The Devil’s Chessboard: Allen Dulles, the CIA, and the Rise of America’s Secret Government

As they sipped liqueur from long-stemmed glasses, Dollmann reflected on how the cardinal always put him in mind of “a delicate alabaster statue.” But Schuster, who had worked with Wolff’s SS team on the Sunrise deal, was not as refined as all that. The wily cardinal was part of the Vatican elite that had collaborated with Mussolini’s fascist regime—and, out of self-interest, he was inclined to help Dollmann now, to avoid an embarrassing war crimes trial. Besides, Schuster thought that men like Dollmann might still play a useful role in postwar Italy; he hoped to recruit the former SS officer in the campaign against the Church’s nemesis, the Italian Communists, who had emerged from the war as a powerful political force.

Dollmann, who was conniving by nature but not political, was uninterested in the cardinal’s plot, but he was in no position to quibble. He allowed himself to be safely hidden away in a Church-run asylum for wealthy drug addicts, where his fellow inmates included a fading Italian film diva and an emotionally fragile duchess. As he languished among the delicato junkies, Dollmann decided to sample some of the forbidden fruit that the screen siren kept stashed in her room, snorting a snowy mound of heroin. For a time, Dollmann—who had much to forget in his life, but was plagued by a detailed memory—seemed in danger of disappearing among the lotus eaters.

Salvation came in the form of James Jesus Angleton, a rising young star in U.S. intelligence who had run the X-2 branch (OSS counterintelligence) in Italy during the war and had stayed behind to use his wiles against the Communists. After tracking down Dollmann in the Milan asylum, Angleton sent a big U.S. Army Buick with a chauffeur to pick him up and drive him to the Eternal City, where he installed Dollmann in the Via Archimede safe house in the Parioli district.

Counterintelligence was the spy craft’s deepest mind game—it was not just figuring out the enemy’s next moves in advance and blocking them, but learning to think like him. Not yet thirty, Angleton was already being talked about in American and British intelligence circles as one of the masters of the field. He had been educated in British prep schools and at Yale, where he had edited the avant-garde poetry magazine Furioso and courted the likes of Ezra Pound and e.e. cummings as contributors, and he seemed to bring an artist’s intuition to his profession. But he could get lost in the convolutions of his own fevered mind, which drove him to prowl the streets of Rome late at night in a black overcoat so big it looked like a cape, on the hunt for clues about the growing Communist menace, and to crawl around on his office floor at 69 Via Sicilia in search of hidden bugging devices.

Angleton was as gaunt as a saint. (His wife, Cicely, would rhapsodize about his “El Greco face.” His colleagues called Angleton “the Cadaver.”) He smoked incessantly, and his bony frame was wracked by consumptive fits of coughing. When he introduced himself to Dollmann, Angleton must have struck the colonel as yet another strung-out soul. But Angleton’s addiction was of a more ideological nature.

As Angleton sat with Dollmann in the comfortable, five-room apartment on Via Archimede, the young spy explained his vision for the new world. Dollmann felt bound to listen politely, since Angleton had gone to the trouble of plucking him from Cardinal Schuster’s madhouse. But Dollmann had heard it all before—with even more fervor—from the Führer himself and his SS overlords: how Bolshevism must be crushed for the new world to be born, why there must be no rules in a clash like this between civilization and barbarity.

Angleton, however, was lost in his own passion. He had found strong support for his views from Allen Dulles in the months after the war, as Dulles lingered in Europe, hoping that President Truman would anoint him commander of the shadow war against the Soviet Union. In October 1945, Dulles visited Rome with Clover, ostensibly to revive their marriage after the strains of separation during the war. But he had another mission as well: to organize the Italian front in the new Cold War. Angleton, who was wired into the Vatican, helped arrange a secret meeting for Dulles with Pope Pius XII, who had maintained a mutually beneficial arrangement with Mussolini’s regime and was a determined foe of Communism.

Angleton looked up to Dulles as a mentor—a powerful figure in the mold of his adored father, James Hugh Angleton, an international businessman who had paved his son’s path into the spy trade and continued to play an influential role in the young spook’s life. Dulles would remain a strong, paternal figure for Angleton junior throughout their deeply entwined intelligence careers. In Rome, the two men conferred about the growing “Red challenge” and “the drastic, sub-rosa measures required to meet it,” as a colleague put it. These extreme measures included recruiting agents “without overscrupulous concern for [their] past fascist affiliations.”

