After two years in the Navy and several unsuccessful stints in the majors, Woodling, a four-time minor league batting champion, stuck with the Yankees in 1949 and played a large role in the club’s record five consecutive World Championships (1949-53).
Yankee manager Casey Stengel usually platooned the lefthanded-hitting Woodling with Hank Bauer in left field, but he sometimes played both in the outfield, getting each about 400 at-bats a season. Woodling was not a typical platooned player. He was, in Stengel’s opinion, the best defensive left fielder Casey managed in New York. He could run and throw, and was a clutch hitter; Old Faithful was particularly effective against the Indians and Dodgers – the Yankees’ main rivals at the time. He topped the .300 mark in 1952 and 1953 and hit a solo HR in each World Series from 1951 through 1953.
Following the 1954 season, Woodling was traded to Baltimore as part of a record 17-player deal. He moved on to Cleveland, with whom he reached career highs of 19 HR, 78 RBI, and a .321 average in 1957. A few months before his 40th birthday, his contract was purchased from Washington by the lowly 1962 Mets, managed by Stengel. “He gave me hell all those years about wanting to play,” said Stengel. “Now he can play all he wants.”