1. Scottie Pippen
New Rocket Scottie Pippen joins forces with Hakeem Olajuwon and Charles Barkley. (1999)
Technically, the move to bring Scottie Pippen to Houston falls as a free agent transaction. Pippen was a free agent at the end of the 1998 season, and the Chicago Bulls were looking to dismantle their dynasty.
Pippen wanted to go to a place where he could win a ring without Michael Jordan to cement his own legacy, and the Rockets seemed to be the perfect fit. A lock-out took place that year and the season didn’t start until late January. Nevertheless, the Bulls agreed to sign Pippen to a 5-year $67 million deal, and traded him to the Rockets in exchange for Roy Rogers and a second-round pick.
Pippen was essentially the replacement to the recently retired Clyde Drexler, and would continue the future Hall-of-Fame trio in Houston alongside Hakeem Olajuwon and Charles Barkley. What started out as something so good, so promising, turned into a Greek tragedy.
Pippen averaged 14.5 points, his lowest scoring output since his rookie season, as the Rockets limped to a 31-19 record. They were over-matched and over-played in their first-round matchup against the Lakers, and fell 3-1.
That’s when it got ugly.
After going on a Nike tour with Barkley in the summer of 1999, Pippen suddenly demanded to be traded. In a public interview, he directed the blame towards Barkley, saying that he was too “fat” and “selfish” to win a championship.
The Rockets shipped him to Portland In August 1999 for Kelvin Cato, Stacey Augmon, Walt Williams, Ed Gray, Brian Shaw and Carlos Rogers. The Rockets weren’t even close to being a playoff team for the next 4 years, while Pippen came close at a chance to win a 7th ring the following season, when the Blazers fell to the Lakers in the Western Conference Finals in 7 games.