Andrew Martin

His name is well-known to every UVA Law graduate, and his penchant for bow ties is almost as famous. Over the course of a career in law, education and government service, Mortimer Caplin ’40 has seemingly lived several lifetimes, each distinguished by remarkable and influential achievements, from his time as an actor and boxer when he was an undergraduate at UVA, to his service in the U.S. Navy on D-Day, to his work as IRS commissioner during the administration of President John F. Kennedy, and beyond. On July 11, Caplin will celebrate his 100th birthday, providing an excellent occasion to look back over the accomplishments of, in the words of former Law School Dean Robert Scott, “an exemplar of a professional life well-lived.” In honor of this milestone, we spoke with Caplin and some of his peers and colleagues about highlights of his life and career.

Undergraduate Success

Caplin boxing
Caplin boxed as an undergraduate at the University of Virginia

Caplin entered UVA as an undergraduate in 1933. In a recent interview, he recalled his first trip to Virginia, a drive from New York City with his father and a family friend who had a son at UVA. They made the trip on Lincoln’s birthday, Caplin said, and there was a light snow falling over Grounds. He was taken to a boxing match — “it was the only winning team they had then” — and developed a passion for the sport. “I hadn’t done much boxing before then,” Caplin said. “But I’d witnessed a lot of boxing bouts, heavyweight fights, things of that sort.”

He had been the captain of his swim team in high school and a swimming instructor at a camp for two months every summer. “Swimming really wasn’t a good sport for boxing — different sets of muscles,” Caplin said. “But that was how I got into athletics.” He was a well-regarded intercollegiate boxer throughout his years at UVA.

He also excelled academically, earning the highest honors and selection for Phi Beta Kappa. Though he knew he wanted to go to law school from an early point in his academic career, he was also very involved in drama. He was president of the Virginia Players and acted in a number of plays as an undergraduate, including the title role in “Julius Caesar.”

“For about 15 minutes I thought maybe I ought to become a stage actor,” he said. This part of his passion lives on at UVA in the Ruth Caplin Theatre, built in 2013 and named for his wife, who was also deeply passionate about and involved with the dramatic arts. She died in 2014. They were married for 71 years and raised five children: Mary Ellen, Jeremy, Cate, Lee ’72 and Michael ’76.

Training in Law and War

After Caplin graduated in 1937, he went to the Law School, where he quickly stood out as well, rising to become editor-in-chief of the Virginia Law Review and first in his class. He went on to a prestigious clerkship with the widely admired Judge Armistead M. Dobie ’04 of the U.S. Fourth Circuit Court of Appeals, a former dean at UVA Law.

“I had a good running start,” Caplin said.

From there, he went on to work for the firm Cohen, Cole, Weiss and Wharton in New York, which eventually became known as Paul, Weiss, one of the leading law firms in the country. However, his work in New York was interrupted by World War II.

He enlisted in the Navy in 1943 and served as a beachmaster on Omaha Beach in Normandy as part of the D-Day invasion, in charge of 40 men, an assistant beachmaster and the Navy doctor. It was his unit’s job to serve as a nexus between the ships and the troops on the beach. It was impossible to prepare for what they were to find the morning after the initial D-Day landing.

“We’d been going through training for almost a year, under less-than-favorable conditions, so we had a basic idea of what to expect,” Caplin said. But still, the carnage they encountered was a shock. He was in France for about a month. Among his important duties were to open landing lanes, assist with casualties on the beach, help bury the dead, repair damaged boats and maintain ship-to-shore communications. Later, he aided in repairing the port of Cherbourg so that that ships could dock there directly.

In 2009, he was named a chevalier of the Legion of Honor by the president of France for his contributions to the U.S. role in the liberation of the country.

After his service on Omaha Beach, he was given new duty in Plymouth, England, as legal officer for the commander of Amphibious Bases and Craft, United Kingdom. He was in London on VE Day. “Picadilly Circus was wild,” he said. “I was at Buckingham Palace and witnessed the speeches of Winston Churchill and King George VI. There were many dividends out of all this. It was a great event.”

The Kennedys and the IRS

Caplin's Time cover
Caplin is the only IRS commissioner to appear on the cover of Time magazine

After the war, he returned to New York. While resuming work at his firm, he took more law classes, this time at New York University under the GI Bill, trying, in his words, “to re-learn everything I’d forgotten.” He returned to UVA Law in 1950, teaching classes on corporations and taxation. It was during this time that he taught Robert and Ted Kennedy of the classes of 1951 and 1959, respectively.

“Bob didn’t volunteer very much, but he was a better student than Ted,” Caplin remembered. “I got to like Bob very much when I came to Washington, when he was attorney general, and we worked very closely together. He was a real star.”