Dollmann was high on their list of such recruitment targets. With his continental sophistication and network of contacts, Dollmann might prove a valuable espionage asset on the strategic front lines in both Italy and Germany. As Angleton sat with the well-groomed colonel in the Via Archimede safe house now, the American opened a bottle of Scotch whisky that he had brought along and carried on with his enthusiastic recruitment pitch. But as he listened, sipping the good Scotch, Dollmann was filled with utter contempt for his guest. “He was talking like a young university lecturer who dabbled a bit in espionage in his spare time,” mused the colonel. His views struck the world-weary German as typically American—naïve and overblown.

As for Dulles, Dollmann had only contempt for his benefactor, whom he later called “a leather-faced Puritan archangel … [the type] who had fled from the European sink of iniquity on the Mayflower and now returned to scourge the sinners of the old world.” He would ridicule the way that Dulles had misrepresented himself at their secret Sunrise meetings in Switzerland as President Roosevelt’s personal emissary, delivering little speeches to Wolff and Dollmann about how “delighted” FDR supposedly was about the SS officers’ selfless mission for peace. “Wasn’t that nice now?” sneered Dollmann. “Such manly, upright and heartening words from President Roosevelt and his special representative in Europe, Mr. Allen W. Dulles!”

While Dollmann was unimpressed with Angleton’s political lecture, he did appreciate the fake identity card the young spy gave him. The document—which identified him as an Italian employee of an American organization—afforded Dollmann the confidence to venture into the streets of his beloved Rome without fear of being molested by the authorities. Sprung from his apartment, the colonel found himself drawn to some of his favorite old haunts. He strolled through the fashionable Via Condotti shopping district, where he paid a visit to the Bulgari jewelry shop.

In the old days, he had been treated like royalty by the Bulgari brothers, who would take him on tours of their vaults beneath the Tiber River, where there was a red room for rubies, a blue room for sapphires, and a green room for emeralds. The Bulgaris would pour him Napoleon brandy as they showed off the crown jewels of the late czar and other dazzling treasures. But those pleasant days were long gone. This time, when he suddenly appeared in the luxury shop, Giorgio Bulgari greeted him as if he were a ghost. “We were all afraid you had been killed,” the jeweler told Dollmann, after he recovered from his shock.

During the war, Giorgio Bulgari had been so revolted by the deportation of Rome’s Jews—an order stamped by Dollmann’s boss, Wolff—that he and his wife hid three Jewish women in their own home. Now, gazing at the resurrected SS colonel, the jeweler undoubtedly wished Dollmann was dead. And Dollmann knew it.

Afraid he’d been killed? That was rich. Bulgari’s false concern infuriated Dollmann, but he adopted his usual droll manner. “How very amusing. People like me don’t just disappear forever like that.”

Dollmann always liked to give the impression that he was too cosmopolitan to indulge in the Nazis’ anti-Jewish mania. But now he felt offended by Bulgari’s forced courtesy; Bulgari “sickened” him—he was a “corpulent Levantine … [with] fleshy lips [and a] greasy smile.” Dollmann turned abruptly and fled the shop.

Once upon a time, Dollmann had had a love affair with Italy, and he was certain that his sunny “arcadia,” as he called it, returned his ardor. But now he was no longer certain. Dollmann had arrived in Italy two decades earlier, long before the war, as a young graduate student in Renaissance history. The young German was well educated, fluent in Italian, and boasted some sort of connection to the doomed Habsburg dynasty. He was also gay and charming, and he quickly shed as much of his stolid German upbringing as he could in favor of la dolce vita. With his slickly groomed hair, sleek Italian suits, and year-round tan, Dollmann went completely native, becoming Eugenio instead of Eugen.

Dollmann had been embraced by the German diplomatic set in Rome, who appreciated his nuanced grasp of the local language and customs, and by the Italian aristocratic set, who found him an amusing decoder of all things Deutsch. His binational skills were increasingly in demand as the two countries’ fates grew more closely linked. He was sought out by a principessa named Donna Vittoria, who was the reigning queen of Roman salons. Her soirees, held at her otherworldly palazzo in the imperial ruins of Teatro Marcello, were frequented by Mussolini’s daughter Edda and her husband, Count Ciano, as well as the leading Italian film stars of the day. She very much hoped to have Hitler, too, as an honored guest someday, the principessa confided to Dollmann.

