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The Spymasters

How the CIA Directors Shape History and the Future

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About The Book

From the New York Times bestselling author of The Gatekeepers, a remarkable, behind-the-scenes look at what it’s like to run the world’s most powerful intelligence agency, and how the CIA is often a crucial counterforce against presidents threatening to overstep the powers of their office.

Only eleven men and one woman are alive today who have made the life-and-death decisions that come with running the world’s most powerful and influential intelligence service. With unprecedented, deep access to nearly all these individuals plus several of their predecessors, Chris Whipple tells the story of an agency that answers to the United States president alone, but whose activities—spying, espionage, and covert action—take place on every continent. At pivotal moments, the CIA acts as a brake on rogue presidents, starting in the mid-seventies with DCI Richard Helms’s refusal to conceal Richard Nixon’s criminality and continuing to the present as the actions of a CIA whistleblower have ignited impeachment proceedings against Donald Trump.

Since its inception in 1947, the Central Intelligence Agency has been a powerful player on the world stage, operating largely in the shadows to protect American interests. For The Spymasters, Whipple conducted extensive, exclusive interviews with nearly every living CIA director, pulling back the curtain on the world’s elite spy agencies and showing how the CIA partners—or clashes—with counterparts in Britain, France, Germany, Israel, Jordan, Saudi Arabia, and Russia. Topics covered in the book include attempts by presidents to use the agency for their own ends; simmering problems in the Middle East and Asia; rogue nuclear threats; and cyberwarfare.

A revelatory, behind-the-scenes look, The Spymasters recounts seven decades of CIA activity and elicits predictions about the issues--and threats—that will engage the attention of future operatives and analysts. Including eye-opening interviews with George Tenet, John Brennan, Leon Panetta, and David Petraeus, as well as those who’ve just recently departed the agency, this is a timely, essential, and important contribution to current events.


Chapter 1: “Stay the hell away from the whole damned thing.” CHAPTER ONE “Stay the hell away from the whole damned thing.”
Richard Helms, Lyndon Johnson, and Richard Nixon

At his transition headquarters on the thirty-ninth floor of New York City’s Pierre Hotel, in a suite with a panoramic view of Central Park, Richard M. Nixon was preparing to become president of the United States. It was Friday, November 15, 1968, and Nixon had been huddling with his closest advisers, meeting with candidates for his cabinet, plotting to bend the Washington establishment to his will. The president-elect was “in the mood of a general about to occupy an enemy town,” wrote author Thomas Powers, “bringing with him a visceral dislike and suspicion of the federal bureaucracy… because it was in his character to see himself always as surrounded by enemies, obstructionists and saboteurs.” Oddly enough, in Nixon’s mind, no one exemplified the Washington elite—those enemies, obstructionists, and saboteurs—more than the man he’d summoned to meet with him, CIA director Richard Helms.

It would be hard to imagine a partnership less likely to end well, more riven with intrigue and mutual suspicion, than Helms and Nixon. Helms personified the CIA, rising through the ranks of the agency to become Lyndon Johnson’s director for the previous two years. Nixon was still seething about the CIA’s role in his 1960 election loss, convinced the agency had helped JFK invent a Soviet-American “missile gap.” He wasn’t about to let Helms forget it. Worse, in Nixon’s mind, Helms was a member of the “Georgetown set,” a tony cabal that spent its evenings sipping martinis and making fun of the president-elect. (Helms did frequent the living rooms of Washington’s high-society doyennes, but he was quick to point out that he’d never lived in Georgetown.)

In their manner and dress the two men were polar opposites. Helms wore Savile Row suits with kerchiefs and was an avid tennis player and ballroom dancer. (Born with nine toes, Helms had shoes specially designed for him in London when he lived there in the 1930s.) Nixon was fumbling and socially inept, and so sartorially clueless he wore dress shoes while walking on the beach.

Helms arrived at the hotel and was shown into Nixon’s suite. He was greeted there by the president-elect and John Mitchell. Jowly and overweight, Mitchell, who’d been Nixon’s law partner and was most recently serving as the president-elect’s confidant, was about to become attorney general—and would later go to prison for his role in the Watergate scandal. After some pleasantries, the president-elect told Helms he wanted him to stay on as CIA director. Helms thanked him and left, promising not to tell anyone until the decision was made public. A month later, on December 18, 1968, Richard Nixon announced Helms’s reappointment as director of Central Intelligence.

Nixon must have had his reasons. Possibly, he’d been swayed by LBJ’s urging him to keep Helms around as an honest broker. “I’ve no idea how he voted in any election and I have never asked him what his political views are,” Johnson told the president-elect. “He’s always been correct with me and has done a good job as director. I commend him to you.” But beyond Helms’s bona fides, other considerations were undoubtedly at work in Nixon’s conspiratorial mind. It was a mind that Helms could never fathom. “He couldn’t figure out Nixon,” recalled his widow, and second wife, Cynthia Helms. “He just could never figure out what Nixon was up to.” What Nixon was up to, it does not seem far-fetched to conclude, was choosing a CIA director who could be blackmailed into doing his bidding.

Surely, anyone who’d been in the spy business as long as Helms must have something to hide, must be malleable, or vulnerable to exposure. “We protected Helms from one hell of a lot of things,” Nixon would say later, as the White House tapes rolled, implying that he’d kept damaging information from coming to light, that Helms owed him, and it was time to collect the debt. Did Nixon and his henchmen have something on Helms, a secret that would make him do their dirty work on Watergate? The fate of Nixon’s presidency would hinge on the answer to that question.

Richard Helms hadn’t set out to become a spy. Born on Philadelphia’s Main Line, he was sent to a Swiss boarding school and then attended college at Williams. In 1936, as a twenty-three-year-old reporter for United Press, speaking passable French and German, Helms found himself at the Nazi Party Congress in Nuremberg, standing next to the German führer, Adolf Hitler. “At arm’s length, Hitler appeared shorter and less impressive than at a distance,” Helms reported in his UP dispatch. “Fine, dark brown hair, rusty in front, slightly graying along the crown; bright blue eyes, coarse skin, with a pinkish tinge.” Helms was appalled by Hitler’s demagogic narcissism. By contrast he was impressed by the quiet modesty of American track star Jesse Owens, whom he met while crossing the Atlantic on the Queen Mary after his dominant performance at the Olympic Games.

After Pearl Harbor, Helms joined the Naval Reserve. Then, two years before the Nazi surrender, he was summoned to the Office of Strategic Services (OSS) in Washington, D.C. The wartime intelligence service, precursor to the CIA, wanted someone who spoke French and German, had lived in Europe, and worked as a journalist.

The OSS was the creation of William “Wild Bill” Donovan, a dashing figure who led an eclectic band of intellectuals and paramilitary adventurers, running spies and saboteurs behind Nazi lines from its headquarters in London. Helms was sent to Maryland for training (knife fighting, hand-to-hand combat, maintaining a cover)—and finally dispatched to London. There, he reported to a rumpled Navy lieutenant named William J. Casey, the chief for secret intelligence collection in Europe.

Restless, indefatigable, and brilliant, Casey, who would later become Ronald Reagan’s CIA director, was as rough around the edges as Helms was silky smooth; he was so excitable during meals, and his table manners such an afterthought, that he often ended up chewing on his tie. The two young OSS recruits became roommates and sent spies into occupied Europe right up until the Nazi surrender.

By 1943 Helms had given up his journalistic ambitions (he’d wanted to own a newspaper) in favor of a career as a spy. “I now realized that I was hooked on intelligence,” Helms wrote years later in his memoir, A Look over My Shoulder. And he intuited that the OSS, or something like it, would still be necessary after the war: “The need for an effective intelligence service in the turbulent and anything but benign postwar world seemed obvious.” But Helms wasn’t done with Hitler yet. At war’s end, as the Third Reich lay in ruins, while he was on a reconnaissance mission in Berlin, Helms seized a chance to sneak into Hitler’s chancellery. He helped himself to the few pieces of crockery that hadn’t been shattered—and Hitler’s personal note cards. On one, Helms penned a note to his toddler son, back in Virginia.

Dear Dennis,

The man who might have written on this card once controlled Europe—three short years ago when you were born. Today he is dead, his memory despised, his country in ruins. He had a thirst for power, a low opinion of man as an individual, and a fear of intellectual honesty. He was a force for evil in the world. His passing, his defeat—a boon to mankind. Thousands died that it might be so. The price for ridding society of bad is always high.



By then both Helms and Casey were focused on a new force for evil, one they considered as threatening as the Third Reich. The struggle against Soviet communism, starting in Eastern Europe and extending across the globe, would shape the ethical choices they made while working for, and later running, the CIA. They believed the morality of their methods shouldn’t be judged in a vacuum, but against those of the KGB. (Helms disliked John le Carré’s classic novel The Spy Who Came in from the Cold, with its gray compromises and cynical, world-weary protagonist.) Helms’s world was black-and-white: The CIA’s spies were honorable men in a fight against evil.

