When Donald Trump wanted to cut Keir Starmer down to size in March, he reached for his hero. "This is not Winston Churchill," the president said in the Oval Office, after Britain initially refused to let U.S. forces use its bases, including Diego Garcia, for strikes on Iran.
Trump has often made clear his reverence for Churchill. On his first day back in the White House in 2025, Trump restored a bust of Churchill to the Oval Office, just as he had in 2017, righting, as he saw it, a wrong made by two Democratic presidents.
During the pandemic, Trump likened himself to the wartime leader who, he said, would "go to a roof in London and speak" as Adolf Hitler’s bombs fell.
Today, like Churchill, Trump is facing an escalating European crisis and a difficult Kremlin. But is Trump as Churchillian as he presents? How does Trump’s handling of Vladimir Putin and the Ukraine war compare with how Churchill dealt with the huge issues he faced during World War II and the Cold War? Put simply: what would Sir Winston do?
Historians of Churchill’s dealings with Moscow have answers that may unsettle Trump’s admirers and critics alike.
Churchill would very likely have sought a summit with Putin, and he might well have leaned on Kyiv to accept a hard bargain. But he likely would have insisted on negotiating from strength, with Europe in the room, for stakes he judged strategic.
Trump is channeling a real Churchill, just not the one he imagines. Not the defiant leader of 1940, but the deal-hungry summiteer of 1944. The difference is that Churchill, playing a weakening hand, still extracted a price.
On October 21, Trump’s envoy Steve Witkoff met Putin in St. Petersburg for the ninth time, and praised the man raining missiles on children’s playgrounds in Ukraine as a "humanitarian."
It followed Trump’s October 9 deal for Russian diesel, and his October 16 waiver of most of the sanctions and tariffs imposed on Russia in a bipartisan law he had signed less than a month earlier.
There is a case for bringing Russia closer in the interests of resolving the Ukraine crisis. But to many observers, this was naked self-serving opportunism ahead of a difficult set of midterms where energy prices are politically toxic.
A deal on Ukraine may be taking shape. Trilateral negotiations look set for November. But those hoping Russia will pay a price beyond the blood and treasure it has charged itself may be left wanting.
A Parley at the Summit
Churchill actually supplied the language of Trump’s diplomatic style. In Edinburgh in February 1950, he called for a "parley at the summit" with Moscow, coining the term.
Professor Richard Toye of the University of Exeter is co-author with Warren Dockter of the forthcoming book Churchill and Russia, and co-host of the podcast "Churchill: The Finest Half Hour."
He told Newsweek Churchill stayed convinced until he left office in 1955 that personal meetings, "man-to-man if you like, were the way to solve big international problems." Toye, a leading expert on Churchill, said he had no wish to flatter Trump, China’s Xi Jinping, or Putin, "but in that sense, they are kind of following in his footsteps."
Nor was Churchill squeamish about bargaining with a dictator over the heads of smaller nations. In the Kremlin on October 9, 1944, he pushed a half-sheet of paper across the table. It proposed 90 percent Russian predominance in Romania and a 90 percent British say in Greece. Josef Stalin ticked it with a blue pencil.
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Dr. Martin Folly, a historian at Brunel University of London, is co-author of Churchill and Stalin: Comrades-in-Arms During the Second World War. He called this percentages agreement "a clear cold-blooded bargain."
At the same meeting, the two leaders agreed to call Poland’s exiled leaders to Moscow for talks. Churchill warned them that refusing would relieve Britain of further responsibility toward them. He was, Folly told Newsweek, "not above bullying his Polish allies."
There are echoes of this with Trump. Diesel averaged $6.18 a gallon in mid-October, up from $3.48 at the start of the year. Trump calls lower prices for farmers, ranchers, and truckers "my Greatest Priority." Trump told Kyiv to stop striking Russian refineries—the economic engine of Moscow’s war—and says he finds Volodymyr Zelensky "more difficult to deal with than Putin."
Folly thinks Churchill, too, "might have counseled the Ukrainians to weigh up the realities of their situation." And Thomas Graham of the Council on Foreign Relations argues that Putin will not be hauled off to The Hague: "peace will have to be made with him."
