Oregon Woman Sentenced to Prison After IRS Says She Used Employee Tax Withholdings to Buy Luxury Real Estate

The owner of a tree removal and landscaping business in Happy Valley, Oregon, 47-year-old Joyce Leard, was sentenced yesterday to 15 months in federal prison for willfully failing to pay owner employment business taxes to the IRS amounting to more than $3.5 million.

According to court documents and statements, Leard was responsible for withholding Social Security, Medicare, and federal income taxes from the wages of her employees to the IRS each quarter from 2017 to 2024, as well as failing to file quarterly income tax returns.

Tidings Context
Employment taxes withheld from paychecks are trust fund taxes. If they are not paid, the IRS can assess a Trust Fund Recovery Penalty and pursue responsible people personally, not just the business.

 

Leard Deducted Income Tax from her Employees but Failed to Pay the Funds to the IRS

Court documents reveal that Leard deducted taxes from her employees’ wages but failed to pay these over to the IRS from the fourth quarter of 2018 to the fourth quarter of 2020. During this time, she also failed to file quarterly employment tax returns,

Tidings Insight
When employers withhold Social Security, Medicare, and income taxes, they are holding employee money for the Treasury. Using it for payroll or expenses can trigger criminal charges and restitution.

instead using the funds in the Mr. Tree business bank account.

During this period, no corporate tax was filed on behalf of the company, and Leard also failed to file a personal income tax return from 2018 to 2020, as required by law.

 

She Used the Business Account to Buy Real Estate Worth $3.5 Million

Court documents reveal that Leard used the business account to purchase $3.5 million in real estate, to pay creditors, and for other expenses.

According to court documents, Leard owned and operated Mr. Tree from 2017 to 2024, although the company was advertised as being in business for 30 years, employing between 50 and 75 people every year.

On January 14, 2025, a federal grand jury in Portland indicted Leard on charges of willful failure to account for and pay over tax, as well as willful failure to file a tax return. Just two days later, Leard pleaded guilty to one count of willful failure to account for or pay over tax.

Tidings Timeline
  • 2017 to 2024 : ran Mr. Tree Inc. and owed payroll tax deposits
  • Q4 2018 to Q4 2020 : withheld taxes, did not pay IRS or file returns
  • Jan 14 2025 : grand jury indictment in Portland
  • Jun 16 2025 : pleaded guilty to one count
  • Feb 18 2026 : sentenced 15 months, restitution $2,880,346.25

Apart from the 15-month prison sentence, Leard was also ordered to pay $2,880,346.25 in restitution, and a $100 special assessment.

Tidings Insight
Restitution is what the court orders to be paid back. It can differ from the headline tax loss because it is tied to proven amounts and how the case is resolved.
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