Angry Trump struggles to understand challenges from Iran’s leaders

Trump considers himself a master at assessing and exploiting his adversaries.

But Iranian leaders have baffled him.

“All they do is make me angry,” he told reporters last week.

“They just make me angry.”

The American president could face more frustrations.

Trump administration officials say a new deal to reopen the Strait of Hormuz could be near, but Iran continues to insist on fees that Trump considers unacceptable.

Trump’s inability to reach a favorable deal with Iran has not only cost him votes among war-weary voters, but continued tension over this crucial shipping lane has caused volatility in oil prices, to the detriment of American consumers and the global economy.

Trump is by no means the first American president who has had difficulty understanding Iran.

Each of his predecessors, from Islamic Revolution 1979, has attempted to decipher the murky Iranian power structure and the mentality of its political leadership.

Most have not been successful; some have suffered serious losses. A rare exception is President Barack Obama, whose 2015 nuclear deal with Iran was the fruit of a 20-month diplomatic effort.

Obama called it a major achievement, despite criticism from Republicans and some Democrats who alleged that Iran had persuaded him to sign a flawed deal by feigning restraint.

But Trump may be the president who has “least understood Iran’s leadership,” said Kenneth Pollack, a former CIA analyst and National Security Council official who has studied Iran for decades.

“In many ways, Trump represents the quintessence of America’s frustrations with Iran,” Pollack said.

“He has been both the one who most wanted to reach an agreement with Iran and the one who used the most force against it. He has discovered that neither of the two things helped him get what he wanted.”

Trump often speaks as if brute force will get a quick deal.

After the start of the war with the February 28 airstrike that killed Iran’s supreme leader, Ali Khamenei, who had held power for almost 40 years, Trump urged the Iranian people to rise up and “take control” of their government.

He added that he would later “choose” Iran’s next leader.

Other senior Iranian officials were also killed in the airstrikes.

But it didn’t happen no popular uprising.

The hardline Iranian government doubled down on its stance. In March, he appointed a new supreme leader, Mojtaba Khamenei, son of Khamenei.

U.S. officials consider him even more uncompromising—and more interested in acquiring a nuclear bomb—than his father.

Iran simply ignored Trump’s public statement that the younger Khamenei would be an “unacceptable” choice.

And Khamenei did not respond to Trump’s public offer for an in-person meeting.

Still, Trump held out hope for major change. “Iran can right its situation if it reaches an agreement,” he declared at the end of April.

Iran, he said, could become “a legitimate country, not a country based on death and horror.”

Iranian officials say they can negotiate with Trump on issues such as the Strait of Hormuz and its nuclear program, although they dismiss many of his key demands.

But in a political system based on hate towards the United States, no one shows interest in a broader reconciliation with that country.

There is little indication that Trump’s months of dealings with the Iranian regime have given him any better understanding.

Throughout the conflict, Trump has constantly revised his assessment of Khamenei and his associates.

He has described them as “lunatic”, “reasonable”, “completely crazy”, “very intelligent” and “completely crazy”.

To some extent, Trump is experiencing the same frustrations that plagued several of his predecessors, who also hoped for big deals with Iran.

“For decades, American policymakers have systematically underestimated the ideological commitment and deeply institutionalized power structure of the Islamic Republic,” said Suzanne Maloney, vice president and director of foreign policy at the Brookings Institution in Washington.

One problem, Maloney noted, is the little direct interaction U.S. officials have had with top Iranian leaders.

No American official ever met with Iran’s first supreme leader, the Ayatollah Ruhollah Khomeini, nor with the late Khamenei, nor with his son.

Maloney stated that the war appears to have strengthened the power of Iran’s religious and military leadership, leaving no “viable alternative power center.”

Iran’s semi-democratic political system, which has a president and parliament under the absolute religious authority of its supreme leader, has at times included senior officials open to friendlier relations with the United States.

But Washington’s previous appeals to those figures have mostly ended in repentance.

