Venezuela’s 20-year downfall featured a weird bromance between Hugo Chávez and Sean Penn, ex-husband of Madonna and ‘One Battle After Another’ actor
Venezuela President Nicolás Maduro’s capture, coming exactly 36 years after the similar seizure of Panama’s Manuel Noriega, has taken U.S. foreign policy back to the future, just as Hollywood grapples with questions of American imperialism in Oscar favorites ranging from Paul Thomas Anderson’s One Battle After Another to Ryan Coogler’s Sinners to Josh Safdie’s Marty Supreme. Life began imitating art when President Donald Trump bluntly declared “we’re going to be running Venezuela” about the U.S.’ role going forward in the country’s governance, recalling the Marty Supreme closing credits needle drop: “Everybody wants to rule the world,” by ’80s greats Tears for Fears.
But Anderson’s One Battle, an adaptation of the always politically minded novelist Thomas Pynchon, has a certain extra resonance in 2026 because of the surprise strike from the White House on Venezuela and because of its casting of an unlikely player in 21st century foreign policy: Sean Penn. The onetime Gen X badboy was famously, briefly married to pop icon Madonna before reinventing himself as one of the greatest actors of his generation, notching an Oscar for 2003’s Mystic River. Shortly after his crowning as Hollywood royalty, Penn emerged as a notable voice endorsing the Chavismo that ultimately led to Maduro and a near 30-year economic unraveling in Venezuela.
In One Battle, Penn’s Col. Steven J. Lockjaw lampoons the sort of right-wing Americans who are angry about immigration in general and left-wing activism in particular, but his real-life politics showed almost a hero worship, certainly a weird bromance, with Hugo Chávez in Venezuela. When Penn first appeared alongside Chávez in Caracas in the late 2000s, Venezuela was still riding high on oil revenue, even as the government tightened control over state institutions and the national oil company. The actor praised the leftist leader as a “model Democrat” and a sort of Robin Hood figure who would be a champion of the poor, at one point even suggesting that critics who called Chávez a dictator should be jailed.
For the Chávez administration, having a Hollywood star onstage delivered more than a photo‑op. Penn’s presence became a form of soft validation for a project that was already spooking investors, undermining private industry through expropriations, and hollowing out checks and balances. Economists were warning the petrodollar‑fueled social model was unsustainable, but the political machinery increasingly prioritized revolutionary narrative and global symbolism over technocratic discipline.
One battle after another
The Penn‑Chávez alliance fit neatly into Venezuela’s broader strategy of courting foreign celebrities and ideological fellow travelers as a counterweight to Washington’s influence. That soft‑power approach helped humanize a government that was simultaneously centralizing authority, pressuring independent media, and neglecting long‑term investment in the oil sector that underpinned the entire economy.
At first, Penn’s endorsement of Chávez was correct, as Venezuela made large expansions in social programs and regional oil diplomacy, such as subsidized exports through Petrocaribe. Chávez passed a new Hydrocarbons Law in 2001 that sharply increased taxes and required the state oil company PDVSA to hold at least 51%–60% in “mixed” joint ventures with foreign firms, reversing the earlier liberalization of the sector. In the years afterward, Chávez’s government forced foreign oil companies to accept new majority‑PDVSA contracts or leave, leading to expropriations and arbitration cases by firms like ExxonMobil and ConocoPhillips.
But Chávez was not as socialist in practice as in theory, firing roughly half of PDVSA’s workforce after a 2002-2003 strike, gutting the company of 18,000 valuable workers and accelerating its operational decline. The country with the largest proven oil reserves suffered stagnating output for years afterward, and maintenance, reinvestment and technical management of its oil fields and refineries suffered.
When oil prices slid and mismanagement came due, the country staggered into hyperinflation, shortages, and mass migration, culminating in a full‑blown humanitarian crisis that outlived Chávez and deepened under his successor, Nicolás Maduro. As opposition leader María Corina Machado told Fortune in October 2025 from hiding, weeks after winning the Nobel Peace Prize, Venezuela had gone from being one of the richest and freest countries in its region to a “narco-terrorist state,” with nearly a third of the population fleeing (many to Florida, not far from Trump’s Mar-a-Lago estate). The International Monetary Fund estimated Venezuela’s economy had declined by roughly 75% as of late 2022, although center-left critics such as the Center for Economic and Policy Research argue that this doesn’t fully reflect the role of U.S. sanctions.
President Trump has alluded to this seizure of oil assets multiple times before the U.S. strike on Venezuela. “They took all of our oil not that long ago,” he told reporters on Dec. 18. “And we want it back.” At the same time, Trump’s legal justification for striking Venezuela rests on narco-terrorism allegations, as he issued an executive order in January 2025 that laid the groundwork for criminal organizations and drug cartels to be named “foreign terrorist organizations.” U.S. intelligence agencies have disputed the claim that Maduro’s administration was working with Venezuelan street gangs.
Penn has previous when it comes to narco-terrorism, too.
The El Chapo detour
Penn’s attempt to leverage his celebrity into geopolitical relevance did not stop in Caracas. In 2015, he traveled in secret to meet Joaquín “El Chapo” Guzmán in the Mexican jungle, arranging an interview for Rolling Stone that appeared days after the drug lord’s capture. Mexican officials later said the meeting was “essential” or “critical” to tracking Guzmán, pointing to surveillance of intermediaries who shepherded Penn and Mexican actress Kate del Castillo to the rendezvous.
In January 2016, Rolling Stone published “El Chapo Speaks,” Penn’s first‑person account of this meeting in the Mexican jungle, complete with photos of the actor shaking hands with the world’s most wanted trafficker and a video Q&A recorded after the fact. Within hours, television networks and newspapers flooded the airwaves with split‑screens of Penn and El Chapo, treating the encounter as a mash‑up of Hollywood thriller and narco‑soap opera rather than a sober examination of cartel terror.
The media frenzy that followed said as much about modern information markets as it did about Penn. Television networks and digital outlets framed the episode as a Hollywood‑meets‑narco thriller, while press‑freedom advocates and Mexican journalists blasted the story as a “vanity project” that gave Guzmán unprecedented story control and downplayed cartel brutality. Penn later said he had “terrible regret” the narrative centered on him rather than on the failures of the drug war, but the episode furthered his reputation as an uncredentialed actor‑journalist in some of the world’s most dangerous conflicts.
Penn’s representatives at CAA did not immediately respond to a request for comment. His CAA page mentions that Penn has written for Time, Interview, Rolling Stone, and The Nation, and that he was the first international journalist to interview Cuban President Raul Castro. (Secretary of State Marco Rubio said Cuban troops were killed in Venezuela as part of the recent U.S. strike, and Trump told reporters that Cuba was “in a lot of trouble.”)
Today, Penn is attracting a different kind of attention for One Battle After Another, which critics groups and awards handicappers describe as a leading Best Picture and acting contender after a strong run at major ceremonies. The movie’s dark satire of revolutionary politics and personal compromise arrives as Venezuela remains mired in low growth, fragile institutions, and an ongoing exodus that has reshaped labor markets across the Americas. But Penn may not have imagined that he would come into contention for another golden statuette when a conflict that he played a visible role in, boiled over. Everybody wants to rule the world, indeed.
This story was originally featured on Fortune.com