{"id":771,"date":"2026-05-20T09:34:34","date_gmt":"2026-05-20T09:34:34","guid":{"rendered":"https:\/\/bostonrelocationinsider.com\/?p=771"},"modified":"2026-05-20T09:34:34","modified_gmt":"2026-05-20T09:34:34","slug":"a-tough-new-englander-meet-the-south-natick-carpenters-son-frustrating-trump-as-a-federal-judge","status":"publish","type":"post","link":"https:\/\/bostonrelocationinsider.com\/?p=771","title":{"rendered":"\u2018A tough New Englander.\u2019 Meet the South Natick carpenter\u2019s son frustrating Trump as a federal judge."},"content":{"rendered":"<article>\n<div>\n<p><span>WASHINGTON \u2014 US District Judge Richard J. Leon is a plainspoken South Natick native known in legal circles for sprinkling his rulings with exclamation points \u2014an idiosyncrasy now getting national attention thanks to President Trump.<\/span><\/p>\n<p>Read more <a href=\"https:\/\/bostonrelocationinsider.com\/?p=770\">Jaylen Brown often rubs people the wrong way, but that doesn\u2019t mean he\u2019s not making some good points<\/a><\/p>\n<p><span>The 76-year-old, bow-tie-wearing judge used 26 exclamation points to convey emphasis or indignation (\u201cThis argument is absurd!\u201d) 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, (\u201ca troubling development in a free country!\u201d) for a video telling US troops that they can refuse illegal orders.<\/span><\/p>\n<\/div>\n<div>\n<p><span>And in a lawsuit to block Trump\u2019s White House ballroom, Leon employed 19 exclamation points (\u201cHe is not &#8230; the owner!\u201d) 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.<\/span><\/p>\n<div>\n<div>\n<div><span>Get Starting Point<\/span><\/div>\n<div><span>A guide through the most important stories of the morning, delivered Monday through Friday.<\/span><\/div>\n<div>\n<div><label>Enter Email<\/label><\/p>\n<div><button>Sign Up<\/button><\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<p><span>\u201cDefendants argue that the entire ballroom construction project, from tip to tail, falls within the safety-and-security exception and therefore may proceed unabated,\u201d Leon wrote in a ruling that has been stayed while the White House appeals. \u201cThat is neither a reasonable nor a correct reading of my Order!\u201d<\/span><\/p>\n<p><span>Leon\u2019s 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 \u201canother dirty judge\u201d and the president has called him a \u201cTrump Hating Judge\u201d who is \u201cout of control.\u201d<\/span><\/p>\n<p><span>But in this instance, their target is no liberal they can brand as politically motivated. He\u2019s a widely respected, Republican-appointed conservative. And those who know Leon say he is highly unlikely to be intimidated by Trump\u2019s criticism.<\/span><\/p>\n<p><span>\u201cI\u2019m just going to laugh and say, \u2018No,\u2019 \u201d said Karen E. Christian, a former Republican counsel on Capitol Hill who was Leon\u2019s first law clerk in 2002 and remains close to him. \u201cI think he has very thick skin. I think he sleeps well at night.\u201d<\/span><\/p>\n<p><span>Leon\u2019s conservative bona fides run deep. <\/span><\/p>\n<p><span>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.<\/span><\/p>\n<p><span>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.<\/span><\/p>\n<p><span>Leon\u2019s 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.<\/span><\/p>\n<p><span>\u201cHe is somebody who is straight as an arrow,\u201d said John Podesta, who has served in multiple Democratic administrations. \u201cThis is a judge who takes separation of powers seriously.\u201d<\/span><\/p>\n<p><span>The two met in 1994 when Leon deposed Podesta \u2014 President Bill Clinton\u2019s White House chief of staff at the time \u2014 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. <\/span><\/p>\n<p><span>Leon often arrives wearing a Red Sox hat, Podesta said.<\/span><\/p>\n<p><span>\u201cHe\u2019s a tough New Englander. He\u2019s going to call balls and strikes based on the merits of the case,\u201d said Wendy Huang Waszmer, another former Leon clerk who worked in the Justice Department. \u201cIt\u2019s not about whether you like someone or don\u2019t like someone. It\u2019s really what is the case that\u2019s been put forward.\u201d<\/span><\/p>\n<p><span>Leon arrived on the federal bench from a modest background with deep Massachusetts roots. <\/span><\/p>\n<p><span>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. <\/span><\/p>\n<p><span>Watching the Senate Watergate hearings in 1973, he was \u201coh so impressed\u201d with Fred Thompson, the young Republican counsel, Leon recalled in a Suffolk lecture in 1997. <\/span><\/p>\n<p><span>\u201cI 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,\u201d Leon said. \u201cOne of my more cynical friends commented back, \u2018Suffolk boys don\u2019t get those assignments.\u2019 We all laughed and we all agreed.