Michael Jordan's love for gambling has been well documented. From having late nights in casinos to betting with teammates, gambling was as much of Jordan's life as was basketball. Jordan especially loved to make bets with teammates, either in shooting contests or unfortunately for Scottie Pippen, on Jumbotron races.
According to ESPN's Amin Elhassan, Jordan one day found out that the animated bull races the Bulls showed on their Jumbotron were prerecorded. So he started asking the Bulls' operations staff before each game, which color bull would win the race that night. They would tell him and then Jordan would use this information to trick his teammate Scottie Pippen into a bet.
So whenever the Jumbotron race would occur during a timeout, Jordan would bet Pippen a hundred dollars that he could name the winner. Unaware that Jordan had insider information on the race, Pippen would agree to the bet and then instantly lose. According to Elhassan, Jordan did this for basically an entire season and Pippen just kept agreeing, losing a hundred dollars to his teammate at every home game.
It is strange that Pippen never realized that Jordan already knew what color bull was going to win the race but perhaps he was just humoring his teammate. After all, they did win six championships together, which is worth way more than a few hundred or thousand dollars.