point, the district court had already observed

that “the money coming to the personal accounts was . . . substantial[,]” that Gildersleeve spent

“lots of [business] money” on personal luxuries, and that Gildersleeve failed to pay income taxes

on the monies received from the business between 2015 and 2019. But the court acknowledged

2
No. 25-3351, United States v. Gildersleeve

that Gildersleeve had experienced a financially challenging childhood. It also recognized that

Gildersleeve’s daughter suffered from autism and required parental care.

Following its analysis, the district court concluded that “[e]ighteen months is not sufficient,

. . . not given the length of time this went on, not given . . . the way the monies were spent, the

waste, the complete ignoring his obligation to both income tax and otherwise.” So, the district

court varied Gildersleeve’s sentence “two levels from the 13 to offense level 15.” And the court

determined that a sentence of twenty-four months was reasonable due to “the nature of this

conduct[.]”

Upon announcing Gildersleeve’s sentence, the district court asked whether the parties had

“any objection[s], corrections, [or] arguments not previously raised.” The parties offered none.

After sentencing, the district court issued a “Statement of Reasons,” finding that additional

punishment was necessary “[t]o reflect the seriousness of the offense . . .[,] [t]o afford adequate

deterrence . . .[, and t]o protect the public from further crimes of the defendant[.]” The district

court subsequently issued a judgment reflecting its sentencing pronouncement, and Gildersleeve

timely filed his notice of appeal.

II. Standard of Review

When a defendant fails to raise a procedural challenge at the sentencing hearing—as

Gildersleeve failed to do here—this court reviews the challenge for plain error. United States v.

Vonner, 516 F.3d 382, 386 (6th Cir. 2008) (en banc). With or without an objection, we review a

challenge to the substantive reasonableness of a sentence under an abuse-of-discretion standard.

See United States v. Nunley, 29 F.4th 824, 830 (6th Cir. 2022). Under that standard, this court

reviews the district court’s legal conclusions de novo and its findings of fact for clear error. Id.

(citing United States v. Battaglia, 624 F.3d 348, 351 (6th Cir. 2010).

3
No. 25-3351, United States v. Gildersleeve

III. Discussion

A. Procedural Reasonableness

Gildersleeve first claims that the upward variance was procedurally unreasonable because

the district court did not give notice that it was considering a variance. In response, the government

argues that the district court did not commit plain error because it was not required to give notice

of a potential upward variance.

We review procedural reasonableness claims to ensure that the sentencing judge “set forth

enough to satisfy the appellate court that [the sentencing judge] has considered the parties’

arguments and has a reasoned basis for exercising his own legal decision[-]making authority.”

United States v. Nunley, 29 F. 4th 824, 833 (6th Cir. 2022).

Gildersleeve’s procedural argument is unconvincing. In Irizarry v. United States, the

United States Supreme Court held that a district court is not required to give notice of its intent to

impose a variance. 553 U.S. 708, 714–16 (2008). Indeed, the Court observed that “[s]entencing

is ‘a fluid and dynamic process and the court itself may not know until the end whether a variance

will be adopted, let alone on what grounds.’” Id. at 715 (quoting United States v. Vega–Santiago,

519 F.3d 1, 4 (1st Cir. 2008) (en banc)). And despite Gildersleeve’s insistence, his case is unlike

United States v. Coppenger, where the district court improperly imposed a variance based on

“extraneous” information—information that the defendant could not have accessed or anticipated.

775 F.3d 799, 804–05 (6th Cir. 2015). The district court here relied on facts contained in the

presentence report. So, Gildersleeve has not established plain procedural error.

4
No. 25-3351, United States v. Gildersleeve

B. Substantive Reasonableness

Gildersleeve next raises several arguments to attempt to show that his sentence is

substantively unreasonable. The government counters that the district court reasonably weighed

the § 3553(a) factors and imposed a sentence that reflected the circumstances of the offense.