It was while they were in London that Casey told Helms about an idea hatched by Bill Donovan: the creation of a peacetime intelligence service that would be assembled from the remnants of the OSS. Upon the disbanding of OSS in 1945, several halfhearted iterations were tried—the Strategic Services Unit (SSU), the Office of Special Operations (OSO), and the Central Intelligence Group (CIG). Then, in 1947, the Central Intelligence Agency (CIA) was born, created by President Harry Truman’s National Security Act.

The first Director of Central Intelligence (DCI) was appointed two years earlier. Rear Admiral Sidney Souers became the first man to hold the title; to commemorate the occasion, Truman threw a lunch—and presented each guest with a black cloak, black hat, and wooden dagger. Souers was the first of four mostly forgettable CIA directors plucked from the military; he was followed in rapid succession by Army Lieutenant General Hoyt Vandenberg, Navy Admiral Roscoe Hillenkoetter, and Army General Walter Bedell Smith. Then, in February 1953, Eisenhower appointed the first civilian CIA director, Allen Dulles.

For the next eight years, allied with his influential brother, Secretary of State John Foster Dulles, Allen Dulles transformed the CIA into a powerful cudgel against communism, overthrowing governments in Iran and Guatemala, and serving as Ike’s covert army general in the Cold War struggle.

Present at the creation, Helms would be at the center of the CIA for the next three decades, privy to its secrets, triumphs, and disasters. It was a time when the agency largely did what it wanted and Congress looked the other way. When it was time to renew the CIA’s budget, the director would pay a visit to Senator Richard Russell, chairman of the Appropriations and Armed Services Committees. As one veteran operative recalled: “Russell would say, ‘How much do you need?’ [The director] would say, ‘Well, here’s my number.’ And Russell would say, ‘Well, how about this number?’ And that was it.” It was accepted that spies were mysterious figures who moved in the shadows. All of this would change soon enough.

Few were better than Helms at navigating the corridors of power in Washington, D.C. “He understood how to operate at the policy level as bravely and as ably as anybody I’ve ever seen,” said veteran CIA analyst Charles Allen. An agency legend who joined the CIA in 1958, Allen would become the National Intelligence Officer (NIO) for Warning, and later the Assistant Director for Collection (ADCI). (This is probably a good place to explain some CIA terminology: “Agents” or “assets” are by definition foreigners who are recruited overseas to spy for the agency; CIA employees, by contrast, are called “officers.” Officers in turn may be “operatives” or “analysts,” depending on the division they belong to.) Allen had never seen anyone with a better survival instinct than Helms. During his steady rise through the Directorate of Plans (DP), as the covert operations division was then called, the paperwork for most clandestine missions crossed his desk, but Helms avoided blame for operations that went sour. “Ducky Dickie,” he was called, for his ability to evade responsibility for ill-fated ventures; like a good covert operative, Helms seldom left fingerprints behind.

Operation ZAPATA, the CIA debacle that came to be known as the Bay of Pigs, was a classic example of Helms’s dodging a bullet that might have ended his career. He was aided by a fortuitous turn of events. In 1958 Helms was the odds-on favorite to be named Deputy Director of Plans (DDP). (This was the CIA’s covert arm, later renamed the Directorate of Operations, or DO.) But Helms was passed over by Director Allen Dulles in favor of Richard Bissell. Bissell, a brilliant technocrat, had spearheaded the groundbreaking development of the U-2 surveillance plane. His promotion was a shattering blow to Helms, but it would turn out to be a blessing in disguise—because it would fall to Bissell, as DDP, to plan the ill-fated invasion that would become the CIA’s worst disaster. Sensing a fiasco-in-the-making, Helms, instead of warning against the operation, made sure that he wasn’t in the loop. An office betting pool was started: How long would it take Helms to attend a planning meeting for the Cuba invasion? He never attended a session.

Helms kept a low profile. He drove old, conservative black cars that wouldn’t be noticed. Not even his son knew what he did for a living. “There is nobody who was more artful at dodging questions than my father,” said Dennis Helms, now seventy-seven, a patent attorney in Princeton, New Jersey. “If you asked him the time, he’d give you the weather. He was guided by the principle that if you don’t say anything, then you can’t say anything wrong.” The stories of Helms’s laconic nature are legion. His second wife, Cynthia, recalled that on the eve of their marriage in 1968 she got a phone call from Alice Acheson, wife of former secretary of state Dean Acheson. “She said, ‘You can’t possibly marry him!’ And I said, ‘Why not?’ And she said, ‘He doesn’t talk!’?”

Despite being the soul of discretion, Helms moved effortlessly from watering holes to embassies to the living rooms of high-society hostesses like Katharine Graham, The Washington Post’s publisher. “He was almost a James Bondian figure,” said Robert Gates, a young CIA analyst who would later become director. “In those days people still smoked. He was a smoker and he drank martinis; he was very suave and clearly was a player in town.” Helms smoked two packs of Chesterfields a day but limited himself to a single, very dry martini. Washington’s literati, among them James “Scotty” Reston of The New York Times and columnist Stewart Alsop, gathered round when the spymaster worked the room, martini in hand. “Run it by Dick,” a New York Times editor once told his star investigative reporter, Seymour Hersh (to Hersh’s dismay). But Helms seldom stayed long at the party. “He knew exactly where the exit was in every embassy in Washington,” said Cynthia.

At his modest suburban house in Chevy Chase, Maryland, Helms threw his own parties: eclectic gatherings of spies, professors, journalists, and diplomats (but rarely politicians). “They used to come on New Year’s Eve, a lot of the old guys in black tie, and we’d play charades,” recalled Dennis, referring to the parlor game in which contestants acted out well-known phrases which the other team tried to guess. “Dad’s friends were a pretty smart crowd: two Williams College presidents, all kinds of people from Yale.”

One regular at these affairs was a CIA legend, a lean, angular, bespectacled Yale grad with a mischievous grin and a mysterious manner. A chain-smoker, he bred rare orchids and designed elaborate fishing flies. At Yale he’d published a literary magazine and befriended the poet Ezra Pound. The phrase he chose for charades, recalls Dennis, was from T. S. Eliot: “garlic and sapphires in the mud, clot the bedded axle-tree.” “So needless to say nobody guessed that, and my mother said, ‘Time out!’?” The man she banned from future charades games was the CIA’s head of counterintelligence, James Jesus Angleton.

Angleton would cause Helms and the CIA no end of grief in the postwar years. But in the immediate aftermath of the Bay of Pigs, Helms had more pressing problems. For his role in the debacle, Director Allen Dulles had been sacked by Kennedy, who appointed John McCone in his stead; Bissell was gone, too. But there’d still be hell to pay because the attorney general, Bobby Kennedy, was furious, out to avenge the president for his embarrassing humiliation at the hands of his generals and spies. “After the Bay of Pigs, Bobby Kennedy became obsessed, which means Jack Kennedy became obsessed, with killing Castro,” said Burton Gerber, an operative who served in the Middle East and Russia. The marching orders, for Helms and his colleagues, were to get rid of Fidel Castro—immediately, by any means necessary.

This was not a new command. The CIA’s murder plots against Castro had begun under Dwight Eisenhower. The schemes had been delegated to the CIA Security Staff, a shadowy division for off-the-radar operations, and a colorful character named William Harvey. Harvey, a rotund ex-FBI agent who’d had a falling-out with Director J. Edgar Hoover, was a bullheaded operative who seldom let rules interfere with a mission; Harvey almost always carried a loaded pistol in his belt. While stationed in Germany, he’d run an ambitious covert operation: Workers burrowed a tunnel under the Berlin Wall, tapping into Soviet cables; unfortunately, the operation was compromised by a Russian mole. At one point Harvey was taken to the Oval Office to meet John Kennedy, who loved pulp spy novels. “They tell me you’re the closest thing we have to James Bond,” quipped the president.

Not that close, in Helms’s opinion. Anyone who thought so “had either never read Ian Fleming’s books, seen a Bond movie, or caught a glimpse of Harvey… who would never win the battle with his waistline.” Harvey was also “deliberately blunt and loudly outspoken, qualities that, with his heavy drinking, were eventually to catch up to him.” In short, the CIA had chosen a gun-toting, hair-triggered loudmouth with a heavy drinking habit to carry out the assassination of a foreign leader. What could possibly go wrong?

Harvey pursued an out-of-the-box idea: Why not reach out to people who did this kind of thing for a living—the Mafia mob boss Sam Giancana and his lieutenant Johnny Roselli? (Giancana’s mistress Judith Exner was having an affair with JFK, though Harvey was probably unaware of this.) Would the mobsters be interested in teaming up with the CIA to knock off Fidel Castro? No gadgets were too outlandish for ZR/RIFLE, as Harvey’s project was called, including poisoned cigars, deadly scuba diving gear, and exploding seashells. (Most of these never got beyond the CIA laboratory.) Roselli managed to have a jar of poison pills smuggled into Havana. But in the end, ZR/RIFLE was a case of life imitating farce, a Peter Sellers and Monty Python movie rolled into one: No would-be assassin got anywhere near Castro.

