Judge Richard Leon. (AP/AP)

Most of Judge Richard J. Leon’s background would not have foretold his new role as the jurist who would become a roadblock in the National Security Agency’s daily collection of virtually all Americans’ phone records.

Before Leon was nominated to the U.S. District Court in 2001 by President George W. Bush, he spent most of his career working for the government, serving as a congressional committee investigator and Justice Department attorney.

Yet in the 11 years he’s been on the bench, Leon has often used his position to hold government officials accountable.

In folksy and colorful language Monday, he took apart the government’s position in his ruling, saying that Founding Father James Madison would be “aghast” at the government’s encroachment on privacy rights and calling the bulk collection program “almost-Orwellian.”

Lawyers and friends say Leon, 64, is a maverick who has strong opinions and a case history that shows he hasn’t been partial to either political party. (Leon declined to be interviewed for this article.)

Conflicting rulings


On Dec. 16, U.S. District Court Judge Richard Leon ruled that a program that collects telephone metadata likely violates the Fourth Amendment. Read his ruling.


On Dec. 27, U.S. District Judge William J. Pauley said the bulk collection of Americans' telephone records is legal. Read his ruling.

“We knew from the Guantanamo litigation that Judge Leon cannot be pigeonholed,” said Stephen R. Sady, chief deputy federal public defender in Portland, Ore., and a longtime challenger of the government’s use of power.

Leon sided with the Bush administration in 2005 when he ruled that a group of detainees at Guantanamo Bay had no legal right to challenge imprisonment and seek release.

Once the Supreme Court reversed that ruling, Leon delivered a stinging indictment in 2008 of the same administration’s detention decisions and ordered the release of a group of detainees. Leon rejected the government’s assertions that the men were dangerous enemy combatants, and he took the unusual step of asking the Justice Department not to appeal his order.

“Seven years of waiting for a legal system to give them an answer . . . in my judgment is more than enough,” he wrote.

Both on and off the bench, Leon’s personality is big and his interests expansive.

“He loves Beethoven and he loves rock-and-roll,” said Richard Hauser, a vice president and assistant general counsel at Boeing, as well as a former law partner of Leon’s.

The judge, who favors bow ties, has retained traces of the accent he picked up during his childhood in South Natick, Mass., and he has a boisterous cackle that can be heard from a distance. Former clerks flock to the annual holiday potluck in his chambers and consider him a mentor.

When he has free time, he enjoys watching his son play lacrosse or joining his buddies for a round of golf and a cigar. Among his friends is Supreme Court Justice Clarence Thomas, who also attended the College of the Holy Cross and who issued the oath of office at Leon’s formal investiture ceremony.

In his courtroom, which has been home to high-profile cases in the District, Leon can be mercurial.

He sternly chastised Kwame R. Brown after the former D.C. Council chairman failed three times to report to authorities by telephone, as required by the court, before his sentencing in a bank fraud case. Leon placed Brown on an 11 p.m. curfew and displayed little patience with Brown’s apology last year.

“Your apology is a little late in the game,” Leon said. “What’s your excuse?”

The judge warned: “This is not the way to position yourself most favorably before sentencing.”

In 2007, when former Washington Teachers’ Union president Barbara A. Bullock faced sentencing for embezzling $4.6 million in union funds that she spent on luxury goods at Neiman Marcus and Tiffany, she told Leon she was deeply remorseful and that her bipolar disorder played a role in her crimes.

Leon responded sharply that only Bullock’s age — she was in her early 60s at the time — saved her from getting the maximum of 10 years in prison.

“This is a tragedy of self-destruction, a tragedy of which you were the architect,” Leon said in sentencing her to nine years. “You so badly abused a vital institution in this city.”

Prior to becoming a judge, Leon was a special counsel to the U.S. House Banking Committee for its Whitewater investigation. (He teaches a class on congressional investigations at Georgetown Law each spring with John Podesta, who formerly served as deputy chief of staff to President Bill Clinton.) In the 1990s, Leon also served as special counsel to the bipartisan Ethics Reform Task Force. In the 1980s, he also advised then-Rep. Dick Cheney during the Iran-contra investigation, which focused on the provision of arms to Nicaraguan fighters with funds obtained by arms sales to Iran.

In Monday’s ruling, Leon found that the government’s widespread collection of telephone records is likely unconstitutional, but he stayed a preliminary injunction while the government appeals the ruling.

In another show of Leon’s independent streak, his opinion contradicts that of bench-mate Colleen Kollar-Kotelly, who in 2004 authored the foundational opinion on bulk collection of telephone data.

In some of the footnotes in his NSA ruling, Leon ditches traditional legal citations for a more conversational style. He hypothetically describes the massive number of phone records, for instance, that the government could inadvertently scoop up if a person suspected of terrorist activity called his neighborhood Domino’s pizza shop.

That’s classic Leon, said David Laufman, a D.C. lawyer and former federal prosecutor who worked with the judge on two congressional committees.

“He’s going to bring to bear the kind of valor under political fire that the situation requires,” Laufman said, “regardless of whose ox might be gored.”

Carol Leonnig contributed to this report.