I was literally born into the Cuban Revolution. My mother was working in Venezuela for the Rockefeller Foundation, my parents met and married in Caracas, and any and all travel back and forth to the United States took place through the Pan Am hub in Havana. The Cuban Revolution began in 1953, with Fidel Castro’s attack on the Moncada Barracks on July 26, 1953. By my birth math, I was three months in utero at the time and while the Batista, Myer Lansky and Lucky Luciano were still playing their Havana Nocturne when I first transited through Havana on my way home from Fort Lauderdale at age one month in early 1954, Fidel was busy fomenting dissent until he overcame Batista on January 1, 1959. Years later, in college, I wrote a senior thesis on the Cuban Revolution that I called “Donna Azucar” about all those events. It was a few months after the actual takeover that we last transited through Havana. I have told the story of my sister Kathy having a hissy fit that had my mother, sisters and I running across the tarmac at Havana Airport with a “Fidelista” carrying a Russian-built AK47 yelling at us to stop or be shot. Lots of drama for a trinket doll, but a great family story.
I have no further connection to Cuba other than as an American school kid living in the Midwest in October, 1962 when we collectively experienced the famous 13 days of tension with Russia. On October 16th, President Kennedy was informed that U.S. spy planes had discovered Soviet nuclear missile installations being built in Cuba. On October 22nd, Kennedy publicly announced the crisis and declared a naval blockade (“quarantine”) of Cuba. On October 27th, the most dangerous day, sometimes called “Black Saturday,” an American U-2 spy plane was shot down over Cuba and the risk of war was at its peak. And then, on October 28th, Soviet leader Nikita Khrushchev agreed to dismantle the missiles in exchange for a U.S. pledge not to invade Cuba, and a secret agreement to remove American Jupiter missiles from Turkey. That incident is widely regarded as the closest the world ever came to nuclear war during the Cold War.
And here we are today in 2026, a full 64 years later, still playing the same game with the two dominant actors, America and Russia, and the monkey in the middle appearing to be Cuba…and yet the real football being kicked around being Iran. What’s changed? The U.S. economy is roughly 12x larger than Russia’s in nominal terms today, compared to 2–3x in 1962. The U.S. remains the world’s largest economy, and has vastly outpaced Russia, especially if you adjust for the fact that defense and security spending accounted for approximately 40% of Russia’s total government spending in 2025, exceeding combined spending on education, healthcare, social policy, and the national economy. Defense spending as a share of the U.S. federal budget was nearly 30% at the end of the Cold War but now sits at around 10%. But that’s now starting to change. The trajectory of U.S. defense and security spending under Trump is steeply upward. The base defense budget is approximately $850–892 billion, roughly flat in real terms from the prior year. Notably, the Pentagon is currently operating on its first-ever full-year continuing resolution, which nearly caps defense spending at the FY2024 level. But the “One Big Beautiful Bill” pushed total planned defense spending past $1 trillion for FY2026, including a $156.2 billion increase on top of the Pentagon’s base request of approximately $848 billion. The FY2026 budget represents a 13% increase in defense spending. And Trump has announced that he wants the FY2027 defense budget raised to $1.5 trillion, which would increase defense spending by $5 trillion through 2035 and add $5.8 trillion to the national debt when interest is included. If enacted, this would be the largest single-year increase in defense spending since the Korean War, dwarfing the increases during the War on Terror and Reagan’s buildup in the 1980s. Trump came in cutting defense spending with DOGE, but then pivoted to massive increases, reflecting the ongoing tug-of-war between fiscal hawks (Musk/Vought) and defense hawks (Wicker, Hegseth). And these numbers do NOT yet reflect the events of the Iran War which are underway and will clearly boost the numbers further just for replacement of munitions if nothing more. If, news alert, there is now an added Pentagon ask for an extra $200 billion to support the Iran War that isn’t really a war…yet. Is it any wonder that MAGA is fracturing over this Iran War issue?