Helms insisted he knew nothing about ZR/RIFLE until he replaced Bissell as DDP in 1962. “After checking into it I told Bill Harvey—who agreed entirely—to close it down,” he wrote later. But the evidence suggests that Helms approved Harvey’s project and kept it secret from those who didn’t need to know. That was the way assassination plots were handled in the agency’s early days; presidents—and even CIA directors—maintained plausible deniability. Helms evidently kept his boss, Director John McCone, out of the loop. McCone, a devout Catholic, professed to be appalled when he learned about the Castro plots years later.

“There is no easy answer to the question of assassination,” Helms would write later. “Clearly, boundless misery would have been avoided if Hitler had been struck down.… That said, in peacetime the assassination of troublesome persons is morally and operationally indefensible.” But though the Mafia hit men were now gone, the pressure on Helms to “get rid of Castro” only intensified. Bobby Kennedy was relentless. “[Robert] Kennedy wanting Mr. Castro killed was a huge issue,” recalled Cynthia Helms, who got an earful about it years later from her husband. “Robert Kennedy was out at the agency and he was obsessed by it. Dick said, ‘you can’t see the lashes on my back but they are there.’?”

Bobby Kennedy never stopped demanding that the CIA eliminate Castro. Helms would nod dutifully, and then go about his business of trying to topple the Cuban government by other means. It wasn’t the first or last time that Helms, faced with an arguably illegal order, would pretend to go along while dragging his heels. “When people wanted to invade Cuba or kill Castro, his attitude was, ‘Oh, God,’?” said Thomas Powers, author of the Helms biography, The Man Who Kept the Secrets. “He just was so against it all,” said Cynthia of the plots to kill Castro. “He said to me one day, ‘I was never going to do it. We were never going to do it.’ But they made his life miserable over it.”

ZR/RIFLE was part of Operation MONGOOSE (so named by presidential assistant Richard Goodwin). Its objective was to overthrow Castro—through sabotage, propaganda, and efforts to spark an insurrection. The operation involved six hundred CIA personnel and five hundred contract personnel, as well as elite counterinsurgency experts General Maxwell Taylor and Edward Lansdale. “The Kennedys were enchanted by those guys,” said Frank Wisner Jr., son and namesake of a legendary Helms CIA colleague. “The Green Berets, John Wayne: ‘Send in a few good men.’ The music plays in the background, the natives are rallied and deal with the hated communists.” But it was mostly a show by Helms; he knew the enterprise was a fool’s errand. MONGOOSE only confirmed Helms’s skepticism toward presidents (and attorneys general) who were clueless about the CIA’s capabilities.

It also clinched Helms’s belief that covert operations were a dangerous gamble. It wasn’t just the “perfect failure” of the Bay of Pigs. In Helms’s view, even the successful CIA coups in Iran and Guatemala—AJAX and PBSUCCESS, respectively—had been flukes, unique situations: they’d depended on ideal circumstances, and on everything going right. “Most of the best clandestine service officers that I’ve ever known thought that way,” said Bob Gates. “I’m not sure that any careers got destroyed by a failure on the espionage side, but many were destroyed by covert action.” Covert action, Helms wrote, should not be “wielded about like an all-purpose chainsaw. It should be used like a well-honed scalpel, infrequently, and with discretion lest the blade lose its edge.”

In 1962 the CIA would find out if it was equal to the ultimate challenge: averting Armageddon. The CIA’s new director, John McCone, in Helms’s opinion, was “exactly the right man” to replace Dulles. A rich conservative who’d run the Atomic Energy Commission, McCone was intelligent and aggressive, not afraid to give the president his unvarnished advice. In the late summer of 1962, JFK would need it. Something strange was going on in Cuba: Eight Soviet ships had docked there; thousands of Russian military specialists were on the island; and a CIA-run U-2 flight showed a Soviet construction site with two surface-to-air (SAM) missiles protecting it.

The foreign policy establishment was unanimous: Soviet premier Nikita Khrushchev wouldn’t risk installing offensive nuclear missiles so close to Florida. Such a move would be rash, provocative; it could start World War III. But McCone, alone in the administration, was convinced the Soviets were doing just that. From the south of France, honeymooning with his second wife, he pressed his case with the president. U-2 photos showed that McCone’s hunch was right. In the end, armed with eyewitness accounts from the island and stolen manuals of Russian intercontinental missiles (provided by a Soviet defector named Oleg Penkovsky), McCone gave Kennedy a decisive edge in his showdown with Khrushchev. The CIA helped to avert a nuclear war.

On November 22, 1963, Helms was having lunch with McCone in a small room adjoining the director’s office when the door flew open: An aide burst in with news that President Kennedy had been shot in Dallas. McCone grabbed his hat and raced to meet Bobby Kennedy at his home in nearby Hickory Hill, Virginia. Helms headed to his office to hold down the fort.

Helms later wrote, “I have not seen anything, no matter how far-fetched or grossly imagined, that in any way changes my conviction that Lee Harvey Oswald assassinated Kennedy, and that there were no co-conspirators.” But Helms was being disingenuous. The truth is, he was deeply concerned that Oswald might have been sent to kill Kennedy by a foreign power.

The Kennedys had tried mightily to have Castro killed. Did Castro get Kennedy first? “Dick thought, and I don’t think I’m exaggerating,” said Cynthia, “that Robert Kennedy suffered from guilt after Kennedy was assassinated, from this relationship with the Castro murder plots. Because Bobby never quite knew… he never quite knew how the thing had played out.” If Bobby Kennedy felt guilty about the Castro plots, it might explain why the first question he asked McCone at Hickory Hill was whether Castro was involved in JFK’s assassination. McCone told him the CIA had no evidence of that.

Helms dismissed the idea of a Cuba-Oswald plot as a figment of conspiratorial imaginations, the tinfoil hat brigade. But Russia was another story. “A much better case can be made that Oswald was put up to it by the Russians,” Helms told a CIA historian, without elaboration. Helms, it seems, was worried about Moscow’s possible involvement.

In the early 1990s, Helms invited a retired head of the KGB, Vadim Bakatin, to dinner at his house in Northwest Washington. “My job was to keep his wife busy,” recalled Cynthia. While the women chatted, Helms took the former Russian spymaster into his study. “Dick obviously wanted to check some things,” said Cynthia, who strained to overhear their conversation. “I noticed he went through some things that he really wanted to know. One was Alger Hiss, he got confirmation of that.” Bakatin confirmed that Hiss, a former State Department star, had in fact been a spy for the Soviet GRU. “And another thing…was Oswald.” Alas, what the ex-KGB head told Helms about the Soviets and Oswald is not known. And Helms never wrote or spoke about this encounter.

The possibility of Oswald’s having been a tool of the Russians triggered a decade of soul-searching at the CIA: a bitter struggle that would almost paralyze the agency and destroy promising careers. And the man at the center of this drama was the mysterious head of counterintelligence, James Angleton. In his book Wilderness of Mirrors, David Martin described his aura: “Angleton. Even the name suggested labyrinthine conspiracies. His body seemed stooped and cocked to one side in a way that hinted of both deformity—as if his very frame had been twisted out of shape by machinations—and conspiracy, as if he were perpetually bending toward someone’s ear to whisper a secret.”

Angleton had an office on the second floor of CIA headquarters, where he sat at his desk, enveloped in cigarette smoke, the blinds closed, barely illuminated by a green desk lamp. Once a bright light of the CIA, Angleton in his later years would become a kind of Death Star, pulling people into his orbit and ruining careers. And Helms, blinded by admiration and loyalty, was at a loss for how to deal with him.

The trouble began with the defection of a Russian major named Anatoliy Golitsyn. Assigned to the Soviet embassy in Helsinki, Finland, Golitsyn escaped to the United States on December 15, 1961, in a dramatic dash with his wife and daughter by train across the Finnish-Swedish border. He was flown to the United States, where Angleton and his counterintelligence (CI) staff were waiting for him.

Golitsyn told Angleton that the CIA had been penetrated at the highest level by Russian spies. Be on the lookout for CIA officers with the letter “K” in their surname, he warned. Moreover, Russian defectors were actually KGB plants, Trojan horses sent to deceive the West with disinformation. It was all part of a sophisticated and diabolical Soviet deception campaign. As Angleton weaved Golitsyn’s warnings into the web of his Master Plot, he would henceforth consider every defector, and many CIA officers, guilty until proven innocent of spying for the Soviets.

