The hair, the headband, the epic Wimbledon battles with John McEnroe and Jimmy Connors: Swedish tennis legend Bjorn Borg had one of the greatest, yet shortest, careers in professional tennis. With his emotionless bearing — perhaps only in comparison to McEnroe's and Connors' notorious outbursts — Borg won his first Wimbledon at barely 20 years old. He would win a total of five titles on the grass at Wimbledon and six more in the French Open, all before retiring at the ripe old age of 26 [source: Collins].
Borg was smart and likeable, and new friends and business partners swarmed the handsome champion. While Borg was living in swinging Monte Carlo, his colleagues and clients would run up monumental tabs on Borg's dime and jet off to exotic locations in his private plane. When his luggage and sportswear venture went south, he was forced to declare bankruptcy in 1989. The only reason he lived in Monte Carlo was to escape the punitive tax rates of Sweden, whose government hounded Borg for $40,000 in back taxes [source: Campbell].
Three marriages and two divorces later, Borg narrowly missed declaring bankruptcy again in 1997, but has restored his wealth through a now-successful clothing and sportswear venture called simply Bjorn Borg. Impossibly, it doesn't sell headbands.