19. Chauncey Billups
It’s crazy to think how much of a career Chauncey Billlups made for himself despite doing very little before he finally got to Detroit at age 26. Billups was traded five times, including each of his first three seasons. He was worth the wait for the Pistons, who made six straight Conference Finals with Billups as their best player in win shares and other advanced metric models.
Detroit made the Finals twice and won it all in 2004, and Mr. Big Shot was named Finals MVP, an apt nickname for a guy consistently even better in the playoffs than in the regular season. Billups finished 5th in a weak 2006 MVP race and had a real case to win it looking back, and he led Denver to the Conference Finals his first season after leaving the Pistons. He’s the highest retired player on this list not in the Hall of Fame yet — and he will be there soon enough.
Achievements: 1x champion, 3x All NBA, 5x All Star