Judge Shepherd began his legal career with the law firm of Bradford, Williams, McKay, Kimbrell, Hamann and Jennings in Miami, Florida, where he maintained both a trial and appellate practice for more than 18 years. In 1981, he was appointed by President Reagan and served as Associate Administrator for Legal Counsel and Enforcement for the United States Environmental Protection Agency. In 1990, he became the founding managing partner of the national law firm of Popham, Haik, Schnobrich and Kaufman, P.A. He was a partner in the law firm of Weissman Dervishi, Shepherd, Borgo & Nordland, P.A., from 1997-1998, and from January 1, 1999, until he was appointed to the Third District Court of Appeal, he was the Florida Senior Attorney for the Pacific Legal Foundation. Judge Shepherd assumed his position as a Judge of the Third District Court of Appeal in 2003. His community and professional activities have included service as a director of the James Madison Institute in Tallahassee, Florida (1987-1995), a member of the research advisory board of the Foundation for Florida's Future (1995-1998), and participation in the Miami-Dade County Guardian ad Litem program. In 1985, he was recognized by the Florida State-Federal Judicial Council for his representation of Raleigh Porter, an inmate then serving on Death Row. Judge Shepherd teaches Florida Constitutional Law.