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Shepherd was a United States magistrate judge for the United States District Court for the Western District of Arkansas from 1993 until he joined the Eighth Circuit. His appointment was only the second time ever a sitting magistrate judge had been elevated directly to a federal court of appeals. From 1991 to 1993, Shepherd was an Arkansas state trial judge for the 13th Judicial Circuit, in the southern end of the state. Previously, Shepherd had been in private practice as an attorney in Arkansas from 1976 to 1990.
Federal judicial service
Shepherd was nominated to the Eighth Circuit by President George W. Bush on May 18, 2006, to fill a seat to be vacated by Judge Morris S. Arnold. Shepherd was confirmed by the United States Senate by voice vote on July 20, 2006. He received his commission on October 10, 2006.