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“History repeats itself,” Karl Marx famously observed, “first as tragedy, second as farce.” When it comes to American presidents and Iran, someone has been holding the repeat button.
In his remarks prior to signing a memorandum of understanding with Iran, President Donald Trump said that the Iranian regime’s leadership was “very rational” and “not radicalized.”
On June 16, the president told reporters, “We’re dealing with people that I think are very rational people. They were nice to deal with. They were strong people, smart people. I think actually they’re smarter than the first and second group, but they’re not radicalized and they’re, you know, looking to help their country.”
For his part, Vice President JD Vance said that “it’s worth seeing” if the “incredible pressure” that the United States has put on Iran will lead the regime to change its behavior.
The vice president is correct to note that the U.S. not only has tremendous leverage over Tehran, but that the circumstances preceding negotiations with the Iranian regime are very different than they were more than a decade ago under then-President Barack Obama.
The Trump administration and its Israeli ally took the fight to Iranian soil and delivered massive and devastating blows. The upper echelons of the regime’s political and military leadership were eliminated and its defense industrial base severely degraded.
The U.S. easily obtained air supremacy and put Iran’s navy into “the bottom of the ocean,” as Secretary of War Pete Hegseth memorably put it.
This is a significant achievement that is singular in the annals of American history.
But the Trump White House’s hopes for “moderates” to suddenly emanate from the Islamic Republic ended in predictable disappointment. By July 8, after weeks of Tehran violating its MOU with Washington, Trump’s opinion of Tehran’s leaders had changed. Trump ordered additional U.S. military strikes on the country and now said of its rulers: “I don’t like them at all … they’re bad people … I think they’re incompetent.”
For now, the administration’s experiment with Iranian “moderates” appears over, having ended in failure — just as it has for successive administrations since the regime’s bloody birth nearly half a century ago.
Iran’s 1979 Islamic Revolution was led by fervent anti-American ideologues. But many top officials in the Carter administration were slow to catch on.
In a November 1978 memo, U.S. Ambassador to Iran William Sullivan called Ayatollah Ruhollah Khomeini a “Gandhi-like” figure. Carter’s ambassador to the U.N., Andrew Young, said that Khomeini was “some kind of saint.”
He was no such thing. And U.S. officials should have known better.
In February 1979, Khomeini arrived in Iran from his exile in France. He immediately set about ushering in Iran’s Islamic revolution and earning a reputation as one of history’s great tyrants. Under his rule, Iran shifted from being a longtime American ally to an avowed nemesis.
The Shah’s ouster might not have been predictable, but what Khomeini would do once seizing power certainly was. Like another antisemitic tyrant before, Adolf Hitler, Khomeini had left a road map of his intentions. Hitler wrote a book. Khomeini made tapes.
The Shah kicked Khomeini out of Iran in 1964, after the aging cleric refused to quit agitating against his government. From his exile, first in Iraq and later in France, Khomeini gained supporters inside Iran thanks to a network of aides that distributed tapes of his virulent anti-American and antisemitic sermons.
But U.S. officials didn’t bother listening to the tapes. As Scott Anderson documented in his 2025 book on the fall of the Shah, King of Kings, CIA and American embassy officers stationed in Tehran had been collecting the tapes, sold on the black market, for years.
But “among those Americans gathering the Khomeini cassettes, none spoke Farsi” and by December 1978 only one “had reportedly been curious enough to have a tape transcribed.” And the CIA didn’t even bother passing that transcript on to the NSC or the State Department. The tapes languished in CIA desk drawers.
The Carter administration would be the first to misread Iran’s bloodthirsty revolutionaries. But it wouldn’t be the last.
Ronald Reagan wasn’t one to fall for the propaganda of dystopian police states. The Gipper famously said that the U.S. must “trust but verify” arms control agreements with the Soviet Union. But even he fell prey to the myth of Iranian moderates.
In a Dec. 7, 1985, diary entry, Reagan described a meeting with top advisers about a “complex plan which could return our 5 hostages and help some officials in Iran who want to turn that country from its present course and on to a better relationship with us.”
Under the plan, Israel would sell weapons to Iran, and in exchange, Tehran would release hostages, he wrote. But “the weapons will go to the moderate leaders in the army who are essential if there’s to be a change to a more stable government,” Reagan optimistically noted.
The 41st president had found his “moderates” in the Islamic Republic. He was describing what would soon be known as the Iran-Contra affair, in which the proceeds from arms sales would be used to fund the Contras, an anti-Sandinista group in Nicaragua.
The idea was a disastrous one and led to the indictments of numerous Reagan administration officials, up to and including the secretary of defense himself.