Meanwhile, back in Cuba at a recent news conference, Trump said: “I do believe I’ll have the honor of taking Cuba.” It’s now rumored that I he administration was in talks with Cuban officials to oust President Miguel Diaz-Canel from power but leave the country’s repressive regime in place. It sounds like Trump is contemplating a Cuban version of what he did in Venezuela… and then Iran (remove the leader)… only this time without the use of military force. Just send Cuban descendant Secretary of State Marco Rubio into Havana with his hands waiving in the air and a few bucks sticking out of his back pocket and get the country onside finally, right? Wait a minute…that sounds a lot like the tactics that Myer Lansky tried to use in 1959…
I wonder what Russia is tanking about all of this? While I’m sure the optics of Cuba coming over to the dark side after 66 years does not thrill Moscow, the reality of proximity in global conflict is mostly an antiquated notion. You no longer need to be 90 miles away to reign havoc down upon the U.S.. All you need is a computer hacker or a very cheap drone. So let’s face it, Cuba has far less strategic value to Russia than it did in 1962. Well…that’s not entirely true. There is Ukraine and there is Taiwan. What do I mean by that? Trump bullying or squeezing or disrupting Cuba is good for Moscow’s ongoing efforts in Ukraine because it gives Putin reason to shrug and say, “What is difference between Zelensky and Diaz-Canel?” And it also gives Xi the opportunity to set up his move on Taiwan in total consistency with the Trump regional hegemony program…you take Cuba, Russia takes Ukraine and China takes Taiwan. We might as well take out our game boards of Risk and figure out who has the rights to Iran in all of this.
The truth is that this is a very active and evolving situation in Cuba that is tied to the ongoing US-Israeli military conflict with Iran that began on February 28, 2026. Instead of Russia putting missiles in Cuba, it has been busy helping Iran with intelligence & targeting data, providing Iran with intelligence about the locations and movements of American troops, ships, and aircraft. Much of the intelligence shared has been imagery from Moscow’s sophisticated satellite network. Russia’s overhead surveillance network, including the Kanopus-V satellite transferred to Iranian operational use under the name “Khayyam,” provides Tehran with round-the-clock optical and radar imagery, giving Iran a precision-strike capability it could not achieve on its own. While we get drone advise from Ukraine, Russia has been sharing advanced drone tactics drawn from its war in Ukraine to help Iran hit US and Gulf nation targets. Western intelligence describes the assistance as evolving from general targeting support to specific tactical advice on drone strike strategies. In January 2025, Russia and Iran signed a comprehensive strategic partnership treaty covering trade, military cooperation, science, and education, deepening defense and intelligence coordination. It’s funny how some alliances bear up under pressure when mutual respect is shown, whereas others splinter and fall away when asked to do little things like help defang the Strait of Hormuz.
Unlike JFK’s indignation at the thought of Russian missiles in Cuba, when confronted about Russia’s assistance, Trump conceded he believes Russia “might be helping them a little bit,” but essentially gave Moscow a pass, comparing it to US assistance to Ukraine — saying “they do it and we do it.” JFK is rolling over in his grave while Putin snickers himself into hysteria. After all, Ukraine is a victim of unprovoked aggression. Russia invaded Ukraine, a sovereign nation, in 2022. US aid to Ukraine is helping a country defend its own territory against an invader. Iran, by contrast, is engaged in a conflict with the US and Israel, making Russian assistance to Iran more directly oppositional to American forces and interests. But wait…I guess Putin would say that he is simply helping poor little old Iran defend itself against big bad American and nasty little Israel. US troops are at risk from Russian intelligence…but then so are Russian troops in Ukraine. Like with Turkish missiles and Cuban missiles in 1962, it all boils down to the fact that Russian targeting intelligence may be directly enabling attacks that kill Americans. Last time I checked, that’s a justification for a defensive action, and isn’t that what a President is charged with defending?
It’s all very confusing, isn’t it? Back in 1962 we picked once fight at a time and stuck to our guns. Today we are doing neither. We attack Venezuela and Colombia, we position ourselves in Ecuador, we threaten Canada, Greenland/Denmark, we fuck up Gaza and now Iran, all while diddling with Russia and China when everyone knows they are the only playground bullies that can match us. I think I will go cover my head and hide under my desk like I was taught to do in 1962.