After graduating from Chicago\'s Leo High School, O\'Toole attended the University of Wisconsin–Madison. He made his Major League debut with the Reds after only one minor league season, with the 1958 Nashville Vols, where he led the AA Southern Association in wins (20), innings pitched, strikeouts and bases on balls.\n', '

From 1961–64, he won 19, 16, 17 and 17 games for the Cincinnati Reds, from 1961 to 1963 respectively 3rd, tied for 8th, and tied for 10th in the National League. He played a crucial role in Cincinnati\'s 1961 National League championship, when he won 19 of 28 decisions, with an earned run average of 3.10, second in the National League behind Warren Spahn. He was named Player of the Month for September with a 5–0 record, 2.53 ERA, and 37 strikeouts. He finished 10th in MVP voting. Though pitching effectively in the 1961 World Series, with an earned run average of 3.00, O\'Toole lost his two decisions to Whitey Ford in games 1 and 4, as the New York Yankees bested the Reds in five games. In 1963, he was the starting pitcher of the National League in the Major League Baseball All-Star Game (his only appearance at the Summer Classic), pitching 2 innings and allowing 1 earned run, not involved in the decision. O\'Toole later said that being selected as the starting pitcher by San Francisco Giants manager Alvin Dark was one of the proudest moments of his career. In 1964, he continued as an elite pitcher, with a career-best earned run average of 2.66, 6th in the National League, and a win-lost percentage of .708, third in the National League behind Sandy Koufax and Juan Marichal, two members of the National Baseball Hall of Fame and Museum.\n', '

O\'Toole played in Cincinnati until his final season, 1967, spent with his hometown team, the Chicago White Sox, but was ineffective due to arm troubles. O\'Toole tried to return with a 1969 expansion team, the Seattle Pilots, but was cut in spring training before the season began.\n', '

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