‘A tough New Englander.’ Meet the South Natick carpenter’s son frustrating Trump as a federal judge.

WASHINGTON — US District Judge Richard J. Leon is a plainspoken South Natick native known in legal circles for sprinkling his rulings with exclamation points —an idiosyncrasy now getting national attention thanks to President Trump.

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The 76-year-old, bow-tie-wearing judge used 26 exclamation points to convey emphasis or indignation (“This argument is absurd!”) in an opinion striking down a Trump executive order targeting the WilmerHale law firm last year. He typed 14 of them into a February ruling blocking Defense Secretary Pete Hegseth from punishing Arizona Senator Mark Kelly, a Navy veteran, (“a troubling development in a free country!”) for a video telling US troops that they can refuse illegal orders.

And in a lawsuit to block Trump’s White House ballroom, Leon employed 19 exclamation points (“He is not … the owner!”) in March in ordering a halt to all but national security and safety related construction on the controversial project until Congress authorized it. Then he dropped three more into a short, follow-up order when the Trump administration tried to exploit that loophole.

“Defendants argue that the entire ballroom construction project, from tip to tail, falls within the safety-and-security exception and therefore may proceed unabated,” Leon wrote in a ruling that has been stayed while the White House appeals. “That is neither a reasonable nor a correct reading of my Order!”

Leon’s rulings have infuriated Trump and his allies, making him one of several perceived enemies on the bench for a president pushing the bounds of executive power. Right-wing influencer Laura Loomer labeled Leon “another dirty judge” and the president has called him a “Trump Hating Judge” who is “out of control.”

But in this instance, their target is no liberal they can brand as politically motivated. He’s a widely respected, Republican-appointed conservative. And those who know Leon say he is highly unlikely to be intimidated by Trump’s criticism.

“I’m just going to laugh and say, ‘No,’ ” said Karen E. Christian, a former Republican counsel on Capitol Hill who was Leon’s first law clerk in 2002 and remains close to him. “I think he has very thick skin. I think he sleeps well at night.”

Leon’s conservative bona fides run deep.

He played a public role on the team supporting the 1991 confirmation of Supreme Court Justice Clarence Thomas, a classmate at the College of the Holy Cross in Worcester. Leon then worked as counsel for congressional Republicans on three high-profile investigations before conservative President George W. Bush appointed him to the Washington, D.C., district court in 2002. And over the years, Leon has spoken at more than a dozen events sponsored by the Federalist Society, a conservative and libertarian legal organization.

Known for running an extremely tight ship in his courtroom and for a gregarious personality outside of it, Leon has ruled against executive overreach no matter the president. In 2008, he was the first federal judge to order the release of detainees at Guantanamo Bay, finding that five Algerian men had been held unlawfully during the war on terror that was the centerpiece policy of the president who picked him for the bench.

Leon’s reputation as an even-handed judge has earned him admiration from both sides of the political aisle. When his portrait was unveiled in 2018 at the Washington courthouse where he still works with a limited caseload as a senior judge, Republicans and Democrats turned out to honor him. According to Christian, they included three members of the Supreme Court: conservatives Thomas and Chief Justice John Roberts and liberal Elena Kagan.

“He is somebody who is straight as an arrow,” said John Podesta, who has served in multiple Democratic administrations. “This is a judge who takes separation of powers seriously.”

The two met in 1994 when Leon deposed Podesta — President Bill Clinton’s White House chief of staff at the time — during a House probe of the Whitewater controversy. Despite that bumpy start and their differing politics, the two became friends and have jointly taught a class on congressional investigations at Georgetown Law School for the past 30 years.

Leon often arrives wearing a Red Sox hat, Podesta said.

“He’s a tough New Englander. He’s going to call balls and strikes based on the merits of the case,” said Wendy Huang Waszmer, another former Leon clerk who worked in the Justice Department. “It’s not about whether you like someone or don’t like someone. It’s really what is the case that’s been put forward.”

Leon arrived on the federal bench from a modest background with deep Massachusetts roots.

Born and raised in South Natick, he is the son of a carpenter and was the first in his family to go to college. After graduating in 1971 from Holy Cross, where he was cocaptain of the lacrosse team, Leon attended Suffolk Law School. It was there he first aspired to work in Washington.

Watching the Senate Watergate hearings in 1973, he was “oh so impressed” with Fred Thompson, the young Republican counsel, Leon recalled in a Suffolk lecture in 1997.

“I even remember commenting to a bunch of my buddies as we watched the hearings one day how nice it would be to have the opportunity to do that,” Leon said. “One of my more cynical friends commented back, ‘Suffolk boys don’t get those assignments.’ We all laughed and we all agreed.”

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Leon’s point was simple and motivational: he got that opportunity and they could, too.

After working for the Justice Department early in his career, Leon was tapped in 1987 by then-US Representative Dick Cheney, the top Republican on the committee investigating the Iran Contra affair, to be the deputy chief minority counsel.

“He’s a big personality and still is a big personality, but was pretty easy to work with — with the caveat that we were not on the same team,“ said Neil Eggleston, a Harvard law professor who was Leon’s counterpart as deputy chief counsel for the Democratic majority.

As with Podesta, the partisan combat didn’t prevent the two from developing mutual respect and striking up a friendship. Eggleston has spoken to their Georgetown class multiple times, he said, with the three usually going out for burgers afterward.

Leon went on to serve as chief minority counsel on the House October Surprise Task Force in 1992-1993 and as special counsel in the House Whitewater investigation in 1994 and worked in private before become a judge. Since taking the bench, Leon has become a longtime mentor to many of his law clerks, often encouraging them to go into public service.

“He takes a great interest in their careers and their families and their children, and he’s just a part of your life forever after you’ve clerked for him,” said Susan McMahon, a professor at the University of California, Irvine, law school who clerked for Leon from 2008-09.

Christian said when her oldest son had cancer last year, Leon called her every other week.

“He turns his chambers into a family,” she said.

He is beloved by his former clerks, who describe him as engaging and entertaining outside the courtroom. “A true Renaissance man” one called him. Leon will let loose with a boisterous laugh, they said, and enjoys dishing out stories along with career and life advice, often during a daily snack time in his chambers or with a cigar on his patio.

The exclamation points he frequently uses reflect his passion for the job and desire to make his rulings on major cases resonate with the public.

“He writes in a very clear, common-sense kind of way that is accessible to people who are not lawyers,” McMahon said. “And I think that’s something that’s important to him, because he knows that some of these decisions have very important impacts.”

That was evident in his ruling in the case against Kelly, who made the “illegal orders” video with five other members of Congress who served in the military or intelligence services. Because Kelly is drawing a military pension, Hegseth censured him in January and began a process to consider reducing his retirement rank.

Kelly sued, and the case landed with Leon, who quickly blocked Hegseth’s punishment in a scathing order that included a typically blunt response to one of the Pentagon’s legal arguments: “Horsefeathers!”

“This Court has all it needs to conclude that Defendants have trampled on Senator Kelly’s First Amendment freedoms and threatened the constitutional liberties of millions of military retirees,” Leon wrote in a ruling the Pentagon is appealing. “After all, as Bob Dylan famously said, ‘You don’t need a weatherman to know which way the wind blows.’ To say the least, our retired veterans deserve more respect from their Government, and our Constitution demands they receive it!”

Ty Cobb, a Republican attorney in Washington who was on Trump’s White House legal team in his first term before becoming a critic of the president, predicted Leon “won’t hesitate to do what the law requires” despite the attacks from the White House.

“The rule of law in D.C. right now is something that the administration dances on,” Cobb said, “and I don’t think he’s happy about it.”

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