“We used to call it Sick Think,” said Gerber, the veteran operative whose friendship with Helms was strained by the Angleton affair. Critics within the CIA dubbed Angleton’s conspiratorial musings “the Monster Plot.” There was no arguing with the byzantine logic of the counterintelligence chief, said Gerber. “I’d say, ‘Here we have this and that and I think such and such.’ And he’d say, ‘Well, I understand, based on what you know, but if you only knew what I know.’ I’d say, ‘Well, tell me.’ He’d say, ‘Well, I can’t tell you.’ I became convinced he was the Wizard of Oz; there was nothing there except a curtain.”

But Angleton’s authority was almost impossible to challenge. And he used that authority to mount a campaign against one of the CIA’s most valuable informants, a Soviet defector named Yuri Nosenko. After Kennedy’s assassination, Nosenko, a KGB lieutenant colonel still working for the Soviets, met secretly with his CIA handlers while on leave in Geneva and assured them that the Russians weren’t involved with Oswald. But Angleton was having none of it; he insisted that Nosenko was lying—he was a KGB plant. Hadn’t Golitsyn warned them about just such a thing?

After he defected to the U.S., Nosenko was put in solitary confinement at Angleton’s insistence—verbally abused and harshly interrogated for nearly two years. Angleton’s suspicions were never confirmed, and Nosenko was later relocated in the U.S. But it was just the beginning of Angleton’s reign of paranoia: More than a dozen CIA officers were fired, or their careers derailed, based on unfounded accusations of spying for the Russians. “He destroyed some agency career people’s lives, there’s no question about it,” said Richard Kerr, a veteran CIA analyst who would become deputy director. “The suspicion of everything, of everybody, was nearly a disease, an infection.”

While the agency was in the grip of Angleton’s infection, Helms, now the DDP, was loath to rein in his old friend; he had Angleton’s back. “It was a question of loyalty there,” said Burton Gerber, the Russia expert who was Helms’s contemporary. “These old boys knew each other. When he writes about Angleton in his memoir, you can see he’s queasy about the whole thing.” No intelligence service, Helms wrote, “can for very long be any better than its counterintelligence component.” And no one was better at counterintelligence than Angleton. Helms’s wife, Cynthia, recalled a pointed conversation about their odd, idiosyncratic friend: “Dick sat me down one day—he didn’t often do this—and he said, ‘I want you to understand something. You are going to have to defend my stance on Angleton, and I want you to understand that I have made up my mind—because I will never have a mole with Angleton there, and that is more important to me than anything.’?”

No doubt, Angleton had an eye for moles and a mind for counterintelligence. The only trouble was, in an almost unbelievably ironic twist, Angleton himself had been betrayed by the most notorious Russian mole of all.

Harold Adrian Russell Philby, better known as “Kim,” was a rising star in the British intelligence service, MI6, a smooth-talking bon vivant who charmed his way into the nerve center of American intelligence. Philby had met Angleton at Bletchley Park in England, the headquarters of the British wartime decoding effort, and saw him again in Rome. While serving as Britain’s chief liaison to the CIA and FBI in Washington, the British spy struck up an intimate, boozy friendship with the American counterintelligence chief over long, martini-soaked lunches. Angleton and his wife, Cicely, often flew to London, where they babysat Philby’s children while he gallivanted around Europe.

But all along Philby was a Soviet spy; he’d been recruited at Cambridge University in his early twenties. When the CIA finally put two and two together and Philby was exposed in 1951, the disgraced British intelligence official was recalled to England at the insistence of the CIA. Philby quit MI6 but was not arrested by the British (no one wanted to face the embarrassment of such a scandalous intelligence breach); he joined The Economist as a foreign correspondent. In 1963, at an apartment in Beirut, an MI6 officer confronted him with evidence of his treason. The next day Philby fled to Moscow, where he spent his remaining years gloating about his betrayal of the West. He died, a hero of the Soviet Union, in 1988.

Angleton was crushed. His friend and intelligence soul mate had not only made a fool of him; he’d given up to his Soviet masters scores of CIA and British agents who were summarily tried and executed. Angleton was never the same after Philby’s betrayal; he drank more and more heavily, and receded deeper into his wilderness of mirrors. But as long as Helms had anything to say about it, Angleton would remain the head of counterintelligence at the CIA. (Decades later, in 2007, at a dinner party at Washington’s Willard Hotel, this author found himself seated next to an elegant, diminutive woman in her nineties. “Mrs. James Jesus Angleton,” she replied proudly when I asked her name. “My God, you must have known Kim Philby!” I said. Cicely Angleton paused for a beat, and then said: “Well, evidently not well enough!”)

One day in 1965, President Lyndon Johnson summoned Helms, then the CIA’s Deputy Director of Plans (DDP), to the Oval Office. Since Kennedy’s assassination, LBJ hadn’t given much thought to the CIA. But now he was ready to make some changes. “John McCone has resigned,” he told Helms, “and I’ve decided to appoint Admiral William Raborn as the new DCI. Do you know him?” “No, sir,” replied Helms. “Well, you will. You’ll be named deputy director at the same time. I want you to go to every meeting with the admiral whether here or around town. You know the agency. Red doesn’t.”

Vice Admiral William “Red” Raborn was evidently chosen to run the CIA because LBJ loved the way he ran the Polaris Missile program. But the agency wasn’t the only thing Raborn didn’t know. Geography was also not his strong suit. At one meeting that became grist for the CIA gossip mill, the new director asked his briefer about Libya: “Is that a land-locked country?” The briefer replied: “Well, mostly.” After just fourteen months, Raborn resigned. On June 30, 1966, LBJ appointed Richard Helms as his new Director of Central Intelligence.

During the two years he served as Johnson’s CIA director, Helms would regard his boss with a mixture of fond admiration and complete exasperation. Helms admired LBJ’s determination to achieve his dream of a Great Society; he was exasperated by his obstinacy over Vietnam. “He really admired Johnson,” said Cynthia. “And he really thought that Johnson suffered so over Vietnam. He said it was agony to see him sitting with his head in his hands.” Helms was not an agonizer; when it came to Vietnam, he was “the coolest of advocates,” as his biographer Powers put it, “presenting his agency’s views on paper, defending them on paper, a paper general in a paper war.” Nonetheless Vietnam was a flesh-and-blood debacle, and it became for Helms “my nightmare for a good ten years. Like an incubus… it seemed I would never be free of it.”

The war had gone from bad to worse after an American-backed coup toppled South Vietnam president Ngo Dinh Diem in 1963. Barely three weeks before Kennedy’s assassination, an aide barged into the Roosevelt Room, where the president was meeting with aides, and announced that Diem had been killed; a cabal of generals had seized power. Kennedy turned ashen and abruptly left the room.

Whether he felt responsible for the death of Diem—whom the U.S. considered an impediment to the war effort—is anyone’s guess, but Kennedy knew that he’d given the generals the green light to proceed. For his part, Helms insisted his conscience was clear. “We were following orders and we were doing what we were supposed to do,” he said later. “But we had no role in this.… It was the Vietnamese who got together and chopped up Diem.… It simply is not true that the agency had anything to do with [it].” There’s no evidence that the CIA conspired in Diem’s murder—but, also, no doubt that the U.S. encouraged the rebellious generals to stage their coup.

In the beginning, Helms was excluded from LBJ’s inner circle. After briefings with the president and his advisers, at Johnson’s request he’d gather his papers and excuse himself. That was fine with Helms, who considered himself a neutral broker of intelligence, content to keep his opinions on policy to himself. “My role was to keep the game honest,” he said. But Helms’s standing with LBJ improved markedly after war broke out in the Middle East in 1967.

In the fall of that year, the Israelis warned the U.S. that without American help they faced defeat at the hands of their Arab enemies. Helms assured LBJ of the contrary. The CIA estimated that not only would Israel defeat her Arab neighbors but that the war would last no more than seven days. That prediction looked prescient after Israel’s lightning victory in the Six-Day War. Helms proudly called it “the intelligence bingo of my time.” Shortly thereafter, newly impressed with his CIA director, LBJ invited Helms to stay behind for lunch. From that day forward, he was a regular guest at Johnson’s famous Tuesday lunches where the inescapable subject was Vietnam.

While Helms was preoccupied professionally by the war, his personal life took a fateful turn. He and his first wife, Julia, had been drifting apart. “She wanted a little more from him, and he didn’t have a lot to give,” said their son, Dennis. “His job was 8:15 in the morning till 7:15 at night, half a day on Saturday.” Helms was restless, too, and in 1965, at a dinner party, he met Cynthia McKelvie, a British expatriate also on the verge of divorce. She was opinionated, curious, and adventurous; as an eighteen-year-old during World War II she’d joined the “Wrens,” Women’s Royal Naval Service, and ran naval harbor craft, often under Nazi bombardment. With LBJ’s permission (he felt compelled to ask for it) Helms divorced Julia. He and Cynthia were married in 1968.

