Early Legal Career
After graduating from law school, Roberts served as a law clerk for Judge Henry Friendly on the Second Circuit Court of Appeals for one year. Roberts frequently cites Judge Friendly in his opinions. From 1980 to 1981, he clerked for then-Associate Justice William Rehnquist on the United States Supreme Court. From 1981 to 1982, he served in the Reagan administration as a Special Assistant to U.S. Attorney General William French Smith. From 1982 to 1986, Roberts served as Associate Counsel to the President under White House Counsel Fred Fielding.
Roberts entered private law practice in 1986 as an associate at the Washington, D.C.-based law firm of Hogan & Hartson. As part of Hogan & Hartson's pro bono work, he worked behind the scenes for gay rights advocates, reviewing filings and preparing arguments for the Supreme Court case Romer v. Evans (1996), which has been described as "the movement's most important legal victory"; as well as arguing on behalf of the homeless, a case which became "one of Roberts' few appellate losses".
Roberts left Hogan & Hartson to serve in the George H. W. Bush administration as Principal Deputy Solicitor General from 1989 to 1993 and as Acting Solicitor General for the purposes of at least one case when Ken Starr had a conflict.
In 1992, George H. W. Bush nominated Roberts to the U.S. Court of Appeals for the District of Columbia Circuit, but no Senate vote was held, and Roberts's nomination expired at the end of the 102nd Congress.
Roberts returned to Hogan & Hartson as a partner and became the head of the firm's appellate practice, in addition to serving as an adjunct faculty member at the Georgetown University Law Center. During this time, Roberts argued 39 cases before the Supreme Court, prevailing in 25 of them. He represented 18 states in United States v. Microsoft. Those cases include:
| Case | Argued | Decided | Represented |
|---|---|---|---|
| First Options v. Kaplan, 514 U.S. 938 | March 22, 1995 | May 22, 1995 | Respondent |
| Adams v. Robertson, 520 U.S. 83 | January 14, 1997 | March 3, 1997 | Respondent |
| Alaska v. Native Village of Venetie Tribal Government, 522 U.S. 520 | December 10, 1997 | February 25, 1999 | Petitioner |
| Feltner v. Columbia Pictures Television, Inc., 523 U.S. 340 | January 21, 1998 | March 31, 1998 | Petitioner |
| National Collegiate Athletic Association v. Smith, 525 U.S. 459 | January 20, 1999 | February 23, 1999 | Petitioner |
| Rice v. Cayetano, 528 U.S. 495 | October 6, 1999 | February 23, 2000 | Respondent |
| Eastern Associated Coal Corp. v. Mine Workers, 531 U.S. 57 | October 2, 2000 | November 28, 2000 | Petitioner |
| TrafFix Devices, Inc. v. Marketing Displays, Inc., 532 U.S. 23 | November 29, 2000 | March 20, 2001 | Petitioner |
| Toyota Motor Manufacturing v. Williams, 534 U.S. 184 | November 7, 2001 | January 8, 2002 | Petitioner |
| Tahoe-Sierra Preservation Council, Inc. v. Tahoe Regional Planning Agency, 535 U.S. 302 | January 7, 2002 | April 23, 2002 | Respondent |
| Rush Prudential HMO, Inc. v. Moran, 536 U.S. 355 | January 16, 2002 | June 20, 2002 | Petitioner |
| Gonzaga University v. Doe, 536 U.S. 273 | April 24, 2002 | June 20, 2002 | Petitioner |
| Barnhart v. Peabody Coal Co., 537 U.S. 149 | October 8, 2002 | January 15, 2003 | Respondent |
| Smith v. Doe, 538 U.S. 84 | November 13, 2002 | March 5, 2003 | Petitioner |
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 traveled to Tallahassee, Florida to advise Jeb Bush, then the Governor of Florida, concerning the latter's actions in the Florida election recount during the presidential election.
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