#6 Steve Kerr
If you play NBA 2K video game series, you can have a match between Chicago Bulls of 95-96 featuring Steve Kerr the player vs Golden State Warriors of today featuring Kerr the coach, and commentated by Steve Kerr the commentator. He's had a solid post-retirement career, to say the least, having won the NBA Championship as a coach with the Warriors in his first year as a head coach in 2015.
After playing for the Bulls, Kerr won a ring with the San Antonio Spurs in 2003. He then went on to serve as the General Manager and President of Basketball Operations for the Phoenix Suns in 2007, a position he retained till 2010.
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After retiring from the Suns, Kerr worked as a commentator on NBA on TNT till 2014 before taking up the mantle of Head Coach for the Golden State Warriors.
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