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In his office on via Dante, Hugh Angleton received visitors from all over Europe. From friends in manufacturing, he learned about the German arms industry. At the Rotary Club, he talked to financiers and industrialists.29 As a member of the Knights of Malta, he knew influential Catholics.30 As a Mason, he drew on his friends in the secretive order to keep himself informed about Italian politics. As a man with connections, Hugh wanted to get to know his son’s friend, the great poet, who dared to say fascism and Americanism were two sides of the same coin. Angleton gravitated toward Pound’s view that Italy and America were not enemies.31 Hugh didn’t disagree.
The newspapers brought more foreboding news every day. Armies were mobilizing across Europe. In August 1914, a global war had erupted, seemingly out of nowhere. In the summer of 1939, the older generation could sense another cataclysm coming.
A few weeks later, on September 1, 1939, Germany invaded Poland, and the war in Europe had begun. Two days later, England and France mobilized to fight Germany. Mussolini rallied to Hitler’s defense, passing a series of anti-Semitic decrees in November 1939. The United States then sanctioned Italy. Angleton’s adopted country was now an enemy of the United States of America.
* * *
IN THE FALL OF 1939, Angleton and Whittemore moved into room 1456 of Pierson College, a pleasant enclosed quadrangle in the heart of the Yale campus.32 They went to work on the second issue of Furioso, which proved even better than the first, flush with poems from the famous and the promising. Pound’s contribution, alas, was again disappointing. Generously titled “Five Poems,” it consisted of five fragments, alternately whimsical, vulgar, and slight.33
In his own writing, Angleton had adopted Pound’s resentment of Jews and verbal abuse of President Roosevelt. In February 1940, he wrote to Pound: “There is hell of a lot of Rooseveltian shillyshally here in America.” He complained the American press favored London over Berlin. “Everything is definitely British and the jews [sic] cause a devil of a lot of stink. Here in New York will be the next great pogrom, and they do need about a thousand ghettos in America. Jew, Jew and Jew, even the Irish are losing out.34
But Angleton did not write to debate politics. He knew Pound was squeezed by wartime financial measures. He wanted to offer money.
“I talked to Dad on the telephone the day before the war and mentioned the little shekel you might need, say a couple of thousand, and he said o.k.,” Angleton wrote. “So I hope you will oblige by writing him and accept it as a favor.”35
Pound responded by return mail, acknowledging Angleton’s offer, if not his own acceptance of money.
“Dear JIM, Thanks fr/ yr/ air mail. I am not yet starved to the wall yet but thanks for the practical intentions in yr/ epistle. Neither, of course do I have any intention of relapsing into reminiscence of the Celtic Twilight during a period when twilight sleep is NOT, by hell, being used, for the birth of a new Euroope [sic].”
Pound had something more important in mind than money: a cause.
“A NEW god damn it NEW EUROPE,” he wrote. “All midwives to hand and ready.”36
As the poet championed the “new Europe” of Benito Mussolini and Adolf Hitler, he sought out Hugh Angleton and his generosity. Pound wrote him in June 1940:
Dear Mr. Angleton,
Jim is all het up for fear that I with poetic imprudence might have failed to putt [sic] by a few biglietti di mille [meaning he had failed to save a few thousand dollars]. I shall still eat/ even if Morgenthau, Hull, and that ass F.D. Roosevelt have succeeded in having the mails blocked and payment on U.S cheques suspended.
In the same letter, he signaled that he was short of funds, at the same time saying that he wished to talk about something “more important than my personal affairs.” He wanted Hugh Angleton’s help in spreading his political views.
“Time has come when I might be a business asset (wild as the idea wd/ appear),” he wrote. “I don’t mean in an office but sitting at the seat of news.”37 Pound wanted to be a practical asset to a businessman like Angleton. Within six months, he began to broadcast his commentaries for Radio Rome, the Italian news outlet heard from Sicily to the Pyrenees.
