1. Michael Jordan
Jordan was the face of the Chicago Bulls for a decade. It’s no accident that they fell apart after he left for Washington. The legendary NBA icon won six championships during his time in the Windy City. He had an amazing career and changed what it means to be a sports superstar. But when he left, the Bulls went into a severe decline.
They were never going to replace Jordan because he was a generational talent. However, their front office mismanaged the franchise for almost two decades. The team became a ghost of itself and never looked like a contender. They could have prepared for life without Jordan and Scottie Pippen but they didn’t plan for the future.