Trump reacts to contentious hearing over deportation flights

(CNN) — James Boasberg wasn’t supposed to be famous.

As the chief judge for the federal court in Washington, DC, Boasberg is well-liked in wonky legal circles and in the courthouse community. He’s a former law school roommate of Brett Kavanaugh and his personality has poked through his rulings with quirky uses of Star Trek quotes and Fugees lyrics.

Even with 23 years as a judge in DC, Boasberg is very far from a household name.

That all changed last week when Boasberg was randomly assigned a case that put him at a loggerheads with President Donald Trump and his administration’s efforts to use colonial-era laws and send undocumented immigrants to a notorious prison in El Salvador.

His attempts to reign in Trump administration officials who appeared to violate his orders with controversial deportation flights to El Salvador earned him the unwanted position of being the target of Trump’s red-hot fury. In a series of social media posts, Trump smeared Boasberg as a “Radical Left Lunatic Judge” and called for his impeachment, drawing a rare rebuke from Chief Justice John Roberts.

You wouldn’t know it from Trump’s angry reaction, but plenty of Boasberg’s past rulings and actions have actually aligned with the president’s political interests.

Boasberg was known for giving lenient punishments to January 6 rioters. In Trump’s first term, he released FISA court materials that exposed huge problems with the FBI’s probe into connections between Trump’s 2016 campaign and Russia’s election meddling. He also paved the way for conservative groups to obtain some of Hillary Clinton’s emails from her private server.

He’s also currently presiding over another high-profile and consequential federal cases: the Federal Trade Commission’s lawsuit against Meta, the parent company of Facebook.

“Boasberg is the opposite of a radical judge,” one former Justice Department prosecutor, who tried several January 6 cases in front of Boasberg, told CNN. “He was always fair and principled. You knew when you went into court with him, that he was going to follow the rules. He was very predictable because he followed the law. He is not a rash judge at all.”

Trump all week has complained about Boasberg, calling him “a Grandstander, looking for publicity,” and saying Friday in the Oval Office that he’s “sitting behind a bench and has no idea what’s going on.” The militant rhetoric from senior Trump officials about disregarding Boasberg’s orders and in-court stonewalling from Justice Department lawyers have raised the specter of a brewing constitutional crisis.

Trump says he sees the moment as a crisis as well – but one of Boasberg’s making, and it’s endangering American lives. Other White House aides said Boasberg was leading “the gravest assault on democracy” and that he committed an “egregious abuse of the bench.”

In some ways, the controversy isn’t really about Boasberg. It’s Trump who has a history of bashing any judge that rules against him – and praising anyone that rules in his favor. And as often happens amid these disputes, pro-Trump influences have followed up his public outbursts with increasingly personal attacks about Boasberg’s family and doxing-esque details about his home in DC.

Still, it’s not every day that the chief justice speaks out to defend a single lower-court judge. Even after Roberts’ public consternation, Trump continued attacking Boasberg and some House Republicans filed articles of impeachment that will likely go nowhere.

But their ire is perhaps misplaced.

Sources told CNN that they’ve never seen Boasberg as a partisan actor. He has handed down plenty of Trump-favorable rulings. Boasberg, 62, was appointed to the DC district court by President Barack Obama and was previously named to DC’s local courts by President George W. Bush.

“Remember who becomes federal judges – people who are willing to take a tenfold pay cut to spend the rest of their lives resolving impossible legal questions,” said CNN legal analyst Elliot Williams, who clerked for two federal judges. “It’s just not a community that seeks out the spotlight. I don’t think there’s a federal judge in America who relishes being tweeted about.”

Like most judges, Boasberg rarely speaks to the press and does not comment about cases. When he took the reins as chief judge in 2023, after his colleague Beryl Howell stepped aside, Boasberg emphasized that they prefer to work quietly, behind the scenes.

“Neither of us will be Time’s person of the year,” Boasberg told CNN at the time.

Decades of public service

According to Boasberg’s official biography, he is a DC native and graduated from an Episcopal college preparatory school for boys. He played college basketball at Yale while getting an undergraduate degree in history and later graduated from Yale Law School.

He eventually joined the Justice Department and prosecuted homicide cases in DC.

Bush appointed him in 2002 to be a judge on the DC Superior Court, which is essentially the state-level trial court for local DC cases. Obama elevated him in 2011 to serve on the DC District Court, which handles criminal and civil cases in DC’s federal jurisdiction.

The Senate confirmed Boasberg to his current court in a bipartisan 96-0 vote.

