After decades of treating the Islamic Republic with kid gloves, American and Israeli hard power exposed the regime’s weakness and fueled historic protests
In 2009, what shocked me about President Barack Obama’s lack of support for the Green Movement protesters in Iran was the failure to launch of the commander-in-chief’s colossal ego. Here were thousands of young Iranians filling the streets of Tehran to appeal to him, even with a wistful pun on his name: “Obama, ba ma bashid!”—Obama, be with us! Anyone in government at the time knew that the Chicagoan lacked nothing in the way of ruthlessness, though he tended to save it for Republicans of the non-Islamic variety; he applied the word enemy to the GOP but never the mullahs. If righteous anger at the regime’s murder of dissidents didn’t meet the threshold for Chicago Rules, I thought, surely vanity might do the job.
But opening to Iran had been an early theme of his presidency that same year, with a mushy Persian New Year message and a secret letter to Supreme Leader Ali Khamenei, whom he knew little about. “Despite his title as supreme leader, Khamenei’s authority wasn’t absolute,” Obama preposterously intoned in his memoir A Promised Land (2020). “He had to confer with a powerful council of clerics”—the Guardians Council. Referring to the clerics, journalist Karim Sadjadpour has observed that “their average age is ‘deceased.’”
“My first impulse was to express strong support for the demonstrators,” Obama records further on in that memoir. “But when I gathered my national security team, our Iran experts advised against such a move. According to them, any statement from me would likely backfire … activists inside Iran feared that supportive statements from the U.S. government would be seized upon to discredit their movement.”
The latter statement was ridiculous on its face, as the demonstrators were openly pleading for outside support, and from him specifically. He may have been ignorant of how Ronald Reagan’s harsh anti-Moscow rhetoric boosted the morale of imprisoned dissidents like Natan Sharansky. But what of that “national security team”? Obama does not name them, but his administration would become known for high-level sentimentalists toward Iran: Rob Malley, Samantha Power, Philip Gordon, Sahar Nowrouzzadeh, and the diplomatic weaklings who would negotiate the nuclear deal.
Iranians have seen the regime and its backers exposed and humiliated by an American administration, and they were quick to exploit this roll of the dice.
So Obama issued a series of statements that he himself would describe as “bland,” “bureaucratic,” and “passive,” bitter that “I had to listen to Republicans howl that I was coddling a murderous regime” (actually, he was six years away from truly coddling it). Our cerebral leader lamented that as president, “my heart was now chained to strategic considerations and tactical analysis, my convictions subject to counterintuitive arguments; that in the most powerful office on earth, I had less freedom to say what I meant and act on what I felt than I’d had as a senator.” In other words, what passed for his convictions were easily defeated by an “America Bad” briefing from his subordinates.
Numbers are still inexact, but Tehran’s thugs made about 4,000 arrests and killed hundreds to quell the 2009 demonstrations. The Green Movement’s leaders were jailed. Globally, dissidents of all stripes, as well as Madonna and U2, spoke out in favor of Iranian democracy. Was it a bitter pill for a cool cat like Obama not to be in that club? I suspect not, as he harbored some sentimentality towards the Islamic Republic, having stated in his first letter to its leader, as well as in his taped video message on the occasion of Nowruz, the Persian New Year, that he sought normalization with the state sponsor of terror—a long step beyond hoping for better relations with Iran someday, as you might do in a holiday greeting.
I was not in Washington at the time but was serving as an intelligence officer in the field, and I was only a peripheral observer of Iran. Everyone knew that the Green Movement’s candidate, Mir Hossein Mousavi, had been cheated out of the electoral win the very night of the election in favor of Mahmoud Ahmadinejad. That was no surprise. It was mildly surprising, though, to see Obama’s later statement that maybe it was no big deal, as the difference between the two Iranians “may not be as great as had been advertised,” a statement that might have been true (the gradations within the Death to America regime are slight) but that succeeded in insulting all Iranian parties involved.
