Who is the losingest manager in Major league baseball?

Answer 1

Depends what you mean by losingest. The manager who has lost the most games, Connie Mack (3948), has also won the most games, because he managed the most games - 7755 games over 53 seasons - waaaaaaay more than anyone else. 16 managers have managed at least one game, and failed to win any - for a .000 winning percentage. The most games below .500 a manager is is 242, by Jimmie Wilson who went 493-735 in the 30s and 40s managing some pretty bad Phillies and Cubs teams. That's a .401 winning percentage though, which is pretty bad, but nowhere near the worst winning percentage for a manager who "qualifies," (320 career games managed, according to Baseball-reference.com) - that distinction is held by Doc Prothro, who guided the Phillies to a 138-320 record between 1939 and 1941, for a paltry winning percentage of .301.

Take your pick.