With President Donald Trump’s decision to intervene in the Iran-Israel war, Iran, a country 6,500 miles away from Washington, D.C., has once again taken an outsize role in the story of an American presidency. In fact, Iran has been a big part of American presidencies for nearly a century.

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Although most people know the story of how the Iranian hostage crisis helped bring down President Jimmy Carter, the truth is that Iran has been a challenge for American diplomats for decades. In 1924, during the Coolidge administration, a mullah-inspired mob in Tehran attacked and murdered American Vice Consul Robert Imbrie, inflicting 138 wounds on him. Imbrie was falsely accused of poisoning a sacred fountain, and his murder made him the first American foreign service officer ever killed abroad. The United States sent a warship to retrieve Imbrie’s body, billing Persia for the cost, and President Calvin Coolidge attended Imbrie’s funeral at the New York Avenue Presbyterian Church in Washington. Three of the killers were caught and executed following an attempt to commute the sentences that angered American officials. Amid the turmoil, head of the Persian military Reza Khan declared himself to be the shah of Persia 18 months after Imbrie’s murder, renaming himself Reza Shah Pahlavi.

The end of the Coolidge administration did not spell the end of trouble for American diplomats in Persia. In September 1932, with President Herbert Hoover reeling from the Great Depression and on the cusp of losing a landslide election to Franklin Roosevelt, three American diplomats were kidnapped by what the New York Times referred to as “brigands.” The motivation for the kidnapping was to secure the release of prisoners held by the Persian government. Persian troops rescued the three diplomats a few days later, but the incident shows that hostage-taking is an old tactic in what is now known as Iran.

Eleven years later, Roosevelt became the first U.S. president to visit what is now called Iran. It was not relations with Iran that drove the visit but the Tehran meeting of the so-called Big Three: Roosevelt, Winston Churchill, and Josef Stalin, the Allied powers of World War II. Still, Roosevelt was gracious, meeting with the shah and thanking him for his hospitality, even as he and his advisers worried about instability in Iran and both Soviet and British ambitions for the oil-rich nation.

Roosevelt’s successor, Harry Truman, was the first president to host an Iranian leader in Washington. Mohammad Reza Shah Pahlavi had taken over after his father, Reza Shah Pahlavi, abdicated in 1941. It would be the first of 12 visits he made to the U.S., and no top Iranian leader has visited since the shah’s last visit in 1977. Only 21 when he took over, the shah was 30 when he came to the U.S. in 1949.

During that 1949 visit, Truman greeted the young shah at the airport and hosted him at the White House. Recognizing Iran’s strategic location near Russia, Truman framed his toast in the context of the emerging Cold War. Truman was deeply versed in the Bible from his childhood reading and quoted the Book of Daniel from memory, saying, “The laws of the Medes and Persians, they are not altered” (Daniel 6:15). Elaborating on the verse, Truman explained that “Daniel meant not that the laws were unalterable but that the Medes and the Persians believed in keeping their contracts. We have been dealing with a great power that does not believe in keeping its contracts. Iran believes in keeping its contracts. The United States of America believes in keeping its contracts.” 

The Eisenhower years would be the first test of those contracts between the U.S. and the shah. In an incident still somewhat shrouded in historical uncertainty, the CIA helped the British oust Mohammad Mosaddegh, an anti-Western prime minister who had been elected by the Iranian parliament. Mosaddegh nationalized the oil industry, which angered the British, who were deterred from engaging in military action because President Dwight Eisenhower dismissed the idea as “paternalistic.” The shah fled to Italy during the turmoil but returned after large anti-Mosaddegh demonstrations forced Mosaddegh to resign. Although Eisenhower did direct the Dulles brothers, Secretary of State John and CIA Director Allen, to oppose Mosaddegh, Mosaddegh was unpopular with much of the Iranian power structure and might very well have been ousted even without the machinations of CIA operative Kermit Roosevelt, the grandson of former President Theodore Roosevelt.

