It's a story too wild to be fiction,
yet it's all true.
A secret alliance between America's most feared criminal
syndicate
and the highest levels of US intelligence.
An audacious Cold War plot to assassinate
Fidel Castro
that reads like a James Bond screenplay,
but with more misfires,
betrayals,
and bodies left behind.
The story begins in Havana, Cuba,
where the mob made millions controlling casinos
until Castro's revolution swept it all away in
1959.
And in the panicked of the Cold War,
the CIA turned to the unthinkable,
hiring mafia gangsters to do its dirty work.
I sat down with investigative
reporter Thomas Mayer, whose book Mafia Spies
blows the lid off one of American history's
darkest
and most secret chapters.
Mayer and I have mutual friends among investigative
journalists.
He is among the best.
I've placed a link in the show notes
to help you keep track of the cast
of characters.
Mayer's journey into this twisted tale did not
start with the mafia.
It began with JFK
and the Kennedys.
I've written previous books about the Kennedys.
I wrote a book about twenty years ago
about their Irish Catholic immigrant experience,
and also wrote another book about ten years
later about the Churchills and the Kennedys.
In both those books, I did tangentially mention
the incident that happened with JFK and
Judith Exner,
who in Mafia Spies is generally known as
Judy Campbell. That Judith Exner was her married
name. But it was a, an affair that
involved JFK,
a Chicago Mobster by the name of Sam
Giancana,
and Judy Campbell.
And so even though I had mentioned them
very briefly,
I was intrigued about perhaps writing a book
about,
Giancana.
And I wasn't really sure if I had
enough meat on the bone, if you will,
to do a book
by itself. And it wasn't until I did
more research, and I learned about,
this particular aspect of how the CIA hired
both Sam Giancana
and another really fascinating
gangster by the name of Johnny Roselli.
It wasn't until I found out about this
plot to kill Castro
by the CIA by hiring
these two gangsters
to go out and kill Castro during the
Cold War, that I realized, that this was
something that was really intriguing, particularly
the friendship between
Giancana
and Roselli. It was almost like if you
ever watch that movie Butch Cassidy and the
Sundance Kid, it's kinda like these two outlaws
who are hired by the government to to
to do really
a dastardly deed,
and kill a foreign leader,
Fidel Castro, at the height of the Cold
War.
Set the scene of what the tension was
between The United States and Cuba.
What was the vested interest of the mafia
in Cuba and then
the US government, I e, the CIA?
Well, in the late fifties, what happened there
were two things that really shook the American
government. One was,
the the shooting off of the Sputnik
rocket. It was the first thing into outer
space,
and that was sent up by the Russians.
And so that really
threw off the US government because we came
out of World War two very preeminent.
We were the first ones to develop the
bomb.
So the idea of having
a rocket that could conceivably have a have
a an atomic bomb attached to it, that
really sent shutters through official Washington.
But the other satellite, if you will, was
the creation of Cuba
as a satellite of the Soviet Union, Russia,
at that time.
And,
the revolution led by Fidel Castro
really sent,
again, shivers down the the spines of the
the US government. And so we couldn't do
anything about shooting
Sputnik out of the sky, but the decision
was made that, Castro
had such held such a
a threat to the defense and the security
of The United States that something had to
be done about it. And it was approved
by president Eisenhower
at the end of his administration,
and it was adopted
by the Kennedy administration,
in the early nineteen sixties.
So the Kennedy administration was aware that there
was a plot to assassinate Castro? You know,
they have said no. You know, people who
associated with,
president Kennedy's administration have said no. But when
you look at the papers,
these documents that particularly have been released in
recent years
pertaining to the JFK assassination,
a lot of them have to do with
the operation by the CIA in Florida.
Essentially, we were running an undeclared
war
out of, the Miami,
the, the Keys area,
of of
Florida. And so even though there's been denials
about it, we were definitely
trying to kill Castro. And, certainly, Bobby Kennedy
was aware of that. Even despite the denials,
when you look at all of the papers,
it's impossible,
it seems to me. I mean, Bobby Kennedy
was flying down to Florida
during the course of this. He was in
he would he had his hands all over
this. He was the attorney general, but he
was, almost in essence, the head of the
CIA
overseeing this operation
to overthrow the Castro government. Well, and here
he is, the attorney general, yet the US
government forms an alliance with the mafia, a
criminal organization.
