Donald Trump is weighing a face-to-face meeting with Venezuela's acting President, Delcy Rodríguez, as early as next week, when both are expected in New York for the United Nations General Assembly, Axios reported citing people familiar with the planning. It would be their first encounter, and a striking marker of how completely relations between Washington and Caracas have been remade since US forces captured former president Nicolás Maduro in a raid in January.

Advisers say Trump has all but made up his mind. "Iran is tough, but Venezuela is without a doubt the president's top success and Delcy is a key to that," one told Axios. A more senior official struck a note of caution, stressing nothing had been locked in: "Nothing is finalised. This is up to the president."

The setting would carry its own symbolism. Any sit-down in New York would unfold barely a few streets from the federal jail holding Maduro, Rodríguez's predecessor, who has been detained there along with his wife Cilia Flores since being abducted in a US raid on Caracas on January 3 and flown north to face narcoterrorism charges, which he denies.

Since taking office in Maduro's place, Rodríguez has forged an unusually close rapport with both Trump, who has called her a “terrific person” who is “doing a great job,” and Secretary of State Marco Rubio, with whom she reportedly maintains a constant line of communication. That relationship culminated on August 28 in what Trump called "the biggest oil deal in world history": an agreement handing a Washington-backed venture effective majority control of 17 Venezuelan oilfields holding an estimated 65bn barrels of crude, with more than $100bn in projected investment and upwards of $209bn in tax revenue promised to Caracas.

Further details released by the White House the following week showed that the Pentagon's investment arm would take a 35%  stake in the venture's operator, North American Blue Energy Partners, headed by controversial Venezuelan businessman Alejandro Betancourt López, while the State Department secured the right to buy a further fifth of its output at cost.

The agreement was driven as much by domestic politics as by Venezuelan crude. It landed as Trump faced mounting pressure over rising US petrol prices ahead of the mid-term elections in November, pushed up by the war between the US and Iran and the resulting squeeze on shipping through the Strait of Hormuz. Washington has since eased sanctions on Venezuela's hydrocarbons, mining and telecommunications sectors, and is separately mulling whether to push Caracas to leave OPEC, a decision Trump has said is "up to them".

The thaw has extended to narcotics diplomacy, too. On September 16, the State Department published a presidential determination taking Venezuela off the list of countries judged to have "failed demonstrably" to fight drug trafficking, the first time Caracas has escaped that designation since 2005. Trump traced the change to the fallout from Maduro's capture, saying cooperation with Rodríguez's government was "paying dividends" and citing a June strike that killed Tren de Aragua leader Niño Guerrero.

The shift is all the more notable given Rodríguez's own murky past: the Drug Enforcement Administration branded her a "priority target" as recently as 2022, on the strength of an intelligence file alleging ties to trafficking and gold smuggling, and the Treasury Department did not strike her from its sanctions list until April, months into her tenure as acting president. Some of that history lingers uncomfortably close to home: the January raid that removed Maduro also killed dozens of Venezuelan and Cuban security personnel and at least two civilians, an operation legal experts have widely criticised as a breach of international law — criticism Rodríguez herself echoed at the time. She has since stopped mentioning Maduro in public and adopted an extremely conciliatory posture towards the White House, turning Venezuela into a de facto US protectorate.

Yet not everyone in Washington's orbit is pleased. According to Axios, Florida's Venezuelan exile community, a politically vocal and largely conservative bloc, has watched the administration's embrace of Rodríguez — a lifelong Chavista who rose through the same socialist movement as Maduro — with mounting discomfort. That unease is sharpened by a conspicuous omission: despite years spent casting Maduro as an illegitimate ruler who stole the 2024 election, neither Trump nor Rubio has clearly demanded a fresh vote in Venezuela. 

Backers of exiled opposition leader and Nobel peace laureate María Corina Machado, whose movement is widely considered the legitimate winner of the last election, have raised a related complaint, accusing the Trump administration of undermining her attempted return to Venezuela following June's devastating earthquakes.

Meanwhile, polling from Caracas offers little comfort to either sitting leader: surveys there show both Rodríguez and Trump viewed unfavourably by most Venezuelans, with Machado still the most popular of the three.