Michael Jordan smiling9 Feb 1997: Michael Jordan #23 of the Chicago Bulls smiles on the court during the NBA All-Star Practice at the Gund Arena in Cleveland, Ohio.The East defeated the West 132-120 .
Former Chicago Bulls star Michael Jordan has a reputation for being ultra-competitive and it appears he was willing to bet on just about anything.

The six-time NBA champion had a penchant for gambling, one of the few things fans thought put a stain on his career. And he was pretty fond of off-court games, no matter the stakes.

Jordan is said to have tried betting on a dice game in 1995 with a then-23-year-old Lisa Kennedy, proposing she should let him take her virginity if she lost. Lisa was known to be a virgin back then – a video jockey for MTV, she was even called “Virgin Kennedy.”

According to Lisa, she was out with MJ and Russell Simmons in New York when he took out a pair of dice and asked her to play. Lisa would have had to sleep with His Airness if she lost but turned down the bet because the guard was married, plus she thought it would be too painful.