“What will remain from this struggle is an idea,” Pound declared in early 1941. “What spreads and will spread from the determination to have a New Europe is an idea: the idea of a home for every family in the country. The idea that every family in the country shall have a sane house, and that means a house well built, with no breeding space for tuberculosis bugs.…”
Pound likened twentieth-century European fascism to nineteenth-century American democracy in its rejection of collectivism. The new Europe, he said, was merely following in the path of the United States.38 Over the next four years, Pound would deliver more than 120 speeches over Radio Rome, most of them rife with folksy language, images of infestation, historical references, and anti-Semitism, all wrapped in a belligerent spirit of racial chauvinism.
Angleton had not been uncomfortable with fascism or fascists at Yale, sometimes to the consternation of his more liberal classmates. Anti-Semitism didn’t seem to bother him. But Pound’s overwrought vehemence did. As his bright college years came to a close in the spring of 1941, Angleton was ready to graduate from Yale College and the school of Ezra Pound. Apparently, they never corresponded again.39
WIFE
ONE RAINY DAY IN September 1941, Cicely d’Autremont, Vassar class of 1944, walked down Brattle Street in Cambridge. An impish sophomore from Arizona, she was out on a date with a Yale boy who wanted her to meet a friend who had just started at Harvard Law School. Cicely and the boy climbed up three flights of narrow stairs in an old apartment building. They walked into a bare living room that was unfurnished save for a reproduction of El Greco’s painting View of Toledo. A tall man stood next to the picture of an unearthly green landscape.
“How do?” he said.
This first encounter so impressed Cicely d’Autremont Angleton that decades later she recalled the moment.
“If anything went together it was him and the picture,” she told a reporter. “I fell madly in love at first sight. I’d never meet anyone like him in my life. He was so charismatic. It was as if the lightning in the picture had suddenly struck me. He had an El Greco face. It was extraordinary.”40
Another decade after that disclosure, when Cicely Angleton was a grandmother, she again relived that chance encounter, writing a poem tinged with rueful hindsight.
Beware, she warned, of hollow cheeks,
and auras sketched in lightning.41
Cicely d’Autremont didn’t know to beware of hollow cheeks. She was barely more than a schoolgirl, born into comfort and privilege. The marriage of her mother and father in 1919 joined two of the wealthiest families in Duluth, Minnesota. Her father, Hubert, was a scion of the d’Autremonts, who had vast holdings in mining and lumber.42 Her mother, Helen, was a Congdon, who had more of the same, in addition to a fabulous mansion. Helen and Hubert moved to Tucson, Arizona, where he became a banker, while she was active in charitable work. During the Depression years, the d’Autremonts were known as the largest contributors to Tucson charities.43 Cicely was born in 1922, their second child and first daughter.44
Cicely was drawn to Angleton’s exotic intensity. “Jim was a Chicano and I loved him for it,” she said. “I never saw anyone as Mexican as he was. He was Latino, an Apache, he was a gut fighter.”45
* * *
ANGLETON DID NOT RETURN Cicely’s passion, at least not immediately. In his last year at Yale, Angleton’s charmed life had suffered unsettling setbacks. At a time when the U.S. Army was welcoming hundreds of thousands of young men, he was rejected by the Selective Service, probably because of his recurring tuberculosis.46 Optimistically, he applied to Harvard Law School, despite the fact that his poor grades pulled him down to the bottom quarter of the Yale class of 1941.47 He was rejected.
Angleton’s friend Norman Holmes Pearson wrote a letter to Harvard, asking them to reconsider.48 Pearson, t
hen thirty-two years old, surely qualifies as the most improbable spymaster in American history.49 An assistant literature professor from a prosperous New England family, Pearson had few obvious qualifications for a life of deception and intrigue. He was a genteel man of unobtrusive appearance who walked with a limp, left over from a spinal injury in childhood. He was also a founding spirit of the global enterprise of espionage, propaganda, and violence known as the Central Intelligence Agency.
Pearson’s letter to Harvard proved convincing, and Angleton was admitted.50 Reprieved from unemployment, Angleton intended to make good by studying international law and contracts and then going into the family business.51 He was headed for a career of selling cash registers or perhaps publishing poets, but Norman Pearson wasn’t done with him.
