‘Mafia Spies’ Creators Explain the Real Reason for  JFK’s Cold War Threesome in Havana, Castro Assassination Attempts and the CIA’s Mob Ties

As a seasoned journalist with decades of experience under my belt, I’ve seen my fair share of complex and intriguing stories. But none have quite captivated me like the tale of “Mafia Spies” – a story that delves into America’s dark past of assassination plots, covert operations, and the blurred lines between politics and organized crime.


Paramount+’s “Mafia Spies” reveals an unearthed collaboration between the CIA, Chicago mafia, and Frank Sinatra’s Rat Pack to plot the assassination of Cuba’s Communist leader Fidel Castro during the pivotal period of the Cold War. This engaging six-part documentary series explores the implications of geopolitics when powerful American politicians are motivated by inner demons.

The TV series “Mafia Spies” is based on Thomas Maier’s book “Mafia Spies: Revealed Secrets of the CIA, Gangsters, JFK, and Castro,” published in 2017-2018. This work utilized declassified documents regarding John F. Kennedy’s 1963 assassination, made available by the National Archives. Tom Donahue and Ilan Arboleda executive produce this gripping series, which explores themes of power, politics, sex, and violence. Castro endured numerous assassination attempts involving various methods such as two poisoned pills hidden in cream, a explosive cigar, a microphone laced with drugs, and bazookas.

The docuseries uses a large number of declassified National Archive documents and interviews with many experts, along with cinematic reenactments, to tell the story of a high-stakes game of cat and mouse during the Cold War. This game took place in various locations including Las Vegas, Miami, and Havana, as Washington officials faced off against some of the most infamous gangsters of the 20th century.

In the extraordinary series “Stranger Than Fiction,” which premiered on Paramount+ on July 16, Donahue spoke with historians and renowned journalists such as Maier (previously known for writing “Masters of Sex” and producing the Showtime adaptation starring Lizzy Caplan), Gerald Posner, Tim Weiner, Geoff Schumacher, Stephen Kinzer, Peter Kornbluh, J. Michael Niotta, and professor Boris Nerey Obregon. The series also includes appearances by Sam Giancana’s daughter Antoinette, entertainer Betsy Duncan, and actor Robert Davi.

EbMaster spoke with “Mafia Spies” showrunners Donahue and Arboleda.

Tom, could you please expand on your statement that the series aims to “inspire viewers to ponder the significance of safeguarding our democracy and keeping those in authority answerable”?

During World War II, the US didn’t have a dedicated intelligence agency due to democratic principles opposing secret organizations. However, one was established during the war and later dismantled. The CIA came into existence in response to the perceived threat from the Soviet Union, which led us to follow England’s successful model of an intelligence agency under the monarchy. Initially reluctant, President Truman eventually gave in due to national security concerns. On the other hand, President Eisenhower, who wanted to prevent another large-scale military conflict like D-Day, supported covert operations. As a result, the CIA was formed to collect intelligence and take actions based on that information without seeking approval from other branches of government.

As a movie critic, I’d say this: In “Arboleda,” the show explores the chilling consequences when those in power believe they have the right to make decisions for everyone, disregarding individual freedoms and transparency. The government’s desperate attempt to hide the truth about the Castro assassination plot is a stark reminder of how the absence of accountability can undermine democracy itself. When we’re kept in the dark, we lose the ability to hold our leaders responsible for their actions – a dangerous scenario that threatens the very essence of a democratic society.

As a film enthusiast, I’m always intrigued by the behind-the-scenes stories that shape history. In this gripping series, we uncover the shocking revelation that in 1960, President Eisenhower had a secret plan to “take care” of Fidel Castro. The plot involved some heavy hitters: CIA director Allen Dulles, Robert Mayhew, a former FBI agent and Howard Hughes associate, Cuban exile Frank Sturgis, and the notorious Chicago Outfit gangsters Sam Giancana and Johnny Roselli. Yet despite their combined power and resources, they failed to carry out the assassination. Why? The answer lies in the twists and turns of history that unfold as the series progresses.

