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Chapter 1
Gentleman Amateurs

THE DATE was May 12, 1938. With three bells announcing his arrival, trailed by trotting Secret Service agents lugging wire baskets of official papers, FDR propelled his wheelchair from the first-floor elevator into the Oval Office where he summoned Missy LeHand. As she came in, the President greeted his secretary with a blinding smile and an expression that said, what does the world have in store for Franklin Roosevelt today?

It was nearly 11 a.m. as the softly attractive LeHand sat down and propped her steno pad on her knee. By now, eighteen years at his side, through his glowing early promise, the catastrophe of polio, the slow resuscitation of his spirits and ambitions, she could read FDR's every mood and need instantly. The President took from a can on his cluttered desk one of the forty-odd Camel cigarettes he would smoke that day and inserted it into a nicotine-stained holder. He chose from a wire basket a letter delivered personally to the White House the day before by Uncle Ted's son Kermit Roosevelt. It was from Vincent Astor. Before he began dictating, FDR reread the nineteen handwritten pages in the familiar script. The letterhead read simply Nourmahal, the name of Astor's yacht. The very word suffused FDR with warm memories. He had first sailed the Nourmahal in 1932 while still president-elect. The luxurious oceangoing vessel, manned by a crew of forty-two, recalled America's Cup races off Newport watched from her deck, fishing trips off Long Island Sound, cruises in the Caribbean, card games, drinking, and, for some of Astor's pals, occasional amorous adventures on board.

It was to the Nourmahal, tied up in Miami, that FDR had retreated in February 1933 after an incident that nearly ended his presidency before it began. He had been seated in the back of an open car after addressing a crowd when, as he later described the moment, "A man came forward with a telegram about five or six feet long and started telling me what it contained. Just then I heard what I thought was a firecracker: then several more." Roosevelt saw a Secret Service agent wrestle the man to the ground. The assailant was Giuseppe Zangara, an unemployed bricklayer and political malcontent whose shots had miraculously missed Roosevelt, but struck Anton Cermak, the mayor of Chicago then visiting Miami, a woman, and a policeman. Roosevelt accompanied Cermak to the hospital, where the fifty-nine-year-old mayor's wound proved fatal. The other victims survived. The president-elect then joined Astor and other friends aboard the Nourmahal, grateful for a respite from the horrors of the day.

Subsequently, FDR had sailed the Nourmahal every year, enjoying himself tremendously, especially his fellow passengers' sophomoric hijinks. He got a kick out of the mock bills Astor sent after each cruise-"Expenses incurred for alcoholic stimulants and repeated correctives, $37.50 per diem. (Note: the Chief Steward reports that consumption of the above stores was so vast as to overwhelm his accounting system.) With a further $1.90 for chipping Mother-of-Pearl surfaces of bell contacts through impatient punching of the above, to hasten the arrival of correctives. Seventeen cigars, Profundo Magnifico, $.90 each." And always the appended note, "The President is exempt."

The letter from Honolulu now in Roosevelt's hands did not, however, recount shipboard capers. Rather, it was Astor's report of an espionage mission the President had entrusted to the yachtsman. This deep trust, granted by a president to a private citizen, had equally deep roots. The names Roosevelt and Astor had echoed down Hudson Valley history since colonial times. The Roosevelts of Hyde Park and the Astors up the road at Rhinebeck stood at the heart of the Dutchess County gentry, their lives a weave of family, professional, and commercial interests. Franklin's much older half brother, James, was close to Vincent's father, Colonel John Jacob Astor IV, heir to the vast fortune founded by a once penniless fur-trading German immigrant, the first John Jacob Astor. Vincent's grandmother was the grande dame who defined New York society by the four hundred guests who could fit into her Fifth Avenue ballroom. When Vincent's father went down with the Titanic in 1912, the son dropped out of Harvard to assume control of the family's holdings, inheriting $75 million and tagged by gossip columnists as "the richest boy in the world." James Roosevelt became executor of the Astor estate and continued as a trusted advisor to Vincent, who prized his counsel and always referred to FDR's brother as "Uncle Rosey."

Franklin and Vincent had known each other as boys, but were not then close since FDR was eight years older. As Astor put it, much later "we grew to be the same age." The two avid sailors met again during the First World War while Franklin was serving as President Woodrow Wilson's assistant secretary of the Navy. They had met to consider how yacht owners and powerboat sailors might organize their vessels into a Volunteer Patrol Squadron, an idea that ultimately became the Naval Reserve. Later, FDR received an urgent appeal from his brother, James, to help locate Ensign Astor. The young scion had donated an earlier yacht, the Noma, to the Navy and was serving aboard her on anti-submarine patrols off the French coast. James Roosevelt, possessing Astor's power of attorney, needed to determine if the young officer was still alive before signing documents affecting Astor business interests, principally huge chunks of Manhattan real estate.

