Shortly after the upswing in business, Jack is contacted by one of his former mob associates, named Louie Vitali, about performing a black bag job in Cuba which the murder victim, Action Jackson, seen in the opening scene, was originally assigned to. Ruby confers with Candy Cane and he ends up inviting her to go along with him to communist Cuba. Once in Cuba, Ruby meets with Vitali and they meet with the elderly and imprisoned Sicilian mobster Santos Alicante, who has been in jail in Cuba since the 1959 communist takeover after his casino hotel was closed down. Vitali tells Ruby that they are to spring Santos from Cuba to put him back in place in the US as part of a complex operation plan. However, after their visit, Vitali accompanies Ruby back to his and Candy's hotel room where he secretly tells him the real reason for this assignment; he wants Ruby to kill Santos because the people that Vitali works for feel that Santos has outgrown his usefulness to them. Vitali gives Ruby an 8 mm film camera that has a pistol encased in it to carry out the killing. But that evening, Ruby instead kills Vitali on the dock near the prison and springs Santos from his cell by bribing the guards, and then he, Santos, and Candy flee Cuba aboard Vitali's boat back to America. After arriving in New Orleans, Ruby makes contact with David Ferrie, an old friend from his days in Chicago, to supply him with the necessary papers enabling Santos to re-enter the country. Shortly after, Ruby and Candy return to Dallas, while Santos goes off on his own.