Donahue: One explanation is that Castro excelled at infiltrating the US intelligence community with undercover agents, making it difficult to discern who was on Cuba’s side. Whenever an assassination plot was uncovered, it seemed as if Castro had prior knowledge. This was likely due to his extensive training from the Soviet Union.

Arboleda adds another explanation: The CIA was winging it without a clear plan or knowledge of the consequences. They believed they had all the answers to global issues. In the series, we depict Jacqueline Kennedy handing Allen Dulles a copy of “From Russia, With Love” and suggesting, “You ought to try some of these tactics.”

In the 1960s, was the fear of Castro in America primarily driven by the perceived danger of communism, or was it more about America’s sense of masculinity being challenged by him?

Donahue: Yes, you’re absolutely correct. The issue was about one person being located 90 miles away and another gaining control over a significant commercial trade route for the US. The CIA officials at that time, who were predominantly white and based in Georgetown, couldn’t accept this development. Racism also played a role in their actions.

According to Stephen Kinzer and Tim Weiner in their respective books, the US’s perception of these countries as evil due to their opposition to American corporate interests often leaves them with few options but to turn towards the Soviet Union for support. This fear of communism projected by the US can significantly influence the decision-making process of these countries, such as Guatemala, the Congo, the Philippines, and Vietnam, leading them to align with the Soviet Union. This dynamic was particularly significant in the case of Fidel Castro.

Have you pondered over the extent of Frank Sinatra’s connections to the mafia, which has been a topic of much discussion? Would it come as a shock to viewers to learn the full extent of his involvement with American gangsters?

Frank had a strong attraction to the mob world without directly being part of it. He admired their tough demeanor and enjoyed their company. However, he found himself right in the heart of various influential forces – Hollywood, CIA, baits, and President John F. Kennedy. It’s hard to believe the impact he had and the role he played. Essentially, Frank Sinatra is the reason why the president and the Chicago mob boss shared a common love interest.

As someone who has always been intrigued by historical mysteries and scandals, I can’t help but be fascinated by the allegations that JFK had a threesome with two Cuban prostitutes while in Havana. However, it is important to clarify some facts.

Donahue: Yes.

At times, I have the feeling that the alleged extramarital affairs of JFK were exaggerated beyond reality for the sake of sensational news titles.

When considering this generation that grew up after World War II, it’s important to take a broader perspective. Many of them experienced deep psychological trauma and coping mechanisms such as excessive drinking and potential addiction to sex may have been their ways to alleviate their stress and pain.

You interviewed many celebrated experts for this series. Did it take any convincing?

Thomas Maier, the first speaker in the series, posed the question: “How do you narrate a tale when everyone involved is dishonest?” Given the abundance of conspiracy theories surrounding these subjects, we understood that this would be a challenging endeavor. To secure a Pulitzer Prize winner like Tim Weiner for our production, we couldn’t risk featuring a conspiracy theorist on camera. Instead, we needed to maintain an unbiased and truthful perspective throughout. This was essential to ensure that the individuals in question would participate in the project.

Have you come across a critique that describes “Mafia Spies” as a gripping account of espionage, a baffling murder mystery, and an unveiling of America’s initial involvement in assassinations? Does this resonate with the current political climate under Trump?

Arboleda is absolutely right, and it’s increasingly clear to everyone now.

Donahue doesn’t limit his analysis to the Trump administration alone. He believes that going back to George W. Bush and the CIA, the WMDs controversy, and the impact of leaders’ inner motivations on foreign policy are all significant factors. As the supposed leader of the free world, these personal demons hold considerable geopolitical weight.

I had the opportunity to follow the release of “Mafia Spies,” a captivating production brought to life by CreativeChaos, Danny Strong Prods., and See It Now Studios. This intriguing series made its debut in the United States and Canada on Paramount+ on July 16, while viewers in the U.K., Australia, Latin America, Brazil, France, Italy, Germany, Switzerland, and Austria could tune in a day later, on July 17.

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2024-07-18 21:17