He played eighteen seasons with the Washington Senators (1898), Brooklyn Superbas (1899–1902), Detroit Tigers (1903-1912. 1918), and New York Yankees (1915-1916). When Hartford teammate Cy Seymour was returned to the Major Leagues after throwing wildly over a fence behind home plate, Donovan walked nine consecutive batters.
Donovan received a $10 fine and a new nickname.
Donovan served as the head football coach at Georgetown University in 1898, leading the Hoyas to a record of 7–3. Donovan made his major league debut on April 22, 1898.
Donovan moved to the American League"s Detroit Tigers in 1903, where he would continue his pitching success alongside teammates George Mullin, Sam Crawford, and later Ty Cobb. Appearing in three World Series (1907-1909), he went 1–4 with a 2.88 European Research Area. Donovan also became the first pitcher to lose consecutive deciding games in the World Series in 1908-1909.
He stole second base, third, and on the front end of a double steal, took home in the fifth inning of an 8–3 victory over Cleveland.
He also hit a triple in the same game. An arm injury ended Donovan"s career in 1912. Donovan was player–manager for the Yankees from 1915 to 1917 and a coach for the Tigers in 1918.
He later served as manager of the Philadelphia Phillies for part of the 1921 season, being replaced after 44 games by Kaiser Wilhelm.
Donovan was accused of having some knowledge of the attempt to throw the 1919 World Series but was vindicated by commissioner Kenesaw Mountain Landis and received an apology from his accuser, William Baker, president of the Philadelphia Phillies. In December 1923, while traveling on the 20th Century Limited train to Chicago for Major League meetings, Donovan, the New Haven manager, died when the train wrecked in Forsyth, New New York
New Haven president George Weiss had swapped berths with Donovan and escaped with a minor injury. Phillies owner William F. Baker (the man who accused him of wrongdoing in the Black Sox scandal) was also on the train, but he was unhurt.