Truck driver, entrepreneur, womanizer - spy. Sophia Di Martino joins journalist Sean O'Driscoll to tell the story of one of the most unusual and effective moles in modern American history. When David Rupert met a woman in an Irish bar in Florida, the meeting sparked an unlikely chain of events that would lead him to infiltrate a deadly Irish Republican terrorist group on behalf of the FBI, MI5 and the Irish state - and put several key players behind bars. But the 'Big Yank' would pay a heavy price for his success. From SPYSCAPE, the home of secrets. A Cup And Nuzzle production. Series producer: Joe Foley. Produced by Max Bower. Music by Nick Ryan. Audio recording of President Bill Clinton used courtesy of the William J. Clinton Presidential Library via Wikimedia Commons. Learn more about your ad choices. Visit megaphone.fm/adchoices