During World War II Hemingway organized a private spy network, which he jokingly called the Crook Factory, and gathered information about Nazi sympathizers on the island. But in a secret, 124-page report on Hemingway, the FBI—which feared his personal prestige and political power—expressed resentment at his amateur but alarming intrusion into their territory, and unsuccessfully attempted to control and vilify him.
In October 1942 the local FBI agent told J. Edgar Hoover that the American ambassador had granted Hemingway’s request “to patrol certain areas where German submarine activity has been reported” and had given him scarce gasoline for this purpose. Hemingway thought that his boat, the Pilar, fully manned and heavily armed but disguised for fishing, would attract the attention of a German submarine. The sub would signal the Pilar to come alongside in order to requisition supplies of fresh water and food. As the sub approached, Hemingway’s men would machine-gun the crew on deck while a Spanish jai alai player would throw a small bomb into the conning tower. Fortunately, for both Hemingway and the Germans, he never actually encountered an enemy submarine.
—Jeffrey Meyers, writing in Commonweal about Ernest Hemingway’s long involvement with Cuba, where Hemingway lived for twenty years.