In 1987, President Ronald Reagan got the chance to appoint the third Supreme Court justice of his presidency. But while the first two justices had sailed through the confirmation process, the third appointment turned out to be much more difficult. The outcome would have far-reaching consequences for the Court and the country.

After Justice Lewis F. Powell Jr., a long-time “swing” vote on the Court, announced his retirement, President Reagan nominated Robert Bork, a federal appeals court judge. Bork had been serving on the U.S. Court of Appeals for the D.C. Circuit, the nation’s second-highest court, for five years at that time.

A die-hard fan of constitutional “originalism,” Bork rejected what he saw as the Court’s liberal judicial activism, including key precedents like the “one person, one vote” principle of legislative representation, civil rights legislation and cases involving privacy rights. In Bork’s view, the U.S. Constitution included no right to privacy.

Bork’s controversial opinions and writings, and the fear that he would decisively shift the Supreme Court to the right, motivated liberals in Congress to launch an aggressive campaign against his confirmation, led by Senator Ted Kennedy of Massachusetts.

“Robert Bork’s America,” Kennedy declared on the Senate floor, “is a land in which women would be forced into back-alley abortions, Blacks would sit at segregated lunch counters, rogue police could break down citizens’ doors in midnight raids, [and] schoolchildren could not be taught about evolution...”

Democrats controlled Congress at the time, and the Senate ended up voting against Bork’s confirmation by a vote of 58-42, the biggest margin of any failed Supreme Court nominee in history. Bork’s confirmation fight, and its result, even spawned a new verb. In the years that followed, politicians on both left and right would adopt the practice of “borking” judicial nominees—vigorously questioning their legal philosophy and political views in an effort to derail their confirmation.

After Bork, Reagan nominated a more moderate conservative, Douglas H. Ginsburg. The 41-year-old former law professor had served on the U.S. Court of Appeals for the D.C. Circuit for less than a year at the time. But soon after Reagan announced the nomination, controversial revelations began to emerge. During Ginsburg’s years at the Justice Department, he had handled a major case involving the cable television industry at the same time he was substantially invested in a Canadian-based cable company. Questions then arose about whether he lied on a form he filled out during his nomination process to the federal appeals court the previous year.

The final damage was done when Ginsburg admitted that he smoked marijuana several times, most recently while he was a professor at Harvard Law School in the 1970s. Reportedly fearing another long, drawn-out confirmation battle, Ginsburg asked Reagan to withdraw his name before he could be formally nominated.

Twice burned, Reagan turned to Anthony Kennedy, a federal appeals court judge from the Ninth Circuit in California, whom Reagan knew from his time serving as that state’s governor. Some conservatives had initially argued that Kennedy was too weak in his support for conservative principles, urging Reagan to choose Ginsburg instead.

Known for approaching each case individually and not seeking to change the basic course of U.S. constitutional law—as Bork had clearly sought to do—Kennedy represented a consensus choice that reflected the Democratic majority in Congress. On February 3, 1988, the Senate unanimously confirmed Kennedy by a vote of 97-0.

During his 30 years on the Supreme Court, Justice Kennedy often served as a swing vote alongside the four more liberal and four more conservative justices. While he sided with conservatives on issues such as campaign finance, gun control and voting rights, he disappointed them by casting the deciding vote in cases involving gay rights (including the right of same-sex couples to marry), abortion rights, affirmative action and limitations on capital punishment.

“He was primarily a moderate libertarian is the way I would put it,” Michael Dorf, a constitutional law professor at Cornell Law School who clerked for Justice Kennedy, told NPR shortly after Kennedy announced his retirement in June 2018. “He, more than anybody else on the court during his tenure—and perhaps in history—was less likely to give deference to the government...And he didn't see that so much as a partisan or ideological commitment so much as a reading of the Constitution's broad language protecting liberty.”

With Kennedy’s retirement, another battle began for the future of the Court. President Donald Trump—like Reagan before him—was presented with a chance to replace a critical swing voter with another conservative justice who would, as Trump promised during his presidential campaign, help overturn Roe v. Wade, the landmark 1973 ruling that legalized abortion in the United States.