With Michael Jordan retiring following the Bulls' sixth NBA title in 1998, the team was broken up. Pippen agreed to a sign-and-trade with the Rockets where he joined Charles Barkley and Hakeem Olajuwon for a season. The Rockets dealt Pippen to the Trail Blazers in 1999 for six players. Pippen spent four seasons in Portland and one more with the Bulls before retiring in 2004. (Vince Bucci/AFP/Getty Images)