As for Eisenhower, he had warm relations with the rejuvenated shah and, in 1959, became the second president to visit Iran. He gave friendly remarks to the Iranian parliament during that visit and shared a message from the American public: “We want to work with you for peace and friendship, in freedom.” Eisenhower’s “Atoms for Peace” program led to Iran getting its first nuclear reactor for civilian energy purposes. When Eisenhower died in 1969, the shah attended his funeral, the only funeral of an American president that the shah attended. 

In the 1960s, the shah was seen as a close American ally, visiting the U.S. five times during the Kennedy-Johnson years. In a 1962 visit, the shah went to see the U.S. space program at Cape Canaveral, was given the honor of a state dinner at the Kennedy White House, and even received a ticker-tape parade in New York City. President John F. Kennedy, while friendly, also recognized that the shah needed to make reforms and encouraged the “White Revolution” that was intended to liberalize Iran. President Lyndon Johnson, who had visited Iran as vice president in 1962, also welcomed the shah at the White House in 1968, where he toasted the shah, saying, “We greet you as an old friend, not just an old friend of ours, but of the United States.”

President Richard Nixon was even friendlier to the shah than his Democratic predecessors. He had met the shah in 1953, while serving as Eisenhower’s vice president, and would be the only president at the shah’s 1980 funeral in Cairo. Nixon greeted the shah in the White House in his first year in office, calling the shah one of the “few leaders, heads of state in the world, who has been a guest in this house and in this room as the guest of President Truman and then of President Eisenhower and then President Kennedy and then President Johnson and now, tonight, as our guest.”  

Nixon also visited Iran in 1972. His aide Dwight Chapin, who accompanied Nixon on the trip, saw Iran as “an oil-rich country moving into the Western sphere. Everything in Iran was lavish, big, and beautiful.” Despite his positive feelings at the time, future events colored how Chapin looked back on the visit. As Chapin wrote in his 2022 memoir, “As it turned out, though, visiting Iran and meeting the Shah at that moment was the equivalent of meeting Czar Nicholas a few years prior to the Russian Revolution.” 

Nixon was a Cold Warrior and saw the shah as an important ally against the Soviet Union. His national security adviser and then-secretary of state, Henry Kissinger, had a similar view, seeing the shah as “that rarest of leaders, an unconditional ally, and one whose understanding of the world enhanced our own.” When Nixon left office as a result of the Watergate scandal in 1974, Gerald Ford took over the presidency, but Kissinger, and his views on Iran, remained. 

The oil shocks of the 1970s complicated relations between the U.S. and Iran. The shah, eager to pursue his ambitious plans for building up Iran, enjoyed high oil prices and wanted to keep them high. The U.S., battered by energy crises, wanted to see them lowered. To do that, some elements in the Ford White House, including chief of staff Donald Rumsfeld, wanted to push Iran for lower prices. Kissinger pushed back, fearing that U.S. pressure could hurt the shah and bring about a “radical regime” in Iran. The issue came to Ford in August 1974, shortly after Ford took office. Kissinger told the president not to press the shah, saying, “The shah is a tough, mean guy. But he is our real friend. … We can’t tackle him without breaking him.” Ford listened. He welcomed the shah to the White House in May 1975, but signs of trouble lay ahead. The shah’s plans were costly, and the CIA was warning of economic and cultural challenges.

When Carter hosted the shah for a state visit in November 1977, he became the eighth American president to meet with the shah. He would also be the last. The next month, Carter visited Tehran on New Year’s Eve, and he made a toast that did not age well, saying, “Iran, because of the great leadership of the shah, is an island of stability in one of the more troubled areas of the world.” The stability would not last much longer.