\u201d<\/span><\/p>\n<p>Read more <a href=\"https:\/\/bostonrelocationinsider.com\/?p=768\">Jason Kidd is out as Mavericks coach, two weeks after Dallas hires new team president Masai Ujiri<\/a><\/p>\n<p><span>Leon\u2019s point was simple and motivational: he got that opportunity and they could, too.<\/span><\/p>\n<p><span>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. <\/span><\/p>\n<p><span>\u201cHe\u2019s a big personality and still is a big personality, but was pretty easy to work with \u2014 with the caveat that we were not on the same team,\u201c said Neil Eggleston, a Harvard law professor who was Leon\u2019s counterpart as deputy chief counsel for the Democratic majority. <\/span><\/p>\n<p><span>As with Podesta, the partisan combat didn\u2019t 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.<\/span><\/p>\n<p><span>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.<\/span><\/p>\n<p><span>\u201cHe takes a great interest in their careers and their families and their children, and he\u2019s just a part of your life forever after you\u2019ve clerked for him,\u201d said Susan McMahon, a professor at the University of California, Irvine, law school who clerked for Leon from 2008-09. <\/span><\/p>\n<p><span>Christian said when her oldest son had cancer last year, Leon called her every other week. <\/span><\/p>\n<p><span>\u201cHe turns his chambers into a family,\u201d she said. <\/span><\/p>\n<p><span>He is beloved by his former clerks, who describe him as engaging and entertaining outside the courtroom. \u201cA true Renaissance man\u201d 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. <\/span><\/p>\n<p><span>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.<\/span><\/p>\n<div>\n<div>\n<blockquote>\n<p>An exclamation point in the first paragraph can only mean one thing: It&#8217;s an opinion by Judge Leon.  https:\/\/t.co\/CeTyxHfcP5 pic.twitter.com\/dxyTSo0i4J<\/p>\n<p>\u2014 Orin Kerr (@OrinKerr) June 13, 2018<\/p><\/blockquote>\n<\/div>\n<\/div>\n<p><span>\u201cHe writes in a very clear, common-sense kind of way that is accessible to people who are not lawyers,\u201d McMahon said. \u201cAnd I think that\u2019s something that\u2019s important to him, because he knows that some of these decisions have very important impacts.\u201d<\/span><\/p>\n<p><span>That was evident in his ruling in the case against Kelly, who made the \u201cillegal orders\u201d 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. <\/span><\/p>\n<p><span>Kelly sued, and the case landed with Leon, who quickly blocked Hegseth\u2019s punishment in a scathing order that included a typically blunt response to one of the Pentagon\u2019s legal arguments: \u201cHorsefeathers!\u201d<\/span><\/p>\n<p><span>\u201cThis Court has all it needs to conclude that Defendants have trampled on Senator Kelly\u2019s First Amendment freedoms and threatened the constitutional liberties of millions of military retirees,\u201d Leon wrote in a ruling the Pentagon is appealing. \u201cAfter all, as Bob Dylan famously said, \u2018You don\u2019t need a weatherman to know which way the wind blows.\u2019 To say the least, our retired veterans deserve more respect from their Government, and our Constitution demands they receive it!\u201d<\/span><\/p>\n<p><span>Ty Cobb, a Republican attorney in Washington who was on Trump\u2019s White House legal team in his first term before becoming a critic of the president, predicted Leon \u201cwon\u2019t hesitate to do what the law requires\u201d despite the attacks from the White House.<\/span><\/p>\n<p><span>\u201cThe rule of law in D.C. right now is something that the administration dances on,\u201d Cobb said, \u201cand I don\u2019t think he\u2019s happy about it.\u201d<\/span><\/p>\n<p>Read more <a href=\"https:\/\/bostonrelocationinsider.com\/?p=766\">Eastern Mass. softball: Players of the Week for May 12-18<\/a><\/p>\n<\/div>\n<\/article>\n","protected":false},"excerpt":{"rendered":"<p>Richard J. Leon&#8217;s rulings have made him one of several judicial enemies of a president pushing the bounds of executive power.<\/p>\n","protected":false},"author":1,"featured_media":82,"comment_status":"open","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[2],"tags":[],"class_list":["post-771","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-politics"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.6 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>\u2018A tough New Englander.\u2019 Meet the South Natick carpenter\u2019s son frustrating Trump as a federal judge. - Boston Relocation Insider<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/bostonrelocationinsider.com\/?p=771\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"\u2018A tough New Englander.\u2019 Meet the South Natick carpenter\u2019s son frustrating Trump as a federal judge. - Boston Relocation Insider\" \/>\n<meta property=\"og:description\" content=\"Richard J. 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