And
do they end up kind of giving them
a free pass on their criminal activities?
Well, you know, it's interesting because
particularly on that point,
the Kennedys,
Bobby Kennedy claimed that he didn't know anything
about it. It's hard to really believe that,
frankly,
given all of the evidence, all of the
documents,
and all of his deep participation
in in this. So, yeah, I I think
what was interesting about the the mafia,
Giancana,
Sam Giancana, and Johnny Roselli with this, is
that
they thought by
agreeing with Frank Sinatra, who was a pal
of Giancana's and Roselli's,
Sinatra was a very prominent supporter of JFK
in the nineteen sixty election.
And they felt by supporting
the the Kennedy effort that they would go
easy
on them. In fact, when Bobby Kennedy became
attorney general, though, he put up he put
more of the heat on the mafia
than had, than had ever been before. And
so Xi and Khan and Roselli were really
upset,
as the Kennedys came to power that they
essentially betrayed or, at least in their perception,
betrayed
the promise of going easy, getting a getting,
like, a get out of jail free card.
And in fact, they were being chased by
the FBI
more than ever.
Well, when you have this alliance,
they start cooking up these schemes to assassinate
Castro. And it's it's James Bond esque.
But it, like to me, it becomes the
gang that couldn't shoot straight.
Yeah. You know, I I think I that
aspect of the almost the, dark comedy or
comedic aspect of of this, particularly when you
look back with some degree of perspective
historically.
Or certainly in, my book was made into
a TV series
on Paramount plus
by the same name, Mafia Spice. And I
think we kinda capture that as well in
the TV show, both the book and the
TV show.
There was a certain level
of craziness about the whole thing that I
think is captured in both. Try to portray
that. I I think there's a level of
hubris,
a a word that we don't hear hear
too much. But hubris, the whole idea that,
whatever I do
will be fine, it will
will never
blow up in my face,
and that this is well intentioned.
And that wasn't the case. It was very
poorly thought out, and it was very suspect
in terms of getting involved. The idea of
the the
United States government getting involved with the mafia
was suspect to begin with, but the fact
that, the attorney general of United States was
overseeing an operation that had any type of
component
with organized crime is something that remained a
secret for for about ten years afterwards.
The all of this really didn't come out
until the mid nineteen seventies, and still many
details are are still coming out with some
of these JFK assassination papers. But it does
give you pause about the overall
judgment of the Kennedy administration.
Well, one of the methods they'd come up
with to kill Castro was a a poison
cigar with botulism
in it and stuff.
Did that come out of the James Bond
movie?
I mean, it it none of this stuff
ever worked.
Right. Well, I guess if you come up
with the idea by watching a movie,
maybe Yeah. That may be that may be
the grounds why it doesn't work.
It is fictional to begin with.
You know, it's interesting to me in in
looking at this time period, the Bond movies
were just getting off the ground.
JFK was a big fan
of James Bond novels. So was Jackie Kennedy.
Jackie Kennedy actually sent a copy of one
of the James Bond novels
to the head of the CIA, Allen Dulles.
And Dulles also heard at at a dinner
party
that the creator of James Bond,
Ian Fleming,
was invited to JFK's
residence for a dinner party. And so Dulles,
who wanted to keep his job,
decided to keep the president happy and his
wife happy and and all of those fans
for James Bond that he directed people in
the CIA to see if that any of
these ideas
from James Bond films might might be doable.
We might be able to take some of
these ideas, exploding cigars or or, other type
of devices,
gadgets that somehow could be killing devices.
These were all suddenly the focus
of a lab at the CIA. The other
thing I found interesting then is that this
assassination conspiracy
meetings unfold
at the Fontainebleau
Hotel
in Miami, which is the big scene of
one of the James Bond movies,
and in Vegas, which is another big setting
for the early James Bond movies.
It is.
Goldfinger,
it begins with somebody jumping off of a
very high diving board at the Fontainebleau Hotel
in Miami Beach. Miami Beach is,
well, specifically, the Fontainebleau
is a fascinating scene
that because the
the the big first meeting between
the
the, CIA
and the mafia takes place at the Fontainebleau.
And it's around the same time that Sinatra
is appearing at the Fontainebleau.
He's hanging out with Sam Giancana, the gangster,
who's getting involved in all of this plot
to kill Castro along with Johnny Roselli.