I did know one thing Obama did not, however, from a casual conversation with an Iranian intellectual who described his sense of how Ali Khamenei and his ruling circle viewed Obama. “They are deeply threatened by him,” he said. “He is young and handsome, intelligent, and well-spoken. He has charisma. He has unparalleled American political and military power, is genuinely popular, and pays attention to Iran. In terms of population and landmass, you know, Iran is comparable to France, and we want the same respect. We don’t get it. We know we don’t get it because of these ugly old mullahs who don’t represent us and aren’t popular. The mullahs know all this. They are Mr. Obama’s opposite. There is this term in Persian, havvu— it is the beautiful second wife who displaces the first wife. Barack Obama is the mullahs’ havvu. They truly fear his appeal to Iranians.”
How relieved they must have been.
It is improbable that Obama could have made much of a difference, even if he had known any of that. His eventual nuclear deal took the greatest of pains, in its evolution and in how it was sold to the public, to brush aside any U.S. interest in addressing Tehran’s terrorism, ballistic missiles, regional destabilization, or domestic repression. The Joint Comprehensive Plan of Action further weakened any U.S. leverage over Iran, because to preserve the deal, Washington had to swallow Tehran’s endless prevarication and cheating. “Anytime, anywhere inspections” turned out to be the joke, it always seemed. Obama deferred to Iran’s murderous sponsors in Russia and China, and its subordinates in Lebanon. Back in my White House years, when the “EU 3” were trying to interest us in going down this road in 2004, my boss, National Security Council Senior Director for Near East and North Africa Elliott Abrams, told the president, and me, that “the Iranians will lure the EU half way down that path, and then everything will start falling apart. The EU will have a stake in not looking foolish, so they won’t be able to turn back. We’re not going there with them.”
The Mahsa Amini murder and the alliterative Zan, Zendegi, Azadi (“Woman, Life, Freedom”) demonstrations 18 years later saw more arrests, nearly 20,000. About a dozen were executed in 2022. Under the notoriously brutal President Ebrahim Raisi, the repression machine, principally the Basij militia in the streets and “digital curfews” imposed against internet and cell phone use, was more drastic than in 2009. Demonstrators were shot and blinded in the streets and subjected to torture, sexual violence, and forced confessions once detained.
Additionally, this time, Tehran had little to fear from the senile caretaker in the White House. Apart from new pro forma U.S. Treasury sanctions against Iran’s morality police (how many of them had American bank accounts to freeze?), the Biden administration limited itself to deploring the violence and expressing good wishes. Biden foolishly stated at a campaign event that “we’re going to free Iran—they’re going to free themselves pretty soon.” The White House was forced to backtrack, saying that this was an “expression of solidarity” with the Iranian people and did not signal any wish to intervene. Whew.
Both Obama and Biden lacked any life experience outside of American politics and had always played for low domestic stakes. They were like their co-partisan John Kerry, who, despite his wartime service, foreign wife, and lavish overseas travel, was a naïf. I remember a gushing New York Times headline touting the six-foot-four-tall talking tree (as Tina Brown once described him) as “America’s Mr. Diplomacy”—because he was apparently such an awe-inspiring presence when you sat opposite him at the negotiating table.
Here is the thing, though. The negotiating table is nothing. It’s everything you have done outside that room that has brought your adversaries there and shaped their approach that matters. Kerry thought his command of details and his wingwoman, the weepy Wendy Sherman, would impress the Iranians. But Obama had created a weak battlespace around them all by calling off the dogs of Project Cassandra, the U.S. government program to squash the Iranian-backed Hezbollah’s global drug-trafficking network. At Obama’s obsequious direction, the FBI stopped pursuing cases against Iranians, weakening counternarcotics, counterproliferation, and counterintelligence efforts, permitting only counterterrorism work to proceed. Obama hoped the Iranians would read this as a positive sign of openness. But the hard men of Tehran read it, and with deadly accuracy, as exactly what it was: craven weakness.
Former U.S. Embassy Tehran hostage and Iranophile John Limbert once told me on a visit to Los Angeles that the Iranians are not great strategists. “You think they’re great chess players, with all the patience for carpet weaving, tile work, reassembling shredded U.S. embassy cables, and figuring out the future. No, what they are is great backgammon players. The dice roll, and they see an opportunity or a challenge, and they react brilliantly. The dice land, and they see a weakness, and they move against it like lightning.” He should have been the frequent White House visitor that former regime official and visiting research scholar at Princeton University, Seyed Hossein Mousavian, was under the Democrats.
