After Khamenei's Death, the Middle East Faces a Familiar Dilemma

On March 1st, Iran's Supreme Leader Ali Khamenei was assassinated. Donald Trump and Israeli Prime Minister Benjamin Netanyahu are celebrating their perceived "success." But does eliminating enemy leadership actually work in the Middle East?

The track record suggests otherwise—and the consequences of this latest gambit could be far more dangerous than the problem it aimed to solve.

The Hollow Victory of Killing an 86-Year-Old

Killing Khamenei wasn't exactly a military masterstroke. The 86-year-old leader was already planning his succession due to failing health. With the combined firepower of the US and Israel, his elimination was more inevitable than impressive.

The real question isn't whether they could kill him—it's whether they should have. Middle Eastern history offers a sobering answer: leadership assassinations don't create peaceful outcomes. They open doors for more radical successors or unleash chaos that spirals beyond anyone's control.

Consider Iraq. When US forces captured Saddam Hussein in 2003 and handed him over for execution, they eliminated a regime openly hostile to Israel. But they also created a power vacuum that pro-Iranian forces quickly filled. For the next two decades, Iraq became the launchpad for Iran's regional proxy strategy, spawning a network of non-state actors that threatened US and Israeli interests far more effectively than Saddam ever had.

The security collapse triggered multiple insurgencies, culminating in ISIS—a force that swept across the Middle East, killed thousands including US citizens, and sent massive refugee waves toward American and Israeli allies in Europe.

When Assassinations Backfire

The pattern repeats with disturbing consistency. Take Hamas: Israel has been targeting its leadership since the early 2000s. In 2004, they successfully killed founder Sheikh Ahmed Yassin, then his successor Abdel Aziz Rantisi, who was considered a moderate.

A few assassinations later, Yahya Sinwar rose to lead Hamas in Gaza—and went on to orchestrate the October 7, 2023 attack. Hezbollah tells a similar story. The late Hassan Nasrallah, who transformed the group into a formidable regional power, only became its leader after Israel assassinated his predecessor Abbas al-Musawi.

Two and a half years of warfare may have devastated both organizations, but Israel failed to kill the idea behind them: resistance to occupation. The current lull in fighting might just be the quiet before another storm.

The Negotiator They Just Lost

In Iran's case, the timing seems particularly counterproductive. According to Omani intermediaries involved in recent talks in Muscat and Geneva, Khamenei was prepared to make significant concessions on the nuclear issue. His replacement is unlikely to have the political capital—or inclination—to continue down that path.

If Israel and the US push for complete regime collapse in Iran, the resulting chaos could dwarf previous disasters. Based on recent experiences in Iraq and Libya, a security vacuum in Iran would have devastating consequences for US allies throughout the region and Europe.

The question becomes: what exactly do Israel and the US gain from this "decapitation" strategy?

Political Calculations vs Strategic Thinking

For Netanyahu, the answer is straightforward. Facing crucial elections and four corruption charges that could end his political career and land him in prison, the short-term popularity boost is worth almost any long-term risk. Israeli leaders rarely plan beyond the next election cycle and don't bear the consequences of military adventurism abroad—especially when Israeli society overwhelmingly supports it.

But Trump's calculation is murkier. He gets to boast about eliminating an 86-year-old ailing leader to a war-weary American public. Yet at a time of ongoing cost-of-living crisis, he's spending billions of taxpayer dollars fighting a country that posed no imminent threat—a war many Americans increasingly see as "Israel's war."

Instead of projecting strength, Trump risks appearing as a president manipulated into starting a costly conflict to ensure the political survival of a foreign leader. He's drawn a line at putting US boots on the ground, but he'll eventually have to end the bombing campaign and withdraw American forces, leaving behind yet another Middle Eastern disaster for US allies to manage.

Domestic audiences will eventually ask hard questions about another expensive military adventure with no clear returns. The hope is that Washington might finally learn what history keeps teaching: in the Middle East, the cure is often worse than the disease.