The Devil's Chessboard

by David Talbot

  As Dulles was well aware, Angleton had even tucked away explosive secrets about the CIA director himself. That is why Dulles had rewarded him with the most sensitive job in the agency, Angleton confided to journalist Joseph Trento near the end of his life. “You know how I got to be in charge of counterintelligence? I agreed not to polygraph or require detailed background checks on Allen Dulles and 60 of his closest friends. They were afraid that their own business dealings with Hitler’s pals would come out.”

  Angleton’s selection as the top hunter of Soviet moles struck many in the agency as peculiar. During and after the war, Angleton had been badly fooled by his close chum in British intelligence, the legendary double agent Kim Philby. The witty, bibulous, stammering Philby, who had betrayed his class and country by secretly going to work for Soviet intelligence as a young Cambridge graduate in the 1930s, forged a tight friendship with Angleton in London during the war. Philby and the Anglophilic Angleton, who had attended the upper-crust British boarding school Malvern, renewed their relationship when Philby was posted to Washington, D.C., in 1949, as the British Secret Intelligence Service liaison. The two men shared long, sodden lunches at Harvey’s, a Washington power restaurant also favored by the likes of Hoover and his companion, Clyde Tolson.

  Angleton’s children remembered the drunken nursery games played by Philby and his friends Guy Burgess and Donald Maclean, who belonged to the same secret ring of Cambridge-bred traitors, when they were invited to the Angleton home in Arlington for dinner. “They’d start chasing each other through the house in this little choo-choo train,” according to Siri Hari Angleton, the spymaster’s youngest daughter, “these men in their Eton ties, screaming and laughing!” At another raucous party, she recalled, “Philby’s wife passed out, and was just lying on the floor. Mummy said, ‘Oh, Kim, don’t you want to see how Mrs. Philby is doing?’ And he said, ‘Ahhh . . .’ and just stepped right over her to get another drink.”

  Angleton struck people as a wispy figure of a man. He was known as the “Gray Ghost” in agency circles—a tall, stooped, ashen-faced figure, with a bony, clothes-rack frame, draped in elegant, European-tailored suits, and wreathed in his customary rings of smoke. But around Philby, Angleton seemed to come alive, to glow. They were boarding school boys again.

  After Philby was finally exposed, ultimately fleeing to Russia, Angleton’s anti-Soviet sentiments hardened into a fundamentalism that clouded his judgment. “I have no doubt that the exposure of Kim Philby was lodged in the deepest recesses of Jim’s being,” Helms later commented. If he were the sort of chap who murdered people, Angleton told a friend in British intelligence, “I would kill Philby.” The betrayal was painfully intimate, and it bred a paranoia that bloomed darkly within Angleton. When he was named counterintelligence chief, he saw traitors and signs of Soviet treachery everywhere. His compulsive mole hunting ruined the careers of dozens of CIA agents, doing more to damage agency security than to fortify it. “I couldn’t find that we ever caught a spy under Jim,” said William Colby, the CIA director who finally terminated Angleton’s long tenure in 1975.

  But under Dulles, Angleton enjoyed free rein to pursue his demons. He dreamed up Cold War phantasms and bogeymen, and then invented all-too-real methods of destroying these horrible apparitions. He operated a kind of virtual CIA within the CIA, reporting only to Dulles himself—and even the top spymaster was not fully aware of his murky activities. “My father once said, ‘I’m not a genius, but in intelligence I am a genius,’” recalled Siri Hari Angleton, who changed her name from Lucy as a young woman, after following her mother and older sister into the Sikh religion.

  Dulles and Angleton went way back together, to the dark maze of postwar Rome. Like Helms, Dulles admired Angleton’s complex mind and the deep calculus of his spycraft. “Jim,” Dulles once told Angleton’s wife, Cicely, “is the apple of my eye.” Angleton, in turn, grew deeply fond of Dulles, whom he looked up to as a father figure, and of Clover Dulles, too, with whom he shared a creative temperament.

