Trump pushing for hazardous meeting with Venezuelan leader at UN Assembly: insiders
FILE PHOTO: U.S. President Donald Trump speaks to members of the press as he arrives at Charlotte Douglas International Airport, while he travels to attend a campaign rally supporting Republican U.S. Senate candidate Michael Whatley, in Charlotte, North Carolina, U.S., September 16, 2026. REUTERS/Kevin Lamarque/File Photo

President Donald Trump could hold a landmark sit-down with Venezuela's interim leader Delcy Rodriguez within days, according to people familiar with the planning — an encounter insiders say comes loaded with political hazards on both sides of the border.

The meeting would likely happen on the margins of Trump's upcoming trip to New York for the UN General Assembly, where talks with Gulf leaders on the Iran war are already on his calendar. Tuesday has emerged as a possible date for adding Rodriguez to the schedule, Axios reported.

One Trump adviser framed the relationship as central to the administration's foreign policy wins, saying, "Iran is tough, but Venezuela is without a doubt the president's top success, and Delcy is a key to that." A senior administration official was more cautious, noting nothing is locked in yet, and the final call rests entirely with the president.

A Manhattan meeting would unfold not far from the detention facility holding Nicolas Maduro, Rodriguez's old political partner turned prisoner, who's been sitting there since American forces snatched him from Caracas in a January raid Trump personally signed off on and now faces narco-terrorism charges. Rodriguez stepped into the power vacuum left behind and has since built a working relationship with Trump and Secretary of State Marco Rubio, most notably through a sweeping oil agreement between the two governments that's drawn its own share of scrutiny.

Not everyone is happy about that partnership. Venezuelan exiles concentrated in South Florida — a politically vocal bloc — have grown increasingly angry watching Washington cozy up to someone they view as cut from the same socialist cloth as Maduro, both having climbed to power under the late Hugo Chavez. Neither Trump nor Rubio has demanded Venezuela actually hold elections, a notable silence given how relentlessly they once painted Maduro as a dictator who stole his own vote.

Backers of exiled opposition figure Maria Corina Machado, who won the Nobel Peace Prize, share some of that frustration too, still stung by administration pushback when she tried heading home after June's earthquakes.

Venezuelan public opinion polling shows both Rodriguez and Trump struggling with weak approval, while Machado sits on top, even as her own support has started slipping. Some people close to Trump privately fret that being seen shaking his hand could brand Rodriguez a U.S. puppet in the eyes of her own citizens. The administration official waved off that worry entirely.

"The fact is POTUS loves Delcy because she's delivering and she's leading," the official said.

Back home, though, political operatives in Florida say voters heading into the midterms are far more consumed by pain at the pump from the Iran conflict and the administration's crackdown on immigration than by anything happening with Venezuelan democracy — suggesting whatever backlash follows a Rodriguez meeting may stay confined largely to the exile community rather than spilling into the broader campaign.