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Lenny Wilkens

Photo: WENN

A former player with the Cleveland Cavaliers and Portland Trail Blazers, Lenny Wilkens would go on to become the NBA’s most winningest coach. Racking up the impressive number of 1,332 victories, he went unchallenged during his retirement. Eventually, another member of this list, Don Nelson, would upset Lenny and take the number one spot.

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