1. Scottie Pippen
It can be difficult to move on. When the Rockets signed Scottie Pippen, they were on the tail end of the Hakeem Olajuwon era. The Rockets had already traded for Charles Barkley to try to extend their title contention.
That didn't work. Barkley's productivity notoriously began to slip shortly after landing in Houston. So why not try another aging veteran, right?
Right...Pippen lasted one season in Houston. He butted heads with Barkley, and like Barkley, his age-related decline began in Houston. He requested a trade in the summer of 1999. Without any leverage, the Rockets had to accept a meager return headlined by Kelvin Cato from the Blazers.