2) Vernon Maxwell
2-time NBA champion Vernon Maxwell started off his career as a member of the Spurs, playing on the 1988–99 team that was in desperate need of a star. While the Spurs had drafted David Robinson in 1987, he didn't actually join the team until the 1989–90 season, resulting in them winning just 21 games with Maxwell and a random roster.
Ironically, the Spurs were much better the following season during Robinson's rookie year, winning a total of 54 games, though Maxwell would be traded during the year to the Rockets, where he got to play with another Hall of Famer in Hakeem Olajuwon.
In Houston, Maxwell found a home. He played six years there and was a starter for most of that time, putting up solid numbers, including averaging at least 17 points per game in back-to-back seasons in 1990–91 and 1991–92. He later helped the Rockets win consecutive titles.
Maxwell later spent a season with the Philadelphia 76ers before rejoining the Spurs for a season. Ironically, like before, he played on a terrible Spurs team the season before a then-future Hall of Famer—this time Tim Duncan—joined the team.
Maxwell had stops in Orlando, Charlotte, Sacramento, Seattle, and another stop in Philadelphia before finishing his career in Dallas, the final leg of the Texas Triangle.