Douglas V. Oakes (Lake County) Pleads Guilty To Tax Evasion

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Orlando, Florida – Douglas V. Oakes has pleaded guilty to tax evasion. He faces a maximum penalty of five years in federal prison. A sentencing date has not yet been set.

According to the plea agreement, Oakes tried to evade and defeat the payment of federal income taxes that he owed for tax years 2002 to 2005. In August 2015, after the IRS initiated collection actions, Oakes submitted a signed statement to the IRS in which he represented that he was not employed or self-employed, earned no income, and did not have a financial interest in any business entities. In fact, at that time, Oakes was working for Dealerindustry.com, LLC (“DI”) d/b/a Automotive Capital Corporation, a company in which he had a significant financial interest and from which he was earning approximately $400,000 per year. To conceal from the IRS his financial interest in DI, Oakes registered his daughters and others as DI’s managing members with the Florida Department of State, removed his name from DI’s website and bank account, and removed his profile from the website LinkedIn.

In addition, in September 2015, Oakes submitted a sham rent agreement to the IRS representing that he and his wife were renting their 4,321 sq. ft. lakefront home in Orlando from DI for $1 per month. In November 2015, Oakes further attempted to conceal his assets from the IRS by purchasing a new beachfront home in Merritt Island for $1 million in the name of a nominee.

In July 2017, following the death of his daughter, Oakes and another individual caused posthumous tax returns to be prepared for Oakes’s deceased daughter in which DI’s income from 2010 through 2015 was falsely claimed to be entirely his deceased daughter’s income. In fact, between 2010 and 2015, Oakes earned approximately $2.2 million in income from DI, including payments that Oakes caused to be made from DI’s business bank account for credit card payments, luxury car payments, and the rent for his lakefront home.

The total tax loss to the United States in this case was $1,112,651.

This case was investigated by Internal Revenue Service – Criminal Investigation. It is being prosecuted by Assistant United States Attorneys Chauncey A. Bratt and Jennifer M. Harrington.

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