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Psychology

A Young Clerk Lured a Modest Judge Into a Limo, and Started a 30-Year Ritual

The farewell prank on the future Supreme Court justice led to three decades of hiking by day and fine dining by night.

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Original Jurisdiction · The Making Of A Celebrity Litigator: Mathew Rosengart

The chauffeured limousine pulled up to the run-down country home in New Hampshire, and out came a judge who, in Rosengart's words, "didn't like a lot of largesse."

The passenger was David Souter, then a justice serving on New Hampshire's highest court, a bookish New Englander with what his young assistant called a Yankee veneer. The ride had been arranged by Rosengart and his co-clerk, junior lawyers hired to help a judge research cases and draft opinions, who had decided that a goodbye lunch would not be enough.

Mathew Rosengart, now a trial lawyer, tells the story as the start of one of the longest friendships of his life. What began as a one night trick became a ritual the three men repeated for about 30 years: a daytime hike together in the White Mountains, followed by drinks and dinner in Boston.

It started with nerve. In 1988, Rosengart was a student at Boston College Law School and was about to accept a prestigious federal clerkship. Souter, who hired one clerk from Boston College and one from Harvard, invited him to interview. Souter asked in a deep Yankee accent which Supreme Court decision of the past 50 years Rosengart would reverse and why.

Rosengart, sweating, answered with a case from his criminal procedure class. Then he turned the question back on the judge. Souter answered, and Rosengart credits what he calls his impudence or confidence for winning him the job over the safer federal post.

The clerkship year, spent in Concord, turned into something more than work. Souter deliberately hired clerks he thought could become lifelong friends, and Rosengart says the three men developed what he calls an alchemy. Souter, though warm, funny, and decent, did not go in for show.

So for the farewell, Rosengart and his co-clerk used what he calls a little subterfuge. Souter agreed to dinner in Boston instead of what Rosengart called "a more mundane lunch on Main Street in Concord." He did not know about the limousine, or the plan for drinks at the Ritz-Carlton on the Public Garden, or what Rosengart described as "dinner at his favorite restaurant the venerable" Lock-Ober Cafe.

They did it again the next year, and the next. Each time, the three hiked a different mountain in the White Mountains presidential range, then drove to Boston for drinks at the Ritz, a stroll through the Public Garden and Boston Common past the moving Augustus Saint-Gaudens sculpture of Robert Gould Shaw and the 54th Regiment outside the State House, and dinner at the Lock-Ober, a spot long visited by the Kennedys, Oliver Wendell Holmes, and Souter himself since his Harvard days.

Souter, who later joined the U.S. Supreme Court, died last May. Rosengart says he has been thinking about those small, intimate reunions, just the two clerks and the justice, that always came at this time of year.

Questions people ask

Who was Justice David Souter?

David Souter was a New Hampshire judge who served on the U.S. Supreme Court from 1990 to 2009. Appointed by President George H.W. Bush, he became known as a quiet, bookish moderate who retired to his farmhouse in Weare, New Hampshire, and died in 2025 at age 85.

What is a judicial clerkship and why does it matter?

A clerkship is a one or two year job in which a recent law graduate assists a judge with research, memos, and draft opinions. Federal and Supreme Court clerkships are highly prized because judges hire only a few clerks, and the credential often opens doors to top law firms, academia, and government.

Where are the White Mountains?

The White Mountains cover much of northern New Hampshire and include the Presidential Range, a line of peaks named for presidents including Washington, Adams, and Jefferson. Mount Washington, at 6,288 feet, is the highest peak in the northeastern United States and is famous for severe weather and sweeping views.