Will Trump Complete JFK's Goal of a Free Cuba?

[Benjamin Cole]

There is little doubt that President JFK, and brother RFK, were dreadnought in their intent to liberate Cuba from communism and Castro. Indeed, so much so that the Kennedy brothers abided by a few assassination attempts of Fidel.

To which Castro publicly responded in September of 1963 that assassinations could go both ways. Two months after Castro's not-so-veiled threat, JFK was dead. Castro's G2 had deeply penetrated Cuban exile groups, and thus parts of US intel services. 

See JFK's speech to the Orange Bowl Miami Dec. 29 1962, if you have any doubts about JFK felt about Cuba: https://www.youtube.com/watch?v=PxVl0x49zwA

JFK in his own words in Miami, and draw your own conclusions. JFK remains the best public speaker of the postwar era, and this presentation, to a packed Orange Bowl, is another gem.

In one of the more curious twists in history, the garish President Donald Trump, a far different character from JFK, may finally execute on JFK's dream of a Free Cuba. Secy of State Marco Rubio, a Cubano who speaks flawless Spanish, is apparently in the lead.

May it be so. The communist government in Havana is the usual thug-state excrement: https://www.hrw.org/world-report/2026/country-chapters/cuba

Trump has but few redeeming features, but he seems willing to take on ghouls in Havana, Caracas and Tehran.

I think JFK, in this regard, would have done the same, although likely much more smoothly.

[Michael Capasse]

There is little doubt that President JFK, and brother RFK, were dreadnought in their intent to liberate Cuba from communism and Castro. Indeed, so much so that the Kennedy brothers abided by a few assassination attempts of Fidel.

To which Castro publicly responded in September of 1963 that assassinations could go both ways. Two months after Castro's not-so-veiled threat, JFK was dead. Castro's G2 had deeply penetrated Cuban exile groups, and thus parts of US intel services. 

See JFK's speech to the Orange Bowl Miami Dec. 29 1962, if you have any doubts about JFK felt about Cuba: https://www.youtube.com/watch?v=PxVl0x49zwA

JFK in his own words in Miami, and draw your own conclusions. JFK remains the best public speaker of the postwar era, and this presentation, to a packed Orange Bowl, is another gem.

In one of the more curious twists in history, the garish President Donald Trump, a far different character from JFK, may finally execute on JFK's dream of a Free Cuba. Secy of State Marco Rubio, a Cubano who speaks flawless Spanish, is apparently in the lead.

May it be so. The communist government in Havana is the usual thug-state excrement: https://www.hrw.org/world-report/2026/country-chapters/cuba

Trump has but few redeeming features, but he seems willing to take on ghouls in Havana, Caracas and Tehran.

I think JFK, in this regard, would have done the same, although likely much more smoothly.

If he is, the method cruel and inhumane.

[John Corbett]

If he is, the method cruel and inhuman.

This brings up an interesting dilemma for the US. One of the concessions we made to the Soviet Union as part of the agreement to end the Cuban Missile Crisis was that we would not invade Cuba then or in the future. Since the Soviet Union no longer exists, is that agreement still binding, and would our attempt to topple the regime through economic pressure violate the provisions of that agreement. I guess we'd have to look at the fine print.

[Michael Capasse]

This brings up an interesting dilemma for the US. One of the concessions we made to the Soviet Union as part of the agreement to end the Cuban Missile Crisis was that we would not invade Cuba then or in the future. Since the Soviet Union no longer exists, is that agreement still binding, and would our attempt to topple the regime through economic pressure violate the provisions of that agreement. I guess we'd have to look at the fine print.

Mexico is sending aid.  Russia is sending oil. China is sending rice.
we suck.

[John Corbett]

Mexico is sending aid.  Russia is sending oil. China is sending rice.
we suck.

Every dollar Russian spends to prop up the Cuban regime is one more dollar they can't spend on the war in Ukraine, so there is some benefit there. Eventually Russia will come to the same conclusion that the Soviet Union did in Afghanistan. They can't afford to keep pouring money into a bottomless pit and will eventual decide to cease hostilities. I truly believe they are continuing the Ukraine war for Putin to save face. If he were to pass on, I think his successors would find a graceful exit strategy very quickly.

[Michael Capasse]

Every dollar Russian spends to prop up the Cuban regime is one more dollar they can't spend on the war in Ukraine, so there is some benefit there. Eventually Russia will come to the same conclusion that the Soviet Union did in Afghanistan. They can't afford to keep pouring money into a bottomless pit and will eventual decide to cease hostilities. I truly believe they are continuing the Ukraine war for Putin to save face. If he were to pass on, I think his successors would find a graceful exit strategy very quickly.

...as people senselessly die in Cuba.

[Tom Graves]

This brings up an interesting dilemma for the US. One of the concessions we made to the Soviet Union as part of the agreement to end the Cuban Missile Crisis was that we would not invade Cuba then or in the future. Since the Soviet Union no longer exists, is that agreement still binding, and would our attempt to topple the regime through economic pressure violate the provisions of that agreement. I guess we'd have to look at the fine print.

Some people (James Angleton and true defector Anatoly Golitsyn included) believed that the Cuban Missile Crisis was planned-in-advance by the Kremlin to be "resolved in America's favor" so that JFK would abandon the Monroe Doctrine.

If true, it would mean that GRU Col. Oleg Penkovsky, "The Spy Who Saved the World" by telling JFK about the specifications of the nuclear-tipped missiles in Cuba (specifically that it took a long time to get them ready to fire) was actually working for the KGB at that point.

We do know from the "Zepp Incident" (look it up) that Penkovsky was betrayed by a mole in the CIA or in British Intelligence within two weeks of his April 1961 recruitment by MI6 and the CIA, and that, in the interest of "source protection," he was ostensibly allowed to continue spying for them until October 1962 when, due to "superior KGB surveillance," he was arrested in Moscow.