Whitehead was born in Tarboro, North Carolina. He attended the University of North Carolina and started his professional baseball career with the Class AAA Columbus Red Birds in 1931. He batted over .300 in each of the next three seasons, helping to lead the 1933 team to the American Association pennant.\n', '

In 1934 and 1935, Whitehead was a utility infielder for the National League Cardinals. He was a member of the 1934 World Series champion team and was friends with future Hall of Famer Dizzy Dean. Whitehead was selected to the All-Star team in 1935.\n', '

Whitehead was traded to the Giants in December for first baseman/outfielder Phil Weintraub and pitcher Roy Parmelee. With a weak bat but a good glove at second base, he helped the Giants win two consecutive pennants in 1936 and 1937. In 1937, he led all second basemen in fielding percentage and putouts, and he was named to the All-Star team for the second time.\n', '

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