Talese spent three months, beginning in November 1965, following Sinatra and observing everything he could and interviewing any members of his entourage who were willing to speak. "Esquire" paid nearly $5,000 in expenses over the duration of the story. Talese was uncertain whether the story could be finished, but ultimately concluded, in a letter to Harold Hayes, that "I may not get the piece we'd hoped for—the real Frank Sinatra, but perhaps, by not getting it—and by getting rejected constantly and by seeing his flunkies protecting his flanks—we will be getting close to the truth about the man." Without Talese ever receiving Sinatra's cooperation, the story was published in April 1966.