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.

MJ’s love for gambling cannot be understated… He’ll bet on anything from blackjack, to golf, to which bag reaches baggage claim first For Jordan, it’s not always about what you win but simply the rush of winning pic.twitter.com/U0VskcP7Ua

— Frank Michael Smith (@frankmikesmith)

She was out for dinner in New York with Russell Simmons and Michael Jordan It was clear MJ was interested in her He yanked a pair of dice from his pocket In the middle of the meal and suggested the two should play

Jordan proposed that if he won…

She instead bet with him for Knicks tickets and won. There’s nothing on whether she actually got the tickets and, to be fair, this story has actually never been confirmed. While Jordan was pretty fond of gambling, he doesn’t exactly have a reputation for trying to snag every woman he could. Lisa now works as a commentator for FOX.