2008. That should have been it for Justin Gimelstob, forever. After all, the man has amassed zero singles ATP titles: That’s zero Grand Slams, zero Masters 1000, zero 250 events. The trophies he does have are in doubles, courtesy of a brief partnership with Venus Williams. Despite his undistinguished record, despite his controversial baggage, he continued to rise in tennis: He landed a coveted and well-compensated position as a commentator for the Tennis Channel. He landed a coaching job with number one American player John Isner. He was elected to the ATP Player’s Council, a post which indicates the approbation of his peers.
While holding such positions, he was arrested on felony battery charges for a Halloween assault on his ex-wife’s friend, hitting him fifty times. His ex-wife had previously charged Gimelstob with domestic violence in seeking a restraining order against him. Suddenly, it was more than Gimelstob’s mouth getting him in trouble.