Trump’s Least Favorite Judge Has Friends in High Places

Before they were federal judges, James Emanuel Boasberg and Brett M. Kavanaugh were classmates at Yale Law School and housemates in a red brick off-campus townhouse, where they forged a bond that carries forward to this day.

Their friendship, according to interviews with six law school classmates, draws on a foundation of commonalities: Both men are the sons of attorneys and attended elite private high schools in Washington — Georgetown Preparatory for Justice Kavanaugh, St. Albans for Judge Boasberg. Both went to Yale as undergraduates. Both were first appointed to the bench by President George W. Bush. As judges, they overlapped for more than seven years at the E. Barrett Prettyman U.S. Courthouse in Washington, D.C.

The two jurists, neither of whom commented for this story, “have a lot in common,” said Amy Jeffress, a former law school classmate, who said Judge Boasberg and Justice Kavanaugh have been close since she knew them in school.

Friends and colleagues describe Judge Boasberg, who goes by Jeb, as a moderate, known for his calm temperament and thoughtful jurisprudence. He is also a particularly well-respected jurist with deep ties to members of the conservative legal establishment, such as Justice Kavanaugh.

In 2018, President Trump elevated Judge Kavanaugh to the Supreme Court. Last month, the president called for Judge Boasberg to be removed from the bench after he issued an order temporarily stopping the administration from using the Alien Enemies Act, a wartime law, to deport men accused of being Venezuelan gang members to El Salvador. Mr. Trump called Judge Boasberg, 62, “a Radical Left Lunatic, a troublemaker and agitator.”

Lawyers, court watchers and other judges who know Judge Boasberg say that out of the 635 trial court judges on the federal bench, Mr. Trump has chosen an especially hard target to paint as an out-of-step radical.

“He and I might have different views about how to interpret a statute or the Constitution, but in every case in which I reviewed his work, I found him to be the epitome of an impartial judge doing his best to apply the law faithfully,” said Thomas B. Griffith, a retired judge who served for 15 years on the U.S. Court of Appeals for the D.C. Circuit after being nominated by President George W. Bush.

In a hearing on Thursday, Judge Boasberg said he would soon rule on whether there was probable cause to hold the administration in contempt for ignoring his order last month barring about 100 Venezuelan deportees from being flown to El Salvador. A contempt ruling would represent a new level of constitutional tension between the judiciary and the administration.

Kenneth Christmas, who lived with Judge Boasberg and Justice Kavanaugh in the townhouse at 61 Lake Place in New Haven, Conn., said Mr. Trump’s characterization of Judge Boasberg did not match up with the man he knew. Mr. Christmas said the commonalities between the two jurists went beyond their backgrounds.

“In our group, they are the ballast,” he said. “They both stand their ground. They have a viewpoint, but they both are eager what the other side has to say.”

Mr. Christmas, now an entertainment lawyer and consultant, recalled that as students, the group called themselves the “cubs” or “cubbies.” For the next 30 years, the eight men have gathered annually for “cub weekends” to “commiserate, commemorate and support each other,” Mr. Christmas said.

Their 2001 weekend, aboard a 55-foot sailboat, surfaced years later when an email Justice Kavanaugh wrote about it came up during his tense Supreme Court confirmation process.

In 2004, Mr. Christmas said, he and Judge Boasberg were among a few dozen guests invited to the White House to celebrate the wedding of their fellow cub Justice Kavanaugh, who was then President George W. Bush’s staff secretary. Judge Boasberg and the other guests enjoyed a Rose Garden dinner, an Oval Office tour and an informal chat with the president, Mr. Christmas recalled.

Judge Boasberg clerked on the U.S. Court of Appeals for the Ninth Circuit and worked in private practice, where he was briefly a colleague of Justice Neil M. Gorsuch’s at Kellogg, Huber, Hansen (now Kellogg Hansen) before becoming a federal prosecutor in Washington.

He was nominated to judgeships by presidents from both parties, first by President Bush to the D.C. Superior Court in 2002, then to the Federal District Court bench by President Barack Obama in 2011, to which he was confirmed the next year by a 96-0 Senate vote.

Among the 44 Republican senators who voted in his favor were Marco Rubio of Florida and Jeff Sessions of Alabama, both of whom would become members of a Trump cabinet. Justice Kavanaugh, who was then a federal appellate judge, administered the oath at Judge Boasberg’s investiture ceremony.

In 2014, Chief Justice John G. Roberts Jr. appointed Judge Boasberg to the Foreign Intelligence Surveillance Court, also known as the FISA court. It is a sensitive assignment that deals with secret warrants for government wiretaps and searches. Chief Justice Roberts named him the court’s “presiding judge” in 2020, a position that put him in charge of its administrative matters. He became chief judge of the D.C. district court in 2023.

