Judge Shepherd was born and raised in Palm Beach County, Florida. He received his B.A. cum laude from the University of Florida in 1968. In 1970, he received a Master of Arts Degree in Government from the University of Massachusetts, and he was awarded his juris doctor from the University of Michigan Law School in 1972.
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 on September 22, 2003.
Judge Shepherd is a member of the Florida Bar, the District of Columbia Bar and the Dade County Bar Association. He is also a member of the United States District Court for the Southern, Middle and Northern Districts of Florida, the Eleventh Circuit Court of Appeals, and the United States Supreme Court. 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. A year later, he received the Radio Station WRHC award for Special Recognition in the Latin Community for his contributions to the Hispanic community of Miami-Dade County, including his assistance and contribution to the establishment of Radio Station WRHC as the first Cuban-exile-owned radio station in South Florida. His publications include: Personal Injury Claims and Defenses-- Some Particular Considerations, §9.15-9.20, Manual of Dispute Resolution, ADR Law and Practice, Vol.1, McGraw-Hill, Inc., 1996. "Tahoe-Sierra Preservation Council v. Tahoe Regional Planning Agency: The Supreme Court’s Latest Word on Regulatory Takings," The Fee Simple: The Newsletter of the Virginia State Bar Real Property Section, Volume XXIII, Number 1, November 2002.
Judge Shepherd is married to Anne Elizabeth Ferguson-Shepherd and has four children.