In the following slideshow, I will discuss which NBA greats are the most winningest, which is a crucial ingredient to any player's success. NOTE: These rankings are based off of a series of calculations of wins per 48 minutes and total minutes, all available in this chart (credit to Arturo).ohn Stockton comes up as the 2nd Winningest Player of All Time on our list. In 19 years, John Stockton led Utah to several finals, but he and Karl Malone were overshadowed by an amazing Bulls dynasty and never won a championship. They did get a lot of wins, however.