Dennis Ross, a veteran of Middle East diplomacy who has worked with presidents of both parties, said that “the Iranians seem to understand us better than we understand them.”

In 1980, the president Jimmy Carter approved secret talks with Iran’s foreign minister in an attempt to free the 52 American hostages kidnapped from the US embassy in Tehran the previous year.

Carter’s diary entries show that, like Trump, he was obsessed with the details of Iran’s political intrigues, including disputes between senior Iranian officials.

In early 1980, Carter believed he had reached a deal to release the hostages in exchange for the release of billions of dollars in frozen Iranian assets and a promise that the United States would not interfere in Iranian affairs, among other things.

But, in what Carter called “a bitter disappointment,” Khomeini rejected the idea, surprising American officials and his own subordinates.

Carter ultimately ordered a hostage rescue mission that failed, before striking a deal that freed the Americans on his last day in office.

Five years later, the president Ronald Reagan He ordered his advisers to investigate a message from an Iranian arms dealer who claimed that moderate Iranian officials would be willing to establish friendly relations once the elder Khomeini had died.

In what Reagan later called a search for “a strategic opportunity,” he approved the secret sale of American weapons to Iran in exchange for the release of American hostages held in Lebanon.

This agreement became part of what is known as the Iran-Contra case, since money from arms sales was clandestinely diverted, in defiance of Congress, to an anti-communist rebel group in Nicaragua known as the Cons.

The revelation of the scandal plunged Reagan’s presidency into deep disrepute, as several US officials pleaded guilty or were convicted of serious crimes; Reagan’s former national security advisor attempted suicide.

The rapprochement with Iran turned out to be a mirage.

No like-minded moderates emerged in Tehran, and the CIA believed the arms dealer who started it all was an imposter. Reagan, denying knowledge of the key events, apologized in a speech to the nation, while defending his original goal of currying favor with Iranian moderates.

In 1997, the president Bill Clinton had a more tangible opportunity when Iran elected a reformist candidate as president, Mohammad Khatami.

Khatami advocated for good relations with the United States and expressed regret over the embassy hostage crisis.

Clinton reciprocated with gestures such as resuming U.S. imports of Iranian pistachios and rugs, and with conciliatory comments that acknowledged some of Iran’s historical grievances.

The Secretary of State, Madeleine Albright, even issued a public apology for the CIA’s support of the 1953 coup that overthrew Iran’s prime minister after he nationalized the country’s Western-dominated oil industry.

But the most intransigent sectors opposed Khatami’s moderate vision, in part because reconciliation with the United States threatened the foundations of his anti-Western ideology.

Days after Albright’s speech, the elder Khamenei, who became supreme leader after Khomeini’s death in 1989, dismissed his words and any possibility of dialogue with Washington.

Khatami later stated privately that Khamenei believed Iran could never make peace with the United States, according to Karim Sadjadpour, an Iran expert at the Carnegie Endowment for International Peace.

alone Obama has reached a major diplomatic deal with Iran, in the form of the 2015 nuclear deal that imposed limits on Iran’s atomic program for up to 15 years in exchange for the lifting of economic sanctions.

Many Obama administration officials hoped that the deal, negotiated with another moderate Iranian leader, Hassan Rouhani, could be a first step towards better relationships.

Khamenei approved the deal, but showed no interest in moving forward; Critics claimed this confirmed their warnings that Rouhani would become a repeat of Khatami.

Iranian suspicions that the United States could not be trusted were soon confirmed.

In 2018, Trump withdrew from the nuclear deal and imposed economic sanctions even more severe than those in place before the agreement.

Iran responded by accelerating its nuclear program, setting it on course for a violent confrontation with the United States and the war that Trump started in February.

Since then, according to Ross, Iran has continued tactically overcoming to Washington, something that Trump’s evident impatience to conclude the war has facilitated.

“They tend to interpret our sense of urgency as a form of pressure,” Ross said.

“We always seem to be in a hurry to get things done. They start from the premise that time is better for them than for us.”