‘All options are on the table.” That was the refrain of the Venezuela policy in Donald Trump’s first term, when, from 2019 through 2020, I was his administration’s special representative for Venezuela following dictator Nicolás Maduro’s theft of the 2018 election. That was what I repeated endlessly to the press, in Spanish and in English, and it wasn’t false. The American president did have plenty of options, including military moves.

But the swashbuckling capture of Maduro in early January 2026 was not really on the table back then, nor was the gigantic flotilla the president assembled in the Caribbean. Trump had heard advice to do more—for example, from his one-time National Security Adviser John Bolton, whom he came to revile—and rejected it. Instead, we relied on rhetoric, diplomatic isolation, indictments, and economic sanctions. And all that failed.

Maduro & Co. didn’t care about our rhetoric and matched it with their own—a version of the ideological patter they had picked up from Fidel Castro and Radio Moscow. Nor did sanctions on Venezuela do the job, because the immiserated condition of their country didn’t matter to Maduro and his cronies as long as they had enough oil money and drug money around to bribe the military and reload their own accounts in Turkey, Qatar, and elsewhere. That 8 million of their countrymen (a fourth of the population) had to become refugees was not a problem for them either: It meant fewer mouths to feed and some dissidents gone. That, too, they had learned from Fidel Castro. Diplomatic isolation was a nuisance, of course, but it was not backed by any real action, and they were willing and able to live with criticism from the European Union and politicians in Washington.

Yes, indictments were handed down against Maduro in 2020, but such actions don’t tend to move officials who think you will never get your hands on them—as we Central American hands in the Reagan and first Bush administrations had discovered when the same action was taken against Panamanian dictator Manuel Noriega in 1988. He turned down a deal to quash the indictment against him if he would agree to leave power, and the Noriega regime ended only when America invaded in 1990, arrested him, tried and convicted him, and sent him to jail in Miami.

So why didn’t we do more during Trump’s first term? Why didn’t Trump take out Maduro in 2020 instead of 2025? The best answer, as usual with Trump, is “Who knows?” But let’s try.

For one thing, the institutions that would carry out more serious action were against it. Take the CIA. In my position as special representative, I dealt with officials on the agency’s Venezuela task force. Its goal pretty quickly became clear to me: to make sure that no one did anything much, and certainly that no one should expect the CIA to do anything. Floating ideas to them was like asking State Department lawyers whether something you planned to do was OK. You didn’t have to finish your sentence before they began shaking their heads. The answer was always no—or, for the CIA, what we used to call the “Arab no.” The answer was never “Are you kidding me” or “Drop dead,” but versions of “Hmm, we’ll take that back.” Or “Yeah, we’ll take a look at that.” Or “Interesting, but a little complicated.” It became obvious these people were less counterparts with the same goals as those of us tasked with getting Maduro out of office than they were case officers—only I was the case they were to handle. Later, for these fine examples of doing nothing, CIA officers were rewarded with promotions.

Why? The agency’s director, Gina Haspel, was opposed to serious action. The director at present, John Ratcliffe, gave different orders, and we have seen the results. CIA teams have been in Venezuela for months, providing the information the strike force would need.

It is also fair to say there was little enthusiasm at the Pentagon, and in any case, the forces permanently assigned to the U.S. Southern Command would never have been able to blockade Venezuelan oil or seize Maduro. SOUTHCOM was basically a headquarters with a total of just over 1,000 civilians and service members assigned to it. Had anyone suggested back then putting 15 or 20 percent of the U.S. Navy in the Caribbean, everyone would have thought that guy was crazy. Nor did we even contemplate a Hollywood-style snatch-and-grab, due to the size and complexity of such an operation—especially when Maduro’s security was protected by large numbers of Cuban guards.

So what changed was Donald Trump. But why? 

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One theory: By the time it became clear that the combination of sanctions, indictments, etc. was not going to work, it was too late in Trump’s first term to gin up a months-long ambitious military action without possibly affecting the election. This time, he acted in his first year, early in his term, and there is no next presidential election for him to think about. 

Another theory has to do with what happened when Trump ordered the killing of Qasem Soleimani, Iran’s leading terrorist, on January 3, 2020. If the attempt failed, and the assassination plan was subsequently leaked, there was time enough for the bad news to dissipate in the 10 months between that day and the 2020 election. But the attack worked, beautifully. So did the attack on the Iranian nuclear sites in 2025, which was executed flawlessly and without any U.S. casualties. Perhaps, as the French say, l’appétit vient en mangeant—appetite comes with eating. These two successes, five years apart, might have led the president to be open to even more complex military strikes. After all, the American attack on Iran came on June 22, and the Navy buildup in the Caribbean began in August—suggesting the president made his decision soon after the Iran strike. Trump clearly loves his role as commander in chief, loves the very clear successes these attacks have achieved, and loves the glory that (at least in his view) they bring him. Not one American killed, all objectives achieved; it looks great, and the Democrats who are carping look petty and unpatriotic. Bunch of spoilsports.

