The Last War of the 20th Century: Why Trump’s Venezuela Raid Was Never a Surprise
Donald Trump is far from the first U.S. president to set expansionist sights on Latin America. Over the past century, at least a dozen of his predecessors operated under the same dangerous assumption: that democracy and profitable access to the region’s resources were just one successful coup away. But the brand of imperial ambition Trump unleashed with his weekend raid on Venezuela is both a throwback to America’s oldest interventionist habits and uniquely tied to his own chaotic, self-serving politics—and it shows no signs of fading any time soon.
Within hours of U.S. special forces’ dramatic seizure of Venezuelan leader Nicolás Maduro, Trump’s public justification for the operation shifted dramatically. What started as vague rhetoric about advancing democracy and rooting out narcotics quickly gave way to open talk of controlling Venezuela’s massive untapped oil reserves. “We’re in charge,” Trump told reporters. “We’re going to run everything, we’re going to go in and fix it.” Even before Maduro made his first appearance in a New York City courtroom on Monday, Trump was already celebrating what he’s dubbed the “Donroe Doctrine” during a Sunday press gaggle on Air Force One, where he explicitly issued threats to six other nations—from Colombia and Cuba to Mexico and even Denmark’s autonomous territory Greenland.
While Trump’s actions in Venezuela—illegal under both international and U.S. law, carried out without any consultation with Congress—have pushed the U.S. into what feels like a dangerous, destabilizing new chapter of his authoritarian regime, it’s critical to situate this moment in its proper historical and personal context. When you look at the long history of U.S. intervention in the region, and more importantly, at how Trump thinks and operates, trapped in the ideological mindset of 1980s America, it becomes clear that Trump is embarking on what future historians may well label the final war of the 20th century. In fact, three core truths help explain how we arrived at this shocking point just days into the new year—truths that reveal this moment, for all its surprise, was entirely predictable:
1. The U.S. excels at coups, but fails catastrophically at everything that comes after
For a century, two defining features have shaped every U.S. interference in Latin America: quick, easy tactical military success, and catastrophic long-term strategic failure. These patterns are woven deep into the core of American political culture. Take E. Howard Hunt, for example: long before he was indicted for his role in the Watergate break-in and meddling in the 1972 presidential election, Hunt built his career as one of the CIA’s most prolific government overthrow specialists.
In the early 1950s, the powerful U.S.-based United Fruit Company grew alarmed at land reform plans pushed by Guatemala’s democratically elected Jacobo Árbenz, and convinced both the Truman and Eisenhower administrations that the new Central American leader leaned toward communism. The CIA, founded just a few years earlier in 1947, was still new to the regime change game in the Americas—but the U.S. was not. Long before the 1950s, the U.S. had occupied Nicaragua on and off between 1912 and 1933, invaded and occupied Haiti from 1915 to 1934, and held Cuba from 1906 to 1909, then again from 1917 to 1922, all to protect U.S.-owned sugar plantations.
Hunt, a mid-tier CIA spy stationed in Mexico City who had helped recruit a young William F. Buckley Jr. to the agency’s orbit, got a massive career boost from helping orchestrate Árbenz’s ouster. “What we wanted to do was to have a terror campaign to terrify Arbenz particularly, to terrify his troops,” Hunt recalled decades later. The 1954 Guatemalan coup was one of the CIA’s few successful regime change operations of that decade, so Hunt was a natural pick for the agency’s planning of the Bay of Pigs invasion.
A key, ultimately fatal, difference from prior 20th century interventions came with Bay of Pigs: to overthrow Fidel Castro’s government, the Kennedy administration relied not on U.S. Marines, but on a force of Cuban exiles. Hunt was put in charge of assembling a U.S.-friendly provisional government that would take power once the CIA-trained invasion force ousted Castro. The invasion, launched just weeks after John F. Kennedy took office, was a spectacular failure. When promised U.S. air support never arrived, more than 100 exiled fighters were killed on the beaches, and 1,200 more were captured within days, with hundreds more executed after surrender.
The Bay of Pigs fiasco did nothing to curb the CIA’s appetite for overthrowing governments across Central and South America. In 1961, the agency supplied weapons to assassinate the leader of the Dominican Republic. That same year, it helped back a coup in Ecuador—then when the new leader turned out to be even less friendly to U.S. interests than the ousted government, it backed a different military junta in a second 1963 coup.
In the decades that followed, the CIA backed more coups—in Brazil (1964) and Chile (1973), most infamously—and supported armed uprisings and right-wing rebel groups across the region (a pattern that culminated in the Iran-Contra scandal of the 1980s). Most U.S. administrations wanted to go even further than they did: Ronald Reagan’s secretary of state Alexander Haig famously pushed to invade Cuba, telling Reagan, “You just give me the word. I’ll turn that fucking island into a parking lot.”
