By Chris Caesar
law of technology
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winter 2026
rule of law
When President Donald Trump issued an executive order targeting the law firm WilmerHale for its ties to former special counsel Robert Mueller and its work on immigration and diversity initiatives, it raised immediate constitutional questions.
U.S. District Judge Richard J. Leon, JD ’74, HLLD ’06, struck down the order as unconstitutional and permanently barred the government from enforcing it.
The order was part of a series of executive actions aimed at major law firms that President Donald Trump issued in the spring of 2025. In WilmerHale’s case, Trump alleged the firm engaged “in activities that undermine justice and the interests of the United States.”
The administration argued that firms engaging in DEI and immigration advocacy posed risks to national security by potentially influencing government personnel and policy through their access to federal facilities and classified information. The order revoked security clearances for WilmerHale employees and sought to bar them from federal property.
Judge Leon—who was appointed by President George W. Bush to the U.S. District Court for the District of Columbia—decisively rejected the administration's position. “The cornerstone of the American system of justice is an independent judiciary and an independent bar willing to tackle unpopular cases, however daunting,” he wrote at the start of his opinion. “The Founding Fathers knew this! Accordingly, they took pains to enshrine in the Constitution certain rights that would serve as the foundation for that independence.”
Leon’s opinion drew unusual media attention for its forceful style. Reporters noted that the 73-page ruling bristled with emphatic language and even exclamation points—rare in federal decisions. Coverage described the opinion as unusually vivid for a case about executive authority, signaling the constitutional stakes at play.
Leon determined the order was unconstitutional on a number of grounds, including abrogating the firm’s—and by extension its clients’—ability to petition the government for redress of grievances by trying to bar its lawyers from government facilities without any compelling reason. “The Order does not explain how WilmerHale’s conduct has threatened national security or how restricting its access to federal buildings or federal employees would remedy those threats,” he wrote.
Leon is one of several judges who have struck down similar orders targeting law firms, although nine firms have settled out of court, agreeing to do pro bono work Trump favors in exchange for protection from the administration’s directives.
The Trump administration has appealed Judge Leon’s ruling and the two other decisions striking down similar orders. The cases are now before the U.S. Court of Appeals for the D.C. Circuit, with outcomes that will help define the limits of presidential power and the judiciary’s role in protecting an independent bar.
By Robert Schlesinger
Judge Richard Leon’s ruling on the WilmerHale executive order is one of many high-profile decisions in a judicial career that began far from the D.C. District Court. Raised in Natick, Massachusetts, the son of a carpenter, the 1974 Suffolk Law graduate was the first in his family to attend college and law school. Judge Leon has maintained ties to Suffolk Law throughout his career, hiring graduates as clerks and returning to campus for events. In November 2024, he joined four other Suffolk Law alumni serving on the federal bench—Judge Gustavo Gelpí, JD ’91, HLLD ’06; Judge Mary McElroy, JD ’92; Judge Marianne B. Bowler, JD ’76, HLLD ’94; and Judge Joan N. Feeney, JD ’78, HLLD ’06—for a panel discussion on their judicial careers.
A Record of High-Profile Cases
During the panel discussion last year, Judge Leon spoke about three of his biggest cases on the federal bench:
U.S. v. AT&T and Time Warner (2018): Leon presided over a six-week trial involving a $108 billion merger, the first fully litigated vertical merger challenge in nearly 40 years. Most antitrust challenges involve horizontal mergers (between direct competitors). Vertical mergers involve companies at different levels of the supply chain. Leon denied the government’s request to enjoin the merger, a decision that the circuit court subsequently upheld.
Boumediene Habeas Cases (2008): Following a Supreme Court decision granting Guantánamo detainees habeas rights, Judge Leon became the first jurist to hear one of the related cases. He ordered the release of five Algerian men being held at Guantánamo, after finding insufficient evidence to justify their detention.
McConnell v. FEC (2003): Leon served on a three-judge panel reviewing the McCain-Feingold campaign finance law, adjudicating what he described as the largest First Amendment case in U.S. history. The district court opinion he co-authored, which upheld parts of the law while striking down others, exceeded 1,600 pages.
From Iran–Contra to Whitewater: High-Stakes Capitol Hill Counsel
Before he was appointed to the bench, Leon served in high-profile congressional investigations involving three sitting presidents, Bill Clinton, George H. W. Bush, and Ronald Reagan—all as counsel for the Republican minority. He was Special Counsel to the House Banking Committee during its 1994 Whitewater inquiry into President Clinton, Chief Minority Counsel for the House Foreign Affairs Committee’s 1992-1993 October Surprise Task Force, and Deputy Chief Minority Counsel during the 1987-1988 Iran–Contra hearings. These roles placed him at the center of politically sensitive investigations long before his judicial career.
From Natick to the Federal Bench: Judge Leon’s career spans Guantánamo and Capitol Hill
Photography: Michael J. Clarke
“The cornerstone of the American system of justice is an independent judiciary and an independent bar willing to tackle unpopular cases, however daunting.”
Judge Richard J. Leon,
JD ’74, HLLD ’06
U.S. District Judge
