In early 1999, Theodore Olson called a group of Gibson, Dunn & Crutcher colleagues into his Washington, D.C., office for an urgent meeting about a case that he was preparing to argue before the U.S. Supreme Court. Olson was getting ready for Rice v. Cayetano. His client, rancher Harold Rice, was challenging a law that allowed only native Hawaiians to vote for candidates for a board that governed the Office of Hawaiian Affairs.

Olson had bad news to announce, according to an attendee at the meeting. The state of Hawaii had hired a new lawyer to argue in defense of the statute: John Roberts Jr., then the head of Hogan & Hartson’s appellate practice, now the chief justice of the United States. Olson had known Roberts since the early days of the Reagan Justice Department. “I knew his reputation and how extraordinarily good he was,” says Olson. The Gibson Dunn partner intensified his preparation efforts, and the court gave Roberts a hard time, ultimately ruling against Hawaii. But the point was made: The mere mention that Roberts had entered a case gave his adversaries heartburn and sent them back to the U.S. Reports.

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