Judge Boasberg is known as a “feeder judge,” with 17 clerks who served in his chambers going on to work at the Supreme Court. Five worked for justices nominated by Republican presidents — three for Chief Justice Roberts, one for Justice Kavanaugh and one for Justice Anthony Kennedy.

Judge Boasberg is “an even-keeled judge who does what judges are supposed to do, which is simply to do the right thing in every case that comes before him,” said Judge Reggie B. Walton, an appointee of Republican presidents who served with him on the both in the district court in Washington and on the FISA court.

At the courthouse, Judge Boasberg, who is just shy of six-and-a-half feet tall, is a visible and popular figure, often seen walking the hallways chatting in a deep voice with reporters, security guards and other judges.

“He had a very easy manner with jurors,” said Ms. Jeffress, who worked with him as a federal prosecutor. “Even though he’s tall and commanding, he has a way of building rapport through his personality.”

Some of Mr. Trump’s most ardent supporters, on the other hand, argue that Judge Boasberg’s deep ties to his jurist peers merely illustrate their critiques of the judiciary as a cozy club. Judge Boasberg is “a political actor,” said Mike Davis of the Article III Project, a conservative judicial advocacy group.

“The chief justice put him on the FISA court, and he’s been longtime buddies with other justices,” said Mr. Davis, who was instrumental in assisting Justice Kavanaugh’s confirmation to the Supreme Court. “He’s way out over his skis on this one, but we’ll see if his buddies protect him or follow the Constitution.”

Despite Mr. Trump’s complaints, Judge Boasberg has ruled both for and against Mr. Trump and his allies in the past.

Weeks before the 2016 election, Judge Boasberg ordered the State Department to process nearly 15,000 emails from Hillary Clinton, then a candidate, for their potential release. The next year, he blocked the release of Mr. Trump’s tax returns, ruling that only he or Congress could force the documents into the public eye.

As presiding judge of the FISA court in 2020, Judge Boasberg handled the fallout from an inspector general’s findings that the F.B.I. had botched wiretap applications in the Trump-Russia investigation; he barred agents involved in them from working on future wiretap applications and imposed new restrictions on the bureau.

He also rejected an attempt to block Vice President Mike Pence from certifying President Biden’s victory over Mr. Trump. That lawsuit “would be risible if its target were not so grave,” Judge Boasberg wrote, “the undermining of a democratic election for president of the United States.”

“Some may view his opinions as conservative, and others may view them as liberal, but they’re all faithful applications of the law to the case before him,” said David Tatel, a retired judge who was appointed to the bench by President Bill Clinton and served for 29 years on the U.S. Court of Appeals for the D.C. Circuit.

Judge Boasberg is “personable” and “his demeanor is excellent on the bench,” said Tom Fitton, the president of the conservative group Judicial Watch who is an outspoken supporter of Mr. Trump. But he disagreed that the judge’s evenhanded reputation was entirely deserved. Mr. Fitton noted that Judge Boasberg had ruled against his organization when they sued for the release of images showing Osama bin Laden’s corpse.

“He deferred to the government,” Mr. Fitton said, of the bin Laden case. “Here, you have President Trump making a proclamation about foreign terrorists being present in the United States, in concert with a foreign government, and he shuts it down within a minute.”

The case dealing with the Alien Enemies Act is not Judge Boasberg’s only high-profile matter. On April 14, he is scheduled to begin the trial of F.T.C. v. Meta Platforms, a blockbuster antitrust case that Mark Zuckerberg, Meta’s chief executive, is lobbying Mr. Trump to drop.

Then there is American Oversight v. Hegseth, a case brought by a government watchdog seeking to preserve the contents of a group chat on the Signal app where Defense Secretary Pete Hegseth and other top Trump administration officials accidentally shared sensitive information with Jeffrey Goldberg, the editor in chief of The Atlantic.

Mr. Trump has accused the judge of “grabbing the ‘Trump Cases’ all to himself,” but the cases were assigned through a normal process of random selection. During a hearing on the Signal case, Judge Boasberg calmly explained that process from the bench and did not appear to be fazed. Then he ordered the officials involved to preserve their Signal messages.

J. Michael Luttig, a former appellate judge and respected member of the conservative legal movement who has become a critic of Mr. Trump’s, called attacks on Judge Boasberg part of a larger pattern of Trump “trying to browbeat judges into submission to his will.”

He disputed that Judge Boasberg was trying to usurp presidential power, as Mr. Trump has asserted, but said instead that the judge had issued a series of temporary orders to allow time for further deliberation about whether Mr. Trump’s use of the Alien Enemies Act is legal.

“That’s what judges do — it’s their quintessential role,” Judge Luttig said. “They determine what the law is.”

Charlie Savage contributed reporting. Sheelagh McNeill contributed research.