Donald Trump’s Least Favorite Judge Embodies Our Legal Elite’s Arbitrary Authority

May 8

James Boasberg’s Inside Glide to Washington Power—and How He’s Abused It

This report originally appeared in Restoration of America News and is reprinted with permission.

In a series of recent reports, Restoration News investigated the lawyers and judges who are currently the most effective opponents of President Trump’s populist constitutional agenda. Their power, flowing from elite law firms and solidified by legal nonprofits, is ultimately predicated on the two drivers of modern politics: National security growth and government-backed mergers, since the 1950s the elevator music of Washington, D.C. The lawyers and judges who facilitate these transactions, like the composers of elevator music, are omnipresent but unnoticed, which makes them hard targets—at least until recently.

A walking embodiment of this legal supremacy has become President Trump’s least favorite judge: Federal District Judge James Boasberg. To call Boasberg the White House’s legal nemesis would be an understatement. Boasberg has not only ruled against Trump in a case regarding deportees to El Salvador, leading Trump to call for his impeachment. He is hearing a case on Trump Administration members’ inadvertent leaking of information about a military strike to a journalist. And he is the judge overseeing the Trump Justice Department’s landmark antitrust case against Facebook.

In the past few weeks, President Trump and his supporters have called Boasberg a “radical left lunatic.” But Boasberg is something worse for American democracy and constitutionalism than a radical. Boasberg is a legal insider: A seemingly unremarkable figure who speaks in reasoned tones which distract from the fact that he’s made his career being a servant of Washington’s two masters, the national security state and the state’s corporate clients.

Investigating Boasberg’s path to power, and the way he cloaks it and exercises it, shows the outsized influence of a single well-placed functionary who knows how to lubricate the gears of establishment Washington. It also shows the arbitrary ways in which operators like this gain and maintain power, to the detriment of accountable government and American democracy.

Boasberg’s Polished Veneer, his Connected Past…

An instructive place to start understanding Boasberg’s rise and impact is a recent, revealing New York Times article, titled “Trump’s Least Favorite Judge Has Friends in High Places.” It serves as a primer into not just Boasberg but into how the legal game works for those adept at playing it.

The story describes Boasberg, misleadingly, as succeeding because of his personality. According to The Times, he is “a moderate, known for his calm temperament and thoughtful jurisprudence” who is “also a particularly well-respected jurist with deep ties to members of the conservative legal establishment, such as Justice [Brett] Kavanaugh.” But “well-respected” doesn’t quite capture Boasberg’s stature in the eyes of his colleagues. One calls Boasberg “the epitome of…doing his best to apply the law faithfully.” Another describes him as “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.” A third testifies that “he ha[s] a very easy manner…even though he’s tall and commanding, he has a way of building rapport through his personality.” A separate article in The Washingtonian, Washington’s politics and society paper, calls Boasberg “perhaps the most powerful Swiftie in the nation,” divulging that Boasberg has cited Taylor Swift, Star Trek, and the Fugees in opinions—the all-around good-time judge.

But the hard facts of Boasberg’s career paint a different picture: Of someone whose prestige is entirely based on what The Times calls “a foundation of commonalities” shared with powerful people based on their membership in powerful institutions.

Boasberg is the son of Emmanuel “Tersh” Boasberg, a Yale undergraduate and Harvard Law graduate who became a civil servant for the Johnson Administration and later a “community icon” in Washington, D.C.—law faculty at Georgetown, chairman of the D.C. Historic Preservation Review Board, member of the D.C. Zoning commission. James Boasberg’s brother, Tom, a Yale undergraduate and Stanford Law graduate, made his career first as a tech entrepreneur in Silicon Valley and then as Denver Public Schools superintendent off an alliance with current U.S. Democratic Senator from Colorado Michael Bennett.

James Boasberg trod a similar early path as his father and brother. According to The Times, Boasberg’s close friendship with Kavanaugh is based on elite institutions: Having attended St. Alban’s private high school (Kavanaugh went to a private high school nearby); going to Yale as an undergraduate and then to Yale Law, where he roomed with Kavanaugh; and ruling from the same courthouse as Kavanaugh in Washington D.C.

…and His Path to Power

The justification for power transfers among connected families like the Boasbergs has always been that these families “give back” to the public, a story which Tersh and Tom Boasberg reinforce with their focus on philanthropy and education. But James Boasberg’s rise to a level of prominence unmatched by any sitting federal district judge doesn’t show much in the way of even surface-level idealism. Instead it shows a hard-nosed operator acquainted with the levers of power who knows how to play them, with a special focus on the two main levers of power in Washington: Corporate mergers and national security.

In the 1990s, straight out of law school, Boasberg worked for two boutique law firms founded by Ivy League graduates. These firms were part of the 1980s elite law boom off of corporate mergers and acquisitions flowing from Washington’s jettisoning antitrust policies of the kind the Trump Administration is helping bring back. At the second of these firms, Kellogg, Hansen, Todd, Figel & Frederick, he worked with Supreme Court Justice Neil Gorsuch.

Boasberg then returned to Washington and made his reputation in the field of national security: Serving as a federal prosecutor in the office of the U.S. Attorney for the District of Columbia. In 2002, the District of Columbia Judicial Nomination Commission recommended Boasberg for a spot on the Superior Court of the District of Columbia, and President George W. Bush appointed him. Almost a decade later, President Obama elevated him to the federal judiciary: The United States District Court for the District of Columbia, where he is now Chief Judge.

