Trump Judicial Foe Was Kavanaugh’s Roommate, Had GOP Support (1)

President Donald Trump says the judge is a “Radical Left Lunatic” who should be impeached. The attorney general says he’s protecting terrorists. Justice Department lawyers say his rulings are undermining a vital effort to deport Venezuelan gang members.

But to those who know Judge James “Jeb” Boasberg personally, through his early work as a homicide prosecutor and later as a judge, the accusations seem wildly off base. They reject Trump’s description of the jurist and say the president and his supporters don’t appear to know him at all.

The standoff reached new heights Monday night when the Trump administration said in a court filing that it wouldn’t hand over data Boasberg requested about deportation flights. Earlier in the day, Justice Department lawyers argued at a hearing that Boasberg’s rulings are trampling the authority of the executive branch. It’s a fight that could wind up at the US Supreme Court.

In the meantime, another high-profile legal fight landed on Boasberg’s docket this week through the court’s random assignment system. He’ll also preside over a lawsuit accusing several members of Trump’s cabinet of violating US laws meant to preserve official records by using the encrypted messaging app Signal.

Boasberg, 62, has a track record of straightforward rulings in complicated cases — including several decisions in favor of Trump — and a history of support from both Republicans and Democrats. He was a homicide prosecutor in 2002 when President George W. Bush tapped him as a judge for the Superior Court of the District of Columbia, and after being nominated to the federal bench in 2011 by Barack Obama, Boasberg was confirmed unanimously by the Senate Judiciary Committee.

James Boasberg on March 13, 2023.

Photographer: Valerie Plesch/Bloomberg

His defenders also point to his long friendship with conservative Supreme Court Justice Brett Kavanaugh, his roommate at Yale University’s law school, as further evidence he harbors no anti-Republican bias. The conservative Supreme Court Chief Justice John Roberts — who issued a rare public rebuke to Trump over the impeachment threat — selected Boasberg in 2014 to serve on the secretive US Foreign Intelligence Surveillance Court, a prestigious role.

Lionel André, a white-collar criminal defense lawyer who overlapped with Boasberg at the US Attorneys’ Office in Washington in the early 2000s, said the accusations made against his former colleague are unfounded.

“These claims that he’s some kind of partisan judge or activist Democrat — nothing is further from the truth,” André said. “You would have never known that he was a Bush appointee unless you read it, and you’d never know he was elevated by Obama unless you read it, because you would never be able to tell from his rulings.”

The criticism of Boasberg is part of the Trump administration’s growing rift with the judiciary over federal powers, particularly related to immigration and the government workforce. More than 150 challenges to Trump’s policies are currently making their way through the courts.

A three-judge panel held a hearing Monday over the government’s efforts to lift Boasberg’s temporary order that restricts new deportations under the Alien Enemies Act of 1798 until those being removed are given an opportunity to challenge their connection to the violent Tren de Aragua gang. Members of the federal appeals court panel appeared divided as they weighed the issue.

Boasberg on March 15 tried to halt deportations that were already underway, certifying a class action lawsuit for those potentially affected and ordering a Justice Department lawyer to tell the government to turn around any flights that had already left the US.

As Boasberg spoke, two planes were already taking alleged gang members to a notorious El Salvador prison. They didn’t turn around. A third flight left after the court hearing ended, and since then Boasberg and the Trump administration have clashed repeatedly.

US Attorney General Pam Bondi blasted Boasberg during an interview on Fox News last week, saying the judge was “meddling in our government” and “trying to protect terrorists who invaded our country.”

Pam Bondi, US attorney general, on March 24, 2025.

Photographer: Samuel Corum/Sipa/Bloomberg

The bitter attacks on Boasberg claim that he’s overstepping his authority and is biased. His family has also come in for scrutiny. Trump’s supporters have cited his wife’s donations to Democrats and his daughter’s work for a nonprofit that operates in underserved communities as evidence that the judge must not be impartial.

Boasberg, through a court spokesperson, declined to comment.

Boasberg grew up in Washington. His mother was a landscape architect and was described in her 2012 obituary as a “dogged advocate” for the city’s green spaces. His father was a lawyer; the couple moved to Washington when he was recruited for a Johnson administration initiative.