In Naples, he was invited to the midnight entertainments at Duchess Rosalba’s decaying mansion, festivities so lavishly debauched that they could have inspired a young Fellini. One night the lady of the house greeted Dollmann as she reclined on a divan and was attended to by two slyly grinning female dwarves and a well-built retainer packed into a form-fitting suit. The dwarves later appeared on a stage with a troupe of other diminutive performers, who enacted a long and baroque melodrama for the amusement of Duchess Rosalba’s guests. Dollmann was haunted not just by the odd performance but by the strange smile that his hostess fixed on him. The duchess, he noted, had “a simultaneously charming and inhuman mouth.” He later learned the story of her deformity. The duchess liked to prowl Naples’s rough waterfront bars for her handsome henchmen, replacing them in quick succession with one rugged seaman after another. One night she was attacked with a knife by one such jealous sailor, who left the mark of his fury on her once beautiful face.

But not even this decadent world could prepare Dollmann for the life he began when he joined the SS, where he would rise to become the link between the courts of Hitler and Mussolini. Dollmann later tried to make sense of why he had enlisted in Himmler’s death’s-head corps. It wasn’t political ambition that drove him—he insisted that he had none. And it wasn’t monetary reward. “I [already] lived well and comfortably, and my life, after I had yielded to my so-called motives, was no better than before, only more arduous.” Was it the way he looked in his trimly tailored SS uniform? Vanity was always a factor with Dollmann. Years later, he proudly displayed photos of himself standing in the very center of history, between Hitler and his visiting Italian dignitaries, gazing into the Führer’s magnetic eyes, ready to translate his every momentous word. Dollmann, always up to date on the latest Rome gossip, became a court favorite of Hitler. He was at the Führer’s side whenever Hitler and his retinue descended on Italy, and he was there whenever Mussolini or his top ministers trekked to summits in Germany.

By serving as the essential diplomatic link between Germany and Italy, Dollmann ensured that his sojourn in his adopted land would not be interrupted by the coming war. Dollmann would point to this as the primary reason why he made his Faustian bargain. Italia was the great passion of his life. “I loved Italy with the doomed love of all German romantics.”

It was the most peculiar of ironies, and one that Dollmann and his intimates no doubt privately relished. The man who kept the Axis partners smoothly aligned, with his impressive language and social skills, was a highly educated, arts-loving homosexual who enjoyed trading in the most salacious gossip about the personalities who ruled Germany and Italy. Dollmann was, in short, precisely the type of person the Nazis sent to the gas chambers. But instead, Hitler’s interpreter was free to attend gay and lesbian orgies in Venice, a city whose shadows offered some protection from the authorities’ prying eyes. And he had the pleasure of going on shopping safaris with Eva Braun, Hitler’s companion, during her Italian holidays.

Braun was mad for crocodile shoes and accessories. “She loved crocodile in every shape and form, and returned to her hotel looking as if she had come back from a trip up the Congo rather than along the Tiber.”

Dollmann was fond of Braun, a sweet and simple young woman who confided her sad life to him. She was known throughout the world as the German strongman’s mistress, but, as she confessed to Dollmann, there was no sexual intimacy between her and the Führer. “He is a saint,” Braun told Dollmann wistfully. “The idea of physical contact would be for him to defile his mission. Many times we sit and watch the sun come up after spending the whole night talking. He says to me that his only love is Germany and to forget it, even for a moment, would shatter the mystical forces of his mission.”

Dollmann strongly suspected that the Führer had other passions besides Germany. On Christmas Eve 1923, when he was a university student in Munich, Dollmann had been invited to an extravagant, candlelit party at the home of General Otto von Lossow, who had helped put down Hitler’s Beer Hall putsch in November 1923. During the evening, Lossow took Dollmann and some of his other guests into his parlor, where he entertained them by reading selections from Hitler’s thick police dossier. “In a café near the university on the evening of, Herr Hitler was observed …” Lossow’s voice was matter-of-fact as he read through the depositions and eyewitness reports about Germany’s future leader. The general’s small audience listened in rapt silence, transfixed by the portrait of a Hitler who was more interested in boyish men than in national politics.

These were the sorts of tales that Dollmann kept tucked away—stories that would help the consummate survivor navigate what he called the “witches’ cauldron” of Rome as well as Berlin’s dark labyrinth. As the Nazis’ main fixer in Rome, it helped to know everything he could about the dangerous men with whom he was dealing.

