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E. Barrett Prettyman, Jr., arrived in Havana in December 1962 with a seemingly impossible task: charm Fidel Castro. An associate at Washington, D.C.’s Hogan & Hartson, Prettyman was one of a handful of private-practice lawyers recruited by then-attorney general Robert Kennedy to negotiate the release of 1,113 Cuban exiles captured 20 months earlier in the botched Bay of Pigs invasion. His mission was to persuade Castro to accept $53 million in food and medicine in exchange for the prisoners. Just two months earlier, Castro and the Kennedy administration had squared off in the Cuban Missile Crisis. Relations between Cuba and the United States were ice-cold. Castro and Prettyman met at a villa outside Havana that had once been owned by Ernest Hemingway. Castro told stories, lapsing into English toward the end of the afternoon. The next morning, Prettyman was on an airplane headed for the United States, surrounded by freed prisoners. His mission had been a success. “When the plane left the ground, boy, they just went crazy,” Prettyman recalls. “They stood up and shook my hand and hugged me. It was a very emotional time.” Castro is just one of the outsize figures that Prettyman, the son of a former chief judge of the U.S. Court of Appeals, has encountered during his career. After his trip to Cuba, he worked in the Kennedy administration, first at the U.S. Department of Justice (Prettyman attended law school with Robert Kennedy) and then in the White House as a special assistant on transportation mergers. Returning to Hogan & Hartson in 1964, he built a client list that included John Lennon, Truman Capote, and Katherine Anne Porter. Chief Justice John Roberts, Jr., credits Prettyman with helping attract him to Hogan as a young lawyer. “In the law firm he has always been regarded as somebody people feel comfortable with, no matter what camp they’re in,” Roberts says. “He has a very open, broad, liberal-in the classic sense-personality.” While at the firm, Prettyman was named the first president of the District of Columbia Bar in the seventies. There he made his mark as a strong advocate for pro bono work. In the late nineties, Prettyman left the firm for about 15 months to work without pay as the District’s inspector general, doubling the size of the office and increasing its congressional grant and caseload. When his term ended, he returned to Hogan, where he currently is of counsel. Although his specialty is administrative and appellate law, “Barrett is really the Renaissance lawyer,” says Hogan partner David Hensler. “He’s done everything.” That includes writing a book, Death and the Supreme Court, which won an Edgar Allen Poe Award in 1962. Now 82, Prettyman is representing several clients, including an inmate on Florida’s death row. The client is no celebrity, but that’s of no concern. Prettyman, Roberts says, “has a way about him that inspires a great deal of confidence in clients from every walk of life.” Back to Main Story

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