Back in 2017, a well-known and respected sports gambler lost one of the biggest gambles of his life. While sitting on a fortune that had allowed him to own seven homes and a $20-million jet, as well as the ability to wager $3.5 million without blinking, Billy Walters turned to insider trading to fatten his wallet and the wager didn’t pay off. He was sentenced to five years in jail and ordered to pay a $10-million fine. As quickly as he rose, he fell and has now had to file for bankruptcy.

Casino.org points out that Walters has filed for Chapter 11 bankruptcy, coincidentally at the same time that Dean Foods has filed for bankruptcy protection. Dean Foods, the company behind the Land O’ Lakes, Dairy Pure and Dean’s brands, is a publicly-traded dairy company that also happens to be the same company that led Walters to the insider trading charges.

Walters reportedly began, in 2008, making trades on Dean Foods that were based on non-public information supplied to him by the company’s chairman at the time, Thomas Davis. Davis reportedly had a gambling problem and used his position at the company to receive payments from Walters to pay gambling debts. Walters continued his activity for six years before getting caught, and his involvement only came to light after an investigation into Davis caused the chairman to come clean. After that, a black-and-white paper trail led clearly to Walters.

The man who made millions gambling, even before turning to illegal enterprises, is still in jail. He sits in a minimum-security penitentiary in Pensacola, Florida and isn’t scheduled to be released until 2022, when he’ll turn 76 years old. A recent appeal attempt to have his sentence reduced, based on his lawyers’ argument that the case had been compromised by the FBI, was denied by the U.S. Supreme Court.