In nearly every case of U.S. intervention across the Western Hemisphere, the aftermath of U.S. meddling was far worse than the status quo it replaced. Chile’s democratically elected socialist leader Salvador Allende was replaced by Augusto Pinochet’s brutal 17-year military dictatorship, for example. (That pattern holds for 21st century interventions too, from Iraq to Afghanistan.) After the U.S. gave tacit backing to Argentina’s 1976 coup that ousted Isabel Perón, a brutal military junta ruled for decades, committing atrocities like dumping dissident citizens from helicopters into the Atlantic Ocean.
Decades of U.S. military training helped cement that instability and authoritarian rule across the region. The U.S. Defense Department trained tens of thousands of Latin American military, intelligence, and law enforcement officers at the infamous School of the Americas in Georgia. A Duke University researcher’s investigation found that many of these alumni went on to become “dictators, death squad operatives, and assassins”—including Manuel Noriega, Bolivian dictator Hugo Banzer Suárez, Haitian dictator Raoul Cedras, Pinochet’s top secret police chief, and even the Venezuelan general who served as Maduro’s defense minister before this weekend’s raid, part of what the researcher dubbed the school’s “Hall of Shame.”
For decades, U.S. presidents justified these interventions and their support for brutal dictators through the lens of the Cold War, arguing that backing authoritarian regimes was preferable to letting them fall to communism. The ironic twist here is that the very ease of U.S. tactical victory—how quickly the U.S. military and intelligence community can depose an unwanted leader—makes these interventions look far more appealing to presidents than they deserve, from Eisenhower to Reagan to Trump. You can almost always win in the short term: depose, overthrow, or kidnap the sitting leader. But the long term is always a dangerous, unpredictable gamble.
And the unintended long-term consequences of these interventions have rippled through U.S. domestic politics for decades, shaping modern American politics in ways most Americans don’t recognize.
Some links are obvious: it was during Bay of Pigs planning that Hunt met the four Cuban exiles he would later recruit to break into the Watergate Hotel in 1972. Other connections are less visible: most notably, U.S. meddling in Honduras, Guatemala, and El Salvador—the so-called Northern Triangle—unleashed waves of instability that drove millions of migrants north to the U.S. border over the past decade. That migration surge stoked nativist fears across the U.S., and directly helped power Trump’s first 2016 presidential victory and his 2024 return to the White House. Many of these migrants were pushed north by climate change and deforestation that destroyed small farms and collapsed local economies; much of that destabilizing deforestation in places like Guatemala happened after military forces burned highland regions to root out rebel hideouts. As Jonathan Blitzer documents in his award-winning book Everyone Who Is Gone Is Here, which examines U.S.-Latin American migration, after the 1980s Salvadoran civil war—a conflict Reagan called “the front line of the battle that is really aimed … at us”—more than a quarter of El Salvador’s population ended up resettling as refugees in the United States.
2. Donald Trump has no endgame plan for Venezuela
Back in November, as the U.S. military carried out a series of lethal strikes on what it labeled drug-smuggling boats off Latin America—strikes that killed more than 100 people and violate nearly every standard of international law—I interviewed former Ambassador John Bolton at the Texas Tribune Festival. Bolton, the hawkish neocon who served as Trump’s longest-serving first-term national security adviser, has pushed for regime change in Venezuela for decades, and worked during Trump’s first term to support opposition efforts to oust Maduro. He told me bluntly: “I think that our failure to overthrow Maduro in the first term was our greatest failure.” Many of those first-term efforts were shockingly clumsy and uncoordinated, as a WIRED investigation by Zach Dorfman later exposed.
Even so, Bolton said he has been stunned by how little groundwork Trump laid for the recent Maduro raid over the past several months. The earlier boat strikes were carried out without any effort to build bipartisan support in Congress, or even to deepen partnerships with Venezuela’s domestic opposition. Over the weekend, Trump casually dismissed leading opposition figure María Corina Machado—who won the Nobel Peace Prize last fall, and according to The Washington Post, was sidelined specifically because of that achievement. “There’s just no comprehension, I think, of what it takes to replace the Maduro regime,” Bolton told me.
The core problem, Bolton explained, is that Trump never thinks beyond the next immediate step. The veteran Washington insider, who was a key architect of the 2003 Iraq War, said the most baffling part of working with Trump in the White House was that he has no consistent ideological worldview or traditional policy positions. Every decision is transactional, temporary, and shaped by what benefits him in the moment.