Helms now had a partner who shared his passion for tennis and ballroom dancing. Years later, during Nixon’s presidency, they found themselves on the White House dance floor, waltzing next to Fred Astaire and his partner, Farah Pahlavi, the glamorous Shahbanou, or empress, of Iran. “Dick on the same dance floor with Fred Astaire was his idea of heaven,” recalled Cynthia. Tight-lipped with everyone else, Helms confided nearly everything that was not classified to his new wife—especially his frustrations with LBJ over Vietnam.

By 1966, when Helms became DCI, 200,000 American troops were fighting in Vietnam out of more than two million who would join that losing cause. LBJ was desperate to give them good news and kept calling Helms in search of it. “You’ve got to give them some hope,” the president pleaded. “Just like a football team: You call them at the half and they are 21–0 behind and say, ‘Goddamnit boys, you can do it, now here’s how to do it. Let’s go!’ That’s what I’ve got to do. So I’ve got to rely on you to get this stuff.”

In an attempt to force the North Vietnamese to the bargaining table, LBJ launched Operation Rolling Thunder, a massive campaign of B-52 bombardments over North Vietnam. Had it intimidated Hanoi and changed hearts and minds? The answer, Helms told him emphatically, was no. In fact, the CIA concluded: “We see no signs that the air attack has shaken the confidence of the regime.… North Vietnam in the short term at least, will apparently take no positive step toward a negotiated settlement.” Analyst Richard Kerr recalled: “Our reporting was consistently negative, in terms of the effectiveness of the bombing and the question of whether the people were being won over.”

If anything, Helms told Johnson, the enemy’s will to fight was stronger. CIA analysts reported that North Vietnam’s ability to move troops and supplies down the Ho Chi Minh Trail, its main supply route to the South, had increased fivefold. In a 250-page study, “The Vietnamese Communists’ Will to Persist,” they concluded: “Nothing happening to the Vietnamese Communists as of mid-1966 is bad enough to make them stop fighting.” By defending the CIA’s relentlessly pessimistic estimates, Helms, who’d come up through the ranks as an operative, won the respect of the agency’s analysts.

He had to play referee between the CIA’s rival camps, who held diametrically opposed views on the conflict. The operatives on the ground in Saigon—including a future director named William Colby—were mostly convinced the war was winnable; they were by nature aggressive, can-do, optimistic—or if not, willing to suspend disbelief. By contrast, the analysts at Langley were deeply pessimistic, convinced there was no light at the end of the tunnel, in the metaphor of the day (or that the light was a freight train coming toward them). Helms chose a different metaphor. Trying to corral his feuding camps, he was “a circus rider standing astride two horses, each… going its own way.”

The third horse was the Pentagon and its Military Assistance Command, Vietnam, or MACV. While American troops were dying at a rate of nearly three hundred per week, the CIA and MACV engaged in a fierce argument over the size of the enemy they were facing. The bone of contention was the Order of Battle, the estimate of enemy troop strength. MACV calculated that the North Vietnamese troops were approximately 250,000 strong. The CIA counted “irregulars”—part-time fighters, guerrillas, and such—and put the number at twice that: about 500,000.

Helms’s special assistant for Vietnam affairs, George Carver, reported that General William Westmoreland, the commander in Vietnam, had simply ordered MACV to ignore the CIA’s estimate.

So far, our mission frustratingly unproductive since MACV stone-walling, obviously under orders.… [The] inescapable conclusion [is] that General Westmoreland… has given instruction tantamount to direct order that [enemy] total strength will not exceed 300,000 ceiling. Rationale seems to be that any higher figure would generate unacceptable level of criticism from the press. This order obviously makes it impossible for MACV to engage in serious or meaningful discussion of evidence.

In the end Helms hammered out a compromise with MACV; he knew that the CIA couldn’t win an argument with the Pentagon over enemy troop strength. But he felt he hadn’t pulled his punches with LBJ. “I was honest about my point of view and stood up to him, I didn’t take a lot of backtalk from him.”

Still, eventually it became clear that the president wasn’t listening. Helms never gave in to Johnson’s hectoring for good news—but he did not pile on with bad news either. “Helms reached a point where, in the morning briefings and the president’s daily brief, we just slacked off on providing information on Vietnam,” said analyst Kerr. “We did not do the aggressive pieces that were negative, because they were counterproductive.” Helms knew that bad news simply got LBJ’s back up. The president was fixated on the Pentagon’s ever-mounting toll of enemy casualties: “the body count.” Cynthia recalled her husband’s frustration: “The body count was a huge issue—who you count, and who it is that goes into that. But it was just endless, and he felt it was focused on the wrong thing.”

Helms thought it was time to reconsider the fundamental assumptions behind the war. It was an article of faith among LBJ’s advisers that allowing South Vietnam to fall would trigger the toppling of one neighboring country after another until all of Southeast Asia succumbed to communism. It was called “the domino theory.” But was there anything to that theory? At a pivotal meeting of LBJ’s senior advisers back in 1965, the war’s controversial architect, Defense Secretary Robert McNamara, made an impassioned argument: “Our national honor is at stake. Our withdrawal would start further probing by the communists. We would lose all of Southeast Asia.” In August 1967, on his own authority, Helms asked one of his analysts to examine what might happen if the U.S. acknowledged that the war was lost and simply packed up and went home.

The resulting thirty-three-page memorandum, on September 11, 1967, was titled “Implications of an Unfavorable Outcome in Vietnam.” It considered what might happen after the U.S. made a “reasonably orderly” withdrawal from Vietnam.

At some stage in most debates about the Vietnam war, questions like the following emerge: What would it actually mean for the U.S. if it failed to achieve its stated objectives in Vietnam? Are our vital interests in fact involved? Would abandonment of the effort really generate other serious dangers?

The memo conceded some risks.

There could be a spectacle of panic[ked] flight from the country, suicidal resistance by isolated groups, and Communist terror and vengeance. Clearly if this worst case came about, the discredit the U.S. would earn, which would be seen by many as not merely political but also a moral discredit, would be far greater.

… if one or more states in Southeast Asia did in fact fall under Communist control… the region could be in a turbulent and regressive condition for a long time. This would mean a major frustration of U.S. policy aims, but we think would not bring any major threats to U.S. security.

It concluded:

If the analysis here advances the discussion at all, it is in the direction of suggesting that such risks are probably more limited and controllable than most present argument has indicated.

The memo was full of caveats, but Helms knew it was damning; given the bitterly contentious debate over the war, just its existence would be politically explosive. Cynthia recalled her husband’s trepidation about showing it to LBJ: “He told me that he was going to stay behind after the Tuesday lunch and talk to Johnson, and give him the memo. He said it’s a little risky because I shouldn’t really be doing that. But he really felt so involved in LBJ’s trauma. He really thought that Johnson should get out of Vietnam.”

Helms gave Johnson the memo in a sealed envelope. And then he waited. Helms would later write that the president never said a word about it: “President Johnson never mentioned the document to me; nor, to my knowledge, did he raise it with anyone else.” But it’s hard not to suspect that Helms was dissembling here, perhaps keeping a presidential confidence. “Did LBJ read it?” I asked Cynthia. “Oh, yes,” she said. “And they talked about it. Dick was saying that there’d be no domestic repercussions if he got out of Vietnam. I suppose you could say that’s advocating. But he really wanted to help him.” Mrs. Helms did not know what LBJ said in reply.

Did any of LBJ’s advisers, or his war cabinet, read the memo? It was addressed to both LBJ and his national security aide, Walt Rostow. Rostow never acknowledged seeing it, but Cynthia believed he read the memo—and destroyed it, realizing how dangerous it would be to the war effort if revealed. Rostow “deep-sixed it,” she said.

Years later, Cynthia was at home alone. The phone rang and she answered it. It was McNamara, who at the time was researching his forthcoming memoir, In Retrospect: The Tragedy and Lessons of Vietnam. When published in 1995, the book would become a sensation with its dramatic mea culpa. More than 58,000 Americans and countless Vietnamese, McNamara now believed, had died in an ill-conceived cause.

Over the phone, more than twenty years after the American defeat, McNamara told Mrs. Helms that he’d just read “Implications of an Unfavorable Outcome” for the first time. He’d found the memo, declassified in 1993, in the archives of the LBJ Library. McNamara was shocked that he hadn’t seen it before. “Why wasn’t I shown this?” he demanded. “This would have helped me! I should have known!” “He was screaming over the phone at me,” said Cynthia. “He was just furious.”

In his memoir, McNamara wrote: “Having a senior adviser submit a memo questioning the fundamental premise underlying our involvement in a war, and not allowing him to discuss it with his colleagues, is certainly no way to run a government.” Helms shared McNamara’s vexation with LBJ’s decision-making process—the keeping of secrets from colleagues, the pitting of advisers against one another, the cajoling and bullying. But Helms also knew that you couldn’t change a president, and that CIA directors shouldn’t try.

“Every president is going to do business the way he wants to do it,” Helms reflected years later. “You say, well, he should discipline himself—but they never do. They do it exactly the way they want to do it. Even if you convince them that they ought to do it differently, they’ll never do it more than twice… and then they go back to the way they wanted to do it before.”