Among the notable Republicans who voted for Boasberg are current Senate Majority Leader John Thune, Secretary of State Marco Rubio, Senate Judiciary Committee chair Chuck Grassley, Senate Majority Whip John Barrasso, and former Senate Majority Leader Mitch McConnell.

He became the chief judge for the DC district court in 2023.

‘He follows the law’

As the chief federal judge in DC, Boasberg presided over secret grand jury matters that impacted the special counsel investigation into Trump’s attempts to overturn the 2020 election. He most notably ruled in 2023 that former Vice President Mike Pence must testify to special counsel Jack Smith’s grand jury, providing key firsthand evidence against Trump.

Like his colleagues on the bench, Boasberg has also seen his fair share of cases against individual January 6 rioters, including members of the far-right Proud Boys extremist group.

“He is principled and fair,” one former Justice Department prosecutor told CNN. “He is widely respected in the community for making principled decisions based on the facts in each case. He’s great to practice in front of, because he follows the law and the rules.”

One January 6 defendant, Jonathan Munafo, who pleaded guilty to assaulting police, publicly said he expected a “Boasberg discount” at sentencing, because of Boasberg’s reputation for handing out lenient punishments. (Munafo got nearly three years in prison.)

William Shipley, a conservative lawyer who has represented dozens of January 6 rioters, posted Sunday on X that, “Boasberg is easily in the top 1/2 of the most lenient sentencing judges, and possibly among the top 1/3,” among the judges who sentenced his clients.

Shipley – who supported Trump’s mass pardons for nearly all charged rioters – said he was defending Boasberg from “100% false” attacks levied by prominent members of the January 6 support groups whose claims about Boasberg went viral.

After a Supreme Court ruling that an obstruction charge couldn’t be used in January 6 cases, Boasberg even reduced the prison term of one Proud Boys member who had called him a “clown” and a “fraud” at his original sentencing, according to the Associated Press.

Other big cases: Clinton, Russia, Facebook

He is currently presiding over one of the most consequential digital monopoly cases: the Federal Trade Commission’s lawsuit against Meta. He has rejected attempts by Meta to dismiss the case, which is set to go to trial next month.

At the behest of a conservative legal group in 2016, Boasberg ordered the State Department to release some of former Secretary of State Hillary Clinton’s emails from her controversial private server, but also dismissed other lawsuits seeking more disclosures.

He rejected a longshot lawsuit to force the IRS to release Trump’s tax returns in 2017.

CNN previously reported that, while Boasberg presided over the Foreign Intelligence Surveillance Court, he encouraged the declassification of information related to the Trump-Russia probe. Trump and top Republicans have celebrated these disclosures.

These and other materials revealed systemic errors and sloppiness in the FBI’s efforts to wiretap a former Trump campaign aide in 2016 and 2017 who had strange Russian ties.

Personality pokes through

While getting his law degree at Yale, “Jeb” Boasberg lived in a house with future Supreme Court Justice Brett Kavanaugh and six other law students. (He graduated in 1990.) CNN has reported that the group is still close and takes annual trips together.

“Jeb is so social,” Amy Jeffress, a prominent defense lawyer in DC, told CNN in 2023.

Most judges do not have a physical presence around the DC courthouse, let alone walk around the building each day. But Boasberg enters the courthouse most mornings greeting security, court staffers and lingering reporters with a smile. Most days, he could also be spotted during the lunch hour, running to an off-site lunch or picking up takeout.

On the day in August 2023 when Trump was arraigned at the DC courthouse for his federal election subversion indictment, CNN spotted Boasberg making the rounds both inside and outside, talking with reporters about the events for the day. The chief judge’s presence was similar to that of a local mayor, shaking hands with everyone as he walked around.

“The first thing that comes to mind is – he was always fair,” a former courthouse employee said about Boasberg, adding that the chief justice was also always “approachable.”

The former employee added that Boasberg was always willing to listen to an argument before coming to a decision – not just with attorneys regarding a case, but with courthouse staff on administrative matters as well – because he was determined “to do what was best for the court.”

“He wasn’t one of those (judges) that had to have his way all the time,” the employee said.

At a tense court hearing Friday, Boasberg pledged to “get to the bottom” of whether Trump administration officials violated any of his order, and said the implications of Trump’s unprecedented use of a 1798 law to hasten the deportations was “awfully frightening.” He also spoke out about the importance of credibility to upholding the rule of law.

“I often tell my clerks before they go out into the world that the most valuable treasure they possess is their reputation and credibility,” Boasberg said.

CNN’s Katelyn Polantz, Tierney Sneed and Emily R. Condon contributed to this report.

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