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Indians owner Bill Veeck obtained Wynn on December 14, 1948 with Mickey Vernon for Joe Haynes, Ed Klieman, and Eddie Robinson, one of the best deals in Indians' history. Wynn came under the tutelage of Cleveland pitching coach Mel Harder, who taught the portly righthander a curve, knuckleball, slider, and changeup. Wynn threw all his pitches with an easy, effortless motion. After a year of adjustment in 1949, he led the AL with a 3.20 ERA in 1950. He had the first of his 20-win seasons in 1951. With Bob Lemon, Mike Garcia, and, first, aging Bob Feller and then Herb Score, Wynn was in one of baseball's all-time great pitching rotations. In 1952 he won 23 games, Lemon and Garcia won 22 each, and the three were named Cleveland's Men of the Year. They made the Indians a close second to the Yankees in 1952 and 1953. In 1954 Wynn and Lemon tied for the AL lead with 23 wins and the Indians won a league-record 111 games before suffering a stunning World Series sweep to the Giants. Wynn allowed an RBI single and a home run to Series star Dusty Rhodes in losing Game Two.
Though he led the AL in strikeouts, Wynn suffered his first losing season with Cleveland in 1957 (14-17). That December, he and Al Smith went to the White Sox for Minnie Minoso and Fred Hatfield. In 1958, Wynn became the first ML pitcher to lead his league in strikeouts in consecutive years with different teams, but still posted a 14-16 record. But at the age of 39 in 1959 he led the White Sox to the AL pennant, leading the AL in wins (22-10), starts, and innings. He won Game One of the WS over the Dodgers 11-0, but was hit hard in his two other starts and lost Game Seven.
In the 1950s, Wynn was 188-119 with more strikeouts, 1,544, than any other pitcher. He led the league with four shutouts in 1960 and pitched well in his illness-curtailed 1961 season (8-2), but struggled to a 7-15 record in 1962 as his 300th win proved elusive. He was released that November and was cut during spring training in 1963, needing just one more victory for the landmark plateau. Signed by Cleveland, Wynn reached the milestone on July 13, 1963, going five innings to defeat the Athletics. He spent most of the year in the bullpen and retired after the season. He pitched more seasons (23) than any pitcher to that time, despite battling gout from 1951 on. Wynn believed in running and kept his legs in great shape. He also walked a record 1,775 batters.
Wynn's distinct personality led him to call the pitching mound his "office." He worked with a grim, fierce appearance, and might be best remembered for saying he would knock down his grandmother if she dug in against him. Feared on the field, Wynn was an easygoing, fun-loving practical joker off the field. A dangerous batter who is among the all-time pitchers' leaders in hits, he was used as a pinch hitter 90 times during his career and hit .270 or better five times. (ME)