And
Sinatra is filming
a TV special
at the Fontainebleau
with Elvis. Actually, you could go on to
YouTube and actually
see Elvis and Frank Sinatra singing,
together. And that's at the Fontainebleau during the
same time period. And then we see other
meetings in Vegas, which in those days, the
mob controlled.
Right. Well, Las Vegas,
particularly became
important.
Las Vegas,
the Las Vegas that we know, its origins
became,
started right after World War two. But at
that time period,
Cuba was still the place that had its
own casinos,
were was run by the mob.
In the fifties, most Americans, certainly on the
East Coast during the winter months, they didn't
go to Las Vegas. They would go to
Havana. And there are a number of different
casinos, including one that was run specifically
by,
Sam Giancana and Johnny Roselli, the San Sushi.
But there are other mob controlled casinos.
When Castro came to power
in 1959,
he shut down
all of the American casinos, all of the
American businesses, but he shut shut down all
of the mob controlled
casinos as well. So that's where it it
really gave a big boost to, Las Vegas.
But that was also why the mob,
who was now losing millions of dollars that
they used to make in Havana. That's why
the mob was so angry
with Castro and what had happened in Cuba.
Did Sam Giancana, who was out of Chicago,
become involved because he had lost so much
money
down in Cuba?
Tell us about him.
I think so. I used to work as
a reporter for the Chicago Sun Times, and
that was also part of the rationale for
me, the curiosity that I had about Gina
as a figure. But, fundamentally, yeah, it's about
money. Money, money, money, money.
The outfit, the the mob as the mob
was known in Chicago,
was headed by Giancana
at that time period. It was on the
scale of a Fortune 500 company in terms
of its revenues.
And so it was all about money. And
so when they lost,
the casinos
in in Havana, it was a place where
the mob ruled. In fact, Meyer Lansky,
another gangster,
was appointed by the Cuban government as the
head of tourism
and such. So it was it was a
little heaven, if you will, for the mafia
and all of its nefarious
activities.
And and Sam Giancana
had big ambitions.
And so his friendship with Johnny Roselli really
was a a a a reflection of those
ambitions as well, because they got involved
not only,
with Las Vegas and and running things in
in Cuba, but the idea of now getting
involved with the government,
becoming hitmen
for the CIA,
that was extraordinary.
That's the type of thing that the average
mobster didn't do. They were concerned about, like,
local stuff, local gambling,
numbers, rackets, stuff like that. No. These two
guys, Roselli and Gene Conner, they were talking
about getting involved in entertainment, the movies,
and and they certainly got involved with the
CIA.
Was Roselli the connection to the CIA? How
do they how do they make that connection?
Yeah. It's it is
a little bit of a complicated one. But,
yes, Johnny Roselli was the main
connection.
He knew
a guy
named Bill Harvey, who was known as the
James Bond, the real life James Bond of
the CIA. I think there's a couple of
people that can make that claim. But, certainly,
Harvey was a very successful
spy for the CIA over in Europe,
and
he was acquainted
with, Johnny Roselli. And so the connections there
were part of it, part of the story.
But there was also a middleman
involved in this. And he also,
this middleman
worked for Howard Hughes, the the then
the wealthiest man in The United States. And
it was, through that middleman that the CIA
was connected to Johnny Roselli, and and Roselli
recruited,
Sam Giancana
into this whole
escapade, if you will.
For those that don't know,
Howard Hughes was the Elon Musk of today.
Right. I was about to say that. Yes.
Yeah. And it He was.
All kinds of technology.
But that connection to Hughes is what, Robert
Mayhew?
Right. Exactly. His name was Robert Mayhew.
And really a fascinating character because he had
been an FBI agent,
had a lot of friends in the CIA,
and he had done other jobs for the
CIA, the type of jobs that the CIA
didn't didn't wanna get its hands dirty, if
you will. And so they kinda hired out
people that they trusted, and Mayhew was one
of those people. And it was Mayhew who
knew Roselli pretty well. He had invited Roselli
to a backyard party, and that's where there
was a couple of CIA people there. That's
where they met Johnny Roselli. So when the
subject came up from very up on high
from the White House and from the upper
reaches of the CIA that we wanna get
rid of,
Fidel Castro,
they said, well, how do we do this
without,
getting it connected directly to to us?
And so they employed
Robert Mayhew,
and then Mayhew recruited the mob into this
whole scheme
to kill Castro.
