Michael Jordan and Scottie Pippen

Scottie Pippen making questionable financial decisions is certainly nothing new. His struggles to accumulate and hold on to his money are well documented. However, it turns out he may have had a little help in losing a small portion of that fortune thanks to his former Bulls running-mate Michael Jordan.

ESPN’s Amin Elhassan made an appearance on fellow ESPNer Zach Lowe’s podcast, The Lowe Post, on Thursday and revealed a pretty incredible anecdote from Pippen and Jordan’s playing days in Chicago.

One day, Jordan arrived at the United Center much earlier than normal and happened upon arena staff members watching the jumbotron races that are usually shown during breaks in game action. This was a revelation to Jordan, who apparently never realized the cartoon bull races were pre-recorded and the winners predetermined. Armed with this knowledge, Jordan figured out who the winners of each race would be ahead of time and started making $100 bets with Pippen every game over who would win each race.

It is unclear exactly how many times Jordan tricked Pippen, but he continued this scheme every few days for the rest of the season, and Pippen was never the wiser to Jordan’s machinations. However, this fact should not come as too much of a surprise based on some of Pippen’s post-playing-career investments.

While this story seems like a perfect illustration of both Pippen’s financial ineptitude and Jordan’s cutthroat obsession with winning, it may be just a little too perfect according to one NBA blogger.

Not sure if we will ever get confirmation on the truth of this tale, but we will update this post if there is.

About Ben Sieck

Ben is a recent graduate of Butler University where he served as Managing Editor and Co-Editor-in-Chief for the Butler Collegian. He currently resides in Indianapolis.