As Chicago Bulls fans witnessed for more than a decade, Michael Jordan routinely accomplished whatever he sought to do on the basketball court. However, while the NBA legend routinely scored 30-plus points on a nightly basis, he failed to complete another feat off the court that involved a former MTV host’s virginity and a pair of dice.

Considering Jordan’s well-documented gambling history, this story ranks right up there as one of the darkest.

Michael Jordan put his body on the line to become the greatest (and wealthiest) NBA player of all time

While he did step away from basketball on two occasions before finally calling it quits, Michael Jordan put his body on the line for 1,072 regular-season and 179 postseason games during his Hall of Fame career.

Thanks to an unrivaled work ethic and plenty of natural skill, His Airness became the greatest NBA player of all time. Jordan led the league in scoring for seven straight years before he briefly retired to play baseball.

He got back in shape for his No. 1 sport and quickly reassumed his position as the NBA’s biggest star. Even after trading in his signature Nike shoes for a pair of cleats, he still led the Bulls to three more titles before he once again walked away from the game for a short period.

Although he didn’t have nearly the same impact with the Washington Wizards as he did in Chicago, Jordan still impressed by averaging exactly 20 points in 82 games in his final NBA season.

Of course, his basketball prowess and marketing power made him a wealthy man. Despite having billions to his name, the 58-year-old has also lost significant sums of money on several occasions because of gambling.

The Chicago Bulls icon made a few eyebrow-raising bets back in the day

Given his lucrative endorsement deals and NBA contracts, Michael Jordan certainly had the financial flexibility to take some risks with his cash back in the day. And his well-publicized gambling history includes several notable instances of the six-time NBA champion putting serious money on the table.

In 2015, former NBA player Jay Williams revealed on The Brilliant Idiots that Jordan once bet $100,000 on rock, paper, scissors. Needless to say, the stakes were much higher in his version of the classic childhood game.

Last April, Scottie Pippen revealed on ESPN that Jordan would bet $100 with one of the Bulls’ security guards to see who could win the jumbotron games. He reportedly won more than $4,000 in his ongoing bet with the security guard.

Jordan’s penchant for betting big carried some dire consequences, too.

In May 1993, Richard Esquinas released a book entitled Michael and Me: Our Gambling Addiction… My Cry for Help in which he claimed the NBA star owed him $1.25 million from golf bets. While Jordan’s former golfing partner later admitted he settled for $300,000, it still showed the potential harmful financial effects of gambling.

However, another story that paints a dark picture of Jordan’s past bets involves a former MTV host’s virginity and a pair of dice.

Jordan’s dark gambling past includes a strange night involving a former MTV host’s virginity and a pair of dice

Two years before Jay Williams informed the world of Michael Jordan’s history of playing rock, paper, scissors, another celebrity revealed a story about the NBA legend’s gambling past.

However, what Lisa Kennedy Montgomery (who goes by Kennedy) experienced on a night out in 1995 certainly does not inspire the same response as reading about Jordan cheating to win money on jumbotron games.

According to the Daily Mail, the former MTV host wrote in her book, The Kennedy Chronicles, that Jordan wanted to have intimate relations with her if he won a bet. Kennedy claimed the incident occurred in 1995 at New York’s Bowery Bar during an outing with Jordan and Russell Simmons.

In the midst of having dinner, Kennedy said Jordan whipped out a pair of dice and said they should “play for something.”

Only 23 at the time, she was scared by the offer since she was a virgin. Kennedy had previously gone by the stage name of “The Virgin Kennedy” during her internship with an LA radio station. However, it remains unclear whether Jordan knew any of that when he made the bet with Kennedy.

Ultimately, the former MTV VJ reminded the NBA star of his marriage status and changed the stakes to include New York Knicks tickets.

Kennedy won the bet, but she never confirmed whether Michael Jordan paid up.

How to get help: In the U.S., contact the National Council on Problem
Gambling helpline at 1-800-522-4700.