One of country music’s most notorious Outlaws is in some serious hot water, and could be facing time in a Federal prison.

76-year-old David Allan Coe has plead guilty to one count of impeding and obstructing the due administration of the internal revenue laws in a Federal court in Cincinnati. The news was announced Monday, September 14th by U.S. attorney Carter M. Stewart of the Southern District of Ohio, and Internal Revenue Service Criminal Investigation Cincinnati Field Office special agent Kathy A. Enstrom. Coe could face up to three years in Federal prison, and a fine of up to $250,000 for the offense.

According to authorities, David Allan Coe played an average of 100 concerts between the years of 2008 and 2013, but failed to pay taxes on the income he generated. Authorities say that even when Coe did file his taxes, he would fail to pay the amount owed, while also owing additional taxes from previous years as far back as 1993. According to authorities, instead of paying his taxes, Coe paid off other debts, including large debts due to gambling.

Furthermore, investigators claim Coe purposely tried to circumvent the IRS. When Coe would perform, he would insist venues pay his booking manager in full before performing. The booking manager would then wire the money to Coe’s personal account. However in 2009, Coe stopped receiving the payments after receiving word from the IRS for his overdue taxes. Instead, Coe would insist in being paid cash before 3 p.m. on the day of a show, and could not be paid in $50 bills because according to investigators, he believed the denomination was bad luck in gambling.

The IRS says that David Allan Coe willfully did not pay his taxes in 2009, 2011 and 2013, and now owes $388,190.94 total in back taxes, interest, and penalties. The actual amount Coe will have to pay will be determined at sentencing.

On numerous occasions, altercations have erupted between David Allan Coe and venue owners when Coe’s terms were not met, including a high-profile spat with TV personality Richard Rawlings who says Coe tried to “extort” the Gas Monkey Bar & Grill in Dallas, TX in July of 2014.

“All taxpayers, regardless of their profession, must comply with their federal tax obligations,” said Kathy A. Enstrom of the IRS. “As is evident from Mr. Coe’s guilty plea, schemes to evade the payment of taxes are a violation of the Federal Tax laws and postpones the eventual need to comply at an even higher cost, including federal criminal prosecution and having to pay back taxes with interest and steep penalties.”

READ: Look, This is the Deal with David Allan Coe (An Editorial)

David Allan Coe is being represented by Memphis-based attorney, Michael Stengel. There is no word on when the sentencing in the case will occur.