How Oil, Drugs and Immigration Fueled Trump’s Venezuela Campaign

On a spring night in the Oval Office, President Trump asked Secretary of State Marco Rubio how to get tougher on Venezuela.

It was just before Memorial Day, and anti-leftist Cuban American lawmakers whose votes Mr. Trump needed for his signature domestic policy bill were urging him to tighten a vise on Venezuela by stopping Chevron’s oil operations there. But Mr. Trump did not want to lose the only U.S. foothold in Venezuela’s oil industry, where China is the biggest foreign player.

The president was considering allowing Chevron to continue. But he told Mr. Rubio, a longtime hawk on Venezuela and Cuba, that they had to show the lawmakers and other doubters they could bring the hammer down on Nicolás Maduro, the leftist autocratic leader of Venezuela, whom Mr. Trump had tried to oust in his first term.

Another aide in the room, Stephen Miller, said he had ideas. As Mr. Trump’s homeland security adviser, he had been talking with other officials about Mr. Trump’s campaign vow to bomb fentanyl labs. For various reasons, that notion had faded, and in recent weeks Mr. Miller had turned to exploring attacks on boats suspected of carrying drugs off the shores of Central America.

Mr. Miller’s deliberations had not focused on Venezuela, which does not produce fentanyl. But three separate policy goals began merging that night — crippling Mr. Maduro, using military force against drug cartels and securing access to Venezuela’s vast oil reserves for U.S. companies.

Two months later, Mr. Trump signed a secret directive ordering the Pentagon to carry out military operations against Latin American drug cartels and specifically calling for maritime strikes. Though the justification was drugs in general, the operation would concentrate enormous naval firepower off the coast of Venezuela.

The result has been an increasingly militarized pressure campaign intended to remove Mr. Maduro from power.

It has been marked by U.S. strikes that have killed at least 105 people on boats in the Caribbean and the eastern Pacific, a quasi-blockade of oil tankers entering and leaving Venezuelan ports and threats by Mr. Trump to carry out land strikes in Venezuela.

It reflects overlapping drives by Mr. Rubio and Mr. Miller, who have worked in tandem on policies against Mr. Maduro. Each has come to it with a focus on long-held goals: for Mr. Rubio, the son of Cuban immigrants who also serves as Mr. Trump’s national security adviser, a chance to topple or cripple the governments of Venezuela and its ally, Cuba; and for Mr. Miller, an architect of Mr. Trump’s anti-immigration policies, the opportunity to further his goal of mass deportations and to hit criminal groups in Latin America.

This account of how Venezuela moved to the center of the administration’s foreign policy agenda this year — to the point of a possible war — is based on interviews with current and former U.S. officials, almost all of whom agreed to speak only on the condition of anonymity because of sensitivities about national security. Among the findings:

• Mr. Miller told White House officials in the spring to explore ways to attack drug cartels around their home countries in Latin America. Mr. Miller wanted attacks that could draw widespread attention to create a deterrent.

• The focus on Venezuela intensified after late May, when Mr. Trump was upset about tough negotiations involving Chevron. Venezuela’s oil has been more central to Mr. Trump’s deliberations than previously reported.

• In meetings in the early summer, Mr. Rubio and Mr. Miller talked with Mr. Trump about striking Venezuela. The president appeared swayed by Mr. Rubio’s argument that Mr. Maduro should be seen as a drug kingpin.

• Mr. Miller told officials that if the United States and Venezuela were at war, he could again invoke the Alien Enemies Act, an 18th-century law, to expedite deportations of hundreds of thousands of Venezuelans the administration stripped of temporary protected status. He and Mr. Rubio had used it earlier in the year to summarily deport hundreds of Venezuelans to a notorious prison in El Salvador, only to be stopped by court rulings.

• The secret order for military action against the cartels that Mr. Trump signed on July 25, calling for maritime strikes, is the first known written directive from the president on such strikes. Administration officials referred to the boat attacks as “Phase One,” with SEAL Team Six taking the lead. They have discussed a vague “Phase Two,” with Army Delta Force units possibly carrying out land operations.

