After law school, Lucchino practiced law with the Washington, D. C., law firm of Williams & Connolly. The founder, famed litigator Edward Bennett Williams, had ownership interest in both the Washington Redskins and the Baltimore Orioles. Lucchino's law practice at Williams & Connolly included a substantial amount of work for those two sports teams. Through that work, Lucchino served on the Redskins' board of directors from 1979 to 1985. He later became president of the Baltimore Orioles, serving from 1988 to 1993, and president and CEO of the San Diego Padres, serving from 1995 to 2001. Lucchino subsequently joined the Boston Red Sox as president and CEO when John W. Henry purchased the team in December 2001.