“He doesn’t do grand strategy,” Bolton told me. “It is very hard for people to understand. It was very hard for me to understand, because you think in government that’s what it’s about—policy is what you do. That's not what Donald Trump does. Therefore, when people talk about a Trump doctrine in international affairs, it’s a complete fantasy to think that there’s any coherence to it at all. It’s all through the prism of what benefits Donald Trump … He wanted to do what he wanted to do.”
Trump frames every decision around winning the next 24-hour news cycle, and rarely thinks any further ahead. The fact that there is no obvious plan for what comes next in Venezuela—for today, this week, next month—is not an accident. That lack of planning is a core feature of Trump’s approach to governing, not an accidental bug.
3. This conflict, no matter how it unfolds, is rooted in the past, not the future
Some political analysts have argued that Trump’s worldview is frozen in the 1980s and early 1990s—his formative years as a New York real estate tycoon during the booming Reagan era, which cemented his views on politics, business, success (think gilded gold everything), and policy (his longstanding support for protectionist tariffs). Even his iconic “Make America Great Again” slogan was originally used by Ronald Reagan.
That 1980s-trapped mindset is why the operation to capture Maduro and topple his government makes the most sense when you stop framing it as a 21st century conflict, and see it for what it is: a retro, nostalgic intervention, the last war of the 20th century.
We know what 21st century warfare looks like: drones are revolutionizing battlefields in Ukraine, and the U.S. military is retooling to operate nimbly in the Pacific ahead of a potential Chinese invasion of Taiwan. The Venezuelan operation, codenamed Absolute Resolve, which killed dozens of people on the ground, has already drawn widespread comparisons to the 1989 U.S. invasion of Panama, Operation Just Cause, which captured dictator Manuel Noriega. Like Maduro, Noriega—who was backed by the CIA before the U.S. turned against him—was brought to the U.S. to stand trial. His prosecution was led by Robert Mueller and Bill Barr, who were top officials in George H.W. Bush’s Department of Justice at the time.
But the world has changed dramatically since 1989, and Trump has failed to think through what comes next, leading to a deep irony: the U.S. went to war over Venezuelan oil at a moment when it’s not clear any major power actually needs that oil in the long run. Stuck in his 1980s mindset, Trump still champions gas-guzzling cars, pampers the coal industry, and rolled back U.S. government support for solar energy, even as the rest of the world moves rapidly away from fossil fuels. Renewable energy has grown by nearly 30 percent annually in recent years, and in the first half of 2025, renewables produced more energy globally than coal for the first time in history. China is scaling up renewables faster than any other nation: in 2025 alone, it added roughly 360 gigawatts of new solar and wind capacity—more than the entire existing solar and wind capacity of the United States—and is on track to cut its carbon emissions even as its economy continues to grow. Global energy prices have fallen so sharply that Australia announced last November that all residents will get three free hours of electricity every day starting this year.
Invading a country for its oil in 2026 will one day seem just as anachronistic as the 19th century U.S. push to seize dozens of small islands rich in bird guano, a critical ingredient for 19th century agricultural fertilizer. Yet history shows that empires rise and fall around what modern gamers would call “side quests,” small expeditions that lay the groundwork for larger expansion. As Daniel Immerwahr documents in his book How to Hide an Empire, the campaign to claim guano-covered islands around the world established the first legal framework for the U.S. to expand globally beyond the North American continent. Within a few decades, the U.S. was regularly invading Latin American nations to advance its interests.
For Trump, who only cares about short-term gains, controlling Venezuelan oil today still spells massive profit. What should worry Americans and people around the world is that Trump has been remarkably open about what he wants in his second term. During his first term, many pundits argued you should take Trump “seriously but not literally”; the defining truth of his second term is that the world needs to take him both seriously and literally. In that context, when the podcaster wife of top Trump aide Stephen Miller posted a photo of Greenland covered in the U.S. flag’s red, white, and blue on X, it should be read less as a joke and more as a highest-alert warning for Europe.
After all, Greenland and Venezuela share at least one troubling common trait: both hold massive natural reserves that Trump’s circle of oligarchs and allies want to exploit for profit. It’s been more than 150 years, since Andrew Johnson purchased Alaska, that any U.S. president has set his expansionist sights north. But Trump’s imperial appetite is clearly larger than that of his predecessors, and it won’t be satisfied by just repeating the 20th century foreign policy mistakes of past presidents.
For an administration that is building its legacy around tearing down the existing global order to create short-term profit for a small inner circle of Trump family members, political allies, and business cronies—a dynamic WIRED labeled “the enshittification of American power” last summer—Venezuela’s oil and Greenland’s rare earth minerals are more alike than different. And the fossil fuel and tech billionaires coveting these resources have more in common with the 20th century United Fruit Company and sugar barons than they would care to admit.
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