Helms almost never raised his voice, rarely betraying annoyance or satisfaction. But one day a CIA analyst named Jack Smith barged into his office and got a rise out of him. Why, Smith demanded, had the president just approved a war initiative that the CIA had trashed in a recent study? “Dick fixed me with a sulfurous look,” recalled Smith. “How do I know how he made up his mind?” Helms snapped. “How does any president make his decisions? Maybe Lynda Bird was in favor of it. Maybe one of his old friends urged him. Maybe it was something he read. Don’t ask me to explain the workings of a president’s mind!”

Yet Helms came to believe he understood Johnson. Why didn’t LBJ cut his losses and extricate the U.S. from the quagmire of Vietnam? Helms thought it was for just one reason: He couldn’t bear to be the first American president to lose a war.

In the summer of 1967, Johnson pushed Helms to go after his enemies at home. LBJ and his inner circle were convinced, despite no discernible evidence, that the leaders of the antiwar movement were controlled and directed by foreign communist powers. The president wanted Helms and the CIA to confirm this supposition—by any means necessary. Specifically, the president wanted the agency to conduct domestic surveillance of anti-Vietnam protesters.

One might have expected Helms, of all people, to refuse point-blank: The CIA was forbidden by its charter to engage in domestic police activities; surveillance of U.S. citizens required court-ordered search warrants. But when Helms tried to object, Johnson cut him short: “I’m quite aware of that. What I want is for you to pursue this matter, and to do what is necessary.” The next day, Helms set up a Special Operations Group (SOG) and MHCHAOS was born. (The prefix MH was for projects with worldwide reach.) Under the program, which ran from 1966 to 1973, the CIA would illegally compile files on 7,200 Americans and infiltrate antiwar groups and even unrelated organizations—from the women’s liberation movement to the Jewish service organization B’nai B’rith.

Why did Helms succumb to LBJ’s pressure? He had a soft spot for Johnson; Helms sympathized with his anguish over the war. He also thought he had little choice but to go along. “Johnson never said to me, ‘do X, Y, Z,’?” Helms explained. “He said, ‘I need this.’ So MHCHAOS was an effort to put in real life terms the solution to his problem.” I asked Cynthia why her husband didn’t draw a line. “Why not simply say, ‘Mr. President. I’m sorry, that’s illegal. We can’t do that?’?” “Well, I think he did,” she replied. “He said he didn’t want to do it. He tried not to, he tried not to break the law. But he did it. He just felt that LBJ needed help.”

As with MONGOOSE, which targeted Castro, Helms reasoned that the way to minimize the danger, and keep it under wraps, was to put the operation under his thumb. As he later explained: “Because the president had directed us to sail so closely to the wind, I wanted to keep this activity compartmented from other operational activity and firmly under my control.” The truth was, Helms was sailing not close to the wind but right up on the rocks: Later, MHCHAOS would be exposed by New York Times reporter Seymour Hersh.

Helms had allowed his sympathy for a president to distort his judgment as director; he’d violated the law and the CIA’s charter. He would face a similar test, and even bigger stakes, with Richard Nixon.

Johnson’s announcement in March 1968 that he wouldn’t run for reelection shocked almost everyone. But it didn’t surprise Helms; he’d seen the war—and LBJ’s heart condition—take a heavy toll on the man he “had thought to be indefatigable.” Helms was worn out, too, but he wanted to stay on as director—and got his wish when Nixon reappointed him. Over the next few years, he’d have ample opportunity to wonder whether he should have retired with LBJ.

In the beginning, Helms barely saw the president. “Nixon just didn’t like to deal with people individually the way Johnson did,” Helms recalled. “They’re just different personalities. He liked to deal through his staff.” The director was told to go through Henry Kissinger, Nixon’s imperious, domineering national security adviser, who would give summaries of his views to Nixon as he saw fit. Moreover, the President’s Daily Brief (PDB)—traditionally the agency’s conduit to the president—would go first to Kissinger and the national security team. Nixon wasn’t reading it. Adding insult to injury, Nixon installed two loyalists as Helms’s deputy directors: General Robert E. Cushman, who’d been Nixon’s military aide when he was vice president, and Vernon Walters, a retired Army general, who’d worked as his interpreter. Helms soon realized they were sent to spy on him.

Nixon didn’t hide his disdain for his CIA director. At NSC meetings, he interrupted Helms frequently—sometimes gratuitously, often correcting him on some niggling point of fact or geography. Nixon’s low opinion of the CIA’s workforce was also on display. “What are those idiots out in McLean doing?” Nixon wondered aloud. “There are forty thousand people out there, reading newspapers.” Helms shrugged off the slights; he worked for one president at a time, and he’d take whatever indignities came his way. “Get on with it!” was his favorite rallying cry (and his advice to beleaguered successors). But he found Nixon puzzling—and bizarre. He told Cynthia he felt sorry for the president’s wife, Pat Nixon. One day he watched as Mrs. Nixon stepped out of a car and stumbled, landing on her face on the pavement. The president didn’t move a muscle to help her.

Nixon was convinced that the CIA’s past was full of skeletons, particularly involving the Kennedys; he surmised that Helms and his ilk must be covering up for them. The president’s close aide and domestic adviser, John Ehrlichman, had assembled a team of oddball investigators known as “the Plumbers,” so named because their original mission was plugging national security leaks. They were told to find dirt on Nixon’s enemies and political opponents—and if that failed, to manufacture it.

One of the plumbers, a veteran ex-CIA operative named Howard Hunt, created a bogus White House cable tying President Kennedy to the Diem assassination. Then, one day in 1971, Ehrlichman called Helms with a request: Would he send over the CIA’s documents on the Bay of Pigs and the Diem assassination? Helms replied that such a request would have to come from the president himself. Ehrlichman arranged a meeting with Helms and Richard Nixon.

Just before the meeting, Nixon and Ehrlichman engaged in a giddy conversation, caught on the White House tapes; they chatted excitedly about all the skeletons they imagined must be hidden in the CIA’s closets. “Helms is scared to death of this guy Hunt that we’ve got working for us—because he knows where a lot of the bodies are buried,” Ehrlichman told Nixon. “Supposing we get all the Diem stuff, and suppose we get something that we can really hang Teddy or the Kennedy clan with… we’re going to want to run with it.” Nixon enthusiastically agreed.

But it was an exercise in wishful thinking; there was no secret cudgel to bring down on the Kennedys—or any hammer involving Helms and the Bay of Pigs. It was all a figment of Nixon’s imagination. (Much like another president’s delusion, more than forty years later, that a computer server from the Democratic National Committee was spirited away to the Ukraine.)

When Helms arrived for his appointment at the Oval Office, he was carrying an assortment of files, apparently innocuous, related to the Bay of Pigs. “I said, ‘Now do you want these papers? Here are the problems and so forth,’?” Helms recalled telling the president. “Nixon said, ‘these things didn’t happen on your watch’… and gave me certain assurances that while he wanted the papers, he would not use them to damage the agency or anything.” Helms agreed to give him the files. Nixon later complained that the Bay of Pigs file was “incomplete.”

A few years later, a congressional report criticized Helms for having given anything to Nixon; future CIA directors, it said, should have their own political base or independent means by which to withstand presidential arm-twisting. Helms was infuriated. “It’s just baloney that you have to have a personal fortune or a big political base to have the guts to stand up to a president,” he fumed. “I stood up to Nixon, I stood up to Johnson—and if anybody can tell me any time when I failed to do so I’d appreciate knowing it.”

As the Vietnam War raged on, Helms had many opportunities to stand up to Nixon. The president had promised a “secret plan” to end the Vietnam War, but Nixon had no plan, only the vaguest notion of getting out without appearing to have lost. Helms thought Nixon’s chances of success were no better than Johnson’s, but he stayed in his lane, continuing to deliver news the president didn’t want to hear. “He would do it in a way that’s polished but that would not pull his punches,” recalled Charlie Allen, the veteran analyst. “Maybe it was his years in journalism, in policy circles, in Europe, his understanding of other cultures and language.” But while Helms was polished around the cabinet table, he would let his hair down with Cynthia. “We were at a dinner party,” she recalled. “I can remember it so clearly. Kissinger got up and said, ‘Peace is at hand.’ And he made this speech. Well, we got going out through the passageway, and Dick said to me, ‘Bloody hell! You haven’t gotten any peace at all.’?”

Yet the crisis that would make Richard Helms a household name, and cause him the most personal anguish, would unfold closer to home. In 1970 a leftist candidate named Salvador Allende was poised to win Chile’s presidential election, threatening to nationalize industry and confiscate foreign-owned property. This unexpected development was anathema to Nixon, who feared that all of South America, from Cuba to Chile, would become a “red sandwich.” Since 1960, the CIA had been disseminating anti-Soviet propaganda and pouring money into the campaigns of Chile’s centrist candidates. It did the same in the run-up to the 1970 election.