Within 10 months of Carter’s toast, U.S. Ambassador to Tehran William Sullivan cabled his prediction to Washington that the shah’s reign was doomed. In a January 1979 Camp David meeting, Carter declared that “a genuinely nonaligned Iran need not be viewed as a U.S. setback.” This poor prediction by Carter led the administration to be disturbingly receptive to the return of the radical cleric Ayatollah Ruhollah Khomeini, who feared that the U.S. could stop his revolution. He signaled, falsely, to the Carter team that he was someone the U.S. could work with, telling an American intermediary, “There should be no fear about oil.” State Department intelligence chief Philip Stoddard said, “We would do a disservice to Khomeini to consider him simply as a symbol of segregated education and an opponent to women’s rights.” On Jan. 11, 1979, only a few months after Carter told the shah that the U.S. would back him “without any reservation whatsoever, completely and fully,” Carter personally directed the shah to “leave promptly.” U.S. Secretary of State Cyrus Vance cabled the news to American consular officials, “We have decided that it is desirable to establish a direct American channel to Khomeini’s entourage.” It was a disastrous misstep.

Khomeini returned to Iran from exile in France on Feb. 1, 1979, and quickly established control. There was little interest in working with America, “the Great Satan.” On Nov. 4, 1979, Iranian “students” took over the U.S. Embassy. They would hold American diplomats hostage for the remainder of the Carter presidency. Carter, who watched 480 movies as president, viewed the Humphrey Bogart movie Sahara in the White House theater the night the hostages were taken, likely unaware of the way that the day’s development would roil his presidency.

The rest of the story is depressingly familiar. The Carter administration was paralyzed by the hostage crisis. ABC News created the nightly news program Nightline to document the crisis. Carter’s rescue attempt failed miserably, showing America to be a paper tiger and leading Vance to resign, not because it failed but because he opposed the attempt. After losing the 1980 election to President Ronald Reagan, Carter stayed up all night the final night of his presidency in a desperate attempt to negotiate a release of the hostages, but the Iranians had one more humiliation in store for him. Khomeini made sure that the hostages would not be released until Reagan was sworn in and Carter was once again a private citizen.

One reason the Iranians let the hostages go was that they were more afraid of Reagan than of the ineffectual Carter. And they were, in some ways, right to be scared. In 1988, when an Iranian mine hit the USS Samuel B. Roberts, damaging the ship and injuring 10 sailors, Reagan had the U.S. directly engage with the Iranian navy, destroying two Iranian oil platforms and sinking an Iranian frigate. Iran backed off. 

Unfortunately for Reagan, his administration was less deft at dealing with the rise of Iranian terrorist proxies such as Hezbollah, which killed 241 U.S. service members in a 1983 Beirut bombing, hijacked a commercial plane, murdered a U.S. Navy diver, and took multiple Americans as hostages in Lebanon. The hostage situation set the stage for the Iran-Contra affair, a failed attempt to trade arms for hostages. (Current Iranian strongman Ayatollah Ali Khamenei was one of the Iranian interlocutors in those frustrating negotiations.) Iran-Contra was the biggest scandal of the Reagan administration and cost multiple administration officials their jobs, including White House chief of staff Donald Regan. The lesson that the Iranians appeared to take from the Reagan years was that direct engagement with the U.S. was dangerous, but the plausible deniability created by the use of terrorist proxies to do their dirty work gave the Iranians lots of running room.

Tensions between the U.S. and Iran relatively eased during the administrations of Presidents George H.W. Bush and Bill Clinton. This was in part because of the U.S. focus on Iraq in those years, and in part because Iran was exhausted by the costly Iran-Iraq War, which ended in a stalemate. (Kissinger’s wry comment on the war was, “It’s a pity both sides can’t lose.”) But both Bush and Clinton took political hits because of Iran-related problems. Bush was dogged during his run for the presidency by his role in the Iran-Contra affair. In fact, his famous 1988 confrontation with CBS News’s Dan Rather came about because Rather, as Bush’s team predicted, pressed Bush on the question, giving Bush his preplanned opening to hit Rather on the anchorman’s snit about a tennis match intruding on his news broadcast. And Bush was angry when Iran-Contra prosecutor Lawrence Walsh issued Iran-Contra-related indictments on the eve of Bush’s 1992 reelection loss to Clinton. As for Clinton, his embarrassing last-minute pardon of the financier Marc Rich was related to Rich’s involvement in the evasion of economic sanctions against Iran.

