A Falmouth man pleaded guilty for nearly a decade’s worth of tax evasion and failing to file a tax return Monday, after he lied about being unable to pay overdue taxes for years and eventually bought an island home.

Jeffrey Riddle, 58, filed income tax returns between 2006 and 2014 that showed he owed substantial federal taxes but did not pay them, the United States Attorney’s Office for Maine said in a written statement.

Riddle faces up to five years in prison, followed by up to three years of supervised release, and up to $250,000 in fines, the office said.

The Internal Revenue Service began trying to collect Riddle’s overdue taxes in 2010 via tax liens on property and levies on his bank account, the office said.

But in 2015, while he was still on the hook for a significant portion of back taxes, Riddle started a new business that entered a consulting agreement with a large tire retailer, the office said. Riddle listed ownership of the company, Silica Marketing LLC, under his then-wife’s name, but she had no involvement in its revenue, and he used company money to pay personal expenses.

Riddle purchased a home on Great Diamond Island in Casco Bay using Silica money in 2016, the office said. The home was purchased under the company’s name. The following year, he created a new company to replace Silica, which continued working with the same tire retailer.

The office did not name either the tire retailer or Riddle’s second company in its release.

Riddle sold a portion of that second company in 2020, netting $400,000, of which $250,000 was put into an escrow account intended to repay the IRS, the office said. But none of those funds were paid to the IRS.

Riddle also bought a Corvette in 2020, titled in the new company’s name.