Inside Donald Trump’s rocky relationship with the Supreme Court

By Joan Biskupic, CNN Senior Supreme Court Analyst

Some Supreme Court justices thought Donald Trump was setting them up. Two days after the official swearing-in of Justice Brett Kavanaugh in October 2018, the president arranged a televised ceremony at the White House and invited all the justices.

Justices had declined to attend similar White House events under previous presidents, resisting the optics that would conflict with separation of powers. This time, they especially worried about being used for political purposes and were concerned that an appearance by the full contingent of sitting justices could look like an endorsement of the president.

In the end, their concerns were justified. Most of the justices sat stone-faced, disturbed by what Trump said during the event and by being unwitting participants in a political exercise.

Trump had a way of ensnarling the court in politics, fomenting rhetoric of personal destruction and conspiracy, all the while generating challenges to the rule of law.

Even today at this historic moment, as the ex-president faces criminal charges in Manhattan, one of Trump’s first responses involved attacking the judge who will preside over his initial proceedings. Trump’s terms of aggrievement and personal affront (“HATES ME”) were familiar.

Trump wrote in a social media post Friday on Truth Social: “The Judge ‘assigned’ to my Witch Hunt Case, a ‘Case’ that has NEVER BEEN CHARGED BEFORE, HATES ME. His name is Juan Manuel Marchan, was hand picked by Bragg & the Prosecutors, & is the same person who ‘railroaded’ my 75 year old former CFO, Allen Weisselberg, to take a ‘plea’ deal (Plead GUILTY, even if you are not, 90 DAYS, fight us in Court, 10 years (life!) in jail.”

During Trump’s term as president, the Supreme Court justices navigated challenges to his administration’s policies, his attempts to block various investigations and, finally, his effort to overturn the 2020 presidential election. Chief Justice John Roberts presided over Trump’s first impeachment trial, in 2020.

Trump’s presidency further propelled the judiciary into a new era of polarization, through his actions, plus the forceful influence of his appointees, seen most strikingly in last June’s reversal of nearly a half century of women’s abortion rights.

Trump’s choice of Kavanaugh for his second Supreme Court appointment triggered an enormous political fight that had not ended with his Senate confirmation. News networks still buzzed that October with coverage of the Senate hearings, especially Christine Blasey Ford’s accusation that Kavanaugh had sexually assaulted her while a teenager and Kavanaugh’s denial.

Some of the justices later privately revealed that they found the hearings too painful to watch. The sessions stirred their own anxieties from their time in the witness chair, and even those who found Ford credible shuddered at the public thrashing of Kavanaugh. They knew he was destined to join their ranks and already felt some institutional allegiance.

Wary of Trump’s invitation after the contentious hearings, Roberts quietly sought reassurance from the White House counsel’s office that the October 8 ceremonial swearing-in would not be overtly political.

With his fears calmed, Roberts and the associate justices went to the White House for the evening event. As the cameras flashed, they took their front-row seats in the East Room. Jane Roberts sat behind her husband. At her side were the other spouses: Ginni Thomas, Joanna Breyer, Martha-Ann Alito and Louise Gorsuch.

Trump immediately highlighted the rare attendance of the full Supreme Court: “Joining us for tonight’s ceremony is every sitting Supreme Court justice.”

He announced their names, individually, like blue ribbons he had just won: “Chief Justice Roberts. Thank you. Justice Thomas. Thank you. Justice Ginsburg. Thank you. Justice Breyer. Thank you, justice. Justice Alito. Thank you. Justice Sotomayor. Thank you. Justice Kagan. Thank you. And Justice Gorsuch.” The audience applauded.

What came next shattered the decorum of a judicial ceremony.

“I would like to begin tonight’s proceeding differently than perhaps any other event of such magnitude,” Trump said. “On behalf of our nation, I want to apologize to Brett and the entire Kavanaugh family for the terrible pain and suffering you have been forced to endure. Those who step forward to serve our country deserve a fair and dignified evaluation, not a campaign of political and personal destruction based on lies and deception.

