Why Trump Is Raging at Enemy Who Keeps Beating Him
Michael Wolff alleges that Iran knows exactly how to get under Trump’s skin.
President Donald Trump is falling victim to Iran’s “trolling,” his longtime biographer alleges.
Author Michael Wolff has claimed on the Inside Trump’s Head podcast that Trump is “stuck” in a war where his enemies know exactly “how to play him.”
Wolff’s statement comes after a chaotic week in which Trump declared his June ceasefire was “over” and that Iran was concocting an assassination plot against him.
“This is the worst mistake he has made,” Wolff told co-host Joanna Coles, referring to the war.
The public appears unhappy with how Trump and his goons have handled the war in Iran.
Jonathan Ernst/Reuters
Wolff said Trump “tried literally everything” to end the war with Iran, which has tanked his approval rating and spiked gas prices. The war began on Feb. 28 and was supposed to last less than six weeks, but it is now in its fifth month.
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Trump said Wednesday that he no longer wants to negotiate with Iran and that its leaders are “scum,” reacting to Tehran’s targeting of three oil tankers in the Strait of Hormuz and launching strikes against U.S. military sites in Bahrain and Kuwait.
The two countries have continued trading tit-for-tat strikes this week, marking the largest exchange of fire between them since they signed a memorandum of understanding for a ceasefire in June. Even if that ceasefire held, it was heavily criticized, with many arguing it gave Iran too many concessions without sufficient returns.
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Wolff said the president had effectively told Iran, “I’ll give you any kind of agreement you want if you just stop this war.” He noted that Trump was even willing to pay Tehran to stop it.
“They keep coming back,” Wolff said of Iran, alleging that “this is a whole process of trolling Donald Trump.”
The MOU signed by Trump included commitments to create a $300 billion fund to support Iran’s reconstruction if certain conditions were met.
It stopped short of outlining concrete measures to ensure Tehran would dismantle its nuclear program or prevent the development of nuclear weapons—the reason Trump said the U.S. needed to go to war in the first place.
Iranian mourners carry a banner threatening Trump on the day of the burial of former Supreme Leader Ayatollah Ali Khamenei, who was killed on February 28 in Israeli and U.S. airstrikes.
Majid Asgaripour/via REUTERS
Iranian Supreme Leader Mojtaba Khamenei accused Trump of acting “out of desperation” and of using “all kinds of leverage” to force the deal through.
Iranians gathered this week for a weeklong funeral procession honoring former Supreme Leader Ali Khamenei, whom Trump killed in an airstrike on day one of the conflict. The younger Khamenei has vowed revenge for the assassination “will most certainly be carried out,” Axios reported.
“It does get under his skin, and he is somewhat paranoid about this,” Wolff said of the threats against the president’s life. Hordes of people at funeral processions have carried posters that read “there will be blood” and “Kill Trump.”

President Donald Trump’s late-night threat to Iran, which he signed off with “PRAISE BE TO ALLAH!”
Truth Social
On Friday, the president took to Truth Social to warn Iran that “1000 Missiles” were pointed at the country should Tehran attempt to take his life.
Wolff believes “the death thing is probably more clearly related to his polling numbers than it is to whatever threats the Iranians are making.”
A nationwide Financial Times/Focaldata survey found that six in 10 voters believe the war was not worth the cost, while the president’s approval rating has fallen to historic lows as the conflict has dragged on.
“These presidents get into these forever wars, and they can’t get out of them,” Wolff said, arguing that Iran has recognized a pattern in U.S. politics where foreign conflicts can “bring presidencies down.”
Find and subscribe to Inside Trump’s Head with Michael Wolff and Joanna Coles on YouTube and wherever you get your podcasts. New episodes of incomparable insight into the psyche of the world’s most talked-about man drop every Tuesday, Thursday, and Saturday evening on YouTube and Wednesday, Friday, and Sunday mornings on other podcast platforms.
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