Pawley navigates his personal yacht, Flying Tiger II, to the Cuban coast with a raiding party bent on spiriting two Russian missile technicians off the Communist island. If successful, President Kennedy will be publicly humiliated before the next election by the technicians’ announcement that there are still missiles in Cuba. People within the CIA are fully aware of the project and give it the codename TILT and use Pawley’s QDDALE cryptonym when referring to him in TILT related documents. Editors from Luce’s Life magazine are involved in the project as well as John Martino, an individual with Mafia contacts from the days when he was involved in security at a Cuban casino. It was “Jay Sourwine of the Senate Internal Security Committee [headed by Senator Eastland] who had asked that QDDALE participate in the operation.” Pawley’s raiding party failed to return.
Would he look for a new way to prevent JFK from being reelected and Castro from staying in power? Could he kill two birds with one stone using his other contacts within the Cuban exile community?
A 51-year-old document declassified in 2011 may provide a clue as to how ruthless Pawley could be be, and if he had the motive, did he also have the means and method to carry out his mission successfully. The February 24, 1960 document is directed to the Ambassador (unnamed) from the Counselor of Embassy of Economic Affairs and has the subject title: Memo of Conversation Dealing with Caribbean Political Tensions, Including Communist Activities in Latin America; and Alleged U.S. Intelligence Deficiencies. The Counselor details a conversation he had with Wallace B. Rouse, a businessman seeking a business deal with Generalissmo Trujillo. who brought up the subject of eliminating Castro. Rouse detailed how someone he referred to as "big bull," who had played golf with President Eisenhower in Washington, DC, sent a man who had been given a gun and money with the promise of "more when he shot Castro. This man made the mistake of going to Mexico first where he was known to the police and jailed."