Practical Tax Planning Will Land You In Jail! (Even in Florida)

According to the DoJ, a former Jacksonville company CEO was sentenced to 32 months in prison for willfully attempting to evade the assessment of his federal income taxes.

According to court documents and statements made in court, in 2015 and 2016, Jason Cory, 49, of Jacksonville, was a manager at a New York-based IT services company and from 2017 through 2019, he was the CEO of a different IT services company based in Jacksonville. From 2015 through 2018, Cory used his positions to cause more than $1.5 million to be deposited into the bank accounts of Gambit Matrix LLC, a shell company he controlled. As CEO, Cory caused transfers to Gambit Matrix under the false pretense that they were payments for consulting services that had never been provided.

Cory did not report the income he earned through transfers to Gambit Matrix on his tax return for 2015 and did not file tax returns for the years 2016 through 2018 as required by law. 

To conceal the fraud scheme from the second company and evade taxes on his income for those years, Cory invented fictitious owners of Gambit Matrix, made false representations to his employer, and falsified emails and IRS Forms W-9 (Request for Taxpayer Identification Number). 

Cory used the money directed to Gambit Matrix to pay for personal expenses such as credit card bills, rent, and club memberships. In total, Cory evaded more than $600,000 in taxes through his actions.

In addition to the term of imprisonment, U.S. District Court Judge Marcia Morales Howard ordered Cory to serve three years of supervised release and to pay approximately $606,195 in restitution to the United States.

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