WASHINGTON — President Trump singled him out for praise even while attacking other members of the Supreme Court. The White House nominated people close to him to important judicial posts. And members of the Trump family forged personal connections.
Their goal was to assure Justice Anthony M. Kennedy that his judicial legacy would be in good hands should he step down at the end of the court’s term this week, as he was rumored to be considering. Allies of the White House were more blunt, warning the 81-year-old justice that time was of the essence. There was no telling, they said, what would happen if Democrats gained control of the Senate after the November elections and had the power to block the president’s choice as his successor.
There were no direct efforts to pressure or lobby Justice Kennedy to announce his resignation on Wednesday, and it was hardly the first time a president had done his best to create a court opening. “In the past half-century, presidents have repeatedly been dying to take advantage of timely vacancies,” said Laura Kalman, a historian at the University of California, Santa Barbara.
But in subtle and not so subtle ways, the White House waged a quiet campaign to ensure that Mr. Trump had a second opportunity in his administration’s first 18 months to fulfill one of his most important campaign promises to his conservative followers — that he would change the complexion and direction of the Supreme Court.
When Mr. Trump took office last year, he already had a Supreme Court vacancy to fill, the one created by the 2016 death of Justice Antonin Scalia. But Mr. Trump dearly wanted a second vacancy, one that could transform the court for a generation or more. So he used the first opening to help create the second one. He picked Justice Neil M. Gorsuch, who had served as a law clerk to Justice Kennedy, to fill Justice Scalia’s seat.
And when Justice Gorsuch took the judicial oath in April 2017 at a Rose Garden ceremony, Justice Kennedy administered it — after Mr. Trump first praised the older justice as “a great man of outstanding accomplishment.”
“Throughout his nearly 30 years on the Supreme Court,” Mr. Trump said, “Justice Kennedy has been praised by all for his dedicated and dignified service.”
That was an overstatement. Justice Kennedy is reviled by many of Mr. Trump’s supporters for voting to uphold access to abortion, limit the death penalty and expand gay rights. Conservatives have called for his impeachment. James C. Dobson, the founder of Focus on the Family, once called Justice Kennedy “the most dangerous man in America.”
Mr. Trump himself said he wanted to appoint justices who would overrule Roe v. Wade, the 1973 decision establishing a constitutional right to abortion. Justice Kennedy has voted to reaffirm Roe’s core holding. And Mr. Trump has not hesitated to criticize far more conservative members of the Supreme Court, notably Chief Justice John G. Roberts Jr.
“Justice Roberts turned out to be an absolute disaster, he turned out to be an absolute disaster because he gave us Obamacare,” Mr. Trump said in 2016, presumably referring to Chief Justice Roberts’s votes to sustain President Barack Obama’s health care law.
There is reason to think, then, that Mr. Trump’s praise of Justice Kennedy was strategic.
Then, after Justice Gorsuch’s nomination was announced, a White House official singled out two candidates for the next Supreme Court vacancy: Judge Brett M. Kavanaugh of the United States Court of Appeals for the District of Columbia Circuit and Judge Raymond M. Kethledge of the United States Court of Appeals for the Sixth Circuit, in Cincinnati.
The two judges had something in common: They had both clerked for Justice Kennedy.
In the meantime, as the White House turned to stocking the lower courts, it did not overlook Justice Kennedy’s clerks. Mr. Trump nominated three of them to federal appeals courts: Judges Stephanos Bibas and Michael Scudder, both of whom have been confirmed, and Eric Murphy, the Ohio solicitor general, whom Mr. Trump nominated to the Sixth Circuit this month.
One person who knows both men remarked on the affinity between Mr. Trump and Justice Kennedy, which is not obvious at first glance. Justice Kennedy is bookish and abstract, while Mr. Trump is earthy and direct.
But they had a connection, one Mr. Trump was quick to note in the moments after his first address to Congress in February 2017. As he made his way out of the chamber, Mr. Trump paused to chat with the justice.
“Say hello to your boy,” Mr. Trump said. “Special guy.”
Mr. Trump was apparently referring to Justice Kennedy’s son, Justin. The younger Mr. Kennedy spent more than a decade at Deutsche Bank, eventually rising to become the bank’s global head of real estate capital markets, and he worked closely with Mr. Trump when he was a real estate developer, according to two people with knowledge of his role.
During Mr. Kennedy’s tenure, Deutsche Bank became Mr. Trump’s most important lender, dispensing well over $1 billion in loans to him for the renovation and construction of skyscrapers in New York and Chicago at a time other mainstream banks were wary of doing business with him because of his troubled business history.
About a week before the presidential address, Ivanka Trump had paid a visit to the Supreme Court as a guest of Justice Kennedy. The two had met at a lunch after the inauguration, and Ms. Trump brought along her daughter, Arabella Kushner. Occupying seats reserved for special guests, they saw the justices announce several decisions and hear an oral argument.
Ms. Trump tweeted about the visit and posted a photo. “Arabella & me at the Supreme Court today,” she wrote. “I’m grateful for the opportunity to teach her about the judicial system in our country firsthand.”
If the overtures to Justice Kennedy from the White House were subtle, the warnings from its allies were blunt. Last month, Senator Charles E. Grassley of Iowa, the Republican chairman of the Senate Judiciary Committee, went on Hugh Hewitt’s radio program to issue an urgent plea.
“My message to any one of the nine Supreme Court justices,” he said, was, “‘If you’re thinking about quitting this year, do it yesterday.’”
Mr. Grassley said speed was of the essence in light of the midterm elections in November. “If we have a Democrat Senate,” he said, “you’re never going to get the kind of people that are strict constructionists.”
Intermediaries pressed the point with Justice Kennedy privately, telling him that Donald F. McGahn II, Mr. Trump’s White House counsel, would in all probability leave after the midterms. Mr. McGahn has been a key architect of Mr. Trump’s successful efforts to appoint wave after wave of conservative judges, they said, and his absence would complicate a Supreme Court confirmation.
There is nothing particularly unusual in urging older justices to retire for partisan reasons. During the Obama administration, prominent liberals called for Justice Ruth Bader Ginsburg to retire so that Mr. Obama could name her successor.
Justice Kennedy waited until the last day of the term to announce his retirement. The move disappointed liberals who had hoped that he would not want Mr. Trump to name his successor. But the justice, saying he wanted to spend more time with his family, betrayed no hesitation.
His departure is a triumph for Mr. Trump, who has taken particular satisfaction in his judicial appointments. Naming justices and judges is easier than forging legislative compromises, and Mr. Trump understands that his judicial appointments represent a legacy that will long outlast his presidency.
Replacing Justice Scalia with another conservative did not alter the basic ideological balance of the court. But replacing Justice Kennedy, who for decades held the decisive vote in many of the court’s closely divided cases, would give Mr. Trump the opportunity to move the court sharply to the right.
Justice Kennedy visited the White House on Wednesday to tell Mr. Trump of his retirement and to deliver a letter setting out the details. Its warm opening words — “My dear Mr. President” — acknowledged a cordial relationship between the two men, as well as the success of the White House’s strategy.
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