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). 1945 Library

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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