Strength, Allies, Stakes
The analogy breaks on what Churchill brought to the table. His belief in the 1950s, Toye said, was that if you "talk tough to these people" and back it with "sufficiently credible threats, including nuclear threats," Moscow could be made to see reason.
At Fulton, Missouri, in 1946, Churchill said of the Russians that there was "nothing they admire so much as strength."
But Trump has spent this October easing the pressure on Russia instead. The Treasury suspended U.S. sanctions on Russian diesel until April 2027. That is the kind of relief Chatham House had warned in May against offering Moscow as an incentive.
Trump also pressed Ukraine to halt a refinery campaign that has degraded Russia’s capacity to produce diesel, a financial lifeline.
Sir Laurie Bristow, Britain’s ambassador in Moscow from 2016 to 2020, judged in February that Putin "has read Trump’s motivations correctly and is playing him accordingly."
Then there is the room. Churchill, a postwar champion of European unity, "would have wanted Europe too to be at such a summit," Folly said.
Trump announced the diesel deal on the day Ukrainian, British, French, German, EU, and NATO officials were meeting his envoys in Florida. He acted, in the words of CFR’s Matthias Matthijs, "without consulting anyone in Europe."
And there are the stakes. Churchill’s half-sheet listed nations whose fate hung in the balance, which he well knew. Trump’s ledger lists tonnage linked to his own political fortunes at home.
Trump’s deal promises more than 300,000 tons of diesel at once. By analysts’ arithmetic, that is less than a single day of U.S. consumption. In return, Moscow gets sanctions relief that lawmakers from both parties warn will help fund Russia’s war.
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Churchill conceded Romania, where Soviet armies already stood—but he secured Greece in exchange.
Toye’s distinction is one of motive: Churchill, he said, was "acting in relatively good faith, whereas I don’t think that Trump genuinely is," instead serving his own personal interests.
Churchill also misread Stalin, Folly said, admiring his humor and intelligence. Folly cannot picture him taking to Putin, a figure "too much of secret policeman/apparatchik for Churchill’s taste."
Yet age brought Churchill closer to Trump’s style. He "becomes more Trump-like as he gets older and as his health declines," Toye said, believing he could "just show up and ramble on and it'll all be sorted out" without much preparation.
After Stalin’s death, Churchill called in May 1953 for a meeting at the highest level. In 1954 he sounded out Soviet Foreign Minister Vyacheslav Molotov about a two-power summit. Objections from Washington and his own Cabinet stopped him.
The big difference with Trump, Toye said, is "the quality of his advisers" and the willingness of those around Churchill "to stand up to him."
The deepest difference of all is temperamental. The romantic in Churchill, Folly said, would have been "far more stirred by the story of Ukrainian resistance against the might of Russia" than Trump appears to be.
Zelensky made the connection himself in March 2022. He told the House of Commons that Ukrainians would fight "in the forests, in the fields, on the shores, in the streets."
Toye warns against pushing 1940 too far: "to compare Putin to Hitler is a bit extreme."
The Test
The most instructive Churchill, then, is the bargainer of 1944. The old giant of British politics sets Trump a clear test.
Suppose the current St. Petersburg channel yields a ceasefire that Kyiv and Europe sign, backed by guarantees that hold through a winter of expected Russian escalation, and lead ultimately to a lasting deal. Trump will have achieved what Churchill tried and failed to do with Stalin’s successors.
But if sanctions relief buys neither a durable truce nor cheaper diesel by the November 3 midterms, then Trump will have spent the strength Churchill thought Moscow respected above all, and with little to show for it in return.
The "finest hour" Churchill summoned in June 1940 was a refusal to bargain. His most transactional moment came four years later, under Stalin’s blue pencil. Even then he made Stalin concede Greece in return for Romania.
Churchill still worried, as he later wrote, that the deal might be thought "rather cynical." It is hard to imagine Trump worrying about perceived cynicism.
But if Trump wants a finest hour of his own in Ukraine, Churchill’s record points one way: talk to Putin, but make him pay.