This is the ayatollah’s war. Now as in June, the pileup of Supreme Leader Ali Khamenei’s mistakes served President Trump a strategic opportunity too inviting to pass up. On Saturday, Khamenei paid with his life.
The proximate error came during negotiations, in which Iran all but announced it still wants to pursue nuclear weapons. What else was Mr. Trump supposed to conclude from Iran’s evasions?
No more domestic enrichment of uranium for nuclear fuel, the president said. This was hardly unreasonable; 23 nations operate nuclear power programs by importing enriched uranium. U.S. negotiators even offered to provide Iran the fuel free of charge, a senior administration official said Saturday. Iran balked. Despite vast oil reserves, Iran claimed to need nuclear power and its own enrichment program. For this, it would risk everything.
One of Iran’s last proposals, the Journal reports, was that it be allowed to maintain thousands of advanced centrifuges and enrich uranium to as much as 20% purity—covering most of the technical effort to reach weapons-grade. As the nonproliferation expert Andrea Stricker put it, the regime’s clear purpose was “to maintain the means to produce nuclear weapons fuel at a time of its choosing.” Each Iranian “compromise” along those lines was more evidence of the regime’s goal: hanging on to the capability to pursue nuclear weapons.
This was the ayatollah’s policy, for which he has made his people suffer for two decades. What made it so damaging this time was the revolutionary context. In January the Iranian people showed that they seek to overthrow the regime. The regime responded by showing that it rules only by the bullet.
“You better not start shooting,” Mr. Trump warned Iran’s leaders amid the country’s protests, “because we’ll start shooting too.” The regime scoffed. “Trump says things like this a lot,” Ali Larijani, Iran’s National Security Council chief, commented. “Don’t take him seriously.”
Khamenei taunted Mr. Trump and crossed his red line as flagrantly as he could, slaughtering thousands in the streets—at least 32,000 in two days, Mr. Trump said. The president was willing to overlook a few dozen killings in the protests’ early days, but the astonishing scale guaranteed a confrontation and made a limited response difficult.
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.
Wouldn’t this have been a good moment to secure some sanctions relief? A compromise on nuclear enrichment could have shored up the regime. From there, it could have waited out the Trump administration to fight another day.
Khamenei refused. The ayatollah may have thought he had to stand firm, or else the U.S. and Israel would never cease pushing him around. The truth is that his own errors had already brought about the collapse of Iran’s deterrence. Pretending that June’s 12-day war had changed nothing only made a sequel more likely.
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: 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.
Israel ruled the skies over Tehran and lost not a single jet, striking Iran’s most sensitive assets at will. Iran’s missiles and drones failed to inflict major damage in reply. Israel’s success was so great, and Iran’s weakness so glaring, that Mr. Trump had as low-risk a shot on the remaining nuclear sites as planners could ever have imagined.
Having lost its crown jewels, Iran fired off some missiles, hit a U.S. radar dome, and asked for a cease-fire. Yet after this meager performance, and weakened in the war, the regime spent the past few months repeating the same threats from before June. This time it would really fight.
Iran has scored some deadly hits, killing at least three U.S. service members and 11 Israeli civilians, but is it any wonder Mr. Trump wasn’t deterred at the outset? Experience had given him confidence that the risks were manageable.
Khamenei 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.
Those proxies were supposed to do the Iranian regime’s bidding, but under the stresses of the Oct. 7 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.
This left Iran alone when it counted in June, as it has been so far in this war. This makes all the difference: Imagine if Israel also had to deal with Hezbollah’s full arsenal. Proxies could still join the fight, but they have been so weakened that the prospect was no longer enough to deter Israel or the U.S.
Today’s Operation Epic Fury owes everything to Khamenei’s mistakes. He squandered his proxies and insurance policy. He 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.
Most disastrously of all, Khamenei continued to underestimate Mr. Trump. He wasn’t the only one. 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.
Wrong. 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.
Mr. Kaufman is a member of the Journal’s editorial board and a co-author of “In the War Room: The Inside Story of Israel’s Fight Against Hamas and the Iranian Axis,” forthcoming in September.