Born in Decatur, Illinois, Dressen was a veteran baseball man when he took the reins in Brooklyn after the season. After a short football career playing quarterback for the Decatur Staleys (a forerunner of the Chicago Bears) in 1920 and in 1922-23 with the Racine Legion, Dressen was a third baseman for the Cincinnati Reds (1925-31) and a late-season utilityman for the 1933 New York Giants, batting .272 in 646 games.
Despite his poor won-loss record in Cincinnati, Dressen made a valuable ally in the Reds’ mercurial general manager, Larry MacPhail. A year after MacPhail took over the Dodgers in , he named fiery shortstop Leo Durocher player-manager and Dressen as his third base coach. Under MacPhail and Durocher, the Dodgers became a hard-playing pennant contender, winning Brooklyn's third NL pennant of the modern era in . But when MacPhail resigned in October 1942 to rejoin the armed forces and was succeeded by Branch Rickey, Dressen was fired from Durocher’s staff – reportedly because he refused to eschew betting on horses. He was on the sidelines for the first three months of the 1943 season before being rehired by the Dodgers that July.
When the Second World War ended, MacPhail returned to baseball as part owner, president and general manager of the New York Yankees. Following the season, he raided the Dodger coaching staff, signing Dressen and Red Corriden as aides under his new manager, Bucky Harris, and causing hard feelings between the Yankee and Dodger front offices.
When MacPhail quit after the Yankees' 1947 world championship (gained at Brooklyn’s expense) and Harris was sacked after the following season, Dressen was forced to move on. He was manager of the Oakland Oaks of the AAA Pacific Coast League in 1949-50 and his teams finished second and first, winning 104 and 118 games. Simultaneously, a power struggle for control of the Dodgers ended in Walter O'Malley forcing Rickey out of the Brooklyn front office. When O'Malley fired Rickey confidante Burt Shotton in the autumn of , he gave the manager's job to Dressen.
Brooklyn charged into first place early in the season, while the New York Giants - led since July 16, 1948 by Durocher himself - struggled (despite the callup of a 20-year-old rookie phenom named Willie Mays). When the Dodgers completed a three-game sweep of the Giants at Ebbets Field, August 10, the Brooklyn lead over the Giants stood at 12½ games. "The Giants is dead," Dressen sang loudly (to the tune of "Roll Out the Barrel") through a door adjoining the teams’ clubhouses. The next day, after another Dodger win and Giant defeat, the Brooklyn lead swelled to 13½ games. As for the ungrammatical remark, Dressen was defended by at least one college professor who pointed out that, since Dressen was not saying that the Giant players were literally deceased, he had more latitude with grammar in a figure of speech. (All the same, when O'Malley later fired the manager, New York newspapers commented "DRESSEN ARE DEAD.")
But then the Giants began to win. With Sal Maglie, Larry Jansen and Jim Hearn anchoring their starting rotation – and (according to some accounts) with a "spy" stealing opponents' signs from their center-field clubhouse at their home field, the Polo Grounds – the Giants won 16 in a row in August and 37 of their last 44 games to force a flat-footed tie at season’s end and a best-of-three playoff. In the ninth inning of the decisive third game at the Polo Grounds, Dodger starting pitcher Don Newcombe had a 4-2 lead and two men on base when Dressen decided to go to the bullpen, where Carl Erskine and Ralph Branca were warming up. "Erskine is bouncing his curve," the manager was told by his bullpen coach, Clyde Sukeforth. Dressen summoned Branca, whose second pitch to Bobby Thomson was hit into the lower left-field stands for a three-run homer, a 5-4 Giants' win, and a National League pennant – Baseball's "Shot Heard ‘Round the World".
Dressen kept his job in (while Sukeforth was fired) and for the next two seasons, his Dodgers dominated the NL, winning the pennant by margins of 4 ½ and 13 games. But each season, they came up short against the Yankees in the World Series, losing in seven games in 1952 and six in 1953. Coming off the pennant and 105 victories, Dressen decided to publicly demand a three-year contract from O’Malley instead of the customary one-year deal the Dodgers offered their managers at the time. O’Malley didn't blink. He let Dressen quit, and replaced him with AAA Montreal Royals manager Walter Alston, who would go on to sign 23 one-year contracts with O'Malley, while winning seven NL pennants, four World Series, and a berth in the Baseball Hall of Fame.
Dressen then rejoined the newly relocated Los Angeles Dodgers to serve as a coach under Alston in 1958-59. After the '59 Dodgers won the World Series, Dressen was in demand as a manager once again, and the Milwaukee Braves, who had lost a pennant playoff to LA at the end of the season, named him their field boss for . But Dressen was not able to reverse the Braves' slow decline to the middle of the NL pack and he was dumped in late , succeeded by Birdie Tebbetts. In 1962, Dressen managed the Toronto Maple Leafs of the AAA International League to 91 victories.
But Dressen began to suffer from failing health. A heart attack sidelined him during spring training in ; then he suffered a second coronary only 26 games into the campaign. He apparently was recovering from the heart attack when he was fatally stricken with a kidney infection, dying at 67 in a Detroit hospital August 10, 1966 - 15 years to the day when he infamously (and incorrectly) celebrated the death of the New York Giants. He is interred in the Forest Lawn Memorial Park Cemetery in Glendale, California.
Known for his sunny self-confidence, Dressen would often tell his highly talented Dodgers, "Just hold them, boys, until I think of something." His career major league managerial record was 1,037-993 (.511).
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