Pearson, like many other young Ivy League professors, went to war by joining the newly created Office of Strategic Services. The OSS, as it was known, resembled an elite university in its mission to collect and disseminate information. The OSS was the brainchild of William Donovan, a Wall Street lawyer known as “Wild Bill” for his aerial heroics in World War I. For years, Donovan had been telling his friend Franklin Roosevelt that the rise of Adolf Hitler’s Nazi Germany meant there would be another war in Europe, one that the United States would have to join. America needed a foreign intelligence service, and probably sooner rather than later, he told FDR. After Pearl Harbor, Donovan had won the argument.
The British already had a foreign intelligence agency, the Secret Intelligence Service (SIS), established in 1909, sometimes known as MI6. So the officers of the new American OSS were sent to school at the British intelligence facility in Bletchley Park, north of London. There, Pearson joined the SIS men in teaching the novice Americans the arts of espionage and special operations as perfected by the world’s greatest colonial power.
* * *
IN LAW SCHOOL, ANGLETON learned the consequences of his friendship with Ezra Pound. The poet’s speeches on Radio Rome did not attract a big audience in Italy, nor were they broadcast in the United States. But the Federal Communications Commission in Washington was recording them,52 and J. Edgar Hoover was listening. In his midfifties, the FBI director was a heavyset man who favored shiny suits. He had built the Bureau of Investigation, a small office within the Justice Department, into a national police force. In April 1942, Hoover ordered his men to investigate Pound on suspicion of aiding America’s enemies.53
An FBI agent visited Angleton at his Brattle Street flat. Angleton explained he admired Pound’s poetry and found his political theories convincing, though distorted by his prejudices against Jews and bankers. Angleton agreed that Pound’s radio speeches were incoherent and indefensible. He said he would testify to that effect and provide the names of others who knew Pound.54
In spring 1943, Angleton was drafted into the army and passed his physical exam. He identified himself as James Hugh Angleton, Jr., proof that he did not care for his given middle name, Jesus.55 Though he could have used his father’s contacts and become an officer, he chose to begin army life as an enlisted man.56
He also proposed to Cicely, although Hugh and Carmen disapproved.57 They didn’t know Cicely d’Autremont or her family. Jim didn’t have a job or professional degree. The couple endured a painful meeting with his parents, but the young lovers did not relent. They set a date for a wedding in July near the army base where Angleton was training. On one of Jim’s few days off, he and Cicely got married at a church outside Fort Custer, Michigan, an unromantic beginning to a troubled lifelong commitment.58
* * *
CICELY WENT BACK TO Arizona and Jim left on a train eastbound to Washington. Norman Pearson had arranged for him to join the OSS. Before long, he was immersed in another form of basic training, this one in the hills of Maryland. Sixty OSS recruits marched up hills, danced through obstacle courses, and took night compass runs through the woods. The men who passed through the OSS training course became Angleton’s colleagues and friends for life.
Some came from similarly privileged backgrounds. Frank Wisner, the scion of a wealthy Mississippi family, had attended the University of Virginia. Others were older men of humbler origins, experienced in ways unknown to Angleton’s Yale classmates. Winston Scott, a former FBI agent, had grown up in a railroad boxcar in rural Alabama. He had a photographic memory and a Ph.D. in mathematics. Tom Karamessines was a taciturn lawyer who had worked as a prosecutor in New York City. Bill Colby was a Princeton man and army paratrooper who would lead sabotage raids in occupied Norway. Dick Helms was a white-shoed navy lieutenant who had worked as a wire-service reporter and once interviewed Adolf Hitler.
Angleton would know these men for as long as they lived.
Before shipping out to England, the OSS Officers’ Training Corps passed through what was known as the New York staging area for some final polishing, including a course in the art of picking locks. The instructor, a muscular and profane whirlwind named George Hunter White, was a career agent with the Federal Bureau of Narcotics.59 White had met Hugh Angleton and took a liking to his son.60
George White was as tough a character as Angleton had ever met. The FBN regulated the transshipment of narcotics in both legal and illegal transactions. Working undercover, White relished breaking the law in order to enforce it, a trait Angleton would come to share.61 He was a new sort of associate for Angleton, a man who expressed himself not with words but with fists or a gun. There was nothing poetic about him.