The Nazi official Dollmann most dreaded escorting around Italy was Reinhard Heydrich, Himmler’s top executioner. “Now there was a man clearly meant to be murdered by someone or other,” Dollmann observed years later. “He was a daemonic personality, a Lucifer with cold blue eyes.” One night, Heydrich demanded that Dollmann take him to Naples’s finest brothel. Two dozen half-naked women representing the full spectrum of the female form—from “slim gazelles to buxom Rubenesque beauties”—were arranged for Heydrich’s inspection in the brothel’s ornate lobby, with its gilt-edged mirrors and frescoes of rosy nymphs. Heydrich gazed at the women on display with his blank, shark eyes. Considering the SS butcher’s reputation, Dollmann did not know what to expect next. Suddenly Heydrich flung a fistful of shiny gold coins across the marble floor. “Then he jumped up, Lucifer personified, and clapped his hands. With a sweeping gesture, he invited the girls to pick up the gold. A Walpurgisnacht orgy ensued. Fat and thin, ponderous and agile, the [women] scrambled madly across the salotto floor on all fours.”

Afterward, Heydrich looked pale and spent, as if he himself had joined in the frenzy. He coolly thanked Dollmann and disappeared into the night. The interpreter was glad to see Heydrich go. He was, said Dollmann, “the only man I instinctively feared.”

History has come to judge Eugen Dollmann as “a self-serving opportunist who prostituted himself to fascism,” in the words of legal scholar Michael Salter, but not a fanatic like the men he served. Nevertheless, as war criminal proceedings got under way in Nuremberg in the fall of 1945, Dollmann knew that he was at high risk of prosecution. The Nuremberg trials, where Foreign Minister Joachim von Ribbentrop and Ambassador Franz von Papen were both convicted, firmly established that diplomats like Dollmann who moved in rarefied Nazi circles were not immune from judicial reckoning.

Dollmann was perhaps at even greater risk in Italy, where passions ran high regarding Nazi massacres of Italian civilians, such as the infamous slaughter of 335 prisoners in the Ardeatine Caves near Rome in March 1944. Although Roberto Rossellini modeled the effeminate, sadistic SS captain Bergmann on Dollmann in his postwar film Rome, Open City, Dollmann was not directly involved in the Ardeatine atrocity; in reality, the colonel had no taste for brutality. After the war, Dollmann claimed that he had once even rescued several Italian partisans who were being burned alive by fascist thugs. Regardless of his degree of guilt or innocence, however, Dollmann was the most visible symbol of the Nazi occupation of Rome. Italians were all too familiar with the numerous newspaper photos of his slim, ben vestito figure taken at social events in Mussolini’s Palazzo Quirinale or the Vatican. In the fall of 1945, as he strolled around Rome with his fake ID card, Dollmann was acutely aware that if he fell into the wrong hands—particularly those of Italian Communists—he could be lynched.

Dollmann’s anxieties were heightened when American agents installed two former SS colleagues in his Rome apartment—including the notorious Colonel Walter Rauff, who had served as Karl Wolff’s second-in-command in northern Italy—because he knew that the hideout might now attract increased interest from Nazi hunters. Dollmann, who regarded Rauff as “one of my most disagreeable acquaintances,” was well aware of his new roommate’s past. In 1941, Rauff had overseen the development and operation of a fleet of “Black Raven” vans, in which victims were sealed inside and asphyxiated with exhaust fumes. As many as 250,000 people on the war’s eastern front were murdered in Rauff’s vehicles, which were eventually replaced by the gas chambers of Auschwitz and Dachau. “In my opinion,” Dollmann mordantly remarked, “he was quite certainly due for the high jump [at Nuremberg] when they got round to him.” But Rauff had managed to save his neck by prudently jumping on board the Operation Sunrise bandwagon with Wolff.

Weary of his roommate’s baleful presence, Dollmann often fled the Via Archimede apartment to go to the movies. As he sat in the dark day after day, he began getting the prickling sensation that he was being followed. One afternoon in November 1946, as the colonel watched a trifle titled Kisses You Dream Of??at his neighborhood cinema, Dollmann felt a firm hand on his shoulder and heard a voice of authority: “Kindly leave the cinema with me.” He was taken into custody by a plainclothes detective who was accompanied by two armed carabinieri and then whisked away to a nearby police station.

