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Lisa Kennedy Montgomery

Michael Jordan was known as a fierce competitor during his eighteen years as a professional basketball player. He was also infamous for his gambling habits, and allegedly the NBA Hall Of Famer played a high stakes game of dice with a former MTV VJ who claims “His Airness” wanted her virginity as his prize.

Lisa “Kennedy” Montgomery,  who writes in her new book, “The Kennedy Chronicles,” about a night back in 1995 where Jordan tried to lure her into his hotel room in New York. Kennedy was having a bite to eat with Jordan and music mogul Russell Simmons when the b-ball legend broke out some dice.

“If I win, you come back to my hotel room with me tonight,” Jordan said, according to Kennedy. Afraid to lose her virginity to the star, Kennedy said she’d rather play for tickets to a Knicks game instead. Kennedy claims Jordan had a change of heart and reminded the VJ he was a married man.

Former MTV VJ Says Michael Jordan Gambled To Win Her Virginity was originally published on

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