Angleton and his OSS brothers then sailed to England on a stormy North Atlantic sea, a stomach-turning ten-day voyage.62 When he disembarked with the duffel-toting throng at Southampton, Angleton had arrived where he wanted to be: the war front.
SECRETARY
THE HIDEOUS CRACK OF the missile blast jolted the floorboards, shattered the windows, buffeted the typewriters, and drove glass into every cranny of the cramped room at 14 Ryder Street in central London. Not long after, Angleton arrived for work at the OSS headquarters. It was raining hard and a brisk gale blew through the jagged panes as he went up to the second-floor office. Many nights, he slept on a cot by the desk. Luckily, Angleton had spent the previous night elsewhere, a twist of fate that might have saved his life.
It was March 1944. Angleton had gone through OSS training school in Bletchley Park, where he was reunited with Norman Pearson, who was responsible for the X-2 indoctrination training of the American arrivals. “X-2” served as shorthand for counterintelligence. Pearson also called on a British colleague, Harold Philby, an SIS section chief known to all as Kim, to explain the workings of a wartime intelligence station.63
After completing his training, Angleton was assigned to the Ryder Street office. The city was under siege from long-range German rockets fired from Flanders across the English Channel. Every day and night, V-2 missiles slammed into apartment blocks, office buildings, pubs, churches, and schools around the city, killing randomly and terrorizing generally.
Angleton’s secretary, Perdita Macpherson, found him stamping around the drafty, shattered office in his overcoat. Angleton swept the glass off his chair and sat down to work.64
* * *
JIM ANGLETON LEARNED THE craft of counterintelligence from two masters: Norman Pearson and Kim Philby.
Pearson was the more intellectual of two. Now living in England, he liked nothing more than to spend his Sundays sipping tea in the flat of his friend Hilda Doolittle, the poet known as H.D.65 The rest of the week, he taught the subtle arts of counterintelligence, defined as “information gathered and activities conducted to protect against espionage, sabotage or assassinations conducted for or on behalf of foreign powers, organizations, or persons.”66 Angleton would prove to be his most brilliant student.
Kim Philby was more of a rising civil servant. He had grown up in a well-to-do and well-traveled family. His father, Harry St. John Philby, had parlayed his livelihood as an Anglo-Indian tea planter into a career as a confidant to the royal family of Saudi Arabia.67 His son, Kim, was educat
ed at Cambridge and dabbled in journalism before joining the Secret Service in 1940. From the start Philby distinguished himself from his more conventional colleagues with a casual wardrobe, incisive memoranda, and a mastery of Soviet intelligence operations in Spain and Portugal. He taught Angleton how to run double-agent operations, to intercept wireless and mail messages, and to feed false information to the enemy. Angleton would prove to be his most trusting friend.
Angleton had found a calling and a mentor.
Once he met Philby the world of intelligence that had once interested him consumed him. “He had taken on the Nazis and the Fascists head-on and penetrated their operations in Spain and Germany,” he said. “His sophistication and experience appealed to us.… Kim taught me a great deal.”68
* * *
SO DID NORMAN PEARSON. He imparted to Angleton his knowledge about one of the most significant activities housed at Bletchley Park: ULTRA, the code-breaking operation that enabled the British to decipher all of Germany’s military communications and read them in real time. By May 1944, the British believed they had, for perhaps for the first time in modern military history, a complete understanding of the enemy’s intelligence resources.69
Pearson also sat on the committee that decided how to use the ULTRA information. He was let in on another, even more closely held British secret: the practice of “doubling” certain German agents to feed disinformation back to Berlin so as to shape the thinking and the actions of Hitler’s generals.
It was a subtle, dirty game that Pearson shared with Angleton. The Germans had infiltrated dozens of spies into England with the mission of stealing information, identifying targets, and reporting back to listening posts on the Continent. When the British captured one of the German spies, they would “double” him—that is, compel him to send back a judicious mixture of false and accurate data, which would give the Germans a mistaken view of battlefield reality. In the run-up to the Normandy invasion of June 1944, the British had manipulated the Germans into massing their troops away from the selected landing point. The deception enabled the Allied armies to land at Normandy and start their drive toward Paris with the German resistance in disarray.