Even in the context of the Cold War, Allende was hardly a serious threat to American national security; Kissinger would later quip, “Chile is like a dagger pointing to the heart of Antarctica.” But the possibility of Allende gaining power alarmed American corporations, including International Telephone & Telegraph (ITT) and Pepsi-Cola. “There was really no heavy U.S. interest except business interest,” said Burton Gerber, the Russia hand. “That’s what was driving it.” That and one other factor. As Helms put it: “Truman had lost China. Kennedy had lost Cuba. Nixon was not about to lose Chile.”

The CIA predicted that a centrist candidate would win the election. Instead, Allende squeaked out a victory in a plurality; when approved by the Chilean Congress he would assume the presidency in a little over a month. The reaction in the White House was apoplectic. At a hastily called meeting with Kissinger and Helms, Nixon was furious with his director, convinced the CIA had failed him again. Helms was to do whatever it took to prevent Allende from taking office, Nixon demanded. As the president fumed, Helms scribbled notes:

One 10 chance perhaps, but save Chile

worth spending

not concerned risks involved

no involvement of Embassy

$10,000,000 available, more if necessary

Full-time job—best men we have

game plan

make the economy scream

48 hours for a plan of action

Helms understood exactly what this meant: “President Nixon had ordered me to instigate a military coup in Chile, a heretofore democratic country.” And he saw no possibility of ignoring, or slow-walking, this command. As Helms later wrote, defensively: “By what superior judgment was I to leave the White House and then decide that the President did not mean what he said?” Yet more troubling to Helms than his marching orders was the impossibility of carrying them out; preventing Allende from taking office would take time, and the CIA didn’t have enough of it.

Ultimately, Allende would take office, only to be overthrown in a military coup that had the CIA’s fingerprints all over it. Allende was an apparent suicide. And an oppressive military regime would rule Chile for a generation.

Helms’s day of reckoning would come a few years later, in testimony before Congress. Asked under oath if the CIA had tried to overthrow the Chilean government, Helms would find himself caught between his oath of secrecy as director and his obligation to answer truthfully. (The story of Chile’s military coup, and Helms’s fateful testimony about it, is told in chapter 2.)

Chile and all the other challenges were about to be overshadowed by the central drama of Nixon’s presidency. As his campaign for reelection began, the thirty-seventh president was overwhelmingly favored to defeat his potential Democratic opponents. But Nixon was taking no chances. His political enemies would stop at nothing to beat him, he believed. Nixon would do whatever was necessary to win.

Early in the morning on June 17, 1972, Helms was awakened by a phone call. It was the CIA’s chief of security. Five men, he reported, had been arrested at the Watergate Complex, planting bugs in the Democratic National Committee headquarters. Helms took a deep breath. “Yes,” he said. The security chief went on:

“Four Cubans and Jim McCord.”

“McCord? Retired out of your shop?”

“Two years ago.”

“What about the Cubans.… Do we know them?”

“As of now I can’t say.”

“Is that all of it?”

“No, not half. Howard Hunt also seems to be involved in some way.”

As far as Helms knew, the Watergate break-in wasn’t a CIA operation. But Hunt had worked for the CIA in Guatemala, Mexico, and Europe—and on the task force of the Bay of Pigs operation. Helms also knew that Hunt had worked as a “security consultant” at the White House. What Helms did not know was that in July 1971, Ehrlichman had telephoned Helms’s deputy Robert Cushman to tell him that Hunt needed some assistance and wanted to come by the CIA.

Without informing Helms, Cushman had said yes to Hunt and given him some “operational gear”: a wig, a voice-altering device, and some fake IDs. When Hunt came back a few months later with more demands—for telephone answering services and a secretary—Cushman got cold feet. He said no—and informed Helms. (The CIA gear Hunt borrowed was used in another botched break-in: at the Los Angeles office of the psychiatrist for Daniel Ellsberg, who had leaked the secret Pentagon Papers.)

As his security chief talked about the incident at the Watergate, Helms took another deep breath. “Is there any indication that we could be involved in this?” he asked.

None whatsoever,” the chief replied.

Helms told him to stay on top of the matter; he would see him Monday morning.

For the next two weeks, as the break-in dominated Washington’s news cycles and political gossip mills, Helms’s instructions to his staff were, in effect: “Keep cool, do not get lured into any speculation, don’t volunteer any information, and just stay the hell away from the whole damned thing.”

But the damned thing was closing in on Helms.

Nixon and his henchmen had hit on a plan: If the break-in could be portrayed as a CIA covert operation, instead of a Nixon campaign plot, the White House could escape scot-free. After all, three of the Watergate burglars—James McCord, Frank Sturgis, and Bernard Barker—had once worked for the CIA. And FBI director Patrick Gray had suspected agency involvement from the start.

H. R. Haldeman, Nixon’s White House chief of staff, kept calling Helms at home. Cynthia had never known her husband to raise his voice, much less shout, but “he and Haldeman had words, definitely.” Haldeman kept pressing Helms to help the White House out of its jam. There was the thorny problem of coming up with hush money for the Watergate burglars. Couldn’t Helms pay it from the CIA’s “unvouchered funds”? Helms emphatically could not. “If the president wants that done, he’ll have to call me himself!” he shouted into the receiver. “I’m NOT doing it!”

Less than a week after the break-in, on June 23, Haldeman summoned Helms and his deputy Vernon Walters to the White House. When they arrived, Ehrlichman, the president’s other close adviser, was there. A moment later, Haldeman walked in.

“What connection did the CIA have with the break-in?” Haldeman asked the director. “The CIA had no connection whatsoever with the Watergate break-in,” Helms replied coolly. Haldeman ignored this and then got to his point. “The [FBI’s] investigation of certain Mexican leads,” he told Helms and Walters, “might jeopardize CIA activity there. Therefore it has been decided to have General Walters go to see [FBI director] Pat Gray and tell him that further investigation in Mexico could lead to the exposure of certain agency assets and channels for handling money.”

Then Haldeman made a bald threat. Even worse things might be exposed, he said darkly. “The President asked me to tell you this entire affair may be connected to the Bay of Pigs, and if it opens up, the Bay of Pigs may be blown…”

Helms leaned forward in his chair. His eyes narrowed as he looked straight at Haldeman. “The Bay of Pigs hasn’t got a damned thing to do with this,” he said. “And, what’s more, there’s nothing about the Bay of Pigs that’s not already in the public domain.” Ehrlichman thought Helms reacted “like a scalded cat.” Haldeman suspected the CIA director’s outraged reaction meant he was hiding something. Helms’s recollection was different: “I did not shout in the White House, and cannot even remember having shouted in my own office.”

Cynthia recalled that Helms was mystified by Haldeman’s talk of CIA operations in Mexico; nor did he have any idea what Nixon’s men were alluding to about the Bay of Pigs. “What the heck’s the president talking about?” he vented to his wife when he got home. Helms telephoned his security chief. “What are they talking about?” he said. “I don’t think we have any other operation in South America. I want you to search the whole agency, because I can’t think what the president’s talking about. He’s threatening me. And I don’t think there’s anything there.”

Threatening him with what? In his references to the Bay of Pigs, Haldeman later wrote that Nixon “might have been reminding Helms, not so gently, of the cover-up of… [plots against] Fidel Castro—a CIA operation which might have triggered the Kennedy tragedy and which Helms desperately wanted to hide.” But the truth was Nixon and Haldeman had nothing on Helms beyond idle suspicions about skullduggery.

Haldeman had completely misread the CIA director. This was the hill Helms was prepared to die on. One thing was clear: If he obeyed the order to block Gray’s investigation, both he and the CIA would be at risk. Helms could end up in prison. Just paying the Watergate burglars might be enough to jeopardize the CIA’s existence: “We could get the money,” Helms reflected. “But the end result would have been the end of the agency. Not only would I have gone to jail if I had gone along with what the White House wanted us to do but the agency’s credibility would have been ruined forever.”

In an intelligence career that spanned three decades, Helms had approved some dubious operations; looked the other way on others; violated the CIA’s charter; and broken the law. But he would not let Nixon make the CIA a scapegoat for White House crimes; nor would he commit obstruction of justice to save his presidency.

But what about Walters? The White House thought Helms’s deputy could be counted on to follow orders. “Walters is a big weapon,” Nixon said to Haldeman on the Oval Office tapes. “Walters is a total loyalist. He is a total believer in the president. Don’t you agree?” In fact, Walters did meet with FBI director Gray, though he stopped short of telling him to end the investigation.

Helms was scheduled to depart on a trip to Australia, and he was taking no chances. As Cynthia recalled: “He was calling Walters and saying, ‘You are not to make a single decision while I’m gone.’ He was yelling at him, like a two-year-old child. He said, ‘I don’t want you doing anything the president or Haldeman asks you to do while I’m out of the country. You understand? Nothing! No decision is to be made!’?”

