Connie Mack is the all-time leader in both managerial wins (3,731) and losses (3,948). He is also the longest-serving manager in MLB history, having managed 7,755 games split between the Pittsburgh Pirates (1894-96) and Philadelphia Athletics (1901-50). During his career, Mack led the Athletics to five World Series titles (1910, 1911, 1913, 1929, 1930).
Dusty Baker of the Houston Astros has the most wins of any active MLB manager with 2,093 (as of March 28, 2023). He ranks ninth overall in all-time winningest managers, and won his first and only World Series title in 2022.
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