The secret history of Trump's Venezuelan oil baron

President Trump's historic Venezuelan oil deal revolves around a colorful and controversial man from Caracas with a long history of supporting U.S. interests — including the operation to remove former strongman Nicolas Maduro.

Why it matters: Alejandro Betancourt, 46, runs the oil company that's entering into an unprecedented partnership with the Pentagon. It gives America access to some of Venezuela's vast oil fields at a time when U.S. reserves are low.

• "No Betancourt, no energy-security deal," a U.S. official told Axios. "And Maduro might still be in power if it wasn't for him."
• Betancourt's life story has an oil-like boom-and-bust aura, replete with billion-dollar deals, international intrigue, a longstanding money-laundering probe and even a Spanish castle raided by authorities.

Inside the room: As Trump demanded Maduro leave Venezuela last year, Betancourt played a crucial role feeling out Venezuelan Vice President Delcy Rodriguez on whether she would run the government as replacement.

• "There was no direct ask from Alejandro to Delcy; it was more getting a sense on where her head was at," said a second U.S. official briefed on the private talks between the two Venezuelans.
• Betancourt was in regular contact with Trump's unofficial Venezuela fixer, Mauricio Claver-Carone, and discussed how to keep oil flowing and the economy running in post-Maduro Venezuela.

On Jan. 3, when the U.S. military seized Maduro, Claver-Carone was communicating via phone with Betancourt, who was also communicating with Rodriguez.

• At first, Rodriguez "thought the U.S. had killed Maduro, that she had been double-crossed, and [she] was very angry and very scared," a Betancourt ally told Axios. "He had to talk her down, playing the good cop" and finally persuaded Rodriguez to talk with U.S. Secretary of State Marco Rubio about taking charge in Venezuela.

The backstory: Betancourt's relationship with the U.S. government began in Trump's first term, when Claver-Carone was the director of Western Hemisphere affairs for the National Security Council and the administration declared Maduro an illegitimate president.

• Trump became the first world leader to recognize the head of Venezuela's national assembly, Juan Guaido, as the nation's rightful leader in 2019.
• Betancourt acted as a go-between, linking Maduro's opposition with Venezuelan political figures and top-level military officials to build domestic support for a nonviolent, democratic transition to a Guaido government, said an opposition figure and Guaido's brother, Gustavo Guaido.
• Betancourt also traveled to Moscow to hand-deliver a letter on behalf of Guaido's government asking Russia to stop backing Maduro.

Friction point: Maduro survived that U.S.-backed ouster effort. Betancourt fled. Maduro ordered his arrest and seized his assets and his oil company.

• Because of the legacy of socialist mismanagement, oil production on the fields of Betancourt's old business fell dramatically, harming Venezuela's fragile economy.
• Rodriguez urged Maduro in 2023 to bring back Betancourt, who had a reputation as a turnaround artist in Venezuela's oil sector.
• Maduro required Betancourt to stay away from the Venezuelan opposition, a source said, and to take on "the only gringo I trust," Palm Beach oilman Harry Sargeant III, whom Maduro nicknamed "El Abuelo" (the grandfather). The two recently parted ways.

The intrigue: Betancourt faced a problem from the U.S. in 2019, when Maduro was after him — an international $1.2 billion money-laundering investigation that led to a federal indictment of his cousin and other Venezuelans in Miami.

• One of Betancourt's attorneys then, Rudy Giuliani, met with top Justice Department officials to argue that Betancourt didn't know about the crime, the Washington Post reported.
• That meeting came a month after Giuliani and two associates stayed at Betancourt's Spanish castle El Alamín and met with an aide to Ukrainian President Volodymyr Zelensky, urging him to investigate Trump's then-opponent, Joe Biden.
• Betancourt was never charged. But six years later, Swiss authorities inexplicably picked up the 2016 U.S. money-laundering case and persuaded Spanish authorities to execute a search warrant at the castle and Betancourt's office in Madrid.

This spring, in a series of phone calls, U.S. officials — including then-Attorney General Pam Bondi — suggested Swiss authorities hold off on the investigation because Betancourt is such an important foreign-policy figure, the Washington Post reported.

• The problem for the U.S.: Betancourt was unable to travel outside of his home in the U.K. — and therefore to meet in D.C. and Caracas to finish Trump's oil deal — because the Swiss had petitioned for his extradition.

In one call, a top Justice official sounded surprised when Swiss officials said that case was in its early stages.

• "Early stages? This is 10 years old," one U.S. official said, according to a participant on the call.
• The matter was cleared up when Swiss officials told the U.K. court they weren't prepared to proceed, allowing Betancourt to travel in June.

Behind the scenes: Betancourt, Rodriguez and officials from the State Department and the Pentagon's Office of Strategic Capital had a handshake agreement on the oil deal by mid-August. Under its terms, officials say:

• Venezuela receives between 16% to 40% of production, depending on the field. It also gets income taxes.
• The U.S. puts no money into the deal, has a 35% equity stake and gets 20% of the after-tax oil at production cost. That's about $30 a barrel (crude was priced at $90 Monday).
• Betancourt's North American Blue Energy Partners gets access to 17 fields and the implied backing of the U.S. military.
• "No other oilman can say he has the Pentagon on his side," one U.S. official told Axios.

The other side: Energy experts have criticized the deal as potentially unworkable and unlikely to lower gas prices anytime soon.

• While U.S. officials praised Betancourt, some Venezuelans denounced the deal as kleptocratic and denounced him as a corrupt "bolichico," a nickname for slick money-hungry elites.

Betancourt's attorney, Jon Sale, said his client has been unfairly maligned.

• "He's been investigated by the Swiss and by DOJ for a long time on very old facts. Not only has he never been convicted but he hasn't even been charged for any criminal activity," Sale said.
• "He's uniquely situated for this moment in history."