Providing such constituent services was among Assistant Secretary Roosevelt's least demanding duties. What genuinely engaged him was what later drew him closest to Astor, the netherworld of espionage. The clandestine had captivated Franklin Roosevelt from his youth. The first recorded signs of his bent for the covert surfaced while he was a student at Harvard. He had devised a code, numerals substituting for vowels, and symbols, such as an asterisk, substituting for consonants, all run together giving no hint of where words started or ended. Though child's play for a serious cryptanalyst, the code nevertheless served Franklin's need for and pleasure in secrecy. He had developed a crush on a beautiful Bostonian named Alice Sohier, not yet sixteen. One coded entry in his diary, dated July 8, 1902, at the end of his sophomore year, raises curious speculation. "Alice confides in her doctor," he wrote. The next day's coded entry read, "Worried over Alice all night." A half century later the subject of his concern would explain only, "In a day and age when well brought up young men were expected to keep their hands off the persons of young ladies from respectable families, Franklin had to be slapped-hard."

Doris Kearns Goodwin, chronicler of Roosevelt's wartime years, has explored the roots of FDR's character that may explain his attraction to the secret and covert. Franklin had been an intuitive child, Goodwin writes, who "learned to anticipate the desires of his parents even before he was told what to do." She quotes Franklin's mother, Sara Delano Roosevelt, saying that her boy rarely required disciplining: "We took secret pride in the fact that Franklin instinctively never seemed to require that kind of handling." Franklin's childhood compulsion to please his parents had grown into an adult reflex to charm and ingratiate, to turn every encounter into a personal triumph, sacrificing candor to achieve likability. By the time FDR became president, dissimulation had become second nature, and subterfuge cloaked in geniality became his stock-in-trade. Harold Ickes, his interior secretary, as crusty and blunt as Roosevelt was smooth and impenetrable, once complained, "You keep your cards up close to your belly."

Franklin D. Roosevelt had first entered upon the national consciousness on March 17, 1913, at the age of thirty-one, with his appointment by President Woodrow Wilson as the youngest person ever to become assistant secretary of the Navy. Franklin particularly savored the moment since his distant cousin and Eleanor's uncle Theodore Roosevelt had held the same position before going on to become, at forty-two, the country's youngest president. FDR's boss, the secretary of the Navy, was fifty-one-year-old Josephus Daniels, former editor and publisher of the Raleigh (North Carolina) News & Observer. This prohibitionist/pacifist/populist could not have been more unlike his urbane, elegant deputy. Daniels, with his string ties, somber suits, and small-town manners and morals, was a figure out of the departed nineteenth century. Roosevelt was a man of the emerging twentieth century. At times, with the nakedly ambitious Roosevelt under him, Daniels must have felt as if he were sitting on a volcano. On one occasion, FDR looked over a site for building barracks for eleven thousand sailors. The next day, he let the construction contract. Four months later, the work completed, he went to Daniels for permission to carry out the project. The secretary had been forewarned. When Daniels initially went to New York's Senator Elihu Root to clear Roosevelt's appointment, Root had asked him if he really understood the Roosevelts. "Whenever a Roosevelt rides, he wishes to ride in front," Root warned, "they like to have their own way." For all his homespun manner, Josephus Daniels was no fool. He knew that a northern aristocrat would complement his southern folksiness, and he possessed that rare quality in a leader-he was not afraid to hire a subordinate who might be smarter than he was.

The component of the Navy Department that quickly captured the assistant secretary's imagination was the Office of Naval Intelligence. ONI, at that point, was the closest equivalent to an American central intelligence agency. In its thirty-first year when FDR came to the department, ONI was a small, elite subempire, one that had planted naval attachés in all significant world capitals, poking into the secrets of foreign powers. ONI's chief, Captain James Oliver Harrison, unhappily observed that Roosevelt and his political mentor and private secretary, an untidy, irreverent man named Louis Howe, were poaching on his turf, organizing their own secret intelligence cell. FDR's amateurs, Harrison complained to the Chief of Naval Operations, were interfering with his professionals. Soon after America entered World War I in April 1917, Harrison was replaced by a more pliant ONI chief, Captain Roger Welles. Welles happily commissioned FDR's socialite pals into naval intelligence, young men who shared the right schools, clubs, and connections, among them FDR's onetime law partner, Alexander Brown Legare, who founded the Chevy Chase Hunt Club; Lawrence Waterbury, star polo player; and Steuart Davis, a Harvard classmate and commander of the Volunteer Patrol Squadron. ONI's roster soon began to resemble the Social Register.

