The oil sanctions pushed Venezuela’s already unraveling economy into a tailspin, but Mr. Maduro has been able to keep some revenue flowing by readjusting the country’s foreign trade to Asia, Russia and Turkey. In April, he quashed Mr. Guaidó’s attempt to provoke a military uprising and doubled down on repression and state surveillance to tighten his grip on power.
Analysts said the new sanctions will allow Mr. Maduro to blame the economic crisis, which began when he took office in 2013, on the trade barriers imposed by the United States. It is a propaganda message long employed by his government’s closest ally, Cuba.
Neil Bhatiya, a sanctions expert at the Center for New American Security in Washington, said it is not clear from the text of Mr. Trump’s order how aggressively the new sanctions will pursue global companies that do business with Venezuela’s government, or firms linked to it.
He suggested the action could amount to a scare tactic — with widespread economic and strategic implications — that could backfire on the United States, as it could push Venezuela closer to United States’ rivals like Russian and China and could isolate American companies in the country for years, he said.
“That would be obviously the opposite of the intent of the administration in pursuing this goal,” Mr. Bhatiya said. “They want to see Maduro leave, but I think it is in the realm of the plausible that he is able to stay for an indefinite period of time, because he is being bailed out by countries we can’t touch.”
In Lima, Mr. Bolton mentioned Cuba nine times in 12 minutes, saying that extreme economic pressure will “work in Venezuela and it will work in Cuba.” The United States has banned most trade with Cuba since 1962, without toppling its government.
But the message seemed aimed at American voters, particularly in Florida, said Geoff Ramsey, head of the Venezuela program at the Washington Office on Latin America. Florida has a large Cuban-American population and is crucial to Mr. Trump’s re-election prospects.