The meeting took place on March 13, 1961, in the Boom Boom Room of the Fontainebleau Hotel in Miami Beach, a place where deals were usually sealed with handshakes and liquor, not death warrants.

A man using the alias “John Roston” sat across from three figures who ruled the American underworld.

Sam Giancana, the volatile boss of the Chicago Outfit.

Santo Trafficante Jr.

, Florida’s most powerful mobster and former king of Havana’s casinos.

And Johnny Roselli, the smooth Hollywood-connected fixer who moved effortlessly between Las Vegas, Los Angeles, and murder scenes.

The man wasn’t really John Roston.

He was Jim O’Connell, a CIA operative acting on orders that traced back through Langley and into the heart of Cold War paranoia.

He placed an envelope on the table.

Inside were poison pills engineered by the CIA’s Technical Services Division—tasteless, fast-acting, designed to kill without leaving obvious traces—and cash.

The United States government was formally proposing assassination and subcontracting it to organized crime.

The logic, in the cold arithmetic of intelligence work, seemed sound.

Fidel Castro had seized power in Cuba in 1959, nationalized American businesses, shut down mob-controlled casinos, and aligned himself with the Soviet Union just ninety miles from Florida.

For the CIA, Castro was a communist threat.

For the Mafia, he was personal.

Havana had been their crown jewel, a sun-soaked money machine of casinos, hotels, and laundering operations.

Castro destroyed it overnight.

Millions vanished.

Empires collapsed.

Hatred burned hot.

The CIA saw opportunity.

The Mafia saw revenge.

What could possibly go wrong?

The irony was suffocating.

As this secret alliance took shape, Robert F. Kennedy—JFK’s younger brother and newly appointed attorney general—was launching an unprecedented assault on organized crime.

Prosecutions for racketeering exploded.

Convictions skyrocketed.

Bobby Kennedy was obsessed, relentless, and personal.

He believed the Mafia was a cancer eating the republic from the inside, and he intended to cut it out.

The same mobsters being courted by the CIA were simultaneously being hunted by the Justice Department.

Neither side fully understood the contradiction they were creating, but the mobsters understood leverage.

They always did.

The CIA couldn’t approach the Mafia directly.

That would have been too obvious, too dangerous.

So they used intermediaries.

Robert Maheu, a former FBI agent with ties to Howard Hughes, was dispatched to make contact.

In September 1960, Maheu met Johnny Roselli in a New York hotel and offered him $150,000 to arrange Castro’s assassination.

Roselli refused the money.

Not out of morality, but because he believed cooperation with the CIA would buy protection.

A favor this big had to pay dividends later.

Roselli also understood something else.

If the CIA was willing to hire killers, it was willing to lie about it.

That meant evidence was power.

So as the plot unfolded, Roselli quietly left a trail—names, meetings, pills, payments—insurance against the day the government turned on him.

The plan itself was crude and chilling.

Poison Castro’s food or drink.

Make it look natural.

The pills were passed to a Cuban official named Juan Orta, who supposedly had access to Castro’s inner circle.

Orta tried.

He failed.

He panicked.

He backed out.

The pills were returned.

Another intermediary was found.

That attempt failed too.

Castro kept living, kept talking, kept embarrassing Washington.

Meanwhile, Bobby Kennedy’s war on the Mafia intensified.

He expanded the Justice Department’s organized crime section.

He forced the FBI, the IRS, and federal prosecutors to work together.

He went after Jimmy Hoffa, Sam Giancana, Santo Trafficante, Carlos Marcello.

He didn’t know—at least at first—that some of these men were technically assets of the CIA.

When he learned fragments of the truth, he was furious.

But by then, the machinery was already moving, and it didn’t stop for outrage.

The CIA’s secret alliance had created a nightmare.

Prosecutors couldn’t fully pursue mob bosses without risking exposure of assassination plots.

The FBI warned that the arrangement made the government vulnerable to underworld blackmail.

That warning proved prophetic.

As the poison plots failed, the CIA escalated.

Under operatives like William Harvey, a hard-drinking, hard-edged spy who despised Bobby Kennedy, the agency began dreaming up increasingly bizarre schemes.

Exploding cigars.

Toxic diving suits.

Chemical agents to make Castro’s beard fall out, hoping humiliation would destroy his image.

Substances meant to make him hallucinate during radio broadcasts.

None of it worked.

Castro survived them all.

By 1963, resentment was everywhere.

CIA operatives felt betrayed and constrained by the Kennedys.

Mobsters felt hunted after being promised protection.

Castro felt hunted by a superpower that couldn’t kill him.

Everyone involved had grudges, and grudges are dangerous things.

Then came November 22, 1963.

When John F.

Kennedy was shot in Dallas, shock rippled through the world—and panic through the intelligence community.

The Warren Commission was formed to investigate the assassination.

Thousands of witnesses were interviewed.

Mountains of evidence were examined.

But one crucial truth was withheld.

The CIA did not tell the commission that it had hired Mafia figures to assassinate Fidel Castro.

It didn’t tell them about poison pills, hotel meetings, or Johnny Roselli.

It didn’t tell them that men with motive, capability, and fury at the Kennedys had been in bed with U.S. intelligence.

Why?

Because revealing that truth would have detonated everything.

It would have exposed illegal assassination plots.

It would have revealed collaboration with criminals.

It would have shown that key suspects might have had government protection.

And it would have raised questions no one in power wanted asked.

The truth stayed buried until the 1970s, when the Church Committee began peeling back decades of intelligence abuses.

Johnny Roselli was called to testify.

He talked.

He confirmed the plots.

He named names.

And then he disappeared.

Weeks later, his body was found stuffed into a steel drum floating in Biscayne Bay, dismembered, executed in classic Mafia fashion.

Sam Giancana was killed too, shot repeatedly in his basement days before he was scheduled to testify.

Santo Trafficante alone survived, carrying his secrets to the grave.

By the time the CIA’s “Family Jewels” documents were released decades later, the outline was undeniable.

The agency had hired the Mafia.

It had lied about it.

It had hidden it from investigators.

What remained unanswered was whether that secret war had any direct connection to JFK’s murder.

No hard evidence proves it did.

But the damage was already done.

The alliance poisoned everything it touched.

It undermined the Justice Department.

It compromised investigations.

It fed conspiracy theories that still refuse to die.

Not because Americans are irrational, but because they eventually learned they had been lied to.

The tragedy of JFK’s secret war is not that the CIA tried to kill Castro and failed.

It’s that in doing so, it surrendered moral authority, blurred the line between law and crime, and crippled the nation’s ability to confront its own trauma honestly.

The Mafia didn’t need to kill a president to win.

It only needed the truth to stay hidden.

And for years, it did.

History isn’t just shaped by bullets and speeches.

Sometimes it’s shaped by envelopes slid across hotel tables, by poison that never reaches its target, by secrets kept too long.

JFK’s secret war wasn’t fought in jungles or missile silos.

It was fought in shadows, and the cost of those shadows still lingers.