Coaching Seasons: 1989-97, 1999-2003, 2005-11
Teams: Bulls, Lakers
Record: 1155-485 (.704)
Perhaps the most glorified head coach the league has ever known, Phil Jackson's legacy lies almost completely in his accolades on the sideline. But the Zen Master was a player in a past life, and enjoyed a fairly lengthy career playing for the Knicks and Nets. Jackson spent 10 seasons in a Knicks uniform from 1967 to 1978, and logged 17 minutes per game on the 1973 banner-raising Knicks team, before finishing his career with the New Jersey Nets.
Of course, more memorably, Jackson's 11 titles and .704 winning percentage as head coach of the Bulls and Lakers rests in NBA lore forever. As far as a successful playing career translating to an even more fruitful coaching run, Phil might be the best example in all of sports.