Trump’s ‘Winston Churchill’ jibe to Starmer was ironic. This is how he would have dealt with Iran war
When Donald Trump criticized Keir Starmer for not sufficiently supporting American and Israeli operations against Iran, he did so with historic flourish. “The person we are dealing with is not Winston Churchill,” he complained.
The implication was clear: Churchill would stand shoulder to shoulder with Washington in a conflict with Tehran. These words raise an obvious question: What would Churchill say about war with Iran?
The answer is not as simple as Trump’s comparison suggests. Churchill’s record shows a mixture of hawkish rhetoric, strategic caution, and abiding concern for preserving Anglo-American unity. Far from embodying a simple instinct for conflict, he tended to see war and diplomacy as inextricably linked.
Churchill’s famous speech in Fulton, Missouri, in 1946 is an example of this. In this speech, he warned that the “iron curtain” had descended on Europe. But the speech, officially called The Sinews of Peace, was not merely a call to arms against Soviet expansion. Churchill simultaneously emphasized the need for understanding between adversaries and the importance of strengthening the United Nations. His basic message was that peace could best be preserved if Western powers demonstrated sufficient unity and force to deter aggression.
Iran was already involved in the geopolitical crisis surrounding this speech. At the time, Soviet troops had failed to withdraw from northern Iran despite wartime agreements. This event formed part of the initial tensions that would harden into the Cold War. So Churchill was already viewing Iran through the lens of great power competition.
This perspective had deep roots. During World War II, Churchill traveled to Tehran in 1943 to meet with Franklin D. Roosevelt and Joseph Stalin at the first conference of the allied “big three”. The meeting took place in Iran’s capital because the country had become an important logistics corridor through which Allied supplies flowed to the Soviet Union.
For Churchill, the conference was a sobering experience. Roosevelt increasingly cultivated Stalin’s good will, sometimes at Britain’s expense. Churchill later rued that he sat “between the great Russian bear and the great American buffalo” while Britain was like “the poor little English donkey”. These words reflected Britain’s growing awareness that it was no longer one of the world’s dominant powers.
This realization reinforced a central element of Churchill’s post-war strategy: the development of a lasting Anglo-American partnership. Fulton’s call for a “special relationship” between the British Commonwealth and the United States was not merely a rhetorical gesture. This was an attempt to anchor Britain’s future security within the emerging American-led order.
Irony of Churchill reference
However, Churchill’s thoughts on Iran did not end with cold war diplomacy. In 1953, during his second term as prime minister, Britain and the United States supported a covert operation that overthrew Iranian prime minister Mohammad Mossadegh and restored the authority of Shah Mohammad Reza Pahlavi. The coup was largely organized by the CIA under the direction of Kermit Roosevelt Jr., but Churchill enthusiastically supported the plan. When Roosevelt later described the operation to him in Downing Street, the aging prime minister reportedly declared that he would gladly serve under his command in such an enterprise.
This episode shows that Churchill could certainly support strong action where he believed Western interests were threatened. But it also highlights a historical irony. The overthrow of Mossadegh became one of the main complaints voiced by Iran’s revolutionary leaders after the Iranian revolution. Since 1979, the Islamic Republic has repeatedly resorted to foreign intervention, particularly the Anglo-American coup, to legitimize its rule and portray itself as the defender of Iranian sovereignty against external domination.
In other words, the legacy of Western intervention in Iran has become one of the regime’s most powerful political weapons.
Churchill was well aware that wars and interventions could have unintended consequences. Reflecting on his experiences as a young officer during the Boer war, he later wrote that statesmen lost control of events when the signal for conflict was given. The war suffered “bad fate, ugly surprises, terrible miscalculations.” This was not the feeling of a pacifist. But this was the observation of someone who has seen how quickly political decisions can unleash forces that no government can fully control.
About the author
Richard Toye is Professor of Modern History at the University of Exeter. This article is republished from The Conversation under a Creative Commons license. Read original article.
What would Winston do?
How might these instincts translate into the current crisis? It was almost certain that Churchill viewed the Iranian regime with deep suspicion. The Cold War mentality led him to view international politics in terms of ideological conflict and strategic balance. He could well argue that weakness in the face of aggressive regimes invited further challenges.
At the same time, Churchill rarely believed that military intervention alone could resolve geopolitical disputes. His preferred approach was to combine decisiveness with diplomacy, negotiating forcefully with enemies while maintaining communication channels. Even at the height of the Cold War, he hoped that the West’s strong position might eventually persuade the Soviet leadership to make a bargain.
Above all, Churchill believed that Britain’s influence depended on maintaining close alignment with the United States. However, in his view, this alignment was aimed at shaping American power rather than reflecting it. The “special relationship” was supposed to be a partnership, not a blank check.
Trump’s mention of Churchill thus relies on a simplistic image of the wartime leader as an instinctive advocate of military action. The historical record reveals a more complex person: a strategist who believed in power, but also in diplomacy, alliances, and the careful management of great power rivalries.
If Churchill were alive today, he might actually be calling on Western governments to show determination. But he would also likely recognize that Iran’s political system is shaped by the memory of past foreign interventions and that any new conflict would risk strengthening the very forces it seeks to weaken.
Churchill once observed that war, once unleashed, rarely follows the orderly paths imagined by those who started it. This warning may be as relevant as any of his more famous statements.
