Rooseveltâs hands did not, however, recount shipboard capers. Rather, it was Astorâs 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. Franklinâs much older half brother, James, was close to Vincentâs 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. Vincentâs grandmother was the grande dame who defined New York society by the four hundred guests who could fit into her Fifth Avenue ballroom. When Vincentâs father went down with the
Titanic
in 1912, the son dropped out of Harvard to assume control of the familyâs holdings, inheriting $75 million and tagged by gossip columnists as âthe richest boy in the world.â James Roosevelt became executor of the Astor estate and continued as a trusted advisor to Vincent, who prized his counsel and always referred to FDRâs brother as âUncle Rosey.â
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 âwe grew to be the same age.â The two avid sailors met again during the First World War while Franklin was serving as President Woodrow Wilsonâs 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 Astorâs 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 Rooseveltâs 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 childâs play for a serious cryptanalyst, the code nevertheless served Franklinâs 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. âAlice confides in her doctor,â he wrote. The next dayâs coded entry read, âWorried over Alice all night.â A half century later the subject of his concern would explain only, âIn 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
âhard.
â
Doris Kearns Goodwin, chronicler of Rooseveltâs wartime years, has explored the roots of FDRâs character that may explain his attraction to the secret and covert. Franklin had been an intuitive child, Goodwin writes, who âlearned to anticipate the desires of his parents even before he was told what to do.â She quotes Franklinâs mother, Sara Delano Roosevelt, saying that her boy