Above all, de la Espriella is more or less Colombia’s answer to Argentina’s Right-wing populist President Javier Milei: bombastic, cartoonishly subservient to US power, wont to break but not to build. His victory is a testament to Colombian progressives’ folly in adopting the climate, security, and identity politics of the Western Left.

Much like President Trump, de la Espriella fits the Right-wing archetype of the outsider businessman, complete with allegedly dubious deals and flamboyant self-promotion. In the Colombian’s case, the millions came from his legal firm and his extracurriculars include recording music videos and shamelessly promoting self-branded luxury goods on his eponymous podcast.

De la Espriella has been derided as el abogado de la mafia, “the mob’s attorney,” for representing clients like Colombian narco-paramilitary warlord Salvatore Mancuso and Colombia’s former President Álvaro Uribe (2002 – 2010). The most consequential is Uribe, who is alleged to have run death camps with Mancuso’s United Self Defense Forces of Colombia, racking up thousands of civilian casualties while conducting war against FARC, the Left-wing guerillas-cum-drug dealers. De la Espriella previously made the unrealistic promise to nominate Uribe as his vice president. For his part Mancuso, who served time in the United States for drug trafficking, claimed in 2025 that he and de la Espriella were childhood friends.

As an attorney, de la Espriella also represented Colombian-Venezuelan businessman Alex Saab between 2014 and 2019, long after the latter’s ties to the former Venezuelan dictator Nicolás Maduro were well known. On May 19, Saab was extradited to the United States for allegedly laundering $350 million via American banks for the Maduro regime. Days later, the Colombian journalist Daniel Coronell published documents showing that de la Espriella received almost $400,000 in illicit funds from Saab’s companies.  

In his own words, de la Espriella’s international role models are Trump, Argentina’s Javier Milei, and El Salvador’s Nayib Bukele. From Bukele, de la Espriella has borrowed his appearance — the two men look remarkably similar — and his hard-line security policies. But by far, his greatest influence is Milei, who anthropomorphizes himself as a lion in accordance with libertarian social Darwinism. In the same vein, de la Espriella styles himself El Tigre, often engaging in song and dance with AI-generated felines at his rallies.

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Like Milei, de la Espriella professed elite libertarian views before launching his presidential bid. Up until recently, his market fundamentalism came paired with vocal support for euthanasia, abortion, and adoption by same sex couples. The issue, of course, is that this combination of progressive social views and market worship is repellent to the working class. De la Espriella now claims that he evolved on these issues, exalting the traditional family and calling abortion “an abomination.”

More dubious still is his conversion from godless globalist to a Catholic patriot. In 2017, de la Espriella stated in an interview that he denied the existence of anything that reason can’t explain. When asked why he married his wife through the Catholic Church, he replied, “We all commit foolishness and stupidities for love.” In the same vein, the millionaire attorney is a tri-citizen of Colombia, Italy, and the United States, and lived abroad in Florence and Miami for at least a decade prior to his campaign.

Recognizing these vulnerabilities, de la Espriella now claims that he found God in 2020 following his aunt’s death from Covid, though pre-campaign evidence of his religiosity is scant. Now, the president-elect champions Christian nationalism and has adopted the slogan Firme por la patria — “firm for the fatherland.”

In practice, this firmness seems to involve a great deal of deference to Washington — or rather, southern Florida’s Trump World. This month, de la Espriella stated that he voted for Trump and is a registered Republican in the United States. He has also celebrated the White House’s extrajudicial killings of alleged “narco-terrorists” near Colombian waters, though none of the victims have been proven to have engaged in drug trafficking. Undaunted, de la Espriella has gone so far as to say that he would welcome US strikes inside Colombia.

Much of this explains why de la Espriella’s victory was so slim. Petro, moreover, will leave office as the most popular Colombian leader since Uribe. After spending much of his term mired in telenovela-esque scandal and identitarian excesses, Petro engineered a stunning turnaround that saw his approval ratings recover to nearly 50%.       

