Ol’ Blue Eyes was one of the most famous singers of his era, and his connections to the Mafia have been well-documented. But it was exactly those connections that made him an irresistible inside operative for the CIA.
Sinatra’s daughter Tina alleges that even though J. Edgar Hoover’s FBI was constantly trying to bring Sinatra in, the CIA often paid him to work as a courier. Because Frank flew on private jets, he could be depended on to transport valuable information and individuals around the world without too much trouble. As usual, he did espionage his way.