Dollmann and his fellow SS escapees had been tracked for months by the 428th U.S. Army Counterintelligence Corps (CIC), a detachment of Nazi hunters based in Rome. Major Leo Pagnotta, the Italian American who was second-in-command of the CIC unit, was a sharp investigator. He figured out that Dollmann, who knew it was unwise to show his face too much on the streets, would sooner or later reconnect with the Italian chauffeur who had driven him around during his SS days. Dollmann did indeed contact the chauffeur, but Pagnotta had gotten to him first, making him an offer he couldn’t refuse. “If you see Dollmann and you don’t tell me,” Pagnotta had told the driver, “I’ll arrest you and you’ll be shot.” The chauffeur quickly gave up Dollmann, pinpointing when and where he would be dropped off at the cinema.

Now, as Dollmann sat waiting in the police station holding room, the door suddenly opened and Major Pagnotta walked in. The two men took an immediate dislike to each other. Dollmann was predisposed to look down on Americans, whom he found in general to be a crass, illiterate, and mongrelized people. To make matters worse, this one was “rather fat”—a cardinal sin with Dollmann—and the American didn’t bother with any social niceties, treating the Nazi fugitive like “a pretty low sort of criminal.”

The situation appeared bleak for Dollmann—his next stop could well be Nuremberg. But he knew that he had an ace up his sleeve, and he immediately played it. Dollmann took a piece of paper from his pocket and handed it to Pagnotta. “Please call this number,” he told him. “Ask for Major Angleton. He knows who I am.”

Major Pagnotta was quite familiar with Major Angleton. In fact, Pagnotta’s team of Nazi hunters was headquartered in the same building on Via Sicilia as Angleton’s rival intelligence operation, the Strategic Services Unit’s X-2 branch. Pagnotta’s CIC unit was on the first floor, Angleton was on the second, and British intelligence was on the third. Pagnotta and his men didn’t trust Angleton—they thought he was “a devious and arrogant son of a bitch,” in the words of Pagnotta’s aide William Gowen. Angleton seemed to work more closely with the British spies than with his U.S. Army colleagues, and the British treated him like one of their own. Before transferring to Rome in 1944, Angleton had been stationed in London, where his X-2 unit was overseen by British intelligence.

The espionage scene in postwar Rome was rife with rivalries and competing agendas. Some U.S. intelligence units, such as Leo Pagnotta’s, were determined Nazi hunters. But other operatives, such as Angleton, had very different objectives. This spy-versus-spy atmosphere made Pagnotta’s investigative work extremely complicated.

As Pagnotta tracked top Nazi fugitives in Italy, many of whom had escaped from the British-run prisoner-of-war camp in Rimini, it became clear to him that he was often working at cross-purposes with Angleton and British intelligence. One of the most notorious fugitives, SS captain Karl Hass, who had overseen the Ardeatine Caves massacre, mysteriously escaped every time Pagnotta’s team tracked him down and turned him over to British occupational authorities in Italy. Finally, after his fourth arrest, Hass escaped for good. It was not until many years later that Hass was tracked down in Argentina and extradited to stand trial in Italy for his role in the massacre. Hass received a life sentence, but by then he was an old man, and his failing health kept him out of prison.

Unsurprisingly, after capturing Dollmann, Pagnotta decided to hang on to him, placing him in a U.S. military prison in Rome instead of handing him over to the British. In the beginning, Dollmann was a cooperative prisoner, readily revealing the address of his apartment on Via Archimede. When Pagnotta’s team raided the apartment, they narrowly missed catching Dollmann’s infamous roommate Walter Rauff, who managed to flee to Bari, on the Adriatic coast, where he boarded a ship for Alexandria, Egypt—the next stop in the Nazi exterminator’s long and winding ratline. Rauff would cap his bloody career in Chile, where he became a top adviser to DINA, military dictator Augusto Pinochet’s own Gestapo. When Rauff died in 1984—at age seventy-seven, after successfully rebuffing years of extradition attempts—hundreds of aging Nazis flocked to his funeral in Santiago, where he was laid to rest amid loud salutes of “Heil Hitler!”

Pagnotta did snare another fugitive who was living in the Via Archimede apartment, SS officer Eugen Wenner, who had also played a part in the Operation Sunrise maneuvers. It soon dawned on Pagnotta’s team that Angleton was operating a safe house on Via Archimede for a stream of Nazi fugitives who were connected to Sunrise and other Dulles operations. They even traced the car driven by Dollmann’s chauffeur to Angleton’s father, who kept a villa nearby in Parioli.