So, after two weeks of the largest nationwide demonstrations in Iran since the Islamic Revolution, what has changed and why? It had nothing to do with negotiating tables and a lot to do with battlespace.
First, let’s note that this month’s huge anti-regime demonstrations in more than 100 Iranian cities were not ignited by a single big domestic event like a blatantly stolen election or the murder of an innocent young woman. The Iranian rial has been crashing past a million to the dollar for weeks, and inflation reached the point where the Tehran bazaar was losing money on every transaction, so it closed. Something else drove the following events such as the South Pars energy strike and reported military defections.
The battlespace started shaping up six years ago this month under Trump, with the U.S. killing of the Islamic Revolutionary Guard Corps-Quds Force commander Qassem Soleimani, the second most powerful man in Iran, by U.S. drones at Baghdad Airport. He had just arrived from Damascus, where he was briefing former Syrian President Bashar al-Assad on a plan to attack the U.S. Embassy in Baghdad, as had been done in Tehran in 1979. Iran’s Iraqi cat’s-paw, Abu Mahdi al-Muhandis, and 10 senior Iranian briefers and bodyguards were also killed in the strike. After 20 years of Bush, Obama, and Biden kid gloves, Tehran was legitimately frightened.
And then after the Tehran-directed atrocity against Israel in October 2023, Israel killed Yahya Sinwar, Muhammed Deif, Hassan Nasrallah, Ibrahim Aqil, Hashem Safieddine, and Ismail Haniyeh in an IRGC safe house in Tehran, and almost a hundred more in Lebanon and Gaza. Deprived of its decapitated Hezbollah Praetorian Guard—the Syrian Ba’ath Party didn’t trust its own people any more than the Bolivarian Maduro trusted Venezuelans more than Cubans—the criminal Assad family fled to Moscow. Then, last summer, the Israeli and U.S. air forces wiped out much of the Iranian military’s general staff and key nuclear sites. The pro-Tehran, Moscow, and Beijing dominoes continued to fall with the capture of Nicolas Maduro, the massacre of his Cuban protection detail, the seizure of Russia’s ghost ships, and the spread of Starlink terminals in Iran.
Iranians have seen the regime and its backers exposed and humiliated by an American administration, and they were quick to exploit this roll of the dice. Unlike pro-Hamas nihilists from Berkeley to Dublin, they have hit their streets in millions without a single keffiyeh or “Allahu Akbar,” motivated by American successes against their regime and its feckless backers.
As of the time of writing, the regime has turned off the internet and all landlines, and Khamenei has emerged from a two-day silence to express defiance. This is no surprise to anyone who knows that Khamenei’s greatest fear is moderation that causes the regime to bend and then break. As expressed in Alex Vatanka’s The Battle of the Ayatollahs in Iran, Khamenei became obsessed with the prospect of an “Iranian Gorbachev” who would impose reforms and usher in a USSR-style collapse; the more so because this was addressed by Tom Friedman, a Jewish American journalist, in a 1996 column titled “Waiting for Ayatollah Gorbachev” after he visited Iran. That pressed all of the leader’s buttons. Expect his defiance to continue as long as he is alive or in power.
Which may not be long, because he faces two threats. The one in front of him is the unpredictable Donald Trump, who has already shed Iranian blood and has promised to “rescue” the Iranian people. The one behind him is the IRGC, which holds all the firepower in Iran and which knows—as Mahmoud Ahmadinejad knew—that the mullahs are despised by nearly the entire population. They are unlikely to lay down their guns or give up the 40% of the Iranian economy they control. They are led by Ahmad Vahidi, an internationally sanctioned terrorist.
“Terrorists are assholes” was a wise saying of one of my counterterrorist colleagues at the CIA. She didn’t just mean that terror plots ruined our weekends and sleep schedules. She meant that terrorists are psychopathic, disloyal, and venal creatures who could and did mistreat each other and turn against each other. The top ranks of the IRGC are full of them.
What might lead the IRGC to sideline or overthrow Khamenei and his weak president, Masoud Pezeshkian? Two kinds of strikes: an anti-regime blow from the United States, or the labor variety that would shut down Iran’s energy sector. If both occur, my money is on a coup, and goodbye mullahs.
