From 1976 until 1978, Leonard worked as a law clerk for U.S. District Judge Franklin T. Dupree, Jr. He then worked briefly in private practice from 1978 until 1979 with the firm of Sanford, Adams, McCullough and Beard before becoming clerk of court for the U.S. District Court for the Eastern District of North Carolina in 1979.
Federal judicial service
In 1981, Leonard was appointed to be a federal magistrate judge, a position he held until becoming a U.S. Bankruptcy Judge in 1992. In his last year at the district court, Leonard received the first Director’s Award for Leadership in the Federal Courts for his work in setting up training programs for judicial employees. While at the bankruptcy court, Leonard was heavily involved in federal court administration nationally. He served on the prestigious Judicial Conference Committee on Court Administration and Case Management. In that capacity, he oversaw the development of the first electronic filing system in the federal courts and played a role in the development of PACER, the public access system to the federal courts. He also served repeatedly as a consultant for the U. S. State Department to emerging judiciaries in sub-Saharan Africa, traveling to Zambia, Tanzania, Namibia, Kenya, and Nigeria more than 30 times. During his time with the bankruptcy court, Leonard was also active in the National Conference of Bankruptcy Judges. He served as a member of the Board of Governors, chaired the Endowment for Education, and was the editor-in-chief of the prestigious American Bankruptcy Law Journal. In 2011, the American Bar Associated gave Leonard the prestigious Robert Yegge Award for his Outstanding Contribution to Judicial Administration.
Nomination to Fourth Circuit
On December 22, 1995, President Clinton nominated Leonard to be an appeals-court judge on the U.S. Court of Appeals for the Fourth Circuit. Leonard was appointed to a newly created post. Almost immediately, Leonard's nomination ran into opposition from North Carolina Sen. Jesse Helms, who objected to Clinton's refusal to renominate Helms' preferred candidate, Terrence Boyle. President George H.W. Bush had nominated Boyle to that Fourth Circuit seat in 1992, but the U.S. Senate never acted on the nomination, and the nomination lapsed with the end of Bush's presidency. The U.S. Senate did not hold a hearing or a vote on Leonard's Fourth Circuit nomination during 1996, and Clinton did not renominate him to the Fourth Circuit after his second term began in January 1997. That seat on the Fourth Circuit eventually was filled by Roger Gregory, whose nomination by Clinton was never acted upon by the Senate. Clinton subsequently installed Gregory on the Fourth Circuit in a recess appointment in December 2000, and President George W. Bush gave Gregory a permanent appointment to the seat the following year.
Nomination to the U.S. District Court for the Eastern District of North Carolina
On March 24, 1999, Clinton nominated Leonard to be a U.S. District judge for the U.S. District Court for the Eastern District of North Carolina. Leonard was nominated to fill the seat vacated in December 1997 by W. Earl Britt, who took senior status. The Raleigh News and Observer reported on March 25, 1999 that the nomination was made at the request of then-Sen. John Edwards, who is a close friend of Leonard. Helms then announced his opposition to Leonard's nomination on the grounds that he had wanted to shift that open seat to the U.S. District Court for the Western District of North Carolina. The Senate also did not hold a hearing or a vote on Leonard's District Court nomination in 1999 or 2000, and the nomination lapsed with the end of Clinton's presidency.
Judge Leonard is the current dean of Campbell University's Norman Adrian Wiggins School of Law. In 2014, North Carolina Lawyer’s Weekly named Leonard the North Carolina Lawyer of the Year.
Personal
Leonard is the father of five children. He and his wife, Dr. Whitney Cain, live in Raleigh, North Carolina, with their three children, all in elementary school. Dr. Cain holds a doctorate from North Carolina State University and has a private therapy practice. His son Matt is a graduate of Northwestern University and New York University School of Law, and lives in Brooklyn with his wife and three children. His son Justin is a graduate of the University of Wisconsin, and lives in Chicago with his wife and four children, where he is a partner in Walton Street Capital.
