Gumpert spent a few years in the minors before deciding to enter military service. He served in World War II as a member of the United States Coast Guard. After finishing his time in the military, he was able to make it to the major league roster for the 1946 season. He played well in his first season as a Yankee, earning an 11–3 record with an earned run average of 2.31. Gumpert played fewer innings the following season, but still received a 4–1 record, and the Yankees won the 1947 World Series. He continued being a relief pitcher for part of the 1948 season before he was purchased by the Chicago White Sox. He finished the 1948 season in the starting rotation for the White Sox. He spent the 1949 season in the starting rotation as well, and managed to keep his spot throughout the year despite allowing the most home runs in the American League. It was also the one season where Gumpert pitched over 200 innings, pitching 234, and the season where he pitched the most complete games and shutouts, with 18 and 3, respectively. The 1950 season saw Randy split time between the starting rotation and the bullpen.\n', '

On May 1, 1951, Gumpert became part of baseball history as he allowed Mickey Mantle\'s first home run. 1951 also saw Gumpert make his only all-star appearance, in which he did not pitch. On November 13, 1951, Gumpert was traded along with Don Lenhardt to the Boston Red Sox for Mel Hoderlein and Chuck Stobbs. After playing 10 games for the Red Sox, he was traded again, this time to the Washington Senators with Walt Masterson for Sid Hudson.\n', '

After spending the rest of the season in Washington, both in the rotation and the bullpen, Gumpert retired. He later became a scout for the New York Yankees, managed in their farm system and served as a temporary member of the Bombers\' 1957 coaching staff, when, in April, Bill Dickey stepped down due to ill health; Gumpert eventually ceded his coaching post to Charlie Keller.\n', '

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