WASHINGTON — Judge James E. Boasberg may be one of Donald Trump's most vocal critics on the bench today, but he also shares a personal history and professional lineage with Supreme Court Justice Brett M. Kavanaugh — a connection that defies the political labels often thrust upon him.

As detailed by Mattathias Schwartz in his article for The New York Times, the two jurists were once housemates at Yale Law School and have remained close for decades. Both are children of attorneys, attended elite prep schools in Washington, and were appointed to the bench by President George W. Bush. Friends describe their relationship as one of mutual respect, shaped by shared values and experiences.

Boasberg, 62, now chief judge of the D.C. District Court and former head of the FISA Court, became a target of Trump’s ire after he temporarily blocked the administration’s use of the Alien Enemies Act to deport Venezuelan nationals. Trump labeled him “a Radical Left Lunatic” and “a troublemaker,” yet many legal experts — including conservatives — describe him in strikingly different terms.

“He’s the epitome of an impartial judge doing his best to apply the law faithfully,” said retired appellate judge Thomas B. Griffith, who served on the D.C. Circuit after being appointed by President Bush.

Even among the “cubbies” — a tight-knit group of Yale classmates — Trump’s criticisms ring hollow. Kenneth Christmas, a fellow housemate and now an entertainment lawyer, recalled that both Boasberg and Kavanaugh served as the “ballast” of the group: grounded, measured, and always ready to listen to opposing views.

Boasberg’s distinguished judicial career has included clerking on the Ninth Circuit, working alongside Justice Neil Gorsuch in private practice, serving as a federal prosecutor, and receiving bipartisan support for his 2012 confirmation to the federal bench under President Obama. He was later appointed to the secretive FISA Court and named its presiding judge by Chief Justice John Roberts in 2020.

Despite Trump’s accusations of partisanship, Judge Boasberg has ruled both for and against Trump and his allies — from ordering the State Department to process Hillary Clinton’s emails in 2016 to blocking the release of Trump’s tax returns in 2017. He also restricted FBI agents involved in faulty surveillance during the Trump-Russia probe and rejected a 2021 lawsuit aimed at preventing Vice President Mike Pence from certifying Joe Biden’s electoral win.

Judge Reggie B. Walton, a fellow FISA Court appointee, described Boasberg as “an even-keeled judge who does what judges are supposed to do.” And J. Michael Luttig, a prominent conservative jurist, framed Trump’s attacks as part of a broader campaign to erode the judiciary’s independence.

Boasberg’s docket remains stacked with high-profile matters. He is set to preside over FTC v. Meta Platforms, a major antitrust trial, and American Oversight v. Hegseth, a case tied to the Trump administration’s handling of encrypted messages on the Signal app. Although Trump has accused Boasberg of cherry-picking politically sensitive cases, court records show the assignments followed a random process.

As Trump continues to challenge the legal limits of presidential power, it’s Judge Boasberg — tall, soft-spoken, and often seen chatting amicably in courthouse hallways — who remains a central figure in the legal resistance. Whether critics see him as a principled jurist or a symbol of judicial overreach, his approach remains firmly rooted in the law.

(Source: Matthias Schwartz and Alan Feuer for the New York Times)