President Donald Trump did not have an unreasonable request. The president warned Iran, “You better not start shooting because we’ll start shooting too.” Iran’s National Security Council Chief scoffed, “Don’t take him seriously. Trump says things like this a lot.”

Supreme Leader Ali Khamenei’s mistake was crossing President Trump’s red line as flagrantly as he could, by slaughtering at least 32,000 in two days. The president, perhaps, was willing to overlook several dozen killings a day, but the astonishing scale made a limited response difficult, writes Elliot Kaufman in the WSJ.

The people of Iran had been driven to the streets by economic immiseration, and the regime had no answer but gunfire. While it smuggled a billion dollars to Hezbollah in the first 10 months of 2025, amid the January protests it offered its own citizens only $7 a month.

If you were thinking this might have been a good time for the regime to secure some sanctions relief, you’d be proven wrong. Refusing to wait and fight the Trump administration another day, the ayatollah may have thought he had no choice but to stand firm. Would the US and Israel ever stop punching him around?

In the lead-up to June, Iran had issued the kind of threats that had deterred U.S. and Israeli action for two decades. Some in the West believed it, reports Kaufman.

Tucker Carlson wrote that “a strike on the Iranian nuclear sites will almost certainly result in thousands of American deaths.” He warned of $30 gasoline and world war. None of it happened.

Ruling the Skies

Not losing a single jet, Israel hit Iran’s most sensitive assets. Iran, unable to retaliate, gave Mr. Trump as low a risk shot on the remaining nuclear sites as planners could ever have imagined.

Why wasn’t Mr. Trump deterred at the outset? As Mr. Kaufman notes, experience had given the president confidence that the risks were manageable.

Khamenei, writes Kaufman, had erred in giving Israel that same confidence before the 12-day war.

He did it by departing from his own strategy of not directly engaging the Jewish state in war, at least not before acquiring nuclear weapons. Massive Iranian ballistic-missile strikes in April and October 2024 showed Israel that it could withstand the assault and allowed it to destroy Iran’s key air defenses in reply. This left the nuclear program exposed, inviting attack.

All the proxy warfare in the world hadn’t done that. Even the Oct. 7, 2023, invasion by Hamas death squads—funded, armed, and trained by Iran for that purpose—didn’t make Iran a target. Neither did the entry into the war of the rest of Iran’s proxy axis.

Weren’t those proxies to have done Iran’s bidding?

With the stress of the 7 October war, Iran ended up intervening more or less on their behalf. Perhaps Khamenei felt it necessary given the beating his proxies were receiving at Israel’s hand. Generational investments in Hamas and Hezbollah were sinking before his eyes.

Hezbollah was the insurance policy for Iran’s regime and nuclear program. It deterred attacks on Iran by threatening to rain down 150,000 missiles on Israel’s major cities. But Khamenei spent that insurance by directing Hezbollah to join Hamas’s war on Oct. 8, 2023, and then to keep firing rockets for 11 months. Keeping this front alive past the point of diminishing returns was another mistake, which allowed Israel to defang Hezbollah in late 2024.

Khamenei lost his air defenses and allowed the U.S. and Israel to test their own.

He risked a war in June that exposed Iran as a paper tiger. He tanked his currency with postwar intransigence, then slaughtered his people when they rose up to protest, trampling over Mr. Trump’s red line. He was transparent in his effort to keep a nuclear option and refused to adapt to a radically altered balance of power.

Khamenei wasn’t the only one to underestimate Donald Trump, notes E. Kaufman.

The conventional Western analysis has long been that this president would settle for an agreement like Barack Obama’s from 2015 and then call it the greatest deal ever made.

In the end, Khamenei presented Mr. Trump with the best opportunity any president was ever likely to have to weaken, transform or topple this Iranian regime, America’s most implacable adversary.