And then there’s the NSS theory, by which I mean that the president came to believe what was later written in the National Security Strategy released in November 2025. It declares in no uncertain terms that this is our hemisphere, as the administration keeps repeating, and we are not going to allow hostile foreign forces and governments to operate here. The NSS states that “we want a Hemisphere whose governments cooperate with us against narco-terrorists, cartels, and other transnational criminal organizations; we want a Hemisphere that remains free of hostile foreign incursion or ownership of key assets.”

Things looked and sounded different in the first term. I have a vivid memory of a National Security Council meeting on Venezuela. Everyone was there: the president, the vice president, the secretaries of state and defense, the CIA director and the director of national intelligence, the national security adviser, and the chairman of the Joint Chiefs. I cannot disclose any classified information about our Venezuela conversation, but at one point the secretary of defense (as the position was called in that ancient time) spoke about FONOPS, or freedom-of-navigation operations. In such an operation, the U.S. sends ships to some location, for example the South China Sea, to show that we have a right to be there and will enforce that right. The idea was to do the same in the Caribbean near Venezuela, sending some destroyers to sail by—

And then the president interrupted; to say he hated the way our new destroyers looked. He just hated the way they looked. As a boy, he had loved the TV documentary about World War II, Victory at Sea (as I had, and as had many of us who were boys in the 1950s), and he remembered the magnificent look of our old destroyers. These new ones were ugly, and it had to stop. Not another one of those ugly things could be built, he ordered. Not one more!

That subject animated him; the discussion of Venezuela did not. Ergo, moving a big part of our global fleet and then undertaking a hugely complex military operation to grab Maduro was simply not one of the options on the table back then. 

There’s another element worth mentioning: Trump’s view of the opposition. Maduro stole the 2018 election and had himself inaugurated again on January 5, 2019. Under the Venezuelan constitution, when the presidency is vacant, the speaker of the National Assembly fills in. The democratic opposition parties claimed the presidency was vacant because Maduro was illegitimate; the United States agreed and backed the speaker, Juan Guaidó, as interim president. With enough U.S. support, and sanctions, indictments, and the like, the regime would crumble and the opposition would take over. 

Guaidó visited Washington, and Trump pointed him out in the gallery at his State of the Union address in January 2020. “Here this evening is a very brave man who carries with him the hopes, dreams, and aspirations of all Venezuelans,” he said. “Joining us in the gallery is the true and legitimate president of Venezuela, Juan Guaidó. Mr. President, please take this message back to your homeland. Thank you, Mr. President. Great honor. Thank you very much. Please take this message back that all Americans are united with the Venezuelan people in their righteous struggle for freedom.”

But the regime didn’t crumble, and who was Trump going to blame? Surely not himself, so it must have been the fault of the opposition, whose leaders were too weak. That was the lesson learned; the brief romance ended. Maduro and his cronies were tough,  like Putin or Xi, the president must have concluded, and the Venezuelan opposition just ordinary politicians. Which was true: They were people who ran for office and made speeches and never picked up a gun.

So Trump has gone with a different approach this time, even going so far as to openly deprecate the Nobel Peace Prize–winning leader of the opposition, María Corina Machado, in his first press conference after the seizure of Maduro. Instead, he is doing business with the regime, including with the defense and interior minister, both of whom are under U.S. indictment as drug traffickers. That the opposition won a huge landslide in the 2024 presidential election, maintaining complete unity and organizing its voters under the worst possible and wholly unfair conditions, seems to be of no interest. Trump threw in his lot with them in 2019 to no good effect. He doesn’t want to do it again, it seems.

This time around, the people handling Venezuela in the first term are long gone, from Mike Pompeo (and me) at State, to Mike Pence and John Bolton at the White House, to other cabinet members who may have been enthusiasts of action. In 2026, Venezuela policy, whether made over dinner at Mar-a-Lago or in the Situation Room, is now part of the new emphasis on dominance in the Western Hemisphere, the new appetite for military risk and glory, and the new debate within the administration and the Republican Party over the true meaning of MAGA foreign policy. Venezuelans seem to be cast as spectators rather than participants. With three years left of Trump’s administration, the military spectacular of January 3 may prove to be the high point (and sole achievement) of the policy. Or it might lead in the end—by January 20, 2029—to a free and democratic Venezuela. Trump may lose interest. Or strike again. Who knows? As the saying goes: All options are on the table.

Photo: Chip Somodevilla/Getty Images

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