The gentleman spy was a well-worn literary trope long before James Bond appeared on the printed page or silver screen. Yet, like many cliches, there is an element of truth to it. American espionage once relied on well-heeled amateurs to a very large degree. They possessed the necessary skill sets and unique expertise for the job. Espionage, the most pragmatic of occupations, requires language skills, knowledge of foreign nations, and, above all, access to those with access to secrets. A name like Vanderbilt, Astor, or Rockefeller opened doors. Others had long standing business relationships and friendships in foreign nations to smooth any inquiries.

There was Vincent Astor, who put the resources of his vast fortune at the disposal of American and British intelligence alongside the hundreds of members of the New York Yacht Club who donated their yachts to use as troop carriers and armed escorts. Then there was the socialite who saved thousands of lives as a honey trap codebreaker as well as Virginia Hall, the "limping lady" the Gestapo deemed one of the Allie's most dangerous spies. What motivated these people who truly had everything? Perhaps it was patriotism or a desire to prove themselves. Perhaps it was boredom. Espionage is many things. Dull is not one of them.

Yet whatever the motivations of the monied class, what Nathan Hale termed a "peculiar service" before undertaking his ill-fated mission has always attracted more than its share of unlikely and colorful characters. And those recruited from the ranks of the Social Register are no exception. They included dandies and debutantes, heiresses and do-gooders, explorers and the wildly eccentric. The Age of Amateurs is a surprising and skillfully told history of these adventures in espionage.