Donald Trump has a Churchill problem. Not the kind he thinks.
When British Prime Minister Keir Starmer hesitated to open UK military bases for the Iran strikes last week, Trump was furious. Standing in the Oval Office beside German Chancellor Friedrich Merz, he delivered his verdict on the special relationship in nine words: “This is not Winston Churchill that we’re dealing with.”
The implication was clear. Churchill would have said yes immediately, bombed enthusiastically, and never flinched. Starmer — cautious, legalistic, quietly horrified — was cast as the timid contrast to the great wartime bulldog.
But here is what Trump’s Churchill invocation leaves out: the real Churchill didn’t just bomb his enemies. He also tried to talk to them. He negotiated. He built alliances painstakingly. He worried constantly about unintended consequences. He wrote, after witnessing the Boer War as a young officer, that once the signal for conflict was given, statesmen lose control of events.
That warning has aged remarkably well. It is, in fact, the story of the past ten days.
“I Got Him Before He Got Me”
The strikes that killed Ayatollah Ali Khamenei on February 28 were not framed by the White House in the language of grand strategy. Trump was more direct than that. “I got him before he got me,” he told ABC News, referencing Iranian-backed plots to assassinate him during the 2024 election cycle. In a separate conversation with The Atlantic, he admitted that Iran had offered significant concessions in the final round of nuclear talks — but that his recent military successes, including the capture of Venezuela’s Nicolas Maduro, had made him feel he could demand more. “A year ago, it would have been great to accept that deal,” he said. “But we have become spoiled.”
Personal vendetta and military overconfidence, in other words, sat alongside any strategic calculation. The killing of Khamenei was, by Trump’s own account, partly about scores settled.
Then the consequences arrived — exactly as they always do.
The Heir Nobody Wanted, the Oil Shock Nobody Needed
Within nine days of Khamenei’s death, his son Mojtaba was installed as Supreme Leader. Brent crude punched above $114 a barrel. The Strait of Hormuz — through which roughly one fifth of the world’s daily oil supply travels — was effectively sealed. Iran kept launching missiles, now with the new supreme leader’s name inscribed on the warheads.
The regime did not crumble. It promoted from within and kept shooting.
This outcome was not unforeseeable. In fact, it was predicted — repeatedly, by historians, strategists, and the kind of sober analysts Trump tends to dismiss. The belief that removing one man from the top of a hostile state will unravel that state is among the most persistent and most thoroughly disproven assumptions in modern warfare. It doesn’t matter how precisely the strike is executed. The system underneath simply replaces whoever falls.
Yamamoto died over the Solomon Islands in 1943, shot down by American fighters after US codebreakers intercepted his travel plans. Japan kept fighting for two more years. Saddam Hussein survived the opening “decapitation strike” of the Iraq War, and when he was eventually caught, dishevelled and hiding underground, the country did not stabilise — it fractured along lines that bled for the next two decades. The CIA tried to kill Fidel Castro at least eight times between 1960 and 1965, deploying methods ranging from poison pills to an exploding cigar. Castro outlasted ten American presidents.
None of these precedents stopped Trump. None of them ever stop anyone, which is precisely the point.
What Churchill Actually Believed
Trump invoked Churchill as the archetype of resolve — the leader who never hesitated, never lawyered, never blinked. The historical record is more complicated.
Churchill’s actual strategic philosophy, documented across decades of speeches, memoirs and private correspondence, rested on a specific combination: negotiate from positions of strength, but always keep channels of communication open with adversaries. Even during the Cold War, at the height of his anxieties about Soviet power, he pursued the idea that western strength might eventually bring Moscow to the table. Firmness and diplomacy were, in his mind, not opposites but partners.
He was also deeply clear-eyed about Iran specifically. Churchill had attended the 1943 Tehran Conference, sitting between Roosevelt and Stalin as allied leaders carved up wartime arrangements. He emerged sobered, aware that Iran sat at the intersection of competing great-power interests and that interventions there carried long historical tails. A decade later, the Anglo-American coup that toppled Iranian Prime Minister Mohammad Mosaddegh in 1953 — in which Churchill’s government was intimately involved — produced exactly the kind of unintended consequence he feared: it handed the Islamic Republic its founding grievance, a story of western interference that the regime has weaponised for legitimacy ever since.
Trump’s Churchill, in other words, is a simplified cartoon of the man — the bulldog without the brain, the fighter stripped of the diplomat.
A War Trump Is Now Fighting Alone
The Churchill jibe has also exposed something Trump didn’t intend to reveal: just how isolated the United States is in this war.
After a year of tariff threats, diplomatic insults, and the systematic alienation of European partners, Trump launched a major military operation with only Israel beside him. Britain eventually allowed limited use of its bases for defensive strikes, but drew a clear legal boundary around wider involvement. France’s Emmanuel Macron declared the strikes illegal under international law. Spain barred American military planes from its jointly operated bases in Andalusia — and received a trade war threat in response. NATO intercepted an Iranian missile near Turkish airspace, but the alliance has moved carefully to avoid being dragged deeper in.
“This is not Winston Churchill we’re dealing with,” Trump said of Starmer. The irony is that Churchill’s entire doctrine of Western power rested on precisely the alliances Trump has spent years eroding.
The War That Was Supposed to End Quickly
Trump told ABC News the Iran operation could last weeks. He demanded Iran’s “unconditional surrender” on social media. He said the strike had been so successful it had killed most of the post-Khamenei candidates he had identified — “second or third place is dead” — as if the problem of Iranian governance could be resolved by eliminating enough people on a list.
At least 1,230 Iranians have been killed since the strikes began, according to the Iranian Red Crescent. Over 120 died in Lebanon. Ten Israelis have been killed by Iranian attacks. Oil is above $114 a barrel. Asian markets recorded their worst single session since the COVID crash of 2020. Mojtaba Khamenei is firing missiles under his own name.
Churchill wrote, reflecting on a lifetime of wars, that once the signal for conflict is given, statesmen lose control of events. That insight didn’t make him a pacifist. It made him careful.
Trump saw Churchill and thought: warrior. History offers a fuller picture — a man who understood that the hardest part of any war is not the killing. It is knowing what you want the morning after.
That morning is arriving in Tehran now. The question of what comes next has no clear answer. And the man who ordered the strike, confident and unilateral, is discovering what every leader who has walked this road before him eventually discovers:
Decapitation is easy. What follows is not.