And these people in the spy craft are
usually referred to as
cutouts.
Yes.
They have
a language unto themselves,
the whole spy world does, and Cutout is
one of those. But, essentially, he was a
he was a a go between. He was
an intermediary.
He was a middleman
between,
or if you ever watched the, Godfather
movies,
there's at one point where somebody says, the
family has a lot of buffers.
Well,
Mayu was, in a way, a buffer
for the CIA. It was a way of
implementing
their plans to kill Castro
without,
in their eyes, hopefully getting directly,
held responsible
for it. But, of course, that didn't happen.
Eventually, it all came out. And then part
of the plot to overthrowing was the Bay
of Pigs invasion,
which
broke down, fell apart. Yeah. This was an
attempt this was the big attempt to overthrow
the Castro government.
The Cuban Americans who fled to Florida were
trained by the CIA.
They had a base down in Florida.
They they were trained in other countries as
well, but but there was a big effort
to train people
in Florida.
And that was it was remarkable to me
that we could run,
essentially, an undeclared war
in Florida, and it really did not come
out.
People were not even fact, there there was
one incident where there was some type of
shooting
incident,
and the the local newspaper in Miami found
out about it. And they were gonna write
a story about it. And the CIA and
the the,
US government
contacted the newspaper,
and they decided not to run the story.
What ends up happening to Sam Giancana and
Johnny Roselli, the
two mobsters
that got into bed with the CIA?
The friendship between
Sam Giancana
and Johnny Roselli,
fascinated me. I think that was one of
the big appeals
of of this book on a personal level.
Just their friendship they had started together in
Chicago. Johnny goes out to Hollywood. He's sent
by Al Capone out there because Johnny suffered
from tuberculosis.
Johnny becomes kinda the mob guy out in
Las Vegas. He was a fixer out there.
He knew a lot of the studio heads.
Sam Jean kinda rises to the head of
the Chicago mob.
His wife
drops
dead, screaming at their kids. They she has
they have three daughters, and suddenly,
Sam Jean kinda finds himself as bachelor father.
Johnny
is kind of a Casanova
character. So these two men together,
to me, just on a personal level, was
fascinating,
how they interacted
with them and with Sinatra, the Rat Pack,
and such.
I think getting involved with the CIA
was part of the ambition that Giancana
had, which was to
grow the mob outside of just Chicago
into,
not not only domestically,
but even in international places like Cuba and
other other places internationally, particularly in terms of
casinos
and things of that nature, things that would
make big, big money, not petty anti type
of gambling.
And so the the relationship
between,
Roselli and and Giancana was based upon their
own ambitions
and and and and getting involved with the
CIA.
Thinking that if they if they did a
favor for the CIA by killing Castro, not
only would they get back into Cuba,
but they would have a
won over on the on the government. They
would they would have a get out of
jail free card.
And,
that sounded
very attractive to them, and that's really why
they got involved
in all of this. And what ends up
happening to them
at the end of this checkered story?
Well, it becomes even more complicated.
Giancana was warned,
don't
draw attention to yourself
because it can be disastrous,
just like it was
with Al Capone or, in more recent vintage
mob history,
John Gotti in New York. In other words,
if you love the limelight, if you love
the celebrities,
and he was told,
don't do that. Gene Conner was told, don't
do that. In fact, he was selected by
the elders in the mob in Chicago,
who were retiring
or semi retired, at least keeping an eye
on things.
But
they thought that Giancana was married, that he
he was known for mowing his lawn out
in the suburbs,
that he was a solid guy. He was
a money earner, and so will give the
job to Sam Giancona.
When his wife drops dead, he starts hanging
out with Johnny Roselli.
He meets various different people, the Maguire sisters.
He starts going out with one of the
Maguire sisters. And now his photos and and
he becomes friends with Frank Sinatra. So now
the, we have Sam Giancana
as a prominent figure in the in in
the tabloid
newspapers and such. So this is the type
of attention that the mafia in Chicago, they
didn't want any of it. And so they
they wound up,
after the JFK assassination,
Giancana
essentially is pushed out of power in Chicago.
He winds up going down to Mexico
and trying to get involved in international,
business and such.
He eventually comes back
to The United States
in the mid nineteen seventies. By that point,
he's got some health problems.
He comes back to Chicago,
and there's a question about whether or not
he'll he'll try to grab the reins of
the Chicago
mob and run it again. He had been
replaced and whether or not he would try
to grab the power there.
