Kennedy, Sinatra and the Mafia (2023)

★ 7.7 1h 30m IMDb

With his mafia wiseguy links and access to entertainment industry star power, Frank Sinatra helped John F. Kennedy into the White House in 1960. But it all came to a bitter end.

Kennedy, Sinatra and the Mafia

Where to Watch

Netflix Netflix
Amazon Prime Video Amazon Prime Video
Disney Plus Disney Plus
HBO Max HBO Max
Max Max
Hulu Hulu
Paramount Plus Paramount Plus
Apple TV Plus Apple TV Plus
Peacock Peacock
Showtime Showtime
Starz Starz
Paramount+ with Showtime Paramount+ with Showtime

Rent / Buy

Rent

Apple TV Apple TV
Google Play Movies Google Play Movies
Amazon Video Amazon Video
YouTube YouTube
Vudu Vudu
Fandango at Home Fandango at Home

Buy

Apple TV Apple TV
Google Play Movies Google Play Movies
Amazon Video Amazon Video
YouTube YouTube
Vudu Vudu
Fandango at Home Fandango at Home

Cast

John F. Kennedy
John F. Kennedy as Self (archive footage) Died 1963 · Brookline, Massachusetts, USA John Fitzgerald Kennedy (May 29, 1917 – November 22, 1963), also known as JFK, was the 35th president of the United States, serving from 1961 until his assassination in 1963. He was the first Roman Ca...
Frank Sinatra
Frank Sinatra as Self (archive footage) Died 1998 · Hoboken, New Jersey, USA Francis Albert "Frank" Sinatra (December 12, 1915 – May 14, 1998) was an American singer and actor. Beginning his musical career in the swing era with Harry James and Tommy Dorsey, Sinatra became a su...
Ronald Reagan
Ronald Reagan as Self (archive footage) Died 2004 · Tampico, Illinois, USA Ronald Reagan (February 6, 1911 – June 5, 2004) was the 40th President of the United States (1981–1989), the 33rd Governor of California (1967–1975) and prior to that an actor. Upon his college gradu...
Dean Martin
Dean Martin as Self (archive footage) Died 1995 · Steubenville, Ohio, USA Dean Martin was an American singer, film actor, television star and comedian. Martin's hit singles included Memories Are Made of This, That's Amore, Everybody Loves Somebody, Mambo Italiano, Sway, Vo...
Ava Gardner
Ava Gardner as Self (archive footage) Died 1990 · Grabtown, North Carolina, USA Ava Lavinia Gardner (December 24, 1922 – January 25, 1990) was an American actress popular in the 1940s and 1950s. Considered one of the most iconic stars of the Golden Age of Hollywood, she was ranke...
Sammy Davis Jr.
Sammy Davis Jr. as Self Died 1990 · Harlem, Manhattan, New York City, New York, USA Samuel George "Sammy" Davis, Jr. (December 8, 1925 – May 16, 1990) was an American entertainer. Primarily a dancer and singer, Davis was a childhood vaudevillian who became known for his performances...

Audience Reviews

CinemaSerf 6/10 Oct 06, 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 photography but bringing very little new by way of contributors, we embark on a conspiracy theorist’s wet dream. Everything is touched upon from the womanising to the money laundering to the eventual role (or not) of the mafia in events in Dallas in 1963. The contributors are a rather dry collection of academics who offer nothing new, and go to prove that books can be written on just about anything where there is no definitive answer for their enjoyable but superficial speculation. The fact that they all existed at the same time, in the same country, and mixed in the same social circles doesn’t require a rocket scientist to explain to us. What we could have done with here was something more scientifically constructed and evidenced. A smoking gun rather than a water pistol. As it is, it’s gossip substantiated with a few press photos and some bourbon. Disappointing, but then what chance this was ever going to deliver something revelatory?

Similar Movies