Born in Bristol, Florida, Sheppard attended the University of North Carolina at Chapel Hill and read law to enter the bar in 1891.
He was the United States Attorney for the Northern District of Florida from 1903 to 1907.
[1] On September 4, 1907, Sheppard received a recess appointment from President Theodore Roosevelt to a seat on the United States District Court for the Northern District of Florida vacated by Judge Charles Swayne.
Formally nominated to the same position by President Roosevelt on December 3, 1907, Sheppard was confirmed by the United States Senate on May 20, 1908, and received his commission the same day.
Sheppard served in that capacity until his death on April 21, 1934.