While Caswell ran three logging and construction companies, he apparently yearned for something more. According to the Department of Justice (DOJ), beginning in 2018, Caswell withheld employment taxes from his employees' wages and retained those funds rather than remitting them to the IRS as required by law.
In addition to failing to pay over the employment taxes, Caswell also moved money between bank accounts by directing customers to pay him personally or through another company under his control. Although the circumstances are detailed in the DOJ press release, Caswell also apparently lied to IRS collection officers.
One important takeaway from this case is never lie to an IRS agent. If you are concerned that something you say to the IRS could expose you to criminal liability, read our guide, Understanding Tax Fraud, and consult an experienced criminal tax attorney before responding.
In addition to the problems Caswell generated for himself by not paying over his employment taxes, he also created fraudulent bank statements and documentation in order to obtain loans from the Small Business Administration (SBA) and other lenders, including the Paycheck Protection Program (PPP) and the Economic Injury Disaster Loan (EIDL) program. At one point, Caswell appropriated the personal information of another individual in order to obtain a residential mortgage.
Caswell used $70,000 of the proceeds from his fraud scheme as a deposit for an Ultimate Frisbee tournament. The venture did not end well. In addition to appointing himself as a player on his struggling Ultimate Frisbee teams, according to media reports, Caswell was arrested in August 2025 in connection with two alleged drive-by shootings at a residence in Medford, Oregon.
In June, Caswell pleaded guilty to tax crimes that included tax evasion, failure to pay over employment taxes, and other charges. Caswell will spend more than three years in prison, followed by five years of supervised release. He owes $1,198,799.83 in restitution. Game over.
The legal group at Robert J. Fedor, Esq., L.L.C., delivers the guidance needed to address tax compliance concerns, including tax evasion or payroll tax fraud, to help clients navigate potential IRS investigations. Speak with our knowledgeable tax attorneys today at 440-250-9709. We serve clients across the U.S. and internationally from our offices in Cleveland and Chicago.