• Defense Secretary Pete Hegseth kept many career uniformed military officials and lawyers from the drafting of the “execute order” that guides the boat strikes. As a result, the order had problematic holes in it, including a lack of language on how to deal with survivors.

Mr. Rubio, Mr. Miller and other principals oversaw an often haphazard process shrouded in secrecy. Their ability to contain planning to a closed circle has been aided by the gutting throughout the year of portions of the federal bureaucracy, including the National Security Council, which coordinates interagency discussions.

In September, the administration pushed into what is so far the bloodiest stage of its anti-Maduro campaign. That now amounts to 29 lethal boat attacks over the past four months, operations that many legal experts say are murders or war crimes. The administration says it has intelligence linking the boats to drug trafficking but has not publicly presented evidence for that assertion.

Anna Kelly, a White House spokeswoman, said in a statement that the administration was working “to deliver on the president’s agenda to keep this poison out of our communities.”

Mr. Rubio told reporters on Dec. 19 that the goal of the boat strikes was to ensure that “no one wants to get on drug boats anymore” by pounding into them a “fear of the reaper.”

And he reiterated that the Justice Department had obtained a grand jury indictment against Mr. Maduro in 2020 on charges of working with Colombian cocaine producers, who sometimes send their product through Venezuela. Mr. Maduro’s government, he said, is “an illegitimate regime that openly cooperates with terrorist elements.”

“Invasion” in Springtime

The seeds of militarizing the approach to Mr. Maduro and Venezuelans were planted in February, when Mr. Rubio struck a deal with Nayib Bukele, the authoritarian leader of El Salvador, at his lakeside villa: The United States would pay nearly $5 million to send about 300 Venezuelans accused of being gang members to El Salvador’s Terrorism Confinement Center, or CECOT.

Soon after his visit with Mr. Bukele, Mr. Rubio designated eight Latin American criminal groups as foreign terrorist organizations. Tren de Aragua, a Venezuelan gang, topped the list.

Mr. Miller had already landed on a legal tool to bypass due process: the Alien Enemies Act, an 18th-century law that permits immediate detention and deportations of citizens of a country that has invaded the United States or is at war with it.

Mr. Trump signed an executive order in March invoking the act, with a title warning of “the invasion of the United States by Tren de Aragua.” In retrospect, the order was an important opening salvo against Mr. Maduro: It was the administration’s first formal framing of Mr. Maduro and the United States as being in a type of war. Contrary to a secret U.S. intelligence assessment, it said Tren de Aragua was an instrument of Mr. Maduro.

Many of the more than 250 Venezuelan men sent to El Salvador had no ties to Tren de Aragua or notable criminal records, and some have described widespread torture and abuse at the CECOT prison.

Courts soon ruled that illegal immigration does not count as the kind of invasion that justifies using the wartime deportation law. But Mr. Miller later talked about reviving the use of the Alien Enemies Act if the United States were in an actual war with Venezuela, a former U.S. official said.

At the same time, Mr. Miller was exploring policies unrelated to Venezuela that, like the deportations, had their roots in the so-called U.S. war on terror. He looked at the idea of bombing fentanyl labs in Mexico. But it became clear that Mexican leaders would not consent, and the administration feared losing their cooperation on drug and migrant issues. The Washington Post reported earlier on Mr. Miller’s discussions about striking cartels in Mexico.

By early May, Mr. Miller’s team began asking for further options for using force against drug cartels.

White House officials and others bandied around relatively more constrained ideas, including using the C.I.A. to carry out covert strikes on docked boats that did not have people in them. But Mr. Miller’s team wanted to publicize the strikes. Officials also discussed blowing up fake drug boats to instill fear in traffickers. But Mr. Miller’s aides wanted the real thing, officials said.

By June, a request to explore a possible maritime operation was circulating in the Pentagon. It was not yet focused on Venezuela, but that would soon change — triggered by Mr. Trump’s yearslong interest in the country’s most valuable resource.