  “Angleton was fascinating,” recalled Joan (Dulles) Talley. “My mother liked him a lot, he was very talkative, very intellectual. He was an odd one, he fussed over the orchids he grew—which I think was a wonderful obsession of his—and he drank too much. But he was lots of fun for anyone to talk to, you’d never know where the conversation was going to go. He’d jump from orchid colors to flyfishing to poetry and music. He was a real scholar, and he was an oddball. A totally unique creation.”

  Angleton expressed an appreciation for Clover’s art, and he once begged her for a self-portrait that she had painted. Clover suspected that the aesthetic spy was “in his cups” when he made the request, but she agreed to give it to him, as she later told Joan, “because Jim labors day and night for CIA and Dad.” The two couples enjoyed each other’s company, and the Angletons were often invited for dinner at Q Street. Cicely Angleton came from a prosperous family that had made a fortune in Minnesota iron ore—and, educated at Vassar, she shared Clover’s interests in spirituality and the arts. Cicely later published several volumes of poetry, taking the creative path that her husband otherwise might have gone down.

  Dulles and Angleton shared a disdain for Washington bureaucracy and for the governmental oversight that comes with a functioning democratic system. Later, in the post-Watergate ’70s, when the Church Committee opened its probe of CIA lawbreaking, Angleton was called to account for himself. As he completed his testimony, the Gray Ghost rose from his chair, and, thinking he was now off the record, muttered, “It is inconceivable that a secret intelligence arm of the government has to comply with all the overt orders of the government.” It was a concise articulation of the Angleton philosophy; in his mind, CIA overseers were a priestly caste that, because the fate of the nation had been placed in its hands, must be allowed to operate unfettered and above the law.

  “Allen wasn’t red-tape and neither was daddy,” said Siri Hari. “You know, back then, people were much more interesting. . . . I don’t think it was a case of resenting bureaucracy, because the bureaucracy just never came that close to them anyway, so why would they resent it? They probably just felt, you know, a little beyond it, a little above it.”

  Dulles entrusted Angleton with the agency’s most vital and sensitive missions. He was the principal CIA liaison with the key foreign intelligence services, including those in frontline Cold War nations like France, West Germany, Turkey, Taiwan, and Yugoslavia, as well as with Mossad, the Israeli spy agency. Angleton developed a special bond with the Israelis, forging a realpolitik relationship, with both parties conveniently overlooking Angleton’s role in the Nazi ratlines after the war. The Israelis maintained close ties to the American espionage oracle until the end of his life. Several members of Mossad came to Angleton’s home as he lay dying in the spring of 1987, to pay their last respects—and perhaps to make certain the vapory Gray Ghost was indeed finally leaving this mortal coil.

  Dulles also put Angleton in charge of the CIA’s relationship with the FBI—a delicate task considering the rivalry between the two agencies. At the same time he was working with the federal bureau in charge of fighting organized crime, Angleton was also pursuing a CIA partnership with the Mafia. Angleton possessed one of those rare intellects—and characters—that allowed him to lead a life filled with contradiction. He easily passed back and forth between Washington’s overworld and the criminal underworld. He was the sort of man who could crossbreed a new orchid, cook a delicious pasta with slivered truffles imported from Ristorante Passetto in Rome, and then sit down with a criminal mastermind to discuss the fine points of murder. Though he dined and drank with Georgetown high society, Angleton’s work also brought him into close contact with the agency’s rougher characters, including Shef Edwards’s security cops, who helped install Angleton’s bugs, and Bill Harvey, the hard-drinking gun nut who figured prominently in a number of the agency’s assassination jobs.

  It was all of a piece, in the intricately wired mind of
Jim Angleton: countering dangerous ideas by publishing CIA-vetted literature, or by eliminating the intellectuals and leaders who expounded these ideas. One day, shortly after Fidel Castro took power in Havana, Angleton had a brainstorm. He summoned two Jewish CIA officers, including Sam Halpern, who had recently been assigned to the agency’s covert Cuba team. Angleton asked them to fly to Miami and meet with Meyer Lanksy, organized crime’s chief financial officer, who had been forced to flee Havana ahead of Castro’s revolutionaries, leaving behind the Mafia’s highly lucrative casino empire. Lansky was part of the Jewish mob but had close business ties to the Italian Mafia. Angleton told Halpern and the other Jewish CIA agent to see if they could convince Lansky to arrange for the assassination of Castro.

