Justice Anthony Kennedy, the current Supreme Court’s longest-serving member, announced his retirement Wednesday, paving the way for Trump to shape the future America’s highest court . Nominated by former President Ronald Reagan in 1987, the 81-year-old justice has served as the crucial swing vote in a number of landmark cases, including rulings that legalized same-sex marriage[1] and preserved[2] abortion rights.

President Trump will now have the opportunity to nominate a second justice to the court, and he has already indicated he will use the same list[3] of conservative judges circulated before the nomination of Justice Neil Gorsuch last year. Whoever he names will have the power to rule on cases that concern, among other things, privacy and surveillance, First Amendment rights in the social media era, and whether tech companies are monopolies[4].

Kennedy’s record on these issues is mixed, but he was a thoughtful voice on how to interpret rights enshrined in the Constitution in light of rapidly changing technologies.

“[Justice Kennedy] has recognized and sought to grapple with the implications of developments that transform privacy, security, and commerce throughout the nation,” says Joshua Matz, a former law clerk to Justice Kennedy and the co-author of Uncertain Justice: The Roberts Court and the Constitution. “Without him, the court will have lost one of its leading thinkers on the question of how our evolving constitution can meet the needs of a more advanced society.”

That question can be difficult to answer, as Kennedy himself admitted. “While we now may be coming to the realization that the Cyber age is a revolution of historic proportions, we cannot yet appreciate its full dimensions and vast potential to alter how we think, express ourselves, and define who we want

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