Showdown Over Oil

For decades, Chevron has clung to a unique prize in the global oil industry: permission from the governments of the United States and Venezuela to produce and export oil in joint ventures.

Because of that, the company became a bargaining chip this year in secret sets of negotiations among Mr. Trump, Mr. Maduro and U.S. lawmakers — and entwined with a pivotal move by Mr. Trump toward military action.

It began when Cuban American lawmakers pressed Mr. Trump early this year to end Chevron’s Biden-era confidential license. After Mr. Trump and Mr. Rubio announced in late February that they would do so, Mr. Maduro stopped accepting deportation flights of Venezuelans. Mr. Maduro had agreed to them on Jan. 31 with Richard Grenell, a special envoy for Mr. Trump.

Chevron’s chief executive, Mike Wirth, lobbied the administration for a license extension, speaking to Mr. Trump several times over the coming months.

The Cuban American lawmakers got wind that the license could be extended, and they threatened to withhold their votes for Mr. Trump’s signature legislation, “the One Big Beautiful Bill.”

At the Oval Office meeting in late May, Mr. Trump told Mr. Rubio and Mr. Miller that he needed to get the bill passed. But he said he had heard about the downsides of ending the license, including that Chinese companies would take over Chevron’s stakes, said an official.

The president demanded options. That was when Mr. Miller offered to help. He had been nurturing his ideas for mass deportations and boat strikes.

Mr. Trump did not renew Chevron’s license when it expired on May 27. His domestic policy bill passed Congress five weeks later.

The president held a series of White House meetings on whether to strike at Venezuela. At one in the early summer that included Mr. Rubio, Mr. Miller and Mr. Grenell, Mr. Rubio argued that Mr. Maduro was a drug kingpin, a characterization that appeared to stick with Mr. Trump, an official said.

In late July, Mr. Trump reversed course on Chevron’s license. He ordered the Treasury Department to issue one with revised terms. That happened around the time Mr. Maduro freed 10 American prisoners in exchange for the more than 250 Venezuelans that the Trump administration had sent to CECOT, the Salvadoran prison. And Mr. Trump had been swayed by Mr. Wirth’s argument that Chevron was a bulwark against China.

But behind the scenes, Mr. Trump set a course for confrontation. On July 25, he signed a secret order telling the Pentagon to take action against drug-trafficking groups, putting in motion the targeting of Venezuelans.

Summer of Secrecy

That secret directive from Mr. Trump was closely held before The Times reported on its existence in early August.

The two-page order contained a previously unreported written proposal for boat strikes. It directed Mr. Hegseth to target vessels in international waters carrying drugs for any of 24 Latin American “narco-terrorist” groups. The attached list included ones from Venezuela.

In past administrations, many uniformed lawyers and operational experts in the Pentagon would have been invited to meetings to discuss the directive. The National Security Council would have convened discussions among agencies. None of that happened.

While the military order initially remained secret, the administration’s public actions pointed to Mr. Maduro being the ultimate target of the campaign.

The secret list of 24 groups included major cartels and groups that the Trump administration had formally designated as terrorists, along with numerous relatively obscure Mexican gangs. The same day Mr. Trump signed the directive, the Treasury Department announced sanctions against “Cartel de los Soles,” a slang term for drug corruption in Venezuela’s military, declaring it a terrorist organization led by Mr. Maduro. The name was at the bottom of Mr. Trump’s secret list.

On July 27, Mr. Rubio declared that Mr. Maduro had stolen an election a year earlier and was the head of a cartel rather than a legitimate president. Slightly over a week later, he and Attorney General Pam Bondi announced the doubling of a reward for information leading to Mr. Maduro’s arrest or conviction, to $50 million.

Around the same time, a Trump appointee with little national security law experience was drafting a Justice Department memo saying boat strikes would be lawful based on Mr. Trump’s wartime powers. The legal blessing was already developed by late July, when the Senate confirmed the top two lawyers responsible for reviewing such an operation — T. Elliot Gaiser, head of the department’s Office of Legal Counsel, and Earl G. Matthews, Pentagon general counsel. They were essentially presented with a done deal.