  Angleton’s emissaries met with Lansky, but the crime mogul drove too hard a bargain for his services and the deal fell through. This was only the beginning of the CIA’s endless, Ahab-like quest to kill the Caribbean leviathan, however. Castro would never stop haunting the dreams of the CIA high command. The Cuban revolutionary was not only intellectually formidable and politically fearless; his dream of national liberation was backed up with guns. Castro and his equally charismatic comrade, Che Guevara, made it clear from the start that they would not share the fate of Jacobo Arbenz in Guatemala: they would fight fire with fire. Che, a twenty-five-year-old doctor and adventurer in search of a grander meaning to his life, was living in Guatemala City when Arbenz was overthrown. He saw what happened when Arbenz’s moderate reforms came up against the imperial force of United Fruit and the CIA.

  “I am not Christ or a philanthropist, old lady,” Che wrote to his mother, Celia, in the bantering style he had developed with her, as he and Fidel prepared to board the leaky yacht Granma in Mexico with their band of guerrillas to make history in Cuba. “I fight for the things I believe in, with all the weapons at my disposal and try to leave the other man dead so that I don’t get nailed to a cross.”

  To avoid Arbenz’s fate, Castro and Guevara would do everything he had not: put the hard-core thugs of the old regime up against a wall, run the CIA’s agents out of the country, purge the armed forces, and mobilize the Cuban people. By militarizing their dream, Fidel and Che became an audacious threat to the American empire. They represented the most dangerous revolutionary idea of all—the one that refused to be crushed.

  It was after midnight, on September 20, 1960, when Fidel Castro came uptown to Harlem. The white, terra-cotta facade of the Hotel Theresa on Seventh Avenue and West 125th Street—“the Waldorf of Harlem”—gleamed under a battery of police spotlights as brightly as a Hollywood movie premiere. Outside the hotel entrance, a boisterous crowd was steadily growing, in defiance of the pelting rain and the intimidating phalanx of policemen, awaiting the international political celebrity who was rumored to be checking in. Suddenly a lusty roar went up from the throng as an official-looking car suddenly glided to a stop outside the hotel and the familiar, tall, bearded figure emerged from the vehicle. “Cuba si, Yanqui no!” shouted the crowd as a beaming Castro swept his arms through the air, before being hustled into the hotel.

  The Cuban leader and his fifty-member delegation, who were in New York for the annual United Nations General Assembly meeting, had not received such a warm welcome at their first choice of accommodations, the midtown Shelburne Hotel. When the Cuban delegation checked in two days earlier at the Shelburne, they were greeted by a militant group of anti-Castro exiles calling itself La Rosa Blanca (The White Rose), which threatened to blow up the hotel. The Shelburne management promptly informed Castro’s party that they would need to put up a $20,000 security deposit, and an outraged Fidel, insisting that his government did not have ready access to that kind of cash, announced that they would leave the hotel and pitch tents outside the UN if necessary.

  Castro’s 1960 trip to New York marked a sharp turning point in U.S.-Cuba relations. The previous year, in April 1959, the Cuban leader had enjoyed a much more hospitable reception during his eleven-day visit to the United States. Fresh from his revolutionary victory on New Year’s Eve, Fidel was still something of a political mystery to the Eisenhower administration, and the media embraced him as the silver-tongued conqueror who had liberated the Cuban people from Fulgencio Batista’s gangster reign. During his earlier visit to New York—a city he loved—Fidel roamed the streets followed by packs of reporters and photographers, dropping by a Queens elementary school, where the children all wore cardboard cut-out beards in his honor, and the Bronx Zoo, where he gulped down a hot dog and an ice cream cone, and alarmed zoo guards by sticking his hand through the bars of a cage to pat the cheek of a Bengal tiger. “This is like prison—I have been in prison, too,” said Fidel, who had survived Batista’s cages. Even the CIA seemed charmed by Castro during his 1959 visit. After meeting with the Cuban leader in his New York hotel suite, an ecstatic CIA agent reported, “Castro is not only not a Communist, but he is a strong anti-communist fighter.”

