Kennedy, Sinatra and the Mafia

10/6/2025

I suppose that if you are looking for all the ingredients for a good conspiratorial story, then you could do much worse than try to connect the Chicago mob with legendary crooner Frank Sinatra and the ill-fated US President John F. Kennedy. What now ensues tries to establish a link between organised crime and Kennedy by way of some facilitation from Frank. It’s basic premise is that Kennedy Senior (Joe) wanted Sinatra to use his long-suspected underworld connections to help ensure his son was elected to the White House. Once there, though, the building blocks for his presidential bid began to crumble with his old allies as JFK and his tenacious brother Bobby started to root out the corruption and evil that dominated in cities like Chicago. Using a collection of oft-seen archive and still p