The New York Times’ Sept. 28 piece on “the mood” inside Venezuela portrays a country bracing, confused, and cynical amid Washington’s lurches between pressure and engagement. A reading that to a great degree can be attributed to the fact that of the sources the report cites, all are sympathetic to the regime. Whether it’s malpractice, considering that a perfect opportunity to ask the Maduro regime uncomfortable questions was missed, is a question worth asking. More importantly, however, is to address how the piece fundamentally misreads President Donald Trump’s strategy while leaving Venezuela’s Nicolás Maduro’s narrative unscrutinized.
The Times’ Julie Turkewitz misdiagnoses not only popular sentiment in Venezuela, by not challenging the regime’s talking points, but also U.S. strategy. What can look from Caracas like whiplash is, in fact, a deliberate “squeeze” designed to narrow Nicolás Maduro’s room for maneuver: brief, reversible openings to secure concrete gains — paired with fast-escalating pressure that steadily raises the cost of loyalty inside the regime. Recent months supply the clearest evidence yet — and there’s a logic reporters like Turkewitz refuse to grasp.
The Trump administration distinguishes means from ends: brief openings function as calculated moves to erode Maduro’s leverage and attain concrete short-term wins—unlike the Biden administration, which blindly accepted hollow promises of democratization. Critics who mistook Trump’s policy changes as incoherence seized on the Trump administration’s seemingly contradictory moves earlier this year.
During the Biden administration, Washington eased oil sanctions in exchange for vague electoral commitments from Caracas — concessions that ultimately produced little democratic reform and allowed Maduro to consolidate power. This approach echoed aspects of the Obama-era policy, which leaned on engagement and multilateral diplomacy. In March, Trump reimposed targeted sanctions just days after Chevron had been allowed to continue operations in Caracas for thirty days — an apparent contradiction that in fact reflected a calibrated effort to extract economic leverage without conceding political ground.
In April, Trump loudly reversed Biden-era oil diplomacy — moving to cancel the sanctions waivers that allowed Chevron and other European oil companies to operate in Venezuela. By February 2025, the State Department set a deadline of May 27 for all foreign oil companies to exit Venezuela, signaling a return to “maximum pressure” via oil sanctions.
Yet by late spring, Trump’s own envoy, Ambassador Richard Grenell, was pursuing a back-channel negotiation with Maduro. In a stunning development, Grenell struck a deal in May to extend Chevron’s license for 60 days — once again, apparently contradicting the hard line from the State Department. In February, after Grenell’s meetings in Caracas, six Americans who had been detained in recent months — on what the U.S. later called politicized, due-process-free charges — were released and flown home with the envoy.
In May, following a separate round of talks in Antigua, U.S. Air Force veteran Joseph St. Clair — detained near the Colombia–Venezuela border under unclear circumstances — was also freed. Grenell accompanied him back to the United States. Both deals led to seven of these Americans released from wrongful detention beginning in February.
The imagery of Grenell shaking hands with Maduro — and the notion that he was offering oil sanctions relief without any additional demands — seemed to confirm the skeptics’ narrative that Trump was putting American oil and hostages above other strategic considerations.
What looked like appeasement sparked furious blowback from within Trump’s own party. Cuban-American lawmakers from South Florida — long-time Venezuela hawks — felt betrayed that Trump would even temporarily ease pressure on Maduro. In fact, three Florida Republicans in the House nearly derailed Trump’s entire tax-and-spending bill in protest, leveraging their votes to force a reversal of the foreign strategy.
Secretary of State Marco Rubio acted on these concerns. Rubio, who for more than a decade was perceived as the most vocal opponent of the Maduro regime in the Senate, advised the President to rescind the oil license. By May 24, Rubio’s desire materialized: he publicly announced that “the pro-Maduro Biden oil license in Venezuela will expire as scheduled” on May 27. The White House, facing a South Floridian revolt in Congress, agreed that no extension would be granted, apparently undercutting Grenell’s approach.
By July 18, 2025, however, a bigger swap was on the table: Venezuela freed 10 Americans in exchange for more than 200 Venezuelans whom the U.S. had deported to El Salvador’s CECOT prison earlier in the spring. With help from El Salvador’s President Nayib Bukele, the three-months-in-the-making deal materialized. Shortly thereafter, Washington quietly resumed its relaxation of its oil stance as the White House partially reinstated the Chevron license extension that it had proposed and then denied in May.
