Dressen never doubted his own baseball savvy. “Hold them, boys,” he often told his team. “I’ll think of something.” The 5’5′ 146-lb extrovert took up diverse challenges: picking racetrack winners, quarterbacking George Halas‘s Decatur Staleys (forerunner of the Chicago Bears) and the Racine Legion of the early NFL, and playing eight years as a NL third baseman.
He is most famous as a major-league manager. He managed successive pennant winners for the Dodgers in 1952-53, but bucked owner Walter O’Malley’s policy by asking for a multi-year contract. O’Malley replaced him with Walter Alston. Dressen spent a year at Oakland of the Pacific Coast League, then returned to the majors with the talent-less Senators. Two seasons after leading Brooklyn to 105 victories, the same tactician took Washington to 101 losses. A second losing season and a poor 1957 start cost Dressen his job.
In 1960, he took over the Milwaukee Braves. Late in 1961, with the team in third place, he was summoned to the front office. Expecting photographers to record his signing of a new contract, he dressed in his best suit. Instead, he was told he was being let go.
Dressen managed Toronto in the minors the next season, then joined the Dodgers as a special scout in 1963. In June, he received his fourth major-league command, with the ninth place Tigers. He brought them in fifth and followed with two straight fourth-place finishes. On May 15, 1966 the 67-year-old Dressen managed his last victory. The next day he checked into a hospital. Twelve weeks later he died of a heart attack.
Dressen had a gambler’s love for number 7 and wore it whenever he could. When the Dodgers acquired star Joe Medwick from St. Louis in 1940, he asked for number 7, then worn by Dressen as a coach. Chuck agreed; the next day he went to his coaches box sporting his new number: 77. As usual, he’d “thought of something.”