Byrd started work as a court officer for the Brooklyn circuit of the New York City Court System. In 1986 he was transferred to the Family Court division in Manhattan. It was in this capacity that Byrd met Judge Judy Sheindlin, who was the Supervising Family Court Judge for Manhattan. In 1989 Hawkins-Byrd obtained a criminal justice degree from John Jay College. A year later, he and his family moved to the San Francisco Bay Area in California when he went to work for the United States Marshals Service.

In 1996, when Sheindlin was offered her own TV series, Byrd wrote her a congratulatory letter, saying: “If you ever need a bailiff, my uniform still fits.” Judge Judy called him at home to offer him the role, which he accepted.