“What happened to the Kavanaugh family violates every notion of fairness, decency and due process,” Trump continued. “[In] our country, a man or woman must always be presumed innocent unless and until proven guilty. And with that, I must state that you, sir, under historic scrutiny, were proven innocent.”

But that was not true. There had been no trial, nor even much of an investigation into Ford’s accusations. But as with so many of Trump’s assertions, the truth did not matter to him or to a certain number of his supporters.

Some justices confided later that they were sorry they had gone.

Justice Clarence Thomas, however, was conspicuously enthusiastic, applauding heartily after Kavanaugh spoke. A Department of Justice spokeswoman, speaking on Fox News, later described Thomas as “the life of the party” at the Kavanaugh event.

Two years later, when Trump hosted a swearing-in for Justice Amy Coney Barrett immediately after her Senate confirmation, Thomas was the only justice present. Thomas administered the constitutional oath in the televised ceremony; the next day she took the judicial oath at the Supreme Court.

Trump and Roberts

That night at the White House when Kavanaugh stepped to the lectern, the new justice began his remarks by singling out Roberts.

“I’m honored to serve on a Supreme Court headed by Chief Justice John Roberts,” Kavanaugh said. “Chief Justice Roberts is a principled, independent and inspiring leader for the American judiciary. As a country, we are fortunate to have John Roberts as chief justice of the United States.”

The move showed that the two justices had established an early alliance at the high court. (A few weeks later Roberts would favorably cite Kavanaugh in a speech, for the ideal of judicial neutrality: “As our newest colleague put it, we do not sit on opposite sides of an aisle, we do not caucus in separate rooms, we do not serve one party or one interest. We serve one nation.”)

Roberts and Kavanaugh had been friends, first working together in the Department of Justice during President George H.W. Bush’s tenure (1989-1993). Their social circles overlapped, too, through their membership in a Chevy Chase club and poker games among DC’s legal elite.

Trump had already made his feelings about Roberts clear as he vilified those who did not act or rule the way he wanted, such as in June 2012 when the chief justice voted to uphold the Obamacare health insurance law. Then known mainly for his New York real estate ventures and reality TV shows, Trump posted on Twitter after the ruling: “Wow, the Supreme Court passed @ObamaCare. I guess @JusticeRoberts wanted to be part of Georgetown society more than anyone knew.”

The chief justice resisted speaking out against Trump when he became president. Roberts also sought to avoid decisions that divided 5-4 and reinforced Trump’s partisan ways.

The sole time Roberts went public to counter Trump came — perhaps fittingly — when Trump railed against a federal judge in a way that struck at the heart of Roberts’ assertions of judicial neutrality. The episode marked an extraordinary clash between the heads of two branches of government.

In November 2018, Trump disparaged a US district judge who had ruled against his administration’s policy regarding asylum-seekers at the southern border. “This was an Obama judge, and I’ll tell you what, it’s not going to happen like this anymore,” Trump said of US District Judge Jon Tigar as he spoke to reporters outside the White House. “We will win that case in the Supreme Court of the United States.”

Roberts responded with a rare statement issued by the Supreme Court that began: “We do not have Obama judges or Trump judges, Bush judges or Clinton judges. What we have is an extraordinary group of dedicated judges doing their level best to do equal right to those appearing before them.”

Trump fired back on Twitter immediately: “Sorry Chief Justice John Roberts, but you do indeed have ‘Obama judges,’ and they have a much different point of view than the people who are charged with the safety of our country.”

Roberts let Trump have the last word, resisting any further provocation. He never again directly addressed a Trump attack on the judiciary.

Trump’s efforts to pick fights with judges

The intemperate Trump has continually tried to pull judges into the political muck with him.

His fixation was evident early. During his presidential campaign in 2016, he tried to disparage US District Judge Gonzalo Curiel, who was then hearing a Trump University fraud case in San Diego, as “a Mexican” judge who was unlikely to give him a fair shake.

As Trump intensified his dismissive comments about Curiel and sowed other doubts about his regard for the rule of law, the justices declined to comment on his candidacy, with one exception: Ruth Bader Ginsburg.

