After starting business ventures with varying degrees of success, Lenny Dykstra founded a high-end magazine that catered to professional athletes. Called The Player’s Club, the company offered many services to athletes, including financial (via The New Yorker). In 2009, stories began leaking about the internal affairs of the company. Reports that involve everything from credit card fraud (via GQ) to paying for rent with bounced checks, Dykstra’s burgeoning empire was full on crumbling. Lenny filed for bankruptcy in August 2009, living out of his car, while his 1986 World Championship ring sold at auction for $56,000 (via ESPN). All of which went toward the $31 million in debt Dykstra owed.

It only gets markedly worse for Dykstra from there. In January 2011, Dykstra was accused of sexual assault by a former housekeeper. Four months later, he was arrested and charged with bankruptcy fraud. Two months after that, in June 2011, Dykstra was arrested again, this time for grand theft auto and identity theft along with possession of cocaine and ecstasy (via ESPN). 

But wait, there’s more. And that more comes in the form of an indecent exposure charge in August 2011 (via Reuters). While Dykstra paid his debt and finished his probation in April 2014, complying with weekly drug testing along the way, he would be back at it again in 2018. In May of that year, Dykstra was arrested for possession of drugs. Just five months later, Nails was indicted once again, this time for cocaine and methamphetamine possession, as well as making terroristic threats (via AP News). It appears for the former MLB All Star, that there might be no bottom.