Trump’s Dilemma with Venezuela
The strategy of “maximum pressure” through sanctions is unlikely to overthrow Nicolas Maduro; negotiating with him inevitably confers legitimacy.
By Jorge Castañeda* (Confidencial)
HAVANA TIMES – Last weekend, Nicolas Maduro once again agreed to receive deported Venezuelans from the United States, with a stopover in Honduras. It’s unclear exactly what he received in exchange, but it seems unlikely that the resumption of repatriation flights came without some sort of negotiation. This clearly reflects the dual approach in President Donald Trump’s policy toward Caracas, an approach that may confuse everyone: Venezuela’s opposition, Maduro’s government, and Venezuelan exiles in the US and other countries.
Trump had already surprised Maduro’s opponents by dispatching Richard Grenell, one of his closest allies, to Caracas to secure the release of a handful of American prisoners and begin the deportation of Venezuelans. The first task was sensitive but relatively simple: Grenell only had to meet with Maduro to secure the prisoners’ release. The second challenge posed greater difficulties.
The TPS (Temporary Protected Status) program covers over 600,000 Venezuelans, but the number grows when including those awaiting asylum decisions, those admitted under President Joe Biden’s humanitarian parole program, and even undocumented immigrants. However, the logistical and legal hurdles of deporting them all are so significant that deporting a small number—with wide media coverage—might suffice.
This seems to be why Trump believed that the flights authorized by Maduro following Grenell’s mission would be enough to sell his voter base on the idea of Venezuelan deportations—particularly of supposed members of the Tren de Aragua, a gang originating in Venezuela, which, according to Trump’s narrative, had begun victimizing US citizens in several states. But the flights slowed, Maduro began backing away from his commitment, and the original plan stopped working.
Trump himself sparked the crisis. The license granted by former President Biden to Chevron to extract, export, and import petroleum products in Venezuela expired in early March 2025. After initial hesitation, Trump decided not to renew the license, seriously affecting Venezuelan oil production and its export prospects. For Maduro, it was a severe blow. Whether causally linked or not, the flights came to a halt.
At that moment, Trump made one of the most controversial decisions of his still-young term. Without trial or even a hearing, he transferred over 200 Venezuelans—accused of being part of the Tren de Aragua—to one of the most notorious prisons in El Salvador, paying six million dollars to President Nayib Bukele’s government to keep them imprisoned. The images of humiliation and excessive use of force at the so-called Cecot Prison spread around the world. Protests and legal actions in the US quickly followed. A judge attempted to reverse the measure, and the prisoners’ families began a movement to rescue them.
For Maduro, the humiliation of the deportees extended to his own presidency. He reacted relatively quickly and supported the families’ demands. As has been reported, the detainees had not been tried in the US or El Salvador and had committed no crimes in the Central American country.
Simultaneously—and perhaps in response—Trump again adopted two contradictory measures. On the one hand, Secretary of State Marco Rubio announced that as of April 2, the US “might impose” a 25% tariff on imports from any country that purchased or resold Venezuelan oil. On the other hand, Trump extended Chevron’s license to operate in Venezuela until May 27, 2025, leaving open the possibility that the license might never actually be canceled. Meanwhile, Maduro authorized the resumption of repatriation flights on March 24.
What stands out in this dance of measures and countermeasures is that Trump is pursuing two simultaneous and contradictory objectives. He wants to maintain pressure on Maduro—fulfilling the demands of Cuban-American senators and representatives, as well as Rubio himself, who have close ties to the Venezuelan opposition and who oppose any normalization with a regime that committed massive electoral fraud in 2024 and violates human rights, according to electoral observers and human rights organizations. But at the same time, Trump wants to deport a substantial number—preferably to Venezuela—of the more than half a million nationals of that country. Unlike people from other nations, these individuals are easier to locate and detain because many have some form of legal status, whether temporary or more permanent.
It could also be assumed that Trump seeks to maintain a high level of Venezuelan oil production—not so much for the US’s own needs (since it is already the world’s leading hydrocarbon producer)—but to influence international prices. While this is a factor, the migration issue seems to be the decisive one.
All of this makes achieving and sustaining both goals in the medium term difficult. The strategy of “maximum pressure” on Maduro—through sanctions, ostracism, and other forms of coercion—is unlikely to bring him down. It’s been tried before and ended in failure. However, such a strategy could contribute to a new and larger exodus of Venezuelans. In contrast, negotiating with Maduro to accept more returnees and treat them properly inevitably grants him legitimacy and normalizes the relationship. At some point—not far off—Trump will have to choose.
*This article was originally published in CCN Español.
Published in Spanish by Confidencial and translated and posted in English by Havana Times.
Analyzing Trump’s Venezuelan policy moves is a fool’s errand. Trump is an idiot and his Venezuela policy depends on what day of the week it is and what interest group just left the Oval office much as anything else.