With a rap of his gavel on June 27, 2018, Chief Justice John Roberts declared another Supreme Court term over, and the nine justices disappeared behind the dark red curtains that hang behind the bench. The assembled journalists politely stood at attention until the last justice was out of view, then rushed to file stories about a non-event—no justice had announced his retirement. Speculation had been running high that Justice Anthony Kennedy, appointed by President Ronald Reagan and nearly eighty-two years old, would be leaving now that a Republican again occupied the White House. Senator Charles Grassley of Iowa had publicly advised the justices in early May that if they were “thinking about quitting this year, do it yesterday.” Grassley, and the powerful Senate Judiciary Committee he chaired, would have to manage the intense confirmation process, and with the midterm elections looming, they would need all the lead time they could get.
The members of the Court retired to their private dining room for the traditional end-of-term luncheon before they dispersed for the summer. As they dined, an armored black car, dispatched from the White House Military Office, pulled into the parking garage three floors below them. After his meal, Justice Kennedy got into the car, where Don McGahn, the White House counsel, was waiting to take him to a meeting with President Trump.
It was a busy day at the White House, the president having held a mid-morning press conference on trade policy and the economy on the South Lawn. After lunch with Secretary of State Mike Pompeo, he would host President Marcelo Rebelo de Sousa of the Republic of Portugal. The press usually lingered around the famous but surprisingly small briefing room at the north side of the mansion, hoping to catch additional stories or details from their White House contacts.
The day before, Steve Engel, the head of the Justice Department’s Office of Legal Counsel, had told McGahn’s trusted chief of staff, Annie Donaldson, that he had just had a meeting with his old boss and needed to talk to McGahn. It took a minute for the significance of what he’d said to register. Engel’s old boss was Anthony Kennedy. He’d clerked for him at the Supreme Court in 2001–2002, and they had remained close.
Engel and Kennedy had met two days before the end of the term at an outdoor café near the National Gallery of Art’s Sculpture Garden. Kennedy had slipped away from a tour of the museum with his clerks to meet Engel, hoping the location was discreet enough to avoid wandering members of the press. After the justice’s security detail evaluated the café for threats, he sat down with Engel and explained that he expected to announce his retirement in the next few days. He wanted to tell his fellow justices immediately after their final sitting on Wednesday but knew the odds were good that the news would leak shortly thereafter.
Hoping to deliver the message to the president in person before it went public, Kennedy wanted Engel to ask McGahn to arrange a meeting without anyone’s noticing. Later that day, Engel called the White House counsel’s office and asked about the president’s schedule. The two offices spoke frequently, so the question didn’t arouse suspicion. He was told the president was leaving for the Midwest on Wednesday evening, so the meeting would need to happen before then.
The next day, Kennedy gave Engel the green light, and the White House counsel’s office quietly arranged the meeting through Jeffrey Minear, counsel to Chief Justice Roberts. A White House car with a pre-cleared driver would make the entry into the White House quick and easy. Chief of Staff John Kelly arranged for President Trump to leave his lunch promptly at one o’clock and come to the White House residence, where the justice would be waiting with McGahn.
That morning, none of the other associate justices knew that Kennedy was stepping down. The scholarly Californian, known as a swing vote on the Court, had hired four clerks for the coming year and had discussed cases coming up in the next term. When the term ended with no announcement from the bench, the justices proceeded to their stately, paneled conference room for one final discussion.
While the nine justices often disagree sharply about the issues before the Court, they know they are working together for life, so they go out of their way to be friendly to one another. But the last conference of each term tends to be a bit testier. The most