Things worsened between Iran and the U.S. during the 2000s, following the 9/11 terrorist attacks on New York and the Pentagon. Former President George W. Bush labeled Iran part of the “axis of evil,” something that caught the Iranians by surprise. Former Vice President Dick Cheney, who had been Rumsfeld’s deputy in the Ford White House, was a frequent critic of the regime and was one of the first U.S. officials to warn of the danger of Iran obtaining nuclear weapons. Bush tried to work with the Europeans to get the Iranians to the nuclear negotiating table in his second term, but a far bigger problem at the time was Iranian actions against U.S. troops in Iraq. Led by Gen. Qassem Soleimani, the Iranian Quds Force provided Iraqi insurgents with explosively formed penetrators that killed hundreds of American troops. The Bush administration, bogged down by wars in Iraq and Afghanistan, did little to punish the Iranians for their actions against the U.S.

When Barack Obama took over as president, he was more interested in engaging with Iran than in confronting it. He even called Iranian President Hassan Rouhani in his car in 2013, marking the first conversation between a president and an Iranian leader since 1979. But Obama’s tenure coincided with the return to office of Israeli Prime Minister Benjamin Netanyahu, who was raising the alarms about Iran’s nuclear ambitions. Obama’s pursuit of the Joint Comprehensive Plan of Action with Iran brought him into conflict with Netanyahu, who saw the agreement as ineffectual in stopping Iran’s nuclear program, silent on Iran’s promotion of proxy terrorist armies in Lebanon, Yemen, and Gaza, and unwisely providing Iran with “pallets of cash” to fund those armies.

When Trump came to office in 2017, he was far more receptive to Netanyahu’s arguments. Trump pulled out of the JCPOA in May 2018 and reimposed sanctions on Iran. According to Trump, “The Iran deal was one of the worst and most one-sided transactions the United States has ever entered into.” Trump also ordered the U.S. military to kill Soleimani in January 2020. Yet even though Trump was tougher on Iran than Obama had been, his administration ended without a plan to stop the Iranians from getting a nuclear weapon.

PENTAGON PROBLEMS: IT’S BEEN A ROUGH ROAD FOR MANY DEFENSE SECRETARIES 

Former President Joe Biden followed Trump and seemed interested in reentering the JCPOA, but the Iranians were not interested. Biden also granted sanctions waivers that gave the Iranians billions of dollars to fund their terrorist proxies. American long-standing inability to deal with Iran’s terrorist proxies cost the West dearly in the Biden years, with Hamas’s deadly Oct. 7, 2023, attack on Israel, which killed dozens of Americans, Hezbollah’s follow-up war against Israel, and the Houthis’ closing of shipping lanes in the Red Sea and the Gulf of Aden. The Biden administration did, to its credit, help provide Israel with missile defense against two Iranian missile barrages in 2024. Still, the Biden administration did little against Iran on either the nuclear front or the proxy front, setting the stage for Trump’s more aggressive actions when he returned to power.

The troubling 46 years since the fall of the shah have seen the loss of an important American ally and a consistent inability by American presidents to deal with a weaker but still irksome adversary. As Hudson Institute Iran expert Mike Doran observed, “I don’t know the magic thinking that the mullahs have had over every other American president [until Trump].” These last four-plus decades demonstrate that the kid-gloves approach toward Iran has not worked. Viewed in this long and depressing historical context, punching the bully in the nose once in a while, or sending some B-2 bombers to take out its nuclear facilities, makes a lot of sense.  

Washington Examiner contributor Tevi Troy is a senior fellow at the Ronald Reagan Institute and a former senior White House aide. He is the author of five books on the presidency, including, most recently, The Power and the Money: The Epic Clashes Between Commanders in Chief and Titans of Industry.