2. Scottie Pippen, Forward
Another case of Krause really screwing up maybe one last shot that the Bulls had to make something out of that dynasty core in the late 1990’s came when he parted ways with Hall-of-Fame forward Scottie Pippen during the 1998-99 offseason. The extended offseason came courtesy of a negotiation lockout that lasted until January 1999.
And neither Pippen nor fellow former Bulls Hall-of-Famer and all-time great shooting guard Michael Jordan were able to get one more stint with this team. At least with the way he made it sound in the final part of the 10-part documentary series highlighting the 1997-98 Bulls team “The Last Dance”, Jordan did want to come back for at least one more run in 1998-99.
However, the Bulls wound up sending Jordan into the second of three retirements during his playing days in the NBA following the 1997-98 season. And they would send off Pippen to the Houston Rockets in one of the more famous sign-and-trade deals of the 1990’s. Pippen didn’t find near as much success with the Rockets as he did the Bulls.
He would not get another All-Star selection after landing with the Rockets, but he was still rather productive alongside the likes of Charles Barkley and Hakeem Olajuwon. It’s hard to know where he would’ve ended up if the Bulls stuck with him and Jordan for at least one more year. But letting that duo go is by far the biggest miss in terms of free agent retention (sign-and-trade counts for this list) of any in franchise history.