2. Casey Stengel
Over 12 years with the Yankees, Stengel went 1149-696 (.623), winning 10 pennants and seven world championships. If that does not make his case, it is hard to find anything that does.
From 1949-1953, New York executed a five-peat, something you may never see in baseball again — a level of virtually unachievable dominance.
Then, after a 103-win second-place finish in 1954, the Yanks ran off five pennants in six years from 1955-1960, including two World Series titles.
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Managing the likes of Mantle, DiMaggio, Berra, Rizzuto, and Ford, Stengel had more than enough to work with. However, even with an all-star team, that level of sustainable success is simply not performed in today’s day and age.
Without that particular roster, that manager, and potentially favorable circumstances, you will never see it again.