Born in Chicago, Illinois, Wakefield was the son of Howard Wakefield, who was a major league catcher from 1905 to 1907. The scouts started taking notice of Wakefield when he was in high school in Chicago. He recalled: "I was a skinny kid who could hit."\n', '

Wakefield attended the University of Michigan where he played only one season, 1941, with the Michigan Wolverines baseball team. In his one season playing for the Wolverines, Wakefield hit for average (.372) and power (9 home runs), as he led the team to a 24–8 record and its first Big Ten Conference baseball crown since 1936.\n', '

In the summer of 1941, Wakefield was a hot prospect who was invited for tryouts with Brooklyn, Chicago, Cincinnati, Cleveland and Detroit. Wakefield later recalled that his "criterion" in choosing the right team was "the highest offer." A photograph of a smiling Wakefield holding multiple "big league offers" is available from the National Baseball Hall of Fame and Museum. Legendary Tigers scout, Wish Egan, persuaded Detroit owner, Walter O. Briggs, Sr. to give Wakefield a $52,000 signing ($885,765 today) bonus and a car.\n', '

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