During an interview in July 2016, Ginsburg, surprised that Trump had become the Republican presidential nominee, told me, “He is a faker. He has no consistency about him. He says whatever comes into his head at the moment. He really has an ego.” Trump fired back, saying she should leave the bench: “Her mind is shot — resign!”

Ginsburg soon afterward expressed regret for her remarks, which were criticized across the ideological divide as improper for a jurist.

Once he became president, Trump continued to openly disdain the judiciary. He constantly tweeted about the justices, alternately viewing the Supreme Court as his savior or tormentor. “See you in the Supreme Court!” he crowed in 2017 when he lost an immigration case before lower court judges. A few years later, when the high court majority turned against his administration on a series of issues, Trump tweeted, “Do you get the impression that the Supreme Court doesn’t like me?”

The court, led by Roberts with a slim 5-4 conservative majority, did become increasingly skeptical of Trump administration policies. In spring 2019, Roberts pulled back on an initial vote for Trump’s plan to add a citizenship question to the 2020 census form. Roberts’ switched vote sealed the 5-4 ruling against the plan that immigrant rights groups feared would diminish Latino completion of the important decennial census questionnaire.

RELATED: How John Roberts killed the census citizenship question

After the ruling, Trump notably declared he would not give up the fight. “I have asked the lawyers if they can delay the Census,” he said in one tweet, following it later with a post that, “We are absolutely moving forward, as we must, because of the importance of the answer to this question.” But Trump soon had to retreat. There was no time to write a new justification for the citizenship question and defend it in court.

Financial records and separation-of-powers

The following year, Roberts quietly brokered strong majorities against Trump as the president was trying to keep his personal tax and other financial records from the Manhattan district attorney and, separately, committees of the US House of Representatives. These two cases represented the most direct separation-of-powers battles with Trump during his presidency.

The pair of disputes traced to business activities Trump had engaged in before becoming president. New York prosecutors were seeking nearly a decade’s worth of documents related to possible fraud committed by the Trump Organization and Trump himself, including whether he had, when a candidate, directed “hush money” to women who claimed to have had affairs with him. Trump has denied the women’s claims. (This New York financial investigation helped lead to Trump’s current charges.)

Separately, committees of the House of Representatives, led by Democrats in 2020, were trying to obtain Trump’s accounting and banking records as they developed ethics legislation to tighten money-laundering prohibitions.

Both disputes, Trump v. Vance and Trump v. Mazars, initially produced splintered, narrow votes among the justices as they privately discussed the cases. Over two months, however, Roberts coaxed and compromised behind the scenes for two 7-2 decisions against Trump’s arguments as he tried to keep his records secret.

Roberts had wanted to lift the issues beyond Trump and show the kind of court unity the justices were able to attain in past separation-of-powers battles, for example with Richard Nixon in 1974 and Bill Clinton in 1997. Also lurking in the background was the chief justice’s effort to distance the court from the most polarizing president in modern history.

As the turmoil continued, Roberts presided over Trump’s first impeachment trial (and acquittal) in the Senate, which arose from Trump’s 2019 apparent bargaining over military aid to Ukraine and a request to President Volodymyr Zelensky to investigate the Ukrainian activities of Joe Biden, whom Trump faced in the 2020 election.

Roberts declined to preside during Trump’s second impeachment trial, in 2021, when Trump had just left office and faced charges related to the January 6 attack on the US Capitol.

The Supreme Court continued to confront Trump post-presidency. In January 2022, the justices rejected Trump’s attempt to block the release of presidential records to a congressional committee investigating the siege of the Capitol. Only Thomas publicly dissented as the majority brushed away Trump’s effort to prevent the National Archives from turning over the documents to a US House select committee.

Trump’s East Room celebration for Kavanaugh in 2018, eclipsed by so many conflicts in the nearly five years since, still epitomizes an uneasy chapter of the Roberts Court in the Trump era. As Trump tried to keep the court in his clutches, he only widened the fissures.

He is out of office, but his presence looms in the judicial system and his legacy at the Supreme Court endures.

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