To skeptics in Washington and many Venezuela-watchers, these moves looked like Trump playing soft with Maduro — leveraging oil and immigration policy to cut deals. But this was not the endgame. By engaging in limited deals, Trump’s team achieved two critical objectives: (1) get Americans home and remove the leverage Maduro had enjoyed by holding these hostages (after the July 18 swap, “every wrongfully detained American in Venezuela is now free and back in our homeland,” the State Department said), and (2) address his administration’s domestic priorities (deportations and stabilizing oil markets) without permanently empowering Maduro. Each concession to extend the oil licenses is temporary and reversible.
Add to this pressure the still-outstanding March executive order threatening a 25% tariff (say, a secondary sanction) on countries trading in Venezuelan oil or gas, and the hawks lamenting a supposed softening begin to look out of step with reality.
The clearest sign that Trump never abdicated on Maduro came just weeks after these supposedly appeasing deals, on August 8, when the U.S. government announced it was doubling the reward for Maduro’s capture to $50 million. This historic reward sets a record as the highest reward ever offered by the United States for a foreign leader’s arrest. By comparison, Osama bin Laden had a $25 million price tag on his head — a figure Maduro’s bounty now doubles.
The $50 million reward did not come out of thin air. It was built on a legal framework established back in 2020, during Trump’s first term, when the Justice Department indicted Maduro and his top associates on drug trafficking and narco-terrorism charges. At that time, an initial reward of $15 million was offered for Maduro’s arrest. The Biden administration later raised it to $25 million, matching the reward set on bin Laden.
U.S. Attorney General Pam Bondi minced no words about Maduro’s status: “He is one of the largest narco-traffickers in the world and a threat to our national security. Therefore, we doubled his reward to $50 million.” Following up in her actions, AG Pam Bondi revealed that DOJ has seized $700 million linked to Nicolás Maduro, describing the scheme as “organized crime, no different than the mafia.”
The timing was no coincidence. With multiple Americans finally safely out of Venezuelan jails, the administration calculated it could escalate this pressure without endangering U.S. lives. The $50 million reward serves two purposes: (1) a symbolic one sending a powerful message about Washington’s priorities, the Trump administration signals that it views the Venezuelan dictator as an equal or greater menace to American security than Bin Laden, and (2) a strategic one as the reward is designed to incentivize Venezuelan middle military and insiders to turn against Maduro — not to attract foreign bounty hunters as people might speculate.
Fifty million dollars is an almost unimaginably high sum in impoverished Venezuela; it plants seeds of doubt and paranoia within Maduro’s inner circle. Who might be tempted to give information or facilitate Maduro’s arrest for such a payout? Can Maduro truly trust his generals and officials, some of whom are already disgruntled? By dangling this golden carrot, the U.S. hopes to encourage fractures in the regime – essentially inviting someone on the inside to do what external force has so far failed to do. The four top officials in Maduro’s regime face an additional $45 million reward, pressure that could cause them to turn on their leader. Former Pentagon official Alex Plitsas says Maduro “reeks of weakness.”
Even more significant than the reward is the Trump administration’s decision to treat Maduro and his network as terrorists, not just criminals. Over the last few months, the U.S. has rolled out a series of terrorism designations aimed at the heart of Maduro’s power structure. Two notorious Venezuelan organized criminal groups — the Cartel of the Suns (Cartel de los Soles) and Tren de Aragua — have been officially labeled Foreign Terrorist Organizations (FTOs) and Specially Designated Global Terrorists (SDGTs) by U.S. authorities.
The Cartel of the Suns is not a traditional cartel in the Mexican or Colombian sense, but rather a nickname for a coalition of high-ranking Venezuelan military and officials (the term refers to the sun insignias on generals’ uniforms). For years, American officials have accused this shadowy network of facilitating massive drug trafficking operations — effectively turning Venezuela’s state apparatus into a cocaine pipeline. A 2024 report by Transparencia Venezuela suggests the volume of cocaine transported by the Venezuelan regime jumped with record Colombian output, estimating ~639 tons transited Venezuela in 2023, nearly 24% of world production. With that amount, you’re looking at about 255–383 million potential lethal doses, enough cocaine to kill the U.S.’s entire population.