On Iran, George H.W. Bush was more cautious. But even he would fall into the same trap, hoping that more prudent leadership would prevail in Iran after Khomeini’s 1989 death.
In February 1990, Bush even took a phone call from someone claiming to be an adviser to Iranian President Ali Akbar Hashemi Rafsanjani. Although the call was vetted and flagged as “suspicious,” Bush nonetheless decided to take it. The caller would later be identified as an imposter. The incident, largely forgotten today, testifies to the deep desperation and desire by U.S. presidents for outreach to Iran.
Rafsanjani would spend decades being described by Western press outlets as a “moderate.” In fact, he was Khomeini’s longtime bagman, and even directly supplied the weapon used to murder Hasan Ali Mansur, a close ally of the Shah, in 1965.
Bill Clinton would also inhale the myth of regime moderates.
In his first term, Clinton eyed Tehran warily. In 1996, the Islamic Republic and its proxies perpetrated the bombing of Khobar Towers, a U.S. housing complex in Saudi Arabia. But even this didn’t stop the former Arkansas governor from being enticed by the idea of detente with the Iranian regime.
In 1997, the election of Mohammad Khatami seemed, at first glance, to offer an opportunity. In an interview with CNN, the new Iranian president said that he wanted to tear down the “wall of mistrust” that existed between the two countries.
Clinton and his advisers leaped at the opportunity.
The Clinton administration eased sanctions against Iran, and Clinton himself said that he “regrets the estrangement of our two nations … and I hope that the day will soon come when we can enjoy once again good relations with Iran.”
Clinton wanted an official dialogue with Iranian leaders and looked to the Swiss, the Omanis, and Saudi Arabia to try to facilitate talks. Clinton officials offered to meet without preconditions, and Secretary of State Madeline Albright even went as far as apologizing for the U.S.’s (greatly exaggerated) role in a 1953 coup in Iran.
In exchange, Tehran gave them the runaround. Iranian officials didn’t show up to scheduled talks, took weeks to respond, and outright ignored messages. Khomeini’s successor, Supreme Leader Ali Khamenei, dismissed Albright’s apology as “worthless.”
Not for the last time, the U.S.’s outstretched hand would be met with an Iranian fist.
The failed rapprochement should have been a lesson: the Islamic Republic is a theocracy. Its clerics and other ideologues have the final say.
But future presidents would prove unable to resist the siren song of detente.
George W. Bush famously labeled Iran as part of the “Axis of Evil.” Critics and revisionists, including a former Middle East director on Bush’s National Security Council, would later charge that the president’s rhetoric effectively ended Khatami’s outreach and paved the way for his more “hard-line” successor, Mahmoud Ahmadinejad.
In fact, the distinction was a false one. The real moderates were either dead, exiled, or held in the notorious Evin Prison. But the refrain would become familiar, and the search for fabled Iranian moderates ongoing.
Colin Powell, who served as secretary of state in Bush’s first term, eventually became a believer that an accommodation could be reached with the Islamic Republic over its nuclear weapons program.
That view was fully embraced by the Obama administration, which prioritized a “deal” with Iran at all costs. Indeed, as Michael Doran of the Hudson Institute argued at the time, Obama sought nothing less than a full accord with the world’s leading state sponsor of terrorism.
In a 2016 interview with The Atlantic, Obama said that traditional allies such as Israel and Saudi Arabia must learn to “share the neighborhood” with Iran. While ostensibly about the regime’s nuclear program, the Joint Comprehensive Plan of Action, popularly known as the “Iran Deal,” was really about ceding American power in the Middle East to Tehran, at the cost of both American interests and longtime alliances.
Unsurprisingly, it was a difficult sell.
Obama and his top advisers created what deputy national security adviser Ben Rhodes infamously called an “echo chamber.” They served up a number of red herrings, variously claiming that the only alternative to the JCPOA was war, that sanctions relief would somehow benefit the Iranian people and not the regime, and that the deal would empower “moderate” elements at the cost of “hardliners.”
The Iran Deal represented a significant departure. Whereas previous administrations had fooled themselves that mythical moderates could be found, the Obama administration took it a step further by trying to fool the American people themselves.
The JCPOA was adopted. Yet Iran never changed its behavior. The Islamic Republic continued to destabilize the region, its proxies, now flush with cash, advancing throughout the Middle East, spreading terrorism and havoc in their wake.
The Biden administration, filled with Obama retreads, continued to look for “moderates” as it lifted sanctions and appeased the regime.
A half-century of looking at the Islamic Republic through rose-colored glasses hasn’t served the U.S. well. Washington would do well to bury one of its most enduring delusions.