11 Grand Slam titles; former #1 men’s tennis player in the world
Estimated earnings: $4 million + $4 million in endorsements per year
Borg’s famous Swede cool never made it off the court. After retiring from tennis, Bork overdosed on drugs. Some people speculate that it was a suicide attempt, though Borg denies it. His wife left him after that. Borg then courted a string of women, one of whom police busted on possession of cocaine. He tried launching a clothing line, but failed miserably. Years later, Borg has rebounded after starting an underwear line and a new dating site.