The Shocking Collapse Of Cuba's Military & Ukraine's Deep Strikes

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**Mike Baker** (0:42)
It's Friday, the 26th of June. Welcome to The Presidents Daily Brief. I'm Mike Baker, your eyes and ears on the world stage. All right, let's get briefed. First up, the Trump administration is turning up to pressure on Cuba, while the communist regime, well, the communist regime vows to fight any potential military intervention. But new reporting reveals just how far Cuba's once feared armed forces have fallen since the Cold War.
Later in the show, Ukraine continues taking the fight deeper into Russia, striking key oil facilities as part of its long range drone campaign. The attacks are reportedly forcing Moscow to reposition air defenses around the capital and other high value sites. Plus, North Korea is entering a new era of naval power, commissioning its first destroyer capable of carrying nuclear armed missiles. And in today's Back of the Brief, Venezuela is reeling from its worst earthquakes in nearly six decades as rescue crews race to find survivors and the death toll continues to rise. We'll have the latest on the devastation and the ongoing rescue efforts. But first, today's PDB spotlight.
The Trump administration continues to turn up the pressure on Cuba with new sanctions, criminal indictments and an ongoing energy blockade. But what if that pressure were ever to become, well, kinetic? If the US found itself in a military confrontation with Havana, what kind of fight would it actually face? Well, according to new reporting from both The Wall Street Journal and CNN, the answer is somewhat more complicated than you might think. For most Americans, Cuba's military is almost an afterthought, considered a relic of the Cold War. During the height of the Cold War, Cuba possessed one of the most formidable militaries in the Western Hemisphere. Backed by billions of dollars in Soviet aid, the island fielded an active-duty force of more than 200,000 troops. It operated modern MiG fighter aircraft, advanced Soviet air defense systems, hundreds of tanks and armored vehicles, and a navy equipped with Soviet-built frigates. Unlike many militaries in Latin America, Cuba's armed forces back then also had something else, real combat experience. Throughout the 70s and 1980s, tens of thousands of Cuban troops deployed overseas in support of Soviet interests, fighting in places like Angola and Ethiopia. Cuban officers gained experience commanding large scale operations, while their troops fought alongside some of the Soviet Union's best equipped units. At the time, some analysts described Cuba as having a first world military in a third world country.
And then, almost overnight, everything changed. When the Soviet Union collapsed in 1991, Cuba didn't just lose an ally, it lost the economic engine that kept its military alive. The fuel shipments stopped, spare parts disappeared, maintenance contracts vanished, new aircraft and armored vehicles never arrived. Cuba entered what became known as the quote special period, an era of economic collapse that affected virtually every aspect of life on the island. And the military wasn't immune.
Fighter jets require constant maintenance, tanks need replacement parts, radar systems need trained technicians, warships require enormous amounts of fuel and upkeep. Without the Soviet Union, Cuba gradually found itself preserving equipment rather than replacing it. Year after year, another aircraft would become sidelined, another vehicle was cannibalized for spare parts, another ship remained tied to the pier because there simply wasn't enough fuel to put to sea. Today, analysts estimate Cuba's active-duty military numbers somewhere between 40,000 and 45,000 personnel. That's roughly one-fifth the size it was during the final years of the Cold War. Its air force, once among the most capable in Latin America, is believed to have only a handful of aircraft capable of flying. Its navy rarely ventures beyond coastal patrols. Much of its heavy equipment dates back to the 1970s and 1980s.
And perhaps nothing captures that transformation more vividly than a series of images recently released, not by American intelligence, but by Cuba's own government. One photograph shows a Soviet-designed anti-aircraft cannon being pulled down a rural road by a pair of oxen. It's the kind of scene you'd associate with the Crimean War of the late 19th century, not a modern times military just 90 miles from the coast of Florida. At first glance, it almost seems absurd, but that image actually reveals something important about how Cuba now thinks about war. Military analysts say Havana no longer plans to fight the US in a conventional conflict. It understands the imbalance is simply too great. Instead, Cuba has spent decades reshaping its doctrine around what it calls the, quote, war of all the people. The idea is relatively straightforward. If you can't defeat the world's most powerful military, make any invasion so difficult, so prolonged and so costly that your opponent begins questioning whether victory is worth the price. That means training local militias, dispersing weapons, preparing civilians, using guerrilla tactics instead of large armored formations, relying on small mobile units rather than expensive equipment that can't easily be replaced. In other words, Cuba's military strategy today isn't built around winning a conventional war. It's built around surviving one. And that brings us back to those remarkable photographs. It's tempting to laugh at the sight of oxen towing artillery or soldiers training with equipment that's older than they are. But that may be missing the point entirely. Those images weren't linked by accident. They were released by the Cuban government. And they appear designed to send a specific message. We know we're outmatched. We know we can't compete with the US, plane for plane or ship for ship. But if you come here, we'll fight with everything we've got. Now, that message has deep roots in Cuban history. Fidel Castro often invoked the ancient Spanish city of Numancia, whose defenders famously chose destruction over surrender to the Romans. It became a symbol of resistance that endured long after the Cold War ended. Whether that strategy would actually deter the US is another question entirely. But as tensions between Washington and Havana continue to rise, these images serve as a reminder that military strength isn't measured only by the sophistication of your weapons. Sometimes it's measured by what a country believes it's willing to endure once the shooting starts.