If Vladimir Putin’s quarter-century of expansionist rule has taught the West anything, it’s that the Russian president shouldn’t be taken at his word.

That hasn’t stopped top US officials from perpetually buying the Russian strongman’s lines. President Donald Trump’s biggest misconception is that Putin wants peace in Ukraine, despite overwhelming evidence to the contrary.

Now, Trump’s team risks falling victim to its own credulity again.

Just as Moscow is helping to target drones threatening US troops in the Iran war, according to a CNN report, the administration may ease more of the sanctions intended to weaken Putin’s Ukraine killing machine. The hope would be to lessen Trump’s political jam over oil prices.

It would be an extraordinary twist if Putin emerged as the first winner of the deepening Middle East crisis because Trump rocked global energy markets by launching his own war.

Putin gloated over the oil shock at a Kremlin meeting two days ago, according to Pulitzer Prize-winning oil expert Daniel Yergin. “Vladimir Putin has won the lottery here. He’s the biggest winner so far because the price of oil is way up to fund his war. And the sanctions are being taken off,” Yergin, vice chair of S&P Global, told CNN’s Erin Burnett on Wednesday.

In the latest US-Russia melodrama of the Trump era, a top Russian official huddled with Trump’s team in Florida on Wednesday. Special envoy Kirill Dmitriev met special envoy Steve Witkoff; the president’s son-in-law Jared Kushner; and White House senior adviser Josh Gruenbaum. “The teams discussed a variety of topics and agreed to stay in touch,” Witkoff said in a readout that touched on none of the suddenly burning US-Russia issues.

But before the meeting, Witkoff downplayed reports that the Russians were providing Iran with intelligence about the movements of US troops, ships and aircraft. He said on CNBC on Tuesday that Moscow had denied such behavior during Trump’s call with Putin the day before. “So, you know, we can take them at their word. But they did say that,” he said.

On CBS’ “60 Minutes” Sunday, Defense Secretary Pete Hegseth downplayed risks to US troops from Russian activity, insisting, “No one is putting us in danger.”

But the plot thickened Wednesday when CNN’s Nick Paton Walsh exclusively reported that Russia was helping Iran with drone tactics learned in Ukraine to hit US and Gulf targets. This is the most overt and concerning such cooperation yet between the anti-US axis allies, a Western intelligence official said.

Also on Wednesday, Ukrainian President Volodymyr Zelensky, who has sent his drone experts to help US forces counter Iranian Shahed drones, said that Russians were helping the Islamic Republic not just with unmanned aerial vehicles, but also with missiles and air defenses.

Zelensky’s offer is the latest sign of how bitter drone duels between Ukraine and Russia have reshaped the character of warfare. This dynamic has now jumped to a new theater as budget-price weapons threaten the world’s most sophisticated military.

Disclosures about Russia’s drone targeting also underscore the complex game Putin plays to exploit global crises even as he cultivates his relationship with Trump to advance his goals in Ukraine.

Trump hopes the Iran war will soon end as a fearsome US and Israeli barrage against the Islamic Republic is complicated by a crisis of the locked-down Strait of Hormuz, a vital oil transportation corridor.

A consequent spike in oil prices is threatening Trump’s already-fragile position, and has prompted his administration to look for ways to respond.

Washington had been successfully coercing India to lessen its dependence on Russian oil to help pressure Moscow into ending the war in Ukraine. But last week it granted a 30-day waiver to allow New Delhi’s refiners to buy oil from Russia’s ghost fleet. Treasury Secretary Scott Bessent told Fox Business on Friday, “We may unsanction further Russian oil.”

His comment drew a call from Democrats on the Senate Banking Committee for an investigation and testimony from Bessent, first reported by Punchbowl News.

An unexpected oil bonanza is only one of the ways Putin can benefit from the war in Iran. The United States and its European allies may divert resources and arms away from supporting Kyiv’s war effort. And while Trump’s team met Putin’s envoy, European allies are still reeling from the president’s fury over their reluctance to join the assault on Iran. This is all grist for Putin’s long-term strategy of fracturing cohesion among NATO states.

These benefits may partly offset blows to Russian foreign policy if the Iranian regime is weakened or eventually topples. Russia lost another ally this year with the US special forces raid that toppled Venezuelan leader Nicolás Maduro in January.

Putin has strong rationales for helping Iran:

Russian help is valuable for Tehran, meanwhile, far beyond the propaganda value of assistance that implies it’s not confronting the fury of the US and Israel alone.

Russia’s murderous raids on Kyiv and other cities have enabled its specialists to refine formations and tactics, often using dozens of drones simultaneously. Such expertise could help Tehran confront US and Gulf air defenses. Moscow also has satellites used for precise targeting.

Still, Putin has a fine line to walk. His core interest is winning the war in Ukraine, in part by prolonging peace talks to allow his ground forces to grind out new territorial gains. He can’t afford a direct clash over Iran with the United States, or a military confrontation.

The Kremlin has not commented on the latest reports that it is helping Tehran directly with its drone program, which are a further embarrassment for the Trump administration.

The president’s empathy with the Russian strongman has helped define both his administrations. Trump once said that he and Putin were victims of a “witch hunt” over intelligence community assessments that Moscow meddled in the 2016 election. Witkoff, the face of the administration’s so-far thwarted attempts to bring peace to Ukraine, has followed his boss’s lead. He often emerges from meetings with Putin sounding like the Russian leader. “I don’t regard Putin as a bad guy,” he said last year of a man who launched an invasion that has killed thousands of Ukrainians.

Then there was a transcript of a phone call reviewed and transcribed by Bloomberg last year that showed Witkoff coaching a top Russian official on how to talk to Trump.

A 28-point peace plan Witkoff drew up last year could have been written by Moscow and took weeks of finessing by Secretary of State Marco Rubio before it could serve as the basis for talks.

Republicans are often forced to dance on the head of a political pin over Trump’s relationship with Putin.

Kansas Sen. Roger Marshall told CNN’s Kaitlan Collins on Wednesday that the global energy situation amid the Iran war was “very delicate.” He added: “I think the lifting (of) the oil sanctions on India, buying Russian oil, I think that’s doing something good for America right now.”

But he went on: “Of course, I have no use for Russia either … I think just as quickly as we took those sanctions away, we can put them back on.”

That may take a while, especially given expectations that turbulence in energy markets could endure for weeks even if the Strait of Hormuz reopens soon. Stunning imagery Wednesday of two tankers burning in the Gulf following suspected Iranian attacks raise the possibility meanwhile of a deepening crisis.

Unless Trump manages to extricate the United States soon, he may share something else with Putin: having started a war that miscalculated an adversary’s capacity to fight back and that drags on longer than he expected.