(upbeat music) (device beeping) (upbeat music) - The message had come.

There's no living with Castro.

- [Speaker 1] The Soviet Union is putting missiles- - 90 miles from Key West.

- [Speaker 2] Kennedy was really keen on getting rid of... - Fidel Castro.

- [Speaker 3] Our operation must be delicate.

- [Speaker 4] Refined.

- [Speaker 5] The big question was, how do we do this?

- [Speaker 6] The CIA came up with an Operation Mongoose.

- A ridiculous plan.

- Probably a little crazy.

- The CIA wants them hired from Mafia to kill Fidel Castro.

(intense music) (gunshot bangs) - There it is.

That's a clip from "Mafia Spies."

Paramount Plus' "Mafia Spies."

Absolutely love this.

Go check it out.

And how that happen?

Gentlemen you see on camera.

Tom Donahue, writer, director, and executive producer of Paramount Plus' "Mafia Spies," and also co-founder of Creative Chaos.

Tom, it's an honor to have you with us.

- It's great to be here Steve, and an honor to meet you.

- Creative Chaos, what is it?

- So Creative Chaos is my production company that I co-founded with my partner, Ilan Arboleda.

And we've been making films for 15 years, unscripted documentary films.

And we do both films about Hollywood, about pop culture, and films that have social impact.

Films about gun violence, films about gender equality.

We did a film about the Hollywood casting director that led to the Oscar category that just came out this year.

- Well, I gotta tell you, I'm obsessed by... I grew up, you know, in a neighborhood in Newark, New Jersey, "Frank Sinatra," let's just say there were a lot of guys in the neighborhood- - Yeah.

- who were on either side of the law.

And so I thought I understood a little bit about organized crime and the Mafia.

But to read about Operation Mongoose that the Feds, the CIA, the obsession from JFK, the President at the time, to get "Castro," was so intense, the Feds through the CIA connect with the Mafia to take out Castro?

- That happened.

And it sounds so bizarre and like such a conspiracy theory, that we knew in going into this, we had to really, really use the FBI and the CIA documents as foundational.

We had to keep going back to them, because nobody would believe this story if we didn't show the proof in the documentation.

- And the feds did not want the federal government, JFK at the time, the CIA, the FBI headed by J. Edgar Hoover at the time, they did not want the American public to know that they were doing business with the mob.

- No, of course not.

- But here's the really weird part about this.

The specific mobsters that are featured in the film, and also the book, "Mafia Spies," Thomas Maier, fascinating book, Sam Giancana, the mob boss in Chicago, who followed up Al Capone, if I'm not mistaken.

Right?

- Mm-hmm, exactly.

Yep.

- And also, Johnny Roselli.

These mobsters were violent mobsters.

They're not like business people who happened to be involved in an organized crime.

These are violent mobsters.

And where does Sinatra's Rat Pack come into this?

- Well, because there's this in the early '60s, I think you start to see this confluence of politicians, celebrity, in all kinds of power, mixing it up in the world and in the United States.

And so you start to see... I mean, basically, Sinatra is playing at clubs that are being run by the mob.

I did a documentary on Dean Martin and Tony O, who was Sinatra's manager for many years, said "Listen, Sinatra hung out with mobsters because if it was the cardinals and the bishops who were running the clubs, he'd be hanging out with the cardinals and the bishops."

- So here's the thing that's fascinating to me, Castro takes over from Batista, who the American government was very much "in bed" with.

The casinos were doing well in Cuba.

American business making money, government, positive relationship.

Castro comes in, the revolution happens.

What is the obsession that Kennedy had with taking out Castro?

- It wasn't Kennedy.

It was Eisenhower.

And it started in- - Pre 1961?

- Yeah, it was 1957.

They launched Sputnik.

Can you imagine the first satellite launched by the Soviets, by the communists, over our heads, is the Soviet Union satellite.

They could drop nuclear bombs on us.

I mean, there was such a feeling of fear in the country that the next step for Eisenhower was whatever we need to do to protect ourselves.

Then Castro, suddenly aligns with the Soviet Union 90 miles south of Key West.

So that's what they were thinking about.

They were not thinking about Castro.

This was geopolitical.

This was about the- - Oh, hold on.

So it's not so much Cuba and Castro, it's the Soviet Union?

- Yeah.

