Remembering Mortimer M. Caplin – July 11, 1916 – July 15, 2019

The Firm mourns the passing of Mortimer M. Caplin, co-founder of Caplin & Drysdale.  Mr. Caplin passed away on Monday, July 15, 2019, just four days after his 103rd birthday. He died peacefully in his home.

Mr. Caplin lived a remarkable twentieth-century life, spanning the decades from his action as a beach master with the landing force on Omaha Beach, to his service as the Commissioner of Internal Revenue under President John F. Kennedy and, following President Kennedy’s assassination, President Lyndon B. Johnson, then to 1964, when he left the government and formed Caplin & Drysdale, which this year celebrates its fifty-fifth anniversary.  

Mr. Caplin was born in New York City, a grandchild of immigrants, on July 11, 1916, coincidentally also the year of birth of the U.S. federal income tax. In a move that would shape the rest of his life, he left New York for Charlottesville, Virginia in 1933 to attend the University of Virginia. After an outstanding academic career, membership in UVA’s winning boxing team, and acting performances on the UVA stage, he graduated with a B.S. degree in 1937 and remained at UVA to earn his LL.B. from the School of Law in 1940. He was first in his class and Editor-in-Chief of the Virginia Law Review, and, in his first witness to history, sat in the audience at the University’s Final Exercises in June of 1940 as President Franklin D. Roosevelt gave his famous “Hand that Held the Dagger” speech, as Italy had declared war on France and Britain that very morning.  

After a clerkship with U.S. Circuit Judge Armistead M. Dobie, he practised law in New York City, but within a short period, he enlisted in the United States Navy. During World War II, Mr. Caplin served in various capacities, culminating with his role in the Normandy invasion, landing on Omaha Beach following the first wave of forces to help sweep the landing area and ready it for more men and matériel, while still under fire and air attack.  He was later awarded the French Legion of Honor by President Nicolas Sarkozy in a ceremony in France in 2012.

In 1950, Mr. Caplin returned to the University of Virginia as a professor of law, specializing in tax law, where his students included Robert F. Kennedy and Edward “Ted” Kennedy, both of whom, he would say later, he had the good fortune to give passing grades. Following President John F. Kennedy’s election, upon the recommendation of the President-Elect’s brothers, Mr. Caplin served on the President’s Task Force on Taxation. In January 1961, President Kennedy appointed him as IRS Commissioner, a position that landed him on the cover of Time magazine wearing his signature bow tie in 1963.  

During his time as IRS Commissioner, Congress passed a tax reform package and the agency installed its first computer systems through a program called the New Direction. “It changed the relationship between practitioners and the IRS and encouraged accurate self-assessment,” Caplin recalled in a 2016 interview with Tax Analysts. In a story he was fond of telling, Mr. Caplin was also the first, and still, only, IRS Commissioner to persuade the President of the United States to visit the IRS building at 1111 Constitution Avenue to speak to its employees. A plaque in an IRS hallway commemorates the visit of President Kennedy on May 1, 1961. Mr. Caplin remained close to the Kennedy family, and at a ninetieth birthday celebration in the Senate Caucus Room in 2006, Senator Edward Kennedy delivered one of the tributes.

Mr. Caplin left the IRS in 1964 and formed his own law firm, Caplin & Drysdale, in Washington, D.C., with a colleague and friend from Charlottesville, Douglas Drysdale (who died in 2018 at the age of 94). There he assembled a team of lawyers from the top staff at the IRS, the Treasury, and the Justice Department to offer companies, organizations, and individuals tax legal services of the highest quality. Mr. Caplin instituted a nimble and efficient style of practice aimed at minimizing clients’ tax liabilities without compromising ethical principles essential to the integrity of the tax system. With Mr. Caplin at the helm, Caplin & Drysdale soon earned a reputation among clients for mastering the complex and ever-changing tax laws, for finding well-conceived, innovative solutions to tax problems, and for handling major tax controversies successfully in both the civil and criminal tax arenas. At the same time, the firm earned the trust and respect of government officials. The Firm has since expanded its practice areas beyond tax into litigation and political law and, in 1986, it opened an office in New York. Mr. Caplin came into the office daily (after his morning swim) until he turned 98 and enjoyed having lunch with colleagues and friends at the University Club. He was always curious and engaged about the Washington events of the day. The tone, culture and sense of excellence instilled by Mr. Caplin in the Firm at its inception remain to this day.

Mr. Caplin’s lifelong dedication to service was extensive. One of his deepest and most emotional connections remained with the University of Virginia, where he served as a trustee of the University of Virginia Board of Visitors, the Chair of the UVA Law School Foundation, a benefactor to the Miller Center on Public Affairs, and, with his wife of 71 years, Ruth Sacks Caplin, a major patron of the arts. He served for over 10 years as chair of the UVA Council for the Arts and, afterwards, was made Honorary Chair. The Ruth Caplin Theatre, the funding for which came from Mr. and Mrs. Caplin, is a major arts venue on the Main Grounds of the University. On the Law School Grounds, generations of law students have now studied in the library’s Mortimer Caplin Reading Room, attended lectures in the Caplin Auditorium, benefitted from the Mortimer Caplin Public Service Fellowship, and socialized in the gorgeous Caplin Pavilion. The University awarded him its highest honour, the Thomas Jefferson Medal in Law, in 2001. Just two years ago, Mr. Caplin visited the Law School, where he was greeted by hundreds of cheering law students who had lined both sides of the main walkway into the building to express their affection and gratitude for his lifetime of service and gifts to his alma mater. 

Mr. Caplin served on the corporate boards of Prentice-Hall, Fairchild Industries, and for many years, Danaher Corporation, during which time he was the oldest serving corporate director in the country. He also worked in various positions for other non-profit organizations, including The George Washington University, the University of the Virgin Islands, the Peace Through Law Education Fund, Arena Stage, the Shakespeare Theatre, and the Wolf Trap Foundation.  

Mrs. Caplin, who, in addition to being a patron of the arts, wrote and produced a major Hollywood motion picture, predeceased Mr. Caplin in 2014. Mr. Caplin is survived by four of his children, Lee, Michael, Jeremy, and Cate, eight grandchildren, and three great-grandchildren. He is honoured by his colleagues in the Firm and elsewhere, and by the many thousands of people whose lives he touched in his work and in his service to the bar and his country.

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Contributing Advisors