Trump Floats Impeaching Kavanaugh's Yale Roommate

United States District Court Judge James E. Boasberg, 2016. Photo courtesy of United States District Court for the District of Columbia. Public domain.

Trump calls him a troublemaker, a radical, an agitator. But the courtroom nemesis of the president just might be the steadiest, most well-connected judge in Washington — and he's not going anywhere.

For more than a year, Judge James "Jeb" Boasberg has quietly, methodically issued rulings that have disrupted key pieces of Trump's second-term agenda — from blocking mass deportations to overseeing cases tied to the Jan. 6 Capitol attack and Trump's past legal woes. Now, their feud is spilling out of the shadows, as Trump publicly calls for Boasberg's impeachment, and the judge — though publicly silent — keeps handing him legal setbacks anyway.

Boasberg isn't just another federal judge. He's at the center of a quiet legal resistance — and his closest friend just happens to sit on the Supreme Court.

Trump's Growing List of Legal Frustrations

Judge Boasberg has issued rulings in some of Trump's most politically explosive cases. He ordered former Vice President Mike Pence to testify to a grand jury in the 2023 special counsel investigation into efforts to overturn the 2020 election, while also shielding some lines of questioning from prosecutors.

He presided over numerous Jan. 6 cases, often delivering sentences lighter than what prosecutors demanded — but consistently described the riot as a violent attack by Trump supporters, not a false flag or government conspiracy. He also oversaw internal reforms following the FBI's surveillance failures during the 2016 Russia probe and criticized the Justice Department's handling of classified information requests.

More recently, Boasberg blocked the Trump administration from using the Alien Enemies Act — a wartime-era law — to deport Venezuelan men alleged to be gang members. Trump's Justice Department pushed ahead with two deportation flights anyway. Boasberg responded by demanding to know whether his ruling had been defied — setting off a showdown between the courts and the executive branch.

Trump responded by calling for Boasberg's removal and impeachment, saying the judge is an unelected "troublemaker and agitator," as reported by the Associated Press. The social media post typed in all caps drew a rare public rebuke from Chief Justice John Roberts, who defended judicial independence and stated impeachment was not a tool for punishing legal decisions.

The Power of Staying Quiet — And Connected

Boasberg, 62, hasn't responded to Trump's public attacks — not in statements, not on social media, not even through intermediaries. He has spoken only through his rulings and official court statements.

But that doesn't mean he's alone. One of Boasberg's oldest friends is Supreme Court Justice Brett Kavanaugh. The two were law school roommates at Yale, housemates off-campus, and early appointees of George W. Bush — both rising through the conservative legal world, despite now sitting on different sides of many rulings.

This friendship has become a quiet buffer against political pressure — and perhaps one reason why Boasberg, though now routinely targeted by Trump and his allies, hasn't faced serious consequences. His bipartisan bona fides also include a 2011 appointment to the federal bench by President Barack Obama and a decade of service on D.C.'s Superior Court after being nominated by President Bush.

Boasberg has a reputation for patience and professionalism — qualities that contrast sharply with Trump's scorched-earth approach to conflict.

Why the Clash Matters

Legal experts say the back-and-forth between Boasberg and Trump is more than a personality clash — it's a microcosm of the broader friction between the judiciary and the executive branch. Some warn that impeachment talk aimed at judges could set dangerous precedents, especially when those calls come from the Oval Office.

Boasberg, meanwhile, keeps working. He continues to lead lunches for federal judges in Washington and returns to Yale for speaking events that promote bipartisan respect for the rule of law. He's described by colleagues as someone who listens — even to people who disagree with him — and fosters calm in an era of chaos, NPR reports.

While Trump moves fast and punches hard, Boasberg plays the long game. That may be what irritates the president most. Because unlike political foes who fade when fired upon, Boasberg doesn't respond. He rules. And for now, the bench still has the final word.

References: Trump's Least Favorite Judge Has Friends in High Places | 4 Things to Know About Judge Boasberg as He Battles Trump Over Deportation Flights | A Look at the Judge Who Blocked Trump's Deportations and Is Now Facing Calls for Impeachment