I'm not absolutely certain, but I would say Chipper Jones under Bobby Cox(Atlanta Braves).
Casey Stengel, who was manager of the New York Yankees from 1949 to 1960, won a record 37 World Series games.
Probably Earl Weaver he was a legend.
Lou Pinella, Chicago Cubs
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.
Joe McCarthy won the most games as Yankees manager with 1,460. Both Joe McCarthy and Casey Stengel have won the most World Series championships with seven.
Whitey Herzog is famous for being an American baseball player and most notably as a baseball manager. He started his baseball career in 1956 with the Washington Senators.
baseball 162 games and playoffs
He most famously got kicked out Iceland after murdering two individuals there.