In 1940, when it became apparent he wasn't in the Cardinals future plans as a player, Alston was given the opportunity to play and manage Portsmouth in the Mid-Atlantic League where he guided them to a sixth place finish. After two more years as Player/Manager for Portsmouth, Alston was promoted to Rochester as a player only. He was released by St. Louis in 1944, but was signed by former Cardinals General Manager and now Brooklyn President Branch Rickey to play and manage in the Dodger minor league system. He led St. Paul to the Junior World Series Championship in 1949 and was immediately promoted to the Dodgers top minor league job in Montreal. Alston spent four seasons with Montreal and managed many players that went on to help win pennants for the big league club
Following the 1953 season, Brooklyn Skipper Charlie Dressen insisted on a multi-year contract to continue as Dodger manager. Brooklyn Owner Walter O'Malley balked at the demand and to everyone's surprise chose the little known Alston to pilot the club. Walt led the Dodgers to a second place finish in 1954, then won the pennant and Brooklyn's only World Series Championship in 1955, defeating the Yankees in seven games. He followed that with another pennant in 1956 securing his position as Dodger field boss, and continued his ritual of extending his stay as manager on a one year contract basis.
Alston's response was predictable and he wasn't going to change. "Look at misfortune the same way you look at success…Don't panic! Do your best and forget the consequences", he said prior to the start of the 1963 season. Once again his philosophy and approach paid off. The Dodgers fought off the surging Cardinals, won the pennant and faced the Yankees in the 1963 World Series. With Koufax, Drysdale and Johnny Podres leading the way with their excellent pitching, Los Angeles swept the mighty Bronx Bombers four straight. After slipping to seventh place in 1964, the Dodgers eked out the 1965 NL pennant and faced off against the powerful Minnesota Twins in the Fall Classic. The Series went to a seventh and deciding game and Alston was faced with one of the most difficult and controversial decisions in World Series history. He had to choose a starting pitcher for the biggest game of the year, and had to decide either on twenty-three game winner Don Drysdale, on his full three days rest, or twenty-six game winner Sandy Koufax, on a short rest of two days. Walt waited until just before game time before announcing in his trademark quiet way that "it will be the lefthander" (meaning Koufax). Sandy justified his Skipper's confidence, and somewhat of a gamble, by shutting out the Twins, 2-0, to win the Series.
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