Roosevelt's intelligence priority had been set before the United States entered World War I. German saboteurs were suspected of blowing up the National Storage Plant on Black Tom Island in Jersey City, New Jersey, on July 30, 1916, a blast that killed seven men, injured thirty-five more, and destroyed millions of dollars' worth of munitions intended for the Allies. FDR became obsessed by the threat of internal subversion, a concern that was to dominate his intelligence thinking for years. No rumor was too wild to enlist his attention. One ONI informant reported that a German-American colony in New Hampshire was plotting to acquire a plane to bomb the Navy yard at Portsmouth. Roosevelt sent out investigators. In October 1917 a friend returned from a visit to Block Island with a possible explanation as to why the battleship Texas had run aground there. Visibility at the time was an ample six hundred yards, his friend told FDR. A sailor who had earlier lived on Block Island with Germans suspected of spying had been the forward lookout on the Texas when she struck the beach. FDR ordered another investigation. ONI personnel, quickly grasping the boss's prejudices, began feeding him what he wanted to hear. A typical report to the assistant secretary on the Krantz Manufacturing Company of Brooklyn noted, "The employees are almost German to a man. Every official has a German appearance . . . and [they] always converse in German." With FDR's fervent support, ONI hired hundreds of new investigators, the rapid expansion justified by threats, fanciful or hypothetical, against Navy installations.

The spy thriller atmosphere pleased Roosevelt to the point of apparently producing spy fiction. FDR later liked to tell how "the Secret Service found a document in the safe of the German consul in New York entitled: To Be Eliminated." The first name on the list was Frank Polk, intelligence coordinator at the State Department. "Mine was the second," Roosevelt would inform rapt listeners. The Secret Service, he maintained, then provided him with a revolver and holster. He wore the gun for only a few days, Roosevelt claimed, then left it in his desk drawer. No evidence supports any part of this story.

On July 9, 1918, the assistant secretary boarded the USS Dyer, the Navy's newest destroyer, to witness the war in Europe. Upon his arrival in England, FDR met his first grownups in the espionage game and was suitably dazzled. He spent two hours in London with Admiral Sir Reginald Hall, director of Britain's Naval Intelligence, known as Blinker for the rapid batting of his eyes, especially when he was excited. Blinker Hall had already influenced American history. It was Hall who created Room 40, the Royal Navy's codebreaking arm, and it was Room 40 that decoded the Zimmerman telegram, which revealed a German plot to induce Mexico and Japan to go to war against the United States. Hall had leaked the telegram to Washington, significantly affecting President Wilson's decision to enter the war. Dr. Walter Page, America's ambassador to Great Britain, said of Hall: "Neither in fiction or fact can you find any such man to match him. . . . The man is a genius-a clear case of genius."

Blinker Hall, in a wing-tipped collar, his head haloed in a ring of frizzy white hair, his eyes batting with anticipation, warmly admitted Roosevelt into the inner sanctum of British espionage. He had been describing German troop movements to his guest when he suddenly broke off and pointed across the room. "I am going to ask that youngster at the other end of the room to come over here," Hall said. "I will not introduce him by name. I want you to ask him where he was twenty-four hours ago." The officer approached, and Roosevelt put the question to him. He had been on enemy soil, inside Germany, "[I]n Kiel, sir," he replied to an astonished FDR. Blinker Hall brushed the feat aside. He had spies passing back and forth between the German-Danish border and England practically every night, he said.

The young agent's tale of derring-do was a charade concocted by Hall precisely to impress Roosevelt. Hall's fiction was the first time, but not the last, in which British intelligence would employ ruses and outright fabrications to bend FDR to its ends-and succeed. In a journal FDR kept, he wrote of this encounter: "Their Intelligence Department is far more developed than ours and this is because it is a much more integral part of their Office of Operations." This failing in U.S. naval intelligence, he added, "will be eliminated." Indeed, by the end of the war, the ONI, led by Roosevelt, could boast an intelligence network spread across Europe, Latin America, and the Far East, employing hundreds of agents and informants.