Herbert signed with his hometown Tigers after attending Detroit Catholic Central High School. After prepping with the Triple-A Toledo Mud Hens in 1949–50, Herbert received his first MLB trial in August 1950. In his debut, he started against the Philadelphia Athletics at Shibe Park. He worked into the eighth inning, and was holding a 3–2 lead when he surrendered a two-run home run to Sam Chapman. Herbert was tagged with the loss, although he registered an eight-inning complete game. In 1951, he made the Tigers out of spring training and appeared in five early-season games, all in relief; remarkably, he was the winning pitcher in four of those contests, and compiled a low 1.42 earned run average in 12​2⁄3 innings pitched. Herbert then joined the military for Korean War service, missing the rest of 1951 and all of 1952.\n', '

When Herbert returned to the Tigers in 1953–54. he got into 85 games, mostly in relief, but was ineffective, winning seven of 19 decisions and posting a poor 5.55 ERA in 172 innings pitched. Then, on May 11, 1955, his contract was purchased by the Athletics during their first season in Kansas City. However, Herbert continued to struggle, winning one game and losing eight in 23 games split almost evenly between starting and relieving. He then spent two consecutive seasons, 1956–57, back in Triple-A. Finally, in 1958, at age 28, Herbert returned to the Major Leagues as a reliable pitcher. Pitching for a succession of poor Athletics teams, he won 36 games while losing 40 (for a winning percentage of .474) before being traded to the first-division White Sox on June 10, 1961.\n', '

Herbert\'s 3​1⁄2 years with the ChiSox were his most successful. He went 48–32 (.600) in 109 games (all but two as a starter) and 710​2⁄3 innings pitched. In 1962, he had his best campaign, winning 20 games (losing nine) and making the American League All-Star Team. Appearing in the second All-Star Game held that summer, on July 30, 1962, at Wrigley Field, Herbert hurled three scoreless innings of relief and was credited with the victory when the AL broke a 1–1 deadlock and went on to a 9–4 triumph. It would be the Junior Circuit\'s last All-Star win until 1971. The following season, he led the 1963 American League in shutouts thrown, with seven. His workload was reduced in 1964, but Herbert was still effective as a spot starter, going 6–7 with a 3.47 ERA in 19 starts.\n', '

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