“John and Robert Kennedy knew what they were doing. They waged a vicious war against Fidel Castro—a war someone had to lose.”       

And the loser turned out to be John F. Kennedy. 

So writes investigative reporter Gus Russo in Live By the Sword: The Secret War Against Castro and the Death of JFK, published in 1998.

In what is almost certainly the definitive account of the assassination of President John F. Kennedy, Russo reaches some startling—but highly documented—conclusions:

• Lee Harvey Oswald assassinated Kennedy.
• He did it alone.
• Oswald, a former Marine, was a committed Marxist—whose hero was Castro.
• The CIA’s ongoing campaign to overthrow and/or assassinate Castro was an open secret throughout the Gulf.
• Oswald visited New Orleans in the spring of 1963.
• There he learned that Castro was in the crosshairs of the CIA.
• Oswald told his Russian-born wife, Marina: “Fidel Castro needs defenders. I’m going to join his army of volunteers.”
• Jack Ruby, a Dallas nightclub owner, murdered Oswald because he was distraught over Kennedy’s death.
• Ruby was not part of a Mafia conspiracy to silence Oswald.
• Skeptics of the Warren Commission—which concluded that Oswald had acted alone—asked the wrong question: “Who killed Kennedy?”
• They should have asked: “Why was he killed?”
• The answer–according to Russo: “The Kennedys’ relentless pursuit of Castro and Cuba backfired in tragedy on that terrible day in November, 1963.”

Another book well worth reading about America’s Cuban obsession during the early 1960s is American Tabloid, by James Ellroy.

Although a novel, it vividly captures the atmosphere of intrigue, danger and sleaziness that permeated that era in a way that dry, historical documents never can.

“The 50’s are finished,” reads its paperback dust jacket. “Zealous young lawyer Robert Kennedy has a red-hot jones to nail Jimmy Hoffa. JFK has his eyes on the Oval Office.

“J. Edgar Hoover is swooping down on the Red Menace. Howard Hughes is dodging subpoenas and digging up Kennedy dirt. And Castro is mopping up the bloody aftermath of his new Communist nation….

“Mob bosses, politicos, snitches, psychos, fall guys and femmes fatale. They’re mixing up a Molotov cocktail guaranteed to end the country’s innocence with a bang.”

Among the legacies of America’s twisted romance with anti-Castro Cubans:

• Following the JFK assassination, there was a coverup.
• Its purposes: To protect the reputation of the United States government—and that of its newly-martyred President.
• Thus, the CIA and FBI concealed the CIA-Mafia assassination plots from the Warren Commission assigned to investigate Kennedy’s murder.
• Other government officials participating in the coverup included Attorney General Robert F. Kennedy and President Lyndon B. Johnson.
• Ironically, this secrecy ignited the widespread—and false—belief that the President had died at the hands of a government conspiracy.
• Robert Kennedy feared that his relentless pursuit of Castro might have led Castro to “take out” JFK first.
• Fearing his own assassination if he continued Kennedy’s efforts to murder Castro, President Johnson ordered the CIA to halt its campaign to overthrow and/or assassinate the Cuban leader.
• The huge Cuban community throughout Florida—and especially Miami—continues to exert a blackmailing influence on American politics.
• Right-wing politicians from Richard Nixon to Donald Trump have reaped electoral rewards by catering to the demands of this hate-obsessed voting block.
• These Cuban ex-patriots hope that the United States will launch a full-scale military invasion of the island to remove Castro.

The Cuban Missile Crisis was the deadliest moment of the Cold War, when the world stood only minutes away from nuclear Armageddon.

That crisis stemmed from America’s twisted obsession with Cuba, an obsession that continues today.

Sixty-three years after that crisis, the world wonders: Could nuclear war erupt over Cuba? 

And, once again, that decision lies in the hands of two men—Vladimir Putin and Donald Trump—out of a world population of more than eight billion. 

The Soviet Union began aiding Cuba in early 1960, shortly after the 1959 revolution, with a formal trade agreement signed in February 1960. This deal involved exchanging Soviet oil for Cuban sugar. The relationship quickly expanded to include extensive economic subsidies and military support that continued through 1990.

On January 29, 2026, President Donald Trump threatened to impose huge tariffs on goods from any country that supplied oil to Cuba. Declaring a national emergency, he aims to cripple the island’s energy supply.

On February 18, Russian President Vladimir Putin met with Cuban Foreign Minister Bruno Rodriguez in Moscow and reaffirmed his support for the island nation. Putin reminded his guest that Russia “will not accept anything of the sort” when discussing the sanctions against the country. 

“I do believe I’ll be having the honor of taking Cuba. That’s a big honor. Taking Cuba in some form,” Trump said on March 16. “Whether I free it, take it, I think I could do anything I want with it, if you want to know the truth. They are a very weakened nation right now.”

Nikita Khrushchev, facing a choice of humiliation or Armageddon during the Cuban Missile Crisis, chose humiliation—so his country could live another day. 

It remains to be seen if Vladimir Putin is willing to make the same decision.