1. Joe McCarthy
From 1931-1946, Joe McCarthy was the epitome of New York Yankees baseball. It is awfully tough to top Casey Stengel, but McCarthy was able to prolong the success of the 1920s and turn the organization into a fierce mainstay.
The Yankees were able to win six world championships (seven pennants) between 1936 and 1943, and seven total in McCarthy’s tenure.
He remains — to this date — atop the franchise’s managing hierarchy, sustaining the longest tenure (16 years), collecting the most wins (1460), and maintaining the highest winning-percentage (.627 — min. three years).
There is no true substantiation to be provided. Barring the unforeseen, this man will be forever alone at the top.