A sentence is substantively unreasonable if it is arbitrary, based on impermissible factors,

or fails to consider or properly weigh any of the relevant 18 U.S.C. § 3553 (a) factors. United

States v. Husein, 478 F.3d 318, 332 (6th Cir. 2007). A within-Guidelines sentence is presumed

reasonable, but a sentence outside the Guidelines is not necessarily presumptively unreasonable.

Id. Moreover, judges may vary from the Guidelines range, but must justify such a variance by

reference to the § 3553(a) factors. United States v. Demma, 948 F.3d 722, 728–29 (6th Cir. 2020).

Such reference may be implicit rather than explicit, and the district court need not engage in a

“ritualistic one-by-one incantation of each factor.” United States v. Coleman, 835 F.3d 606, 616

(6th Cir. 2016) (internal quotation marks omitted).

At sentencing, the district court weighed the § 3553(a) factors. Addressing the nature and

circumstances of the offense, the district court emphasized that (1) Gildersleeve transferred

business funds to his personal account, (2) he failed to pay individual income taxes on the

transferred funds, (3) he spent large sums on personal luxuries using a business account, and (4)

Gildersleeve’s conduct continued for many years. The district court also addressed Gildersleeve’s

history and characteristics by observing that Gildersleeve suffered financial difficulties in

childhood and that his daughter required parental care. And the court noted the seriousness of the

offense, deterrence, and public safety concerns in its Statement of Reasons.

The district court reasonably weighed the relevant § 3553(a) factors. On this point, the

record supports the finding that the nature of the offense was severe, especially given that

5
No. 25-3351, United States v. Gildersleeve

Gildersleeve continued his crimes for nearly a decade. The district court also expressed

appropriate concern regarding Gildersleeve’s self-dealing with business funds, his failure to pay

income taxes on those funds, and his extravagant consumer spending using the funds. So, the

district court did not abuse its discretion in weighing the § 3553(a) factors.

Despite the above, Gildersleeve first contends that his sentence is too long because of his

low odds of recidivism. Gildersleeve then asserts that, like the defendant in United States v. Perez-

Rodriguez, 960 F.3d 748 (6th Cir. 2020), he did not “exhibit an extensive pattern of criminal

activity, or an ongoing risk of harm to the public.” Next, Gildersleeve believes that the district

court did not sufficiently distinguish his case from cases involving similar crimes. Relatedly,

Gildersleeve maintains that the guidelines range adequately accounted for his conduct.

Gildersleeve’s arguments do not carry water. His chance of recidivism is not a relevant

consideration in the circumstances of this case. Moreover, because Gildersleeve engaged in a

pattern of criminal activity by repeatedly failing to pay taxes, he is unlike the defendant in Perez-

Rodriguez, who reentered the United States illegally only once. 960 F.3d at 756. Likewise, the

duration of his criminal conduct distinguishes Gildersleeve’s case from others involving the same

type of crime. Finally, the broader context of his conduct—self-dealing with business funds,

failure to pay personal income taxes on those funds, extravagant consumer spending using the

business funds, and the duration of his conduct—supports finding that the sentencing guidelines

range did not adequately account for his acts. Therefore, because Gildersleeve has not established

an abuse of discretion, his substantive reasonableness claim fails.

IV. Conclusion

For the above reasons, we AFFIRM the judgment of the district court.

6

Source

Analysis generated by AI. Source diff and links are from the original.

Classification

Agency
6th Circuit
Filed
March 20th, 2026
Instrument
Enforcement
Legal weight
Non-binding
Stage
Final
Change scope
Minor
Document ID
Case No. 25-3351
Docket
25-3351

Who this affects

Applies to
Employers
Industry sector
5221 Commercial Banking
Activity scope
Tax Evasion Employment Tax Compliance
Geographic scope
United States US

Taxonomy

Primary area
Criminal Justice
Operational domain
Legal
Topics
Tax Evasion Sentencing

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