3. Dealing away Scottie Pippen too early
If not for the differences that were established between Hall-of-Fame forward Scottie Pippen and Krause early on in the 1990’s (even some friction stemming back to the 1980’s), then this relationship might have ended better. Instead, it felt like Pippen was ready to get away from the Bulls the second that this core broke apart.
Krause and the Bulls sent Pippen away to the Houston Rockets in a sign-and-trade deal that only saw them get a second round draft pick and big man Roy Rogers. What the Bulls got from that second round pick was Jake Voskuhl (who would only spend about one year in a Bulls uniform) and a current assistant coach under Jim Boylen’s direction.
The Rockets did wind up overpaying Pippen compared to the amount of production they got out of him. But that was largely due to poor fit in what amounted to a big name frontcourt rotation. Pippen played alongside Charles Barkley and Hakeem Olajuwon with the only other team in the NBA that had won a title from 1991-1998 outside of the Bulls.
The Bulls definitely could’ve got more production out of Pippen prior to leaving the Windy City if they had valued his contributions more and earlier on in his NBA career. He had already shown he could do great things being the sole superstar with the Bulls, and could’ve thrive with a supporting cast of Dennis Rodman and Toni Kukoc if given the opportunity following the 1998 offseason.