And,
when that happens in that time period,
he subpoenaed
by the senate
to talk about,
what was
had happened in the early 1960s and the
attempts to kill Castro.
Again, with the a lot of things are
complicated. There's a lot of spinning plates in
this story. After the Watergate
investigations of the early 1970s,
the senate was looking at the operations of
the CIA, and they became aware of the
plot to kill Castro
involving the two gangsters, Giancana and Roselli. And
so the senate
subpoenaed both of them. And in the case
of Giancana,
there were investigators who flew out to see
him. And that night, he had dinner with
his family. And and when the family went
home, Sam was cooking up a little snack
for himself. He had, like, a little man
cave in the cellar of his home in
Oak Park, and it was late. And I
brought 11:00
or so. And somebody, we still don't know
who, came in with a silencer
and put six bullets
into Giancana's head.
And he did the the assassin did so,
with the telltale mark of putting the shots
around his mouth, which basically was a message.
Anybody who talks like this will wind up
just like Sam Giancana. They'll wind up dead.
By that point, Johnny Roselli
realized
that he was had a target on his
back. He he went, down to Florida, start
started hanging out with his sister, living with
his sister.
But he was subpoenaed. He did initially
say virtually nothing to the senate.
But then the FBI, who was investigating
Johnny and Johnny had gotten in trouble,
some cheating scandals at the Friars Club in
Beverly Hills. So the FBI, the government was
looking to deport Johnny
Roselli because Johnny Roselli
had a a big secret in his life.
He was an illegal immigrant
from Italy. His mother came over.
He he did not have the proper papers,
and he was feared being deported. In fact,
Johnny Roselli
was not even his real name. It was
completely made up by Roselli himself.
His real name was,
Filippo Sacco.
And when the government found this out after
much investigation of Johnny,
they said that we're going to deport you.
So Johnny, by the mid seventies, was worried
he would be deported, and he intimated that
he knew something about the JFK
assassination. His lawyers intimated that to the senate
committee. And so they subpoenaed him again.
And just before he was to be
deposed
about what he knew,
Johnny
was murdered. He went off to play golf,
and they later found his body in a
55 gallon barrel that was thrown into the
bay
in Miami Beach in that area. And that
was the end of Johnny.
As they say, sleeping with the fishes.
Exactly.
So it's quite a story.
And both the murder of Giancana
and both the murder of Roselli
are unsolved.
Readers of my book,
Mafia Spies, will come to the conclusion
well, you get a pretty good idea of
who I think was responsible,
had his hand involved,
in the murder
of of both Giancana and Roselli. And that's
the last man standing. Castro is the last
man standing on one level, but there's a
mobster who was involved in all of this,
guy named Santo Trafficante.
And I think he had a hand in
both murders.
The secret plot and partnership between the CIA
and the mafia to kill Fidel Castro
first became public during the investigation of the
Watergate scandal in the mid-1970s.
Some of the ex CIA operatives involved in
the plot to kill Castro
played a part in the bungled burglary
of the Democratic National Committee headquarters office at
the Watergate Office condominium
complex in Washington, DC
on 06/17/1972.
President Richard Nixon, facing likely impeachment for his
role in covering up the scandal,
resigned two years later.
Nixon became the only US President to resign.
At the time of the break in, I
was a new congressional aide to Representative
Wright Pattman, chairman of the House Banking Committee.
I would later conduct Watergate related investigations on
his behalf
for the Joint Committee on Defense Production.
Since then, I've watched the revelations
explode into an industry of conspiracy theories
about the assassination
of President John F. Kennedy.
Did the CIA do it? Did the mob
do it? Did Castro do it? Did the
FBI miss warning signs about Lee Harvey Oswald?
Well, the latest batch of JFK documents released
by President Donald Trump
reveals that the KGB
had Oswald under surveillance
during his time in The Soviet Union.
Covertly observing Oswald at a firing range,
they concluded he was a bad shot.
So, how did Oswald, perched in the Sixth
Floor window of the Schoolbook Depository in Dallas,
hit the president with a deadly headshot in
a moving motorcade?
In my next episode,
Mayer reveals a new revelation about the Warren
Commission
and how then CIA Director Allen Dulles
steered the murder investigation
away from the CIA mafia plot to kill
Castro.
You'll wanna stay tuned for this one.
This is Robert Riggs reporting.