Despite having a Big 3 of Pippen Hakeem Olajuwon, and Charles Barkley, the 1999 Rockets lost to the Los Angeles Lakers in the first round of the NBA Playoffs. After the disappointing campaign, Pippen asked the Rockets to trade him, preferably to the Lakers, where his former mentor Phil Jackson was coaching.

There were significant tensions between the management specifically general manager Jerry Krause and the players, which hit the tipping point when Krause nearly traded away Bulls legend Scottie Pippen in 1997 for Tracy McGrady.