According to Michael Wolff, a well-known biographer of Donald Trump, only one person truly knows the president’s intentions regarding the war against Iran, and it is not a general or a Cabinet member. Wolff, who had rare access to the White House during Trump’s first term, believes that person is Trump’s son-in-law, Jared Kushner. Meanwhile, Trump and his inner circle have given little clarity on their strategy, causing unease even among Republicans. Wolff stated on the Inside Trump’s Head podcast that “He has consulted with nobody. Nobody knows what is going on. Literally zero.” He added that if you are looking for the “brains of this operation,” it would be Jared Kushner. In his view, Kushner is the only person truly “inside Trump’s head” and the one person Trump actually listens to on this matter. Although Kushner does not hold an official senior adviser role in this second Trump administration, he has been acting as a key diplomat alongside businