Cuba – A Look in the History Mirror
By: Obie Usategui
3/6/2026

As of late, you all may have heard headline news regarding President Trump’s plans to the end of the Castro regime in Cuba, this, in the aftermath of the recent takeover by the U.S. of Venezuela’s Communist dictatorship of Nicolás Maduro.

I am well-aware that, Cuba’s overthrow of the Castro Communist Revolution has not yet come to fruition. That said, however, it all points like it is not a matter of “if,” but “when,” and it is also pointing out to be like it is going to be sooner rather than later when this epic landmark finally takes place after waiting sixty-seven long years for it to happen.

I will preface the rest of my narrative today with a disclaimer that all my thoughts today assume and/or presume that, the fall of the Castro regime is, indeed, inevitable, a sure thing, based on what we all now know of Donald Trump, namely, this a man that does what he says. Promises made, promises kept. The “Cuban” matter for Trump is just a given, moreover considering the very favorable relationship that he has with his Cuban American, Secretary of State, Marco Rubio.

As a proud Cuban American that I have remained, despite the many legitimate reasons for letting my heritage slip away and letting it be usurped by another culture, much like what happened to many compatriots, I have, proudly stayed true to my heritage, to my lineage, to my legacy. Yes, I am sorry to say, many of those in my baby-boomers generation compatriots, at a point in time, disenfranchised themselves from our culture, some even tried to become more American than George Washington and Abraham Lincoln.

Some went as far as refusing to speak in their native Spanish language for fear of being identified as “Hispanics” – that culture they were trying hard to alienate themselves from. All the while, I am proud to say, while I left Cuba when I was just fourteen years old, Cuba never left me. I guess the best proof I have for this claim is, at a very early age in my life, I took my first Spanish guitar lesson back in the 1960’s with iconic Lily Batet Contreras, my mentor in Spanish guitar playing, that was the start of a lifetime of singing some of the most folkloric Cuban songs which became the main part of my repertoire. Proud to say, I have taken our music all around the world as I travelled extensively while working in the airline industry.

Anyways, today’s narrative deals with my very own thoughts on why it has taken sixty-seven years for the demise of a regime which only brought misery, gloom, desolation, and sadness to various generations of Cubans? As I look back into the mirror of Cuban history, it is exceedingly difficult for me to try and understand, why has it taken this long for the U.S. to do away with a political cancer that sits just ninety miles from its shores.

In trying to look for answers to this question, I could not help realizing that, since 1960, there have been twelve different U.S., presidents, 6 Republicans and 6 Democrats, so there is, if you will, equal guilt to throw around between the two main political Parties. You can really blame either Republicans or Democrats. You even had, among the presidents a Ronald Reagan, who, singlehandedly provoked the fall of the Soviet Union, so question is, whatever happened with Cuba that none of the presidents, including Reagan dared do what Donald Trump is about to do?

Again, as I look back in Cuba’s mirror over the past sixty-seven years, I guess the only answer that could make sense albeit not a justification nor a defense, but merely an objective perspective, has to do exclusively with a geopolitical analysis since Castro first came to power, back on January 1st, 1959. I think it is fair to say this was a whole different world than today’s world, thus conditions throughout all this time were not as ideal as they are today.

To begin with, back in the 1960’s, you could say we were at the height of the “Cold War”. Meaning that one of the principal actors in world supremacy was the Soviet Union – a Soviet Union quite different from a 2026 Russia. Back in the 1960’s the Soviet Union was Cuba’s main protégé. The dissolution of the Soviet Union in 1991 was a momentous change in the world’s geopolitical landscape. Back then, is fair to say, any attempts to eliminate Castro by the U.S. was looked upon as a threat to the Soviet Union and to their competition over world supremacy as proven to be the case during the Cuban missile crisis that followed.

To me, the failed Bay of Pigs invasion after John F. Kennedy betrayed us, sealed our destiny. It marked the beginning of a confrontation between the United States and the Soviet Union which culminated in the October 1962 missile crisis, the closest the Cold War ever came in escalating into a full-scale nuclear war – at the time an eminent and very real threat to mankind. Today, there is no more Soviet Union, and there is no more eminent nuclear threat. As a matter of fact, Russia’s protégé role of Cuba is no longer the case and Russia today is but a weakened nation that is already involved in a war with Ukraine that would prevent them from any considerations of aiding and abetting a Caribbean Island from the threats posed by a U.S. takeover of the island. So…there is your reason number one.

Other than the Soviet Union / Cuba / U.S. interrelatedness, it is fair to say that Cuba was of no particular interest to the U.S. and its former presidents over the past sixty-seven years. Here is an example of the point I am trying to make. Take Taiwan for example. Unlike Cuba, Taiwan, even though is a faraway island across the world, has a crucial strategic location, while being the first island chain anchoring a network of U.S. allies and partners from Japan to the Philippines, essential to the balance of power in the Indo-Pacific region of the world.

Again, unlike Taiwan, Cuba to the U.S. and its former presidents was of no particular interest. It was not of any economic importance. As far as the U.S. was concerned, in the aftermath of the Kennedy / Khrushchev missile crisis pact, Cuba posed no threat to the U.S. mainland, and to the U.S. The so-called U.S. embargo, a comprehensive economic, trade, and financial blockade was sufficient punishment with no real need to change the Castro administration. I personally, to this day, think that the U.S., utterly lost sight and/or pretended to lose sight of the fact that Cuba’s Castro’s government served as the main hub for the exportation of Communism all over Central and South America, including but not limited to nations such as Venezuela, Nicaragua, and other Latin-American nations. I think that the U.S., also totally missed or overlooked Cuba’s drug-trafficking role in the hemisphere.

As far as other of Cuba’s potential Communist protégés, i.e., The Peoples Republic of China, here again, China could not care less about this Caribbean Island. Whereas China has grown exponentially over the past sixty years, I think it is fair to say that their growth is more governed by economic prosperity than world dominance as they have realized that with leaders such as is Donald Trump they better keep a low profile, such as they have proven by not coming in Iran’s defense in the present “Operation Epic Fury.” Chinese know damn well what could happen to them if they rear their ugly head in conflicts between the U.S. and other nations around the world.

In closing, I should say thanks to Donald Trump, we have, definitely, a changing world for the better in our hands. Mind you, a world where democracy, capitalism, God, and family are all making a strong comeback. You may have noticed, till now, I have laid all blame for Cuba’s Communist regime lengthy control of power on the U.S. and still do. That said, however, I also contend that we, Cubans, as a people must also share in some of the guilt for Castro’s clan staying in power for over sixty-seven years. I am not exactly sure what we could have done as a people in overthrowing Castro during all these years. What I do know is that, for many reasons, we have never been as united in our cause as we should have been and, for that, we have only to blame ourselves and no one else.

One way or the other, like I said in one of my earlier essays on the subject, I know when it finally happens, when Trump finally ends the Castro regime, it will be a joyous, unprecedented day in our history, long overdue as it may have been. The joy of the moment will only be overcast by the sadness of knowing that, unlike our fellow-Venezuelan brothers and sisters, there will be a whole generation of Cubans that are no longer with us and will not be here to enjoy the moment that all of them longed for while they were alive. This narrative is dedicated to them. To our fathers, mothers and many other relatives that passed away and cannot experience the joy of this long-overdue redemption day. Viva Cuba Libre!