  But there had been many changes over the following year, as Castro moved to deliver on the promise of the revolution, nationalizing the sugar and oil industries, and beginning to transform Cuba from a vassal state of the United States to a sovereign nation. By early 1960, Dulles had resolved the debate within his intelligence agency over Castro’s true identity, deciding that he was a dedicated Communist and a serious threat to U.S. security. The CIA director’s hardening line mirrored that of friends in the business world like William Pawley, the globetrotting entrepreneur whose major investments in Cuban sugar plantations and Havana’s municipal transportation system were wiped out by Castro’s revolution. One of a coterie of vigorously anti-Communist international businessmen who provided the CIA with foreign information and contacts, as well as guns and money, Pawley began lobbying the Eisenhower administration to take an aggressive stand against Castro when he was still fighting Batista’s soldiers in the rugged peaks of the Sierra Maestra. After Fidel rode into Havana on a tank in January 1959, Pawley, who was gripped by what Eisenhower called a “pathological hatred for Castro,” even volunteered to pay for his assassination. As the Eisenhower administration took an increasingly belligerent posture toward the Castro regime, Pawley found himself at the center of the action, boasting that he was “in daily touch with Allen Dulles.”

  The Eisenhower administration responded to Castro’s expropriation of American-owned plantations, factories, and utilities by cutting imports of Cuban sugar—the country’s economic lifeblood—and by launching a secret campaign aimed at sabotaging Castro’s government. In February 1960, mercenary pilots hired by the CIA dropped bombs on Cuban sugar mills, and in March, a French freighter loaded with Belgian weapons was blown up in the Havana harbor, killing dozens of sailors and stevedores. A second explosion killed many more, including firefighters and emergency medical workers, as they rushed to the scene. The same month, President Eisenhower approved a plan to train a paramilitary force outside of Cuba for a future invasion of the island. The operation, which was spearheaded by Vice President Nixon and the CIA, would culminate the following year on the beaches of the Bay of Pigs.

  The explosion in Havana’s harbor was a milestone in the Cuban revolution. At a funeral ceremony the next day at Colon cemetery, an emotional Castro vowed that “Cuba will never become cowardly” in the face of U.S. aggression. He ended his oration with the declaration that became a ringing slogan of the Cuban revolution: Patrio o Muerte, Venceremos! (Motherland or Death, We Shall Win!) Determined that Cuba would not become another Guatemala, Castro turned to the Soviet Union for economic and military aid, and the tragic dance began, locking Cuba, the United States, and Russia in a fateful embrace for years to come, and nearly ending in a nuclear inferno.

  When Castro and his retinue landed at New York’s Idlewild Airport on September 18, 1960, he appeared to be in a “subdued mood,” reported The New York Times, for reasons that were not yet known to the American people. The Cuban airliner that flew the delegation to the United States had to be immediately refuele
d and flown back to Havana, to avoid being impounded, as a result of legal claims against the revolutionary government by U.S. business interests. It was just one of the numerous ways that Castro’s delegation was subjected to harassment during his weeklong visit to New York, as the Eisenhower administration maneuvered against the Cuban leader on multiple fronts. By the time his retinue was forced out of the Shelburne Hotel, Castro seemed persona non grata in New York. The State Department had ruled that the Cubans could not leave Manhattan, and no city hotel was willing to accommodate them. If New York was incapable of providing hospitality to world leaders, Castro fumed, perhaps the UN should be moved to another city, such as Havana.

  But then Castro turned his humiliation into a propaganda triumph. As the Cuban delegation was preparing to leave the Shelburne, a political sympathizer put them in touch with Black Muslim leader Malcolm X, who intervened on their behalf with the operators of Hotel Theresa. The tallest building in Harlem, the thirteen-story hotel was a lofty—if somewhat worn-down—landmark in the black community. In its heyday, the Theresa had accommodated a glittering array of African American celebrities when they were not welcome at New York’s downtown hotels, including Josephine Baker, Louis Armstrong, Duke Ellington, Nat King Cole, and Lena Horne. In June 1938, Joe Louis celebrated his heavyweight championship victory over Max Schmeling, Nazi Germany’s great white hope, at the Theresa, as thousands of fans cheered on the streets outside.