It was through the younger Kennedys, and Bill Battle ’47, a partner in a Charlottesville law firm, that Caplin met John F. Kennedy, who was visiting the University during his campaign for president. After Kennedy was elected, Caplin received a phone call from Ted Sorensen, Kennedy’s chief advisor and speechwriter, asking if he wanted to join his “tax task force.”

“I didn’t wait very long to give the answer,” Caplin said.

Caplin jumping rope
Caplin, in 1962, still found time to jump rope and box in the Pentagon gym while serving as IRS commissioner.

In 1961, Caplin became the IRS commissioner under President Kennedy, and in 1963 he appeared on the cover of Time magazine in that role. “We were trying to change the underlying philosophy” of the IRS, Caplin explained. “We put the emphasis on better self-assessment, and not so much on putting people in jail.”

George K. Yin, Edwin S. Cohen Distinguished Professor of Law and Taxation at UVA Law, said that Caplin’s commitment to the rule of law and to public service were vividly illustrated in his time as IRS commissioner.

“He really emphasized the importance of full compliance with the law and promoted policies and practices to help taxpayers achieve that objective and help the agency enforce it,” Yin said. “He is extremely proud — rightfully so — to have gotten President Kennedy to visit the IRS to speak to the employees during his tenure as commissioner — the only president to do so. Mort understood full well that the work of the staff who perform the thankless task of collecting taxes really epitomizes public service.”

Caplin with Kennedy
Mortimer Caplin with President John Kennedy

When Caplin left the IRS in 1964, he received the Alexander Hamilton Award, the highest honor conferred by the secretary of the Treasury.

Soon after leaving the government, Caplin founded the tax firm Caplin & Drysdale with a former law student of his, Doug Drysdale ’53.

“Mort had identified a number of very talented young lawyers working for the Treasury and in the IRS chief counsel’s office,” Drysdale said. “That first year or so a number of those lawyers joined us. Our objective was to have a firm of highly talented people and do good work.” The firm emphasized hiring people with a sense of public service, and did very little lobbying.

“Mort was very generous, both in a financial sense and in relation to the management of the firm,” Drysdale added. “It was possible for a young person to advance more quickly than in most typical firms.”

The boutique firm has now been in business for more than 50 years — “a good sign,” Drysdale joked.

Caplin with Drysdale
Mortimer Caplin with his law firm co-founder, Doug Drysdale '53, in 2014

Michael Graetz ’69, a tax law expert and former member of the Law School faculty currently serving as the Columbia Alumni Professor of Tax Law at Columbia Law School, noted that Caplin played an important role in institution-building in his time as IRS commissioner and in founding Caplin & Drysdale. “He’s a far-sighted individual,” said Graetz, who has also served on the annual Virginia Tax Study Group, a conference hosted by the Law School, with Caplin. “He saw an opportunity to create a law firm and build it by hiring Supreme Court clerks, which was not an obvious thing for a tax practice. He hired the best people he could possibly find.”

A Cherished Alumnus

Over the years, Caplin has been an integral part of the Law School, giving both his time and money to the institution where he learned and taught. In addition to the Ruth Caplin Theatre, for which he and his wife donated $4 million to the University, there is the Law School’s Caplin Auditorium, the Mortimer Caplin Professorship, the Mortimer Caplin Public Service Center, the Mortimer Caplin Public Service Fellowship and Caplin Pavilion. This year he pledged to match up to $50,000 of gifts made on Thomas Jefferson’s birthday.

Scott said Caplin was the first alumnus he called when looking for a chair for the executive committee of the Law School’s capital campaign in 1992.

“He could have said, couldn’t you pass that to a younger person?” Scott recalled with a laugh. “But of course, he didn’t. He hosted events at his offices, he came to every meeting. You couldn’t ask for a more loyal, honorable embodiment of the highest levels of skill and integrity as a lawyer.”

The campaign eventually raised $200 million, the most ever by a law school campaign at that time. 

Caplin also served on the University’s Board of Visitors from 1992 to 1997 and on the Board of Trustees of the Law School Foundation for 18 years, becoming an honorary member in 2001. Caplin taught at the Law School from 1965 to 1988 as a visiting professor. 

In 2001, he received the Thomas Jefferson Memorial Foundation Medal in Law, the highest honor the University gives. 

In reflecting on his time as a UVA student, Caplin said his education had a “major impact” on the course of his life. He, in turn, has had as substantial an impact on his alma mater as anyone could hope to have, an impact that will continue to be felt for the century to come. 

As Graetz observed, “If anybody ever deserved to live a great life for a hundred years, he’s the most deserving I can imagine.”

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