The younger Boasberg played forward for Yale’s basketball team as an undergraduate all four years at college, though he wasn’t a regular starter. After graduating from law school, he worked in California for a few years, then returned to Washington in 1995.

Boasberg’s confirmation hearings provide insight into his bipartisan appeal. At his hearing to become a Superior Court judge, the late US Senator John Warner of Virginia, a Republican and former US Navy Secretary, praised Boasberg as a “fine man.” Warner’s son John had been close friends with Boasberg since the 4th grade, when they attended Washington’s elite St. Albans School together.

The senator read into the record a statement by his son that said Boasberg had long reminded the younger Warner of Abraham Lincoln, not just because of his stature, but due to his “leadership, morality, wisdom, and just plain good looks.”

“He has kept these values intact to this day,” the senator’s son wrote. “He is also one heck of a good basketball player.”

At Boasberg’s confirmation hearing to become a federal judge nearly nine years later, Senator Dick Durbin, a Democrat, asked the nominee about his temperament on the bench. The judge said that he took pride in working through tough issues, saying he’d “never flown off the handle” and never held anyone in criminal contempt.

“I think that judges who are best able to control their courtrooms are ones who don’t threaten contempt all the time,” Boasberg said.

But the case over the Alien Enemies Act has been contentious. Trump’s proclamation invoking the act claimed gang members were conducting “irregular warfare” on behalf of the Venezuelan government, engaging in murders, kidnappings and other crimes.

In this photo released by the El Salvador Presidency, alleged gang members arrive in El Salvador by plane.

Source: El Salvador Presidency/Anadolu/Getty Images

On March 17, the judge held a hearing to determine how many people were deported based on Trump’s proclamation and whether the government’s flights carrying people out of the country violated his order.

A Justice Department lawyer, Abhishek Kambli, said he couldn’t disclose any information about the flights, citing national security concerns. He said the judge lost jurisdiction over the planes “the moment they were outside of US airspace.” The government also didn’t have to comply with the judge’s oral order, only his written order, Kambli said.

“The idea that because my written order was pithier, that this could be disregarded, that’s a heck of a stretch,” Boasberg told Kambli.

Read more: Judge Denies Trump Bid to Resume Deporting Accused Gang Members

The case isn’t the first time Trump has crossed paths with Boasberg, who has handled a series of cases related to his first term in office and later legal troubles. In 2017, he rejected a lawsuit seeking to force the Internal Revenue Service to release Trump’s tax returns. In 2020, he ordered the Dakota Access pipeline to shut down after finding environmental law violations by the Trump administration, though an appeals court overruled that decision.

When he became chief judge in 2023, Boasberg took over handling nonpublic proceedings between Trump’s legal team and then-special counsel Jack Smith related to grand jury activity and materials. He was responsible for ordering former Vice President Mike Pence to testify in one of the criminal probes into Trump. That same year, Boasberg denied requests by media outlets including Bloomberg News to pry loose more records from grand jury proceedings related to Trump.

“His academic accomplishments were really remarkable,” said Glenn Kirschner, who worked closely with Boasberg in the early 2000s when they were both federal prosecutors. “But when you get to know him and spend time with him and see him interacting with folks — whether it’s witnesses, victims, police officers, FBI agents, court reporters — he had this ability to instantly connect with everyone from every walk of life.”

Before becoming a judge, Boasberg clerked for Judge Dorothy W. Nelson on the 9th Circuit federal appeals court in the early 1990s before working as an associate at Keker & Van Nest in San Francisco and Kellogg, Hansen, Todd, Figel & Frederick Pllc in Washington.

André, the lawyer who overlapped with Boasberg at the US Attorney’s Office, said the government may have had better luck if the Justice Department had simply offered the judge a full explanation about why the deportations were taking place.

“You have to lay down the facts to support your case,” André said. “He’s the kind of judge who will listen.”

(Updated with information about a new case assigned to the judge.)

--With assistance from David Voreacos.

To contact the reporters on this story:
Erik Larson in New York at elarson4@bloomberg.net;
Zoe Tillman in Washington at ztillman2@bloomberg.net

To contact the editors responsible for this story:
Ben Bain at bbain2@bloomberg.net

Brendan Walsh, Pratish Narayanan

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