Should Trump Have Authorized Khamenei’s Assassination?

President Donald Trump answers questions during a press briefing at the White House in Washington, D.C., February 20, 2026. (Aaron Schwartz/Getty Images)

A familiar historical example might shed some light on the wisdom of the decision.

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A familiar historical example might shed some light on the wisdom of the decision.

T he joint U.S.–Israeli attacks on Iran have raised a host of questions. Will Iranian sleeper cells in Western nations retaliate? Will a regime more friendly to the West take power in Iran? Will the new state stop sponsoring international terrorism? Also, has President Trump set a new precedent?

In January, Trump sent U.S. special forces to extract Venezuelan dictator Nicolás Maduro and bring him to the U.S. to stand trial. Clearly, there was also a desire to change the regime in Venezuela. Now, the U.S. military has cooperated with the Israeli forces that bombed Iranian command centers and killed Ayatollah Ali Khamenei and 47 of his associates. Trump has openly called for “regime change” in Iran and justified the killing of its leaders.


Nations are usually wary about killing the leaders of other countries, for a variety of legal and practical considerations. In 1981, President Ronald Reagan issued Executive Order 12333, which states: “No person employed by or acting on behalf of the United States Government shall engage in, or conspire to engage in, assassination.” It originated from revelations in the 1970s that exposed CIA involvement in plots against leaders such as Fidel Castro (in Cuba), Patrice Lumumba (in Congo), Rafael Trujillo (in the Dominican Republic), and others during the Cold War. Reagan’s order followed one made by President Gerald Ford in 1976, which held that assassinations violated international law and were against long-term U.S. interests.

Every U.S. president since has upheld a version of that ban on assassinations. President Obama tested its limits when his State Department lawyers argued that drone strikes in Pakistan, Yemen, and Somalia did not constitute assassinations but were uses of “lethal force in self-defense” against high-value terrorists who posed an “imminent threat.” President Trump has his own interpretation of what constitutes a legitimate use of force against foreign targets. He will not be moved by faux moral outrage from the likes of Vladimir Putin, who said that the targeting of Khamenei was “a cynical violation of all norms of human morality and international law.”




It is no surprise that many historians and philosophers have long debated whether the evil that Adolf Hitler represented would have justified his elimination before the beginning of World War II, which led to untold devastation, the loss of 70 million people, and the Holocaust. Many argue that Hitler’s complete control of the German government and his ideological fanaticism meant that he was central to the decisions to wage war and eliminate Europe’s Jews. Without him in charge, the Nazis would likely have been much less united and led by less aggressive figures, such as Hermann Göring. They argue that there was plenty of evidence prior to World War II of Hitler’s malign intentions, from his seizure of Austria and the Sudetenland in 1938 to the Kristallnacht pogrom later that year.

Others scoff at what they call the “hindsight bias” of some historians and argue that these historians ignore the anti-war sentiments of many Western voters at the time, not to mention what might have been the unintended consequences of any attempt on Hitler’s life prior to September 1939. They also claim that his assassination was never seriously contemplated before the war.


But that’s not entirely true.

In March 1939, just after Germany’s occupation of Czechoslovakia, Noel Mason-Macfarlane, the British military attaché to Berlin, warned his superiors in London that Hitler was a unique menace. He proposed to assassinate Hitler from his drawing room window, which had a perfect view of the podium at the reviewing stand where Hitler received his birthday salute from the armed forces on April 20 of every year. Mason-Macfarlane reportedly said that the distance of only 100 yards would have made for “an easy rifle shot.” He was convinced that the cheering of the crowd would conceal the location of the shooter. “I could pick the bastard off from here easy as winking.”

As the Sunday Times reported, Mason-Macfarlane also thought Hitler’s death would prompt the German army to move “against the Nazi regime.” He claimed that “the Prussian officer class in the army command had long been distrustful of, and distrusted by, Hitler,” so “this would be their opportunity.” He argued that “the risk of ferocious reprisals against British embassy staff should the Gestapo pinpoint the assassin would be nullified by a swift military coup that would remove the entire Nazi regime.”


Mason-Macfarlane attracted the attention of the British Secret Intelligence Service (SIS), led by Colonel Stewart Menzies, who summoned Mason-Macfarlane to London and was “cautiously interested” in the plan. However, it was rejected further up the chain of command. Lord Halifax, Prime Minister Neville Chamberlain’s foreign secretary, summed up his opposition by saying: “We have not reached that stage . . . when we have to use assassination as a substitute for diplomacy.” Mason-Macfarlane’s daughter, Mona Macfarlane-Hall, confirmed the existence of the plot to the German magazine Der Spiegel. She said it was rejected on the grounds that it “would not be sportsmanlike behavior.”

We’ll never know what would have happened. We do know that Mason-Macfarlane showed up on the reviewing stand for Hitler’s parade, along with other foreign envoys, and was captured by a photographer’s camera scowling. Before the war broke out, he was recalled from Berlin. He later served as governor of Gibraltar, and he died in 1953.


President Trump doesn’t share the Chamberlain government’s view that assassinating a foreign leader is not “sportsmanlike.” I myself have little sympathy for foreign leaders who reject out of hand the removal of dangerous dictators who threaten world peace out of abundant caution or because of international law. I find a bit more reasonable those who may not act for fear that they will in turn be targeted.

In April 1993, three months after leaving the White House, George H. W. Bush visited Kuwait to mark the victory over Saddam Hussein’s Iraq in the Gulf War. There, 16 people were discovered with a large explosive device and charged with planning a car-bomb attack against Bush. The suspects confessed to the FBI that Iraqi intelligence had orchestrated the plot. The CIA concluded that Saddam Hussein himself had green-lit the operation. One can argue that the plot to assassinate his father might have helped motivate President George W. Bush to invade Iraq a decade later, a decision that ultimately turned out badly for the U.S.

While my default position is always against war, there are times when the removal of a key instrument of evil can prevent a wider war that would kill many more people. Still, it is rare for any political leader to be willing to take on the personal risk of reprisal for having targeted an adversary. While we can and should question the wisdom or prudence of such a decision, we should also recognize the courage it takes to make it. In President Trump’s case, the fact that he has already experienced at least two assassination attempts makes his acquiescence in Khamenei’s killing all the more remarkable.


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