Any occasion on which a member of the U.S. Supreme Court leaves the bench through retirement (or death) is a significant political event, providing the incumbent president with the opportunity to nominate a successor who is ideologically congruent with the party in power and (in most cases) will remain on the bench for decades to come. The requirement that a Supreme Court nominee be confirmed by a vote of the U.S. Senate often touches off bitter fights between the two parties on the floor of that chamber.
When Justice Anthony M. Kennedy announced his imminent retirement at the end of June 2018, it set the stage for a particularly momentous shift in the makeup of the Supreme Court, as Kennedy had long been the bridge between the court's liberal and conservative sides on a number of contentious social issues:
Justice Kennedy, 81, has been a critical swing vote on the sharply polarized court for nearly three decades as he embraced liberal views on gay rights, abortion and the death penalty but helped conservatives trim voting rights, block gun control measures and unleash campaign spending by corporations.
His replacement by a conservative justice — something Mr. Trump has vowed to his supporters — could imperil a variety of landmark Supreme Court precedents on social issues where Justice Kennedy frequently sided with his liberal colleagues, particularly on abortion.
Many critics still smarting over the Republicans' successful (and unprecedented) efforts at blocking approval of Merrick Garland, who had been nominated by outgoing president Barack Obama in 2016 after the death of Justice Antonin Scalia -- thus allowing incoming president Donald Trump the opportunity to fill the vacant court seat instead -- immediately jumped on a conspiracy theory involving the timing of Kennedy's resignation and his son's employment:
The details of this conspiracy theory were somewhat hazy, most versions of it seemingly implying that President Trump somehow leveraged his financial connections with Kennedy's son Justin to convince or coerce the jurist to retire ahead of the November 2018 U.S. mid-term elections (during which Democrats might pick up enough Senate seats to block confirmation of Trump's preferred nominee).
The most coherent form of the conspiracy theory posited that Kennedy's retirement was a sudden and unexpected event, a strategic move intended to allow Trump to nominate a friendly successor who would vote favorably on any issues involving Justin Kennedy that might come before the court as a result of the ongoing Mueller investigation into Russian election interference (whereas Kennedy would have to recuse himself from such issues if he remained on the bench):
As the New York Times noted, Donald Trump did have a business relationship with Deutsche Bank, where Justin Kennedy once worked (he left the company in 2009), that went back many years to a time when many other banks were leery of doing business with Trump:
[Anthony Kennedy and Donald Trump] 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.
And, of course, many news outlets have reported on the potentially suspect coincidence that right about the time Trump was sworn in as U.S. president, Deutsche Bank was fined an aggregate $630 million for their involvement in a $10 billion Russian money-laundering scheme — and Deutsche Bank's records were later reportedly subpoenaed by special prosecutor Robert Mueller’s investigation into Russian interference in the 2016 U.S. elections:
[Trump] took out two mortgages against a resort in Miami and a $170 million loan to finish his hotel in Washington, D.C. According to Bloomberg, by the time Trump was elected president of the United States in November 2016, he owed Deutsche around $300 million, an unprecedented debt for an incoming president. (His June financial disclosure showed he owes the bank $130 million, which is due in full in 2024.)
The loans to Trump weren’t the only abnormal behavior at Deutsche. Around the same time he received his new line of credit, the bank was laundering money, according to the New York State Department of Financial Services (DFS). Russian money. Billions of dollars that flowed from Moscow to London, then from London to New York — part of a scheme for which European and American regulators eventually punished the bank.
Was the timing of this illicit operation and the loans to Trump coincidental? Or evidence of something more sinister — a critical chapter in the president’s long history of suspicious business deals with Russian and post-Soviet oligarchs?
Little hard evidence suggests that the Kennedy rumors are more than political conspiracy-driven speculation, however. Justin Kennedy left Deutsche Bank before the money laundering activity referenced above took place, and some sources have asserted that Justin Kennedy had little or no involvement with Trump's Deutsche Bank dealings:
MSNBC host Stephanie Ruhle, who worked for eight years at Deutsche Bank before joining the news network, cautioned about reaching conclusions because there are multiple parts of the bank that "can easily get confused and lumped together."
"While I know and it has been well-reported, Deutsche was a massive lender to Mr. Trump, I want to put a new context," she said. "A lot of this comes from multiple sides of the bank, specifically the private bank, and that was not where Mr. Kennedy worked."
Citing two former members of senior management, Ruhle said, "a lot of the recent lending comes from the private bank ... most of which was done after Justin left the bank."
"The business Mr. Kennedy ran was part of a real estate team that did some business. It was not part of the private bank business," Ruhle continued. "To say that he was the point guy that lent all of this money to Trump, I think, is short-sided. It's a lot more complicated."
The level of engagement Justin Kennedy might have had with Donald Trump's financial dealings at Deutsche Bank remains ambiguous for now, but the New York Times gave little weight to the notion that Anthony Kennedy was directly pressured into retiring, observing that it's not unusual for presidents to be mindful of when an open seat on the Supreme Court bench might be in the offing and strategize around the possibility:
There were no direct efforts to pressure or lobby Justice Kennedy to announce his resignation, 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.
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.”
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.
Moreover, Politico reported back in April 2017 (before the Mueller investigation into Russian interference was even underway) that the Trump White House might have been utilizing connections between Trump's and Kennedy's children to ease the elder Kennedy into retirement. Notably, Politico referenced Justin Kennedy's having a connection with Donald Trump, Jr., not President Trump himself, and made no mention of Deutsche Bank:
While the White House is focused on shepherding Trump’s first Supreme Court nominee, Neil Gorsuch, through the Senate confirmation process, the president and his team are obsessed with the next possible vacancy.
The likeliest candidate is Kennedy, who has sat at the decisive fulcrum of the most important Supreme Court cases for more than a decade. Replacing him with a reliable conservative would tip the court to the right, even if no other seat comes open under Trump — whose team has taken to exploring every imaginable line of communication to keep tabs on the justice and to make him comfortable as he ponders a potential retirement.
One back channel is the fact that Kennedy’s son, Justin, knows Donald Trump Jr. through New York real estate circles. Another is through Kennedy’s other son, Gregory, and Trump’s Silicon Valley adviser Peter Thiel. They went to Stanford Law School together and served as president of the Federalist Society in back-to-back years, according to school records. More recently, Kennedy’s firm, Disruptive Technology Advisers, has worked with Thiel’s company Palantir Technologies.
The White House has also closely monitored retirement chatter by tapping into the network of former Kennedy clerks, a group that includes Gorsuch himself. Some in the legal world viewed Gorsuch’s selection — he would be the first Supreme Court clerk to serve alongside a former boss — as an olive branch to Kennedy that, should he retire next, his seat would be in reliable presidential hands.
Those close to Trump’s judicial-selection process stress that they’re not pressuring Kennedy to hang up his robe, only seeking to put him at ease.
It may be true, as outlined above, that members of the Trump administration undertook efforts to "assure Kennedy that his judicial legacy would be in good hands should he step down at the end of the court’s [current] term." But no substantive evidence yet suggests anything more than that President Trump and other members of his administration might have sought to curry favor with a justice who was already mulling retirement to influence the timing of that event.