A native of Chelsea, Massachusetts, Whittaker played baseball at Somerville High School, where he was the winning pitcher in eight of the team's 15 victories in 1911. He then attended Worcester Academy and Tufts University. While at Tufts in 1914 and 1915, he played summer baseball for the Falmouth Cottage Club in what is now the Cape Cod Baseball League. One of the top pitchers in the league, he threw a no-hitter for Falmouth against Oak Bluffs in 1915. Whittaker played a key role in what has been called the "greatest college baseball battle ever waged," a 1916 championship game between collegiate baseball powerhouses Tufts and Harvard.
Whittaker's only major league appearance came for Baseball Hall of Fame manager Connie Mack's historically poor-performing 1916 Philadelphia club. Whittaker tossed the final two innings for the Athletics on July 6 at Shibe Park in Philadelphia's 9-4 loss to the Detroit Tigers, whose lineup featured Hall of Famer Ty Cobb.
Upon graduation from Tufts, Whittaker pursued a career in dentistry. He died in 1965.

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