The FBI investigation continued. And as prosecutors closed in, Nixon decided to act on the hunch he had expressed to Haldeman two years earlier: “Maybe the lesson is: Just get rid of Helms.”

On February 2, 1973, Helms was summoned to meet with the president at Camp David, the presidential retreat. Helms assumed Nixon wanted to talk about the CIA budget. When he arrived at Aspen Lodge, the president was in the sitting room, flanked by Haldeman, and motioned Helms to sit down. Then Nixon got to his point. It was time for “new blood”: He planned to appoint a new DCI. While Helms digested the news of his firing, Nixon asked him if he’d like to be an ambassador: “What about Moscow?” Still stunned, Helms said that the home of the KGB might be a stretch for an ex-CIA director; perhaps Tehran would be more suitable.

When Helms got home and broke the news to Cynthia, she went into the bedroom and cried. It wasn’t just her husband’s firing that upset her; it was the prospect of leaving friends behind. I asked Helms’s son Dennis if he ever spoke to his father about that day. “No, no, no,” he said. “Wouldn’t have been like him to talk about it. He never talked about any conversation with the president.”

Two years later, on August 5, 1974, following an 8–0 decision of the Supreme Court, transcripts of Nixon’s tape-recorded White House conversations were released to the public. Among them was a talk between the president and Haldeman, six days after the break-in, and just hours before Helms and Walters came to the White House.
  • Haldeman: The only way to solve this… is for us to have Walters call Pat Gray and just say, “Stay the hell out of this… this is, ah, business here we don’t want you to go any further on it”… it’s got to be Helms and what’s his name? Walters?
  • President Nixon: Walters.
  • Haldeman: And the proposal would be that Ehrlichman and I call him.
  • President Nixon: All right, fine.… How do you call him in, I mean you just—well, we protected Helms from one hell of a lot of things.
  • Haldeman: That’s what Ehrlichman says.
  • President Nixon: Of course this… Hunt… that will uncover a lot, a lot of—you open that scab and there’s a hell of a lot of things in it that we feel that this would be very detrimental to have this thing go any further. This involves those Cubans, Hunt and a lot of hanky-panky that we have nothing to do with ourselves.…

The conversation continued:
  • President Nixon: When you get in these people… say “Look, the problem is that this will open the whole, the whole Bay of Pigs thing, and the President just feels that… they should call the FBI in and say that we wish for the country, don’t go any further into this case.” Period.

In the case for Nixon’s impeachment and removal from office, this conversation was the “smoking gun,” proof that the president had obstructed justice. Almost overnight, Nixon’s staunchest supporters abandoned him; impeachment and conviction were inevitable. A delegation of senior senators, led by Arizona’s Barry Goldwater, paid a visit to the Oval Office. It was time, they told the president, to resign.

In the end, what struck Helms was Nixon’s arrogance, and contempt for the government that served him. He “constantly disparaged everyone.… He would describe the State Department people as a bunch of pin-striped cookie-pushers who really didn’t have America’s interests at heart… the implication being the only smart fellow in town was Nixon.… But along comes Watergate, where he uses the most terrible judgment in the world and this to me is the crowning irony of his administration. That here he thought he was such a bright guy and he pulls the dumbest trick that anybody could pull and loses the presidency.”

It wouldn’t be the last time a president’s obsession with enemies brought him to the brink of disaster. More than four decades later, Donald Trump’s delusion that he’d been the victim of a plot hatched in Ukraine would lead him to withhold foreign aid in return for bogus investigations into mythical Democratic servers and dirt on a political opponent.

Helms had sacrificed his job to protect the CIA. But the agency’s troubles were just beginning; its doors were about to be thrown open and many of its secrets revealed. The intelligence world would change forever, bound by new rules and congressional oversight. And Helms himself would be hauled before Congress to testify about what the CIA had done in Chile.

The people Helms blamed for all this weren’t the press or the Congress or the KGB, but rather, his successors as CIA director: James Schlesinger and William Colby.

About The Author

Photograph by David Hume Kennerly

Chris Whipple is an author, political analyst, and Emmy Award–winning documentary filmmaker. He is a frequent guest on MSNBC, CNN, and NPR, and has contributed essays to The New York TimesThe Washington PostLos Angeles Times, and Vanity Fair. His first book, The Gatekeepers, an analysis of the position of White House Chief of Staff, was a New York Times bestseller. His follow-up, The Spymasters, was based on interviews with nearly every living CIA Director and was critically acclaimed. Whipple lives in New York City with his wife Cary. 

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Raves and Reviews

New York Times Book Review Editors' Choice

The best book about the CIA I’ve ever read. Its revelations are eye-popping, alternately exhilarating and depressing…How Whipple managed to pull so much history together, how he extracted such a wealth of detail from his principal sources—the CIA leaders themselves—is quite simply mind-boggling. This is an important book. And one hell of a story.”
—Christopher Buckley, New York Times bestselling author of The White House Mess and Thank You for Smoking

“A genial, engaging portrait of the men and one woman who have run the C.I.A. over the past six decades….[Contains] a richly textured account of the operation targeting the Hezbollah leader Imad Mughniyah….In weighing success and failure, Whipple offers measured, sympathetic, on-the-one-hand-on-the-other-hand tallies of the merits and demerits for each of his spymasters.”
The New York Times

“A study of how the C.I.A. has at different times over the decades been both a target of presidential animus and a clandestine presidential plaything….All of this can make for some great reading….Whipple’s interviews give plenty of rope for some of the former spy chiefs to hang themselves.”
Mark Mazzetti, Washington investigative correspondent for The New York Times and author of The Way of the Knife, writing in the digital weekly Air Mail

"A page-turner. Chris Whipple gives the reader tales of intrigue and masterfully tells the history of the nation’s spymasters and their relationships to presidents, and how those interactions shaped history…..An engaging read of politics, off-the-books plots, and struggles for CIA identity and access…Rating: 3.5 out of 4 trench coats."
—The Cipher Brief

“If you’re an American, The Spymasters is required reading.”
Chicago Review of Books

“Whipple’s access and interviews are impressive [and his] exploration of the different dynamics of the directors themselves, the presidents they served, and the challenges each faced is fascinating….[The] writing is breezy, accessible, and compelling.”
—The Diplomatic Courier

“Compelling…Chris Whipple does for the CIA and Washington DC what Plutarch did for those whose job it was to expand and defend the glory of Rome—paint an indelible portrait of how the servants of government seek to know and control the world….One theme emerges from the career of each director—how difficult it is to tell presidents anything they don’t want to hear.”
—Thomas Powers, Pulitzer Prize-winning author of The Man Who Kept the Secrets: Richard Helms and the CIA

"An expert chronicle of the CIA through the actions of its directors….This lively, opinionated history makes it clear that presidents and CIA directors sometimes deserve each other.”
—Kirkus Reviews

“Riveting…a timely reminder of the outsized influence of our nation’s intelligence bureaucracy—and the men and women who live in this wilderness of mirrors. ‘They were all asked to do things they shouldn’t do,’ says Cynthia Helms, wife of the legendary CIA Director Richard Helms. Whipple explores these ethical quandaries with nuance and fairness.”
—Kai Bird, Pulitzer Prize-winning author of The Good Spy: The Life and Death of Robert Ames

“Fascinating…Whipple parts the curtains on the dark art to show the triumphs and failures, the personalities and rivalries of those who work in the shadows of espionage.”
—Tom Brokaw, Special Correspondent for NBC News and bestselling author of The Greatest Generation

“Chris Whipple is an accomplished historian, hard-nosed journalist, and master storyteller…A must-read for anyone interested in America’s intelligence gathering and national security.”
—James A. Baker, III, 61st U.S. Secretary of State

“Whipple makes excellent use of insider accounts and provides enough color to keep readers turning the pages. This well-written and accessible survey illuminates a neglected role in American history.”
—Publishers Weekly

“Provides astute profiles of the men, and one woman, in charge of the modern Central Intelligence Agency, and the presidents for whom they have worked…Accurate, fair and informative.”
—John W. Dean, Nixon Administration White House Counsel and bestselling author of Conservatives Without Conscience

“Better than anyone, Chris Whipple knows how to root out the secrets buried deeply in the federal bureaucracy…When he gives the most secret of our agencies a good shaking the headline stories and secrets come tumbling out…This is the CIA with the bark off, and Washington reporting at its best.”
—Bob Schieffer, CBS News

“Engrossing…Whipple is at once clear-eyed and fair-minded while giving us a riveting read.”
—Evan Thomas, New York Times bestselling author of The Very Best Men: The Daring Early Years of the CIA

“A highly readable, fair, and well researched history of the CIA over the past fifty years. Whipple comes neither to pillory the CIA nor to praise it but, rather, to understand it—and he fully succeeds.”
—Max Boot, New York Times bestselling author The Road Not Taken: Edward Lansdale and the American Tragedy in Vietnam

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