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President Trump’s angry claim on Monday that Iran was being “unbelievably duplicitous” in its dealings with the United States was just the latest sign of his struggle to understand his rivals in Tehran.
Mr. Trump considers himself a master of sizing up and exploiting his adversaries. But Iran’s leaders have baffled him.
“All they do is make me angry,” he told reporters last week. “They just make me angry.”
More frustration could be in store for the American president. Trump officials say a new deal to reopen the Strait of Hormuz may be near, but Iran continues to insist on collecting fees there that Mr. Trump has ruled unacceptable.
Mr. Trump’s inability to strike a favorable deal with Iran has not only cost him politically among war-weary voters, but continued strife around the crucial waterway has made for volatile oil prices at the expense of American consumers and the global economy.
Mr. Trump is hardly the first U.S. president who has struggled to read Iran. Each of his predecessors since the country’s 1979 Islamic Revolution has tried to decode Iran’s murky power structure and the mind-set of its political leadership.
Most have come up short; some have been burned badly. A rare exception is President Barack Obama, whose 2015 nuclear deal with Iran was a 20-month diplomatic effort. Mr. Obama considered it a major achievement, despite criticism from Republicans and some Democrats that Iran had lured him into a flawed deal by feigning moderation.
But Mr. Trump may be the president who “has least understood Iran’s leadership,” said Kenneth Pollack, a former C.I.A. analyst and National Security Council official who has studied Iran for decades.
“In many ways, Trump represents the epitome of America’s frustrations with Iran,” Mr. Pollack said. “He has been both the most desirous of making a deal with Iran, and the one who used the most force against it. He has found that neither got him what he wanted.”
Mr. Trump often speaks as though massive force will produce a quick deal.
After the war opened with a Feb. 28 airstrike that killed Iran’s supreme leader of nearly 40 years, Ali Khamenei, Mr. Trump called on Iran’s people to rise up and “take over” their government. He added that he would then “choose” Iran’s next leader.
More senior Iranian officials would also be killed in airstrikes. But no popular uprising emerged.
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Mourners gathered at Azadi Square in Tehran last month, holding flags during the funeral procession for Ayatollah Ali Khamenei, the supreme leader killed by an airstrike at the beginning of the U.S.-Iran war in February. Credit…Arash Khamooshi/Polaris for The New York Times
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