In tandem, the Tren de Aragua — a brutal, vertically-unorganized Venezuelan gang turned transnational crime group — was also hit with the terrorist label; the same group held responsible for the murder of Laken Riley and Jocelyn Nungaray. Critically, U.S. officials suggest Maduro’s regime has given oxygen, even led, such groups — using them as proxies to do dirty work. The Treasury Department alleges that the Cartel of the Suns ”provides material support to Tren de Aragua and the Sinaloa Cartel,” effectively acting as a facilitator for their narco-terrorism activities. In return, Tren de Aragua is reportedly helping Maduro flood the U.S. with cocaine (even fentanyl-laced cocaine) as a “weapon” against American society.
Moreover, Trump’s assertive military moves in the past few months show that he is meeting Maduro’s serious cross-border criminality with an equally serious regional security focus, unmatched since President Ronald Reagan. Maduro has largely inoculated himself against domestic democratic pressure — by jailing opponents, rigging institutions, and insulating his inner circle with security patronage — and he diffuses sanctions pain onto ordinary Venezuelans while funding the regime through illicit oil, gold, and cocaine routes. Trump’s decision to expand military operations within the sea borders of Venezuela isn't simply a prelude to invasion so much as a high-visibility lever: it gives Washington interdiction muscle, intelligence reach, and — above all — coercive signaling that backs indictments and sanctions with steel. It confronts Maduro in an arena he understands: force.
Moreover, the administration’s Caribbean build-up shows it is meeting Maduro’s cross-border criminality with a regional security response — not saber-rattling for its own sake. In August, Washington surged three Aegis destroyers (USS Gravely, USS Jason Dunham and USS Sampson) toward Venezuela; within weeks an amphibious ready group with the 22nd Marine Expeditionary Unit (USS Iwo Jima, USS San Antonio and USS Fort Lauderdale), plus the USS Lake Erie, USS LCS Minneapolis–Saint Paul, P-8 patrol aircraft, and at least one fast-attack submarine joined the theater. A fourth destroyer, USS Stockdale, then transited the Panama Canal to reinforce the presence.
In September, U.S. forces conducted multiple strikes on alleged Venezuelan-linked drug boats — the first publicly acknowledged U.S. airstrikes in the region in decades — killing 11 in the initial attack and at least 17 across the month; in a joint follow-on operation, the Dominican Navy recovered hundreds of packages of cocaine from the first boat.
The Times piece misreads Venezuela by centering regime-aligned voices — regime-bought “militiamen,” contested vice-president Delcy Rodríguez, and Henrique Capriles (a former presidential candidate that now cooperates with Maduro’s regime) — while sidelining the movement that actually contests Maduro’s power. By still referring to Nicolás Maduro as the “president” after the stolen July 28, 2024 vote in which Venezuelans overwhelmingly backed the opposition, the New York Times appears to be riding an anti-Trump narrative, even if it means cozying up to a foreign tyrant.
By not reporting that many Venezuelans who support U.S. involvement — especially targeted pressure and enforcement — rather than blanket “hands off” sloganeering, the New York Times granted the Maduro regime a concerning amount of sway in their story. And lastly, by framing recent U.S. moves as mere inconsistency, ignoring the strategic picture that lays behind the moves, the Times is giving its readers unsophisticated analysis.
The result is a piece meant to critique Trump that, in practice, launders a pro-Maduro narrative — normalizing an illegitimate ruler and obscuring the coalition of Venezuelans and international partners pressuring for a democratic transition.
Recent military escalation in the Caribbean, coupled with all the measures that preceded these, show the true intentions from the Trump administration. They are willing to engage in hard power as they ratchet up a coercive “inside-out” strategy — pairing visible hard power with law-enforcement tools and economic squeeze points — not to launch a conventional intervention, but to raise the cost of loyalty within Caracas to intolerable levels, encourage elite defections, and force Maduro to play on Washington’s terms.
What the Times piece captures in color, it misses in structure. Maduro still sits in the Miraflores Palace, but the walls may be closing in. Those who describe President Trump’s Venezuela policy as incomprehensible oscillations between softness and bruteness mistake the moves for the endgame. Now, with terrorist labels as shackles, a $50 million reward for Maduro’s arrest, and an armada on his front yard, the pressure has reached its crescendo.
Somewhere in his palace, Maduro must be wondering which of his own pieces could turn against him first. And that is exactly the point. Washington is no longer reacting to events — it is setting the incentives, and forcing the game onto its terms.
