Angleton’s activities ranged from purloining documents at foreign embassies to opening the mail of American citizens (he once jocularly referred to himself as “the postmaster”) to wiretapping the bedrooms of CIA officials. It was his job to be suspicious of everybody, and he was, keeping a treasure trove of sensitive files and photos in the locked vault in his office. Each morning at CIA headquarters, Angleton would report to Dulles on the results of his “fishing expeditions,” as they called his electronic eavesdropping missions, which picked up everything from gossip on the Georgetown party circuit to Washington pillow talk.

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.”

Talbot, David. The Devil’s Chessboard: Allen Dulles, the CIA, and the Rise of America’s Secret Government (pp. 333-334). HarperCollins. Kindle Edition.

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.

Talbot, David. The Devil’s Chessboard: Allen Dulles, the CIA, and the Rise of America’s Secret Government (p. 335). HarperCollins. Kindle Edition.

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.

Talbot, David. The Devil’s Chessboard: Allen Dulles, the CIA, and the Rise of America’s Secret Government (pp. 336-337). HarperCollins. Kindle Edition.

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.

Talbot, David. The Devil’s Chessboard: Allen Dulles, the CIA, and the Rise of America’s Secret Government (p. 336). HarperCollins. Kindle Edition.

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.

Talbot, David. The Devil’s Chessboard: Allen Dulles, the CIA, and the Rise of America’s Secret Government (pp. 337-338). HarperCollins. Kindle Edition.