- And Cuba's connection.

So hold on.

Help us understand this.

- Yeah.

- I don't want... - This is, I think, the tragedy of it, Steve, is, I think we could have- - Right, talk about that.

- accommodated Castro if we had played it smarter.

But with the Dulles brothers, they were so vehemently anti-communist that they could not take those- - Hold on the Dulles... Hold on.

You're talking about Allen Dulles?

- Sorry.

Allen Dulles was, yeah, the secretary.

- Fed's secretary?

- I'm sorry.

Allen Dulles was the head of the CIA, and John Foster- - Okay.

- was the Secretary of State.

They were brothers.

- And what was... So they had the obsession?

- They were incredibly obsessed.

Yeah, they overthrew the leader in Guatemala.

They were responsible for killing Allende in Chile.

- Is the whole thing... It's so weird that we're in 2026, and the term communist... "You're a socialist communist," it gets thrown around all over the place.

Help folks understand, Tom, how intense the fear slash hatred, and paranoia in the post, if you will, Senator Joe McCarthy era, "looking for any red," which means a communist.

How intense was it in the country at the time?

Not just with Eisenhower and Kennedy, but among American citizens?

- I know for me, growing up in the 1980s, and maybe you too, I had nuclear nightmares.

I would walk home the night thinking, God, a nuclear bomb could drop suddenly in the cornfield.

I mean, I was that... There was that much, I would say, anti-communist propaganda.

But in our country, it was really kind of embedded in that propaganda.

Did it turn out to be... Were they as scary as we thought?

No.

They turned out to be... It kind of was a shell game.

I mean, ultimately, as we know, when Reagan built up and then they built up more, their economy collapsed as a result of the Cold War between us.

But at the time we thought, you know, they have nuclear weapons, we have nuclear weapons, we're ideologically opposed to each other, we could end up in a nuclear war.

And it all came down to that.

- By the way, the Mafia, they obviously failed to get Castro, but there were attempts to assassinate him.

- Yeah, there were something like over 630 attempts to assassinate Castro.

- What?

(chuckles) - Yeah.

Recorded events.

Documented.

- And the mob involved in many of them?

- The mob involved in many, many of them.

Yes.

Other ones were guerrilla groups out of Florida who were aligned with anti-Castro forces.

- Is that how the Bay of Pigs went south?

Because the Bay of Pigs disaster with Kennedy, and Castro's folks were ready for them in the jungles of Cuba, right?

Is that- - Exactly.

Bay of Pigs was a parallel operation with the exile community in Florida to basically have the United States prop up the exile community as if it's an "independent group," going and attacking and trying to take over Cuba from Castro.

Meanwhile, the mob was still working their angle.

So what I loved about the story is, you have, you know, J. Edgar Hoover hated Allen Dulles, did not like the CIA, he felt like that should be his purview.

So he finds out the mob is working with the CIA, he goes after the mobs.

And now you have to see the FBI going after the mob.

Well, the mob actually believes they're doing their patriotic duty in helping the American government and the CIA.

(laughs) - And by the way, don't think the mob didn't want certain things from the feds in terms of the FBI laying off them.

- You're right.

I'm not defending the mob.

But there was this patriotic streak within the mob, and certainly with Johnny Roselli.

I think he did... He was born on the 4th of July.

He was an an illegal immigrant.

- Yes.

- But he really loved America.

- Tom Donahue, writer, director, and executive producer of Paramount Plus' "Mafia Spies."

Hey, listen, if you can find it, watch it.

It's worth it.

It's about a piece of American history that folks don't really understand or appreciate, and it's worth it.

And also co-founder of Creative Chaos.

Hey Tom, thanks so much.

We appreciate it.

- Thank you, Steve.

Good questions.

- You got it.

Stay with us.

We'll be right back.

- [Narrator] One-On-One with Steve Adubato is a production of the Caucus Educational Corporation.

Funding has been provided by EJI, Excellence in Medicine Awards.

A New Jersey health foundation program.

The Adubado Center for Media Leadership.

NJM Insurance Group.

The North Ward Center.

PSEG Foundation.

The Russell Berrie Foundation.

New Jersey Sharing Network.

United Airlines.

And by Newark Board of Education.

Promotional support provided by CIANJ, and Commerce Magazine.

And by NJBIZ.

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