Born in Brenham, Texas, Shepard was a private in the Confederate States Army from 1864 to 1865.

[1] Shepard was nominated by President Grover Cleveland on April 14, 1893, to the Court of Appeals of the District of Columbia (now the United States Court of Appeals for the District of Columbia Circuit), to a new Associate Justice seat authorized by 27 Stat.

His service terminated on January 19, 1905, due to his elevation to be Chief Justice of the same court.

[1] Shepard was nominated by President Theodore Roosevelt on December 16, 1904, to the Chief Justice seat on the Court of Appeals for the District of Columbia (now the United States Court of Appeals for the District of Columbia Circuit) vacated by Chief Justice Richard H. Alvey.

[1] Concurrent with his federal judicial service, Shepard was a lecturer in law at Georgetown University from 1895 to 1910.