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Trump, Venezuela and the Tug-of-War Over a Strongman

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Among those Mr. Claver-Carone contacted, according to the opposition leaders, was Mr. Gorrín.

By then, he was technically a fugitive from American justice. The prior summer, U.S. prosecutors had charged him in an alleged money-laundering scheme. He dismissed the indictment as political persecution, but Mr. Ballard had dropped him as a client and Mr. Gorrín was added to the sanctions list.

Now, American officials and the Venezuelan opposition needed back channels of their own. According to the opposition leaders, Mr. Gorrín and other intermediaries were asked to convey U.S. offers of leniency to cooperative regime figures.

Mr. Gorrín had attended university with the chief justice of Venezuela’s supreme court; the Americans believed they had a deal with Mr. Gorrín to help deliver the judge and others to Mr. Guaidó’s side. That March, the Trump administration quietly took Mr. Gorrín’s wife off the sanctions list.

Mr. Gorrín, whose discussions with regime figures were reported by The Wall Street Journal last year, denied playing any role in the effort, and said he had no contact with Mr. Claver-Carone after their 2017 meeting.

An attempted uprising failed. The promised supreme court ruling never materialized. Mass demonstrations led by Mr. Guaidó fizzled, and Mr. Maduro deployed paramilitaries to torture and kill protesters.

Mr. Sargeant, whose oil deal had been scuttled by the new sanctions, saw an opening. That summer, he teamed up with Robert Stryk, a lobbyist who had earned millions representing foreign leaders in Washington. Mr. Stryk’s White House contacts told him that the president felt misled by his advisers on Venezuela. Eager to cut foreign policy deals that administration hawks opposed, Mr. Trump was clashing with Mr. Bolton. By September, he was gone.

The next month, Mr. Sargeant and Mr. Stryk flew to Caracas to meet with Mr. Maduro. When they arrived in the presidential palace, there was another guest: Mr. Gorrín.

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