Office of Legal Counsel officials orally advised the administration that the operation would be legal, then finalized their written memo on Sept. 5. When lawyers from other agencies raised concerns, they were told there was nothing to debate because the Justice Department had already signed off.

At the Pentagon, a small circle of officials dove into the secret operational planning for boat strikes.

Mr. Hegseth signed an execute order that created the operational framework for the attacks. Dated Aug. 5 and written without input from many career Pentagon officials, it lifted language from previous orders developed for drone strikes against Al Qaeda targets in places like rural Yemen.

It lacked elements crucial to maritime operations — including any mention of what to do with shipwrecked survivors of an attack, officials said.

During the planning, an aide to Mr. Miller, Anthony Salisbury, pushed the Pentagon for ways to expand the scope of the operations, including loosening standards — like the level of confidence military officials would need that a target meets the criteria. Gen. Dan Caine, the chairman of the Joint Chiefs, advised that the military establish targeting criteria using lessons learned from the post-Sept. 11 wars.

Mr. Hegseth largely froze out of the process Adm. Alvin Holsey, the head of the Southern Command, which oversees the region’s forces. Admiral Holsey had begun to raise questions about the plans. For several months, Mr. Hegseth had contended that the admiral was not pursuing the drug-trafficking mission aggressively enough. Admiral Holsey abruptly announced in October that he would leave his position early, at the end of the year. His reasons remain unclear.

The Pentagon also bypassed a process called the Maritime Operational Threat Response, used to get input from various agencies when proposing a maritime action with international implications, said William D. Baumgartner, a retired Coast Guard rear admiral and lawyer who oversaw Caribbean operations.

On Sept. 2, when U.S. forces detected a speedboat with 11 people aboard, Mr. Hegseth gave the order to attack. Mr. Trump posted an edited video showing a single strike blowing the boat apart.

Among the Wreckage

In fact, after the first missile hit, two men climbed from the water atop the overturned hull and waved, said people who had seen a full video of the attack.

Frank M. Bradley, the three-star commander of the Joint Special Operations Command, the force carrying out the attack, had rehearsed in August for scenarios where there might be survivors. He ordered the additional strikes, sinking the wreckage and killing the initial survivors.

Other attacks soon followed. While Mr. Rubio became the public defender of the strikes, Mr. Miller became the White House overseer — he convened regular group meetings that included the Pentagon and other agencies. The Guardian reported earlier on his role.

Then on Oct. 16, after an attack in the Caribbean Sea, military officials spotted two survivors.

This time, a helicopter picked up the men and brought them aboard the USS Iwo Jima. The U.S. government soon sent them back to their home countries of Colombia and Ecuador. They have not been charged at home.

The episode set off a secret — and belated — scramble in the Pentagon on the question of survivors. In separate calls with the State Department, Pentagon officials even proposed sending them to CECOT, the Salvadoran prison, or having them repatriated or shipped to a third country.

Military lawyers revised the bare-bones “execute order” several times to include language on survivors, officials said. Some other officials said the changes reflected earlier planning. The revisions said the military had to treat detainees according to international law.

But senior officials made it clear in internal conversations that the best option, if survivors were spotted in the water, was to ask a nearby government to pick them up rather than have U.S. forces do it, an official said.

The Pentagon did not comment, following its standard practice on execute orders.

As the strikes continue, Mr. Trump, Mr. Rubio and Mr. Miller have moved on to the next stage of the campaign against Mr. Maduro: seizing oil tankers to deprive Venezuela of revenue. They say Mr. Maduro must return oil and other assets “stolen” from the United States before they lift the what Mr. Trump has referred to as a blockade.

In its first weeks, the tactic has shaken Venezuela’s economy by paralyzing its oil industry. Critics call it gunboat diplomacy or, as Mr. Maduro puts it, “a warmongering and colonialist pretense.”

Eric Schmitt contributed reporting from Washington.

Edward Wong reports on global affairs, U.S. foreign policy and the State Department for The Times.

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