Boasberg’s insider route to the federal bench is not unheard of among the judicial and the legal elite, regardless of politics. Supreme Court Justice Neil Gorsuch’s mother, Anne Burford, ran the EPA for Ronald Reagan. Supreme Court Justice Kavanaugh's father was a highly influential government lobbyist. But Gorsuch and Kavanaugh embrace originalist jurisprudence, which can lead to a reduction of national security prerogatives and a reduction of corporate capture of government. Boasberg’s rulings, by contrast, have served to increase the power of unaccountable institutions, particularly the national security state, to his own career advantage.

Boasberg’s Use of the Law…

Tom Fitton, the president of the conservative advocacy group Judicial Watch, the one interviewee in The New York Times article who dissented from its rosy portrait of Boasberg, gave a telling example. He noted “that Judge Boasberg had ruled against his organization when they sued for the release of images showing Osama bin Laden’s corpse,” instead taking the position for suppressing the photos pushed by intelligence agencies. According to a report at the time of the ruling, “U.S. District Judge James Boasberg accepted the CIA’s assertion that release of any photos and video of the body of Osama bin Laden – former leader of al-Qaeda – would pose a major threat to national security, and that he would not overturn the agency’s decision to classify the records.”

Interestingly, Boasberg issued this ruling in 2012, and in 2014 he was appointed to the prestigious Foreign Intelligence Surveillance Court, the purpose of which is to rule on whether the government can secretly conduct wiretaps. The FISA Court was set up by post-Watergate legislation in the 1970s, but the Court’s importance is because of the War on Terror, which has turned it into a center of influence in Washington, D.C. Surely Boasberg, who after his appointment to the FISA court became its presiding judge, knew that his ruling in favor of the government in the bin Laden Case would strengthen his credentials for the FISA court, whose members are appointed by Chief Justice Roberts: A former federal prosecutor and strong backer of national security agencies.

And Boasberg’s rulings on the FISA Court could only have reinforced Roberts’s confidence in him. According to The Washington Post, “Boasberg oversaw changes to the FISA court after the Justice Department inspector general uncovered numerous errors and omissions in the FBI’s requests to wiretap Carter Page, a Trump campaign adviser, in its investigation into Russian interference in the 2016 election.” This kind of clean-up act is suspicious on its face, since Boasberg was one of the judges on the Court when the errors and omissions occurred. But Boasberg’s clean-up actions compounded the harm. According to The Post,

Boasberg…ordered a review of all actions by FBI lawyer Kevin Clinesmith, who the inspector general said altered an email that one of his colleagues relied on to surveil Page. However, Clinesmith pleaded guilty in district court . . . Boasberg sentenced Clinesmith to probation instead of prosecutors’ request for prison time . . . .

This is exactly the lack of accountability that encourages national security agencies to wiretap presidential candidates and communicate their findings to law firms. It is also the lack of accountability that has kept elected Presidents since John F. Kennedy and Richard Nixon from exercising firm oversight of these agencies, substituting for their oversight the arbitrary decisions of security agents overseen by judges. But judges like rulings like this: Tellingly, the judge who told The Times for its recent story that Boasberg “does the right thing in every case” is Republican-appointed Federal District Judge Reggie Walton, a predecessor of Boasberg’s as presiding judge of the FISA court. Chief Justice Roberts also likes Boasberg’s rulings. In 2020, Roberts appointed Boasberg to the Chief Judgeship of an even more exclusive court, the United States Alien Terrorist Removal Court, composed of five judges and “established in 1996 to determine whether an alien should be removed from the country for being a terrorist.”

…And His Abuse of It

Boasberg is eager to insert himself, and therefore the judiciary, into cases where the power of Washington’s permanent national security and corporate establishment is under threat, and he is not picky about disregarding procedural niceties to do so. When it came to Boasberg’s participation in the recent case involving the Trump Administration’s deportations, U.S. Senator Eric Schmitt, a Republican and former Missouri Attorney General, has commented that, as Chief Judge of the DC Circuit,

[Boasberg] inserted himself in that role . . . He was on vacation. The case was filed at 2:30 in the morning, somehow he ended up with that case. He wasn’t the emergency judge on duty, so I think this requires further investigation and legislation.

Boasberg has made a similar play regarding the seminal antitrust case brought by the Trump Justice Department against Meta over which he’s presiding. He has not recused himself from the case despite the fact that, when he worked at Kellogg, Hansen, Todd, Figel & Frederick at the start of his career, one of his bosses was Mark Hansen, the second named partner of the firm; and it is Mark Hansen who is appearing before Boasberg arguing why Meta should not be broken up, after Boasberg dismissed the initial government filing against Meta in 2021.

Tellingly, no one outside of a few antitrust advocates has mentioned this fact. Indeed, just a week before hearing the case against Meta, Boasberg actually spoke at an antitrust conference hosted by the American Bar Association—and, as Restoration News has reported, he brought down the house with a sly joke about his enmity with Donald Trump. Reinforcing the legal elite’s indirect support of Boasberg has been the direct defense of him from Chief Justice Roberts, who issued a pointed defense of judicial power and impartiality immediately after President Trump criticized Boasberg. According to Roberts, in a statement criticized by prominent conservative news outlets including The Federalist, the threat of judicial impeachment Trump made against Boasberg is neither appropriate nor merited.

But impeachment is a democratic process, and Boasberg’s authority as well as the way he uses it—withholding information and incentivizing government falsehoods; recusing and assigning himself to cases at will; blocking executive policies supported by the American majority—is anything but democratic. In fact a person like Boasberg having the authority he does is anathema to American democracy. Boasberg’s life and career has been the epitome of insularity: He is inexperienced with most of America, but, thanks to Washington policies on war and corporate consolidation, he nonetheless has enormous power over Americans. He is one of the most powerful members of a caste of rulers in robes who aren’t only failing to responsibly regulate politics; they’re also failing to responsibly regulate each other. So Americans have to do it for them.

Matt Wolfson