Born on the family plantation in Wayne County, North Carolina, Whitfield's father Richard A. Whitfield moved the family to Leon County, Florida around 1860 to start a cotton plantation. The family later moved to Tallahassee. Whitfield was educated at the West Florida Seminary in Tallahassee and the University of Virginia (bachelor of law, 1886).

After service as a county judge and the clerk of the Florida Supreme Court, Whitfield was appointed state treasurer in 1897, serving until 1903. Whitfield served as Florida's Attorney General 1903-4 before being appointed to the Florida Supreme Court, where he served until resigning in 1943. One of his most significant decisions was a 1908 opinion that prohibited excluding African-Americans from juries.
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