1982 as a special assistant to U.S. Attorney General William French Smith, then from 1982 to 1986 as an associate with the White House Counsel. He then entered private practice in Washington, D.C., as an associate at the law firm Hogan & Hartson (now Hogan Lovells) and worked in the field of corporate law. In 1989, Roberts joined the Administration of president George H. W. Bush as Principal Deputy Solicitor General. He served as the acting solicitor general for the case of Metro Broadcasting, Inc. v. FCC when the solicitor general, Ken Starr, had a conflict of interest. In the case, Roberts argued against policies of the FCC intended to increase minority ownership of broadcast licenses, arguing that the racial preferences were unconstitutional. Roberts's decision to argue that a federal agency's policy was unconstitutional surprised many lawyers within the Solicitor General's office. In 1992, Bush nominated Roberts to a seat on the U.S. Court of Appeals for the D.C. Circuit, but no Senate vote was held, and Roberts's nomination expired at the end of the 102nd Congress. Following Bush's defeat by Bill Clinton in the 1992 presidential election, Roberts left government service and returned to Hogan & Hartson as a partner. He became the head of the firm's appellate practice, and also became an adjunct professor at the Georgetown University Law Center. During this time, Roberts argued 39 cases before the Supreme Court, prevailing in 25 of them. He represented 19 states in United States v. Microsoft. Those cases include: During this time he worked pro bono for gay rights advocates, reviewing filings and preparing arguments for the 1996 Supreme Court case Romer v. Evans, which was described in 2005 as "the movement's most important legal victory". Roberts's involvement with the case was minimal, as he later stated that he had been involved for less than ten hours in preparing oral arguments. He also argued on behalf of the homeless, in a case which became one of Roberts's "few appellate losses." He also represented, pro bono, a man who was sentenced to death for killing eight people in Florida. During the late 1990s, while working for Hogan & Hartson, Roberts served as a member of the steering committee of the Washington, D.C., chapter of the conservative Federalist Society. In 2000, Roberts advised Jeb Bush, then governor of Florida, concerning Bush's actions in the Florida election recount during the presidential election.