In 2024, the administration passed a pension reform expanding coverage for almost 14 million Colombians, including some 3 million seniors living in extreme poverty. Petro also restituted around 1 million out of a total of 3 million hectares for victims displaced by guerrilla conflict. Jhon, an ex-soldier and displaced person from rural Tolima, told me that his hometown had since flourished thanks to government investment, including improved infrastructure and rural health care. “People are growing coffee and bananas again,” he said.

The Petro administration also passed a historic labor reform, reducing the workweek to 42 hours and restoring workers’ rights and benefits that were previously cut by Uribe. Workers now receive overtime worth an additional 35% of wages after 7 p.m., as opposed to 9 p.m. previously, in addition to 90% overtime on weekends and holidays in 2026, set to rise to 100% next year. Additionally, the government has raised the minimum wage around 40% in real terms since 2022, including an unprecedented 23% hike for 2026. Contrary to scaremongering about job losses and “Venezuelization,” poverty and unemployment have fallen to record lows. 

So why, then, did so many Colombians vote for a politician who can only be described as a MAGA-Miami asset? 

The answer is that Petro’s pro-worker turn proved too little, too late. In recent years, much of the Latin-American Left has taken to the activist-academic progressivism of the Western Left, which largely appeals only to credentialed cosmopolitans. Cepeda’s margins with working-class Colombians fell decisively relative to Petro in 2022. Supporters will inevitably fixate on de la Espriella’s surge among fickle, middle-class voters, but this ignores serious failings of policy by the Leftist establishment.  

Colombia produces virtually no fossil-fuel emissions, yet Petro halted all novel oil exploration under the pretense that humanity has 12 years to avoid extinction from climate change. Around half of government revenue derives from the sale of petroleum, most of which comes from the state firm Ecopetrol. Yet Petro resolved to destroy Ecopetrol, whose revenue collapsed by more than half during his term. Up until 2025, Colombia was wracked with stagflation — low growth, high inflation — a predictable consequence of the government’s energy sabotage. 

Catastrophically, Cepeda’s campaign remained committed to the outgoing president’s climate fundamentalism, despite a spiraling energy crisis. In a show of sheer stupidity, Petro and Cepeda put Ecopetrol’s union in the impossible position of choosing between labor rights and the promise of renewed exploration under de la Espriella. To his credit, the president-elect has committed to a commonsense, all-of-the-above strategy that includes fracking (which Petro has described — try not to roll your eyes — as a “crime against humanity”).

Security was also a top concern among Colombians. When it came to tackling common crime, particularly in urban areas, Petro has embraced “criminal-justice reform” of the kind that has hobbled cities run by Democrats the world over. His government attempted — and thankfully failed — to reduce prison sentences for crimes like murder. He also condemned building prisons for fear of perpetuating “mass incarceration.”

Asked by a youth influencer about how he would respond to someone breaking into his own home, Petro waxed philosophical on criminals as victims of society. In contrast, de la Espriella has promised to build mega-prisons modeled on Bukele’s in El Salvador.

Dealing with the militarized cartels, guerrillas, and Right-wing paramilitaries that dominate parts of the Colombian countryside is a different matter, however. Petro’s record on this front, while poor, is roughly comparable to that of his post-Uribe predecessors. Since 2022, Colombia’s high national homicide rate, about 25 per 100,000, has remained stable. While cocaine production has soared to a record high, critics omit that production has risen consistently since 2012. Accordingly, Petro has seized record amounts of the drug.

In contrast, Petro’s “Total Peace” initiative — negotiating peace deals or terms of surrender with multiple armed groups simultaneously — has created more problems. In May, infighting within a FARC splinter group led to nearly 50 dead in the Colombian Amazon. The competing factions were allegedly torn between guerrillas interested in negotiating with Petro and others keen on exploiting illicit economies.

Norberto, a schoolteacher and de la Espriella supporter, told me he wasn’t opposed in principle to talks with armed groups but felt that Petro lacked an iron fist and follow-through during negotiations. Indeed, the architect of Total Peace was none other than Cepeda, Petro’s heir and would-be successor, who doggedly refused to explain what, if any, changes he would make to the policy as president. Then again, de la Espriella’s promises of mass bombings, perhaps conducted by Washington, are unlikely to meaningfully improve security in the countryside; Petro’s predecessor, Iván Duque, tried a similar strategy with mixed results. 

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More broadly, the problem with the president-elect’s promise to imitate Bukele on law and order, is that Colombian courts, unlike their Salvadoran counterparts, are unlikely to tolerate an indefinite suspension of due process. Even then, the example of Noboa’s Ecuador shows that autocratic methods may still prove insufficient against militarized cartels as opposed to simple street gangs; de la Espriella himself has noted that Colombia’s drone-specialized armed groups are far better-equipped than El Salvador’s street gangs.

Colombians have taken a gamble on de la Espriella. Yet — as with Petro — they are likely to be disappointed. Indeed, it is likely that Colombia will descend into mass unrest by year’s end. Like his Right-wing peers elsewhere in the region, the president-elect is enamored with Milei’s “chainsaw austerity,” which he aims to enact via a Trumpian executive decree. Promises to privatize all state companies and slash 40% of public employees are certain to deliver mass protests identical to those in Argentina, Bolivia, Ecuador, and Chile.

The saddest part about the president-elect’s market fundamentalism is that — unlike with the cartoonishly mismanaged Argentina — there simply is no case for mass cuts in Colombia. The Andean nation’s debt-to-GDP is just 60%, compared to Argentina’s whopping more than 150% in 2023. Colombia’s deficit is admittedly high at more than 6%, yet critics neglect that mass cuts would kill economic growth, thereby increasing total debt. Much like Petro’s dogmatic capture on climate change, de la Espriella is equally captured by a fanatical hatred of public services; ironically, the bulk of Colombian public employees form part of the country’s desperately needed armed forces.

There is a painful lesson here for the Latin-American Left. Mexico’s Morena under Presidents AMLO and Claudia Sheinbaum remains the only ruling party Left-of-center in the region to have won re-election since 2020. Sheinbaum, a climate scientist, has championed the state oil firm Pemex and even pushed to expand fracking in tandem with renewables. And contrary to her image as a progressive heroine, the Mexican president and her hard-line security minister, Omar García Harfuch, have tripled Mexico’s incarceration rate, leading to a historic reduction in homicides. Wage hikes have likewise been steeper in Mexico.

Until Left and Right can get it into their heads that voters despise their respective groupthink — on climate change, crime, market fundamentalism, and worship of foreign interests — they will continue to alternate power in the most destructive manner possible. It remains to be seen whether de la Espriella and the current crop of Right-wingers in the Americas stave off a bloodbath in the next wave of elections. 

The administration’s reasoning is not merely that momentum is on its side, but that Maduro’s Venezuela — particularly its oil — had long served as one of very few lifelines available to a Cuban economy teetering on the edge of collapse. Now that Venezuela under Delcy Rodríguez has cut off that supply, an energy crisis is adding to an already bleak economic picture on the island. 

By 1 January, two days before Maduro’s removal from Venezuela, Cuba had lost over 10% of its population over the previous five years. Over the same period, the country’s GDP declined by 11%. Around the country, Cubans are today frequently in the dark, owing not only to energy shortages but a disintegrating power grid. Cuba continues to sort through the rubble of Hurricane Melissa, which last October damaged almost 100,000 homes and much of eastern Cuba’s farmland, while the country also faces an epidemic of dengue fever. 

To topple the government of Cuba — one which has held its population to early-20th century living standards, repressed all political dissent, and been a thorn in the side of US policy for six decades — has long been an impossible dream for American presidents. Only two years after Fidel Castro and Che Guevara’s revolution, in 1959, President Kennedy failed multiple times to dislodge the new regime, whether by covert invasion force or assassination. 

Eventually, the US settled on an indefinite extension of the 1960 trade embargo, a policy designed to ensure that if a longtime friend and ally of Washington was suddenly going to embrace a political ideology antithetical to American values and interests, it would have no support from American commerce in doing so. The policy, which has persisted to this day, succeeded in washing America’s hands of communist Cuba. It failed entirely, however, to pressure Cuba to pursue a different course. 

The embargo’s failure would become synonymous with the axiom that one cannot starve revolutionaries out of their ideologies merely by disengaging with them. As both Cuba and the hermit kingdom of North Korea have shown, communist leaders can use their control over the flow of information to blame their citizens’ poverty on the very nations they have alienated, thus instilling an “us against the world” mentality that dulls the gnaw of poverty, keeps counterrevolution at bay, and preserves leaders’ power.

But even despots cannot ignore the needs of their people forever. After the Soviet Union’s fall in 1990 deprived Havana of a longtime source of international aid, Cuba’s GDP fell by a third. Its economy limped along for two decades. Desperate Cubans regularly left the island on unseaworthy crafts to seek asylum in America, in a manner reminiscent of the South Vietnamese “Boat People” of the Seventies. By 2010, Castro’s brother and successor Raúl was declaring that “we reform, or we sink”. 

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In the early 2010s, Cuba conducted a surface-level political and economic reform sufficient to convince US President Barack Obama to normalize diplomatic relations with the island in 2014, for the first time since the Kennedy presidency, in exchange for Cuba allowing American investment in the island. But over the years that followed, most of those investments went nowhere, waylaid by a command-and-control economy that government insiders still controlled. There was therefore little American political resistance when President Trump cut off diplomatic relations again in 2017. In 2021, Cuba experienced its widest-reaching anti-government protests since the 1959 revolution. 

Today, Cuba — as a nation, a polity, and an economy — is at its lowest ebb since the collapse of the Soviet Union. With Fidel dead and Raúl retired, the family that held the Cuban communist project together is now gone. President Trump is right to see an opportunity. But to take advantage of that opportunity, he will need to bear in mind that Cuba is nothing like Venezuela. 

For one thing, Cuba is a bureaucratic government with power diffused among a large group of party elites. President Díaz-Canel was hand-picked by Cuba’s Communist Party apparatus, and elected by a congress controlled by it. While Venezuela also has a congress, Maduro was a strongman elected by popular (sometimes rigged) elections. Because Maduro was the main locus of political power, a “decapitation” strategy of removing him from the country stood a chance of drastically changing Venezuelan government policy even as the rest of the government structure remained intact. In the few weeks since Maduro’s arrest, this does indeed seem to be happening. But in Cuba, there is no Maduro figure to remove. Power resides in Cuba’s Communist Party and its congress. 

Another difference is ideology. Cuba is a one-party state. Venezuela, at least officially, is not. Venezuelan Chavists follow a populist socialist program with considerable ideological flexibility, whereas Cuba is notorious for its legalistic interpretation of Marxist-Leninist communism. While both nations have always had their share of graft, Chavist Venezuela’s lodestar is self-enrichment for the politically connected, whereas Cuba’s is Marxism-Leninism, even when it impoverishes everyone. 

And then there’s the question of historical memory. Whereas Venezuela was a functional democratic country within the memory of most Venezuelans, Cuba has been a communist dictatorship for as long as most Cubans have been alive. And even those few born during the reign of Cuba’s pre-revolutionary dictator Fulgencio Batista will find few lessons from that grim era.

Based on these contrasts, the Trump administration should instead base its Cuba policy on six decades of US experience with the country — as well as a century of experience with other communist regimes. These encounters might suggest that neither decapitation nor further economic sanctions are, in themselves, viable pathways to change in Cuba. An effective strategy, if it involves a stick in one hand, must be balanced by a carrot in the other.

The most powerful carrot in our arsenal is the prosperity that comes from friendship with the United States. American strategy must make it painfully clear to Cuban leaders and citizens alike what they are missing by not being full members of the international community and the Western Hemisphere specifically. Today’s American leaders can learn a great deal here from the statesmen of the late Cold War, particularly men like Secretary of State George Shultz, who used Western economic dynamism to persuade the Soviet Union’s leaders essentially to legislate themselves out of existence.

Creating a functional democratic government in Cuba is going to require hand-holding. Cuba has been steeped only in communist political philosophies for the lifetimes of most Cubans. To learn anything else will take a great deal of external commitment. Cuba — like many other communist adversaries — also has a history of feigning reforms to attract concessions: as President Obama learned to his cost in 2014. To stick with the late Cold War theme, then, “Trust but Verify” will need to be the watchword of any US strategy toward Cuba, just as it was for Ronald Reagan and the Soviet Union.

Yet if the administration’s current strategy as widely reported, covertly convincing a critical mass of public officials to turn on the government is unlikely to work. If the Cuban Communist Party knows one thing, it is how to sniff out and imprison counterrevolutionaries. And even were this strategy to succeed, pandemonium would be the likeliest result in a nation that has known nothing but one-party rule for the better part of a century. Far better would be a policy that unequivocally shows an exhausted people the perks of friendship with the United States, and persuades them to leave communism behind. No coups required; a whimper, not a bang. 

Trump’s first priority, then, should be to open the information environment in Cuba. An advantage here is Elon Musk’s Starlink, which could connect the whole island cheaply (or even, knowing Musk’s tendencies toward political philanthropy, for free). Reliable internet needs electricity, and Cubans are struggling with broken-down power grids. Happily, American firms have the dollars to help them rebuild. All Cuba’s government would need to do to receive these fabulous benefits would be to end online censorship. Were Cuba to do so and then go back on its word, meanwhile, those benefits could be taken away just as easily. 

Once information is flowing more freely, the Trump administration should set to work on two initiatives at once — one economic, one political. First, Trump should work with US businesses to put together a massive package of potential investment for Cuba. In doing so, it should pretend to be living in a parallel universe with no trade embargo. It is difficult to overstate just how much American imports could contribute to the Cuban economy were the embargo to be lifted, even in part. One might compare Cuba to the Dominican Republic, a US ally with a similar population but which earns seven times as much export income as Cuba.

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How might trade with the US uplift Cuba? Take the example of cigars. Cuba remains, in the estimation of most aficionados, the undisputed quality king. At the moment, though, Cuba’s total international cigar sales are around $1 billion. The country’s total exports, in all categories, are barely above $2 billion. The US market for premium cigars alone is $4 billion. Were American cigar smokers to choose Cuban cigars even half the time, US demand for Cuban cigars alone would equal the total exports of the entire island of Cuba. And that’s just cigars. Cuba also has some of the world’s best land for the cultivation of sugar and fruit, and some of the world’s largest deposits of nickel — a metal vital for producing electronics from phones to electric vehicles.

Once Trump puts together a suitably impressive list of hypothetical commitments, he can begin selling them to the Cuban government and its people. He could offer those investments individually, alongside matching abatements of the embargo, in exchange for specific political changes in Cuba. These could start with concessions in economic policy — allowing private businesses to compete with state-owned monopolies, for instance, or else setting exchange rates, tax policies, and legal frameworks to encourage foreign investment. As the economic rewards get bigger, meanwhile, Trump might exchange them for ever-greater political reforms ending, finally, with the abolition of Cuba’s one-party state, the freeing of political prisoners, and free movement between Cuba and the US. 

Cuba is a once proud and vibrant country that has been hollowed by 65 years of Marxist-Leninist dictatorship. Rebuilding will take time, and such an ambitious program might seem optimistic given the long decades of failure. Yet here it’s useful, perhaps, to return to Venezuela, which the US currently controls. Maduro’s regime was Cuba’s closest ally, and Havana is watching what happens in Venezuela very carefully. If Trump can prove that by bringing a longtime enemy into alignment with Washington, and is able to better the lives of Venezuela’s people, Cubans are likely to be far more receptive to similar ideas for their own country. 

President Trump is an extraordinarily effective salesman, and this is fundamentally a strategy of salesmanship. The greatest obstacle to its success might be the President’s own capriciousness. Rebuilding Venezuela is a years-long project, and at times it seems that Trump has already lost interest in it. Cuba will take far longer, and will require a new level of patience for his administration. But if Trump can retain focus on the long haul of rebuilding Venezuela and Cuba, however, he will have done more to advance American leadership in its near-abroad than any president in decades. And conversely, he will not be able to achieve his goal of reasserting the Monroe Doctrine and reestablishing US dominance over the Western Hemisphere with a blood enemy in Cuba.