RIP: Attorney E. Barrett Prettyman Jr. dies at 91

E. Barrett Prettyman Jr., Lawyer Who Fortified Desegregation Ruling, Dies at 91

E. Barrett Prettyman Jr., a prominent Washington lawyer who played crucial backstage roles in the Supreme Court’s unanimous school-desegregation decision, the first expulsion by Congress of one of its members in more than a century, and the release of prisoners captured in the abortive Bay of Pigs invasion of Cuba, died on Friday in Washington. He was 91.

His death was announced by his law firm, Hogan Lovells, which he joined six decades ago after becoming the only person to clerk successively for three United States Supreme Court justices, and where he took the present chief justice, John G. Roberts Jr., under his wing.

Justice Roberts, in a statement on Tuesday, recalled Mr. Prettyman as “a singularly insightful mentor and dear friend” and a “towering member of the Supreme Court bar.”

The son of a federal appellate jurist and a law school classmate of Robert F. Kennedy’s, Mr. Prettyman crusaded against the death penalty, championed press protections and vigorously prodded lawyers to provide free legal services to clients who could not afford representation.

In a career that he began as a newspaper reporter, he clerked for Justices Robert H. Jackson, Felix Frankfurter and John M. Harlan. He was the founding president of the District of Columbia Bar Association. He argued 19 cases before the Supreme Court and represented an all-star client roster that included Truman Capote, John Lennon and Katherine Anne Porter. And he won an Edgar Allan Poe Award in 1962 for his true-crime book “Death and the Supreme Court.”

But for all his courtroom skills, the arguments he marshaled behind the scenes in various negotiations might be his most enduring legacy.

Chief among them was the role he was credited with playing in the landmark Brown v. Board of Education case in 1954.

As revealed by Richard Kluger in 1976 in “Simple Justice: The History of Brown v. Board of Education and Black America’s Struggle for Equality,” Mr. Prettyman urged Jackson not to write a separate opinion, which, though concurring in the decision, would have intimated that racial segregation was lawful in some circumstances and might have undermined public confidence in what otherwise was a unanimous ruling.

“I told him quite candidly,” Mr. Prettyman recalled in 1996 in an oral history interview with the Historical Society of the District of Columbia Circuit, “that it sounded more like a dissent than a concurring opinion.”

After Chief Justice Fred M. Vinson died in 1953, his successor, Earl Warren, presented Jackson with a draft of what would become the final Brown decision. After reviewing it, Mr. Prettyman, by his account, told Jackson, “You know, it meets a lot of the problems that you had, as expressed in your unpublished opinion, and while it certainly doesn’t contain a lot of law, it makes sense, it hangs together, it doesn’t offend people, it reads well, anybody can understand it.”

Jackson, he said, replied, “Exactly.”

On May 17, 1954, the court ruled unequivocally that, “in the field of public education, the doctrine of ‘separate but equal’ has no place.”

In his book, Mr. Kluger concluded: “It is doubtful if any of the many excellent young men who have come fresh out of the law schools or soon thereafter to serve the justices of the Supreme Court ever served more faithfully or usefully than Barrett Prettyman served Robert Jackson. What part Prettyman’s memo played will never be known, but it is a fact that Jackson, having written this much on the segregation cases, wrote no more.”

In 1962, Mr. Prettyman, a lifelong Democrat, was recruited to help the Kennedy administration, covertly, to speed the donation and shipment of more than $50 million in agricultural and medical supplies to Cuba as ransom for more than 1,000 hapless Cuban exiles who had been captured the year before while trying to retake their homeland from Fidel Castro.

Unbeknown to Mr. Castro, the supplies included surplus products that American companies were dumping as a way to take tax deductions. To prevent Mr. Castro from immediately finding out, Mr. Prettyman flew to Havana and persuaded him to accompany him for the day on a visit to Ernest Hemingway’s old house outside Havana. By the time they returned to the docks, all Mr. Castro could see was a bountiful supply of baby food.

“I did get in the fact that because of the way we had to load, he might be getting some things he could throw away, but by then he was sufficiently pleased with what he’d seen,” Mr. Prettyman said, “and he ordered that the prisoners could start to leave right away.”

In 1980, Mr. Prettyman was counsel to the House ethics committee in its investigation of six members of Congress who were ensnared in the Federal Bureau of Investigation sting operation known as Abscam. At his recommendation, the House voted to expel Representative Michael J. Myers, a Pennsylvania Democrat, after he was convicted of bribery. It was the first time the expulsion penalty had been imposed since 1861.

A year later, when the committee declined to file charges against Representative John P. Murtha Jr., another Pennsylvania Democrat, who had been named as an unindicted co-conspirator in the Abscam affair but who had never been prosecuted, Mr. Prettyman resigned in protest.

Mr. Prettyman’s association with Chief Justice Roberts continued after he had mentored him at Hogan Lovells, though in more contentious circumstances.

“It was my great good fortune to learn from him as his associate early in my career,” Chief Justice Roberts said in his statement, “and later to put to the test what he had taught me when I argued against him in the court.”

Elijah Barrett Prettyman Jr. was born in Washington on June 1, 1925. He was descended from a family that settled in colonial Jamestown in 1608. His grandfather, a Methodist minister, was chaplain of the Senate during the Woodrow Wilson administration. His father, also known as Barrett, was chief judge of the United States Court of Appeals for the District of Columbia; its courthouse in Washington bears his name. Mr. Prettyman’s mother, the former Lucy Hill, was a nurse.

Mr. Prettyman’s marriages to Evelyn Savage and Victoria Keesecker ended in divorce. His third wife, the former Dr. Noreen McGuire, died in 2011. He is survived by two children from his first marriage, E. Barrett Prettyman III and Jill Prettyman Lukoschek, and three grandchildren.

Mr. Prettyman served in the infantry in Europe in World War II and graduated from Yale in 1949. After going to work for The Providence Journal, he decided that studying jurisprudence would improve his earning potential as a reporter. But he became so enthralled by the law that he gave up journalism for a legal career and received a degree from the University of Virginia Law School, where he became a protégé of Robert Kennedy.

Soon he achieved a coveted clerk position at the Supreme Court and found himself playing challenger to the justices for whom he worked, from 1953 to 1955. “My job was to hammer him so hard that he would feel really good about how he was coming out,” Mr. Prettyman said of each of the three.

He found he was less argumentative once he got home, however, when he, a Supreme Court clerk, gathered for dinner with his father, a federal judge, and his sister, an employee of the Central Intelligence Agency.

“There’d be these long silences at the table,” Mr. Prettyman recalled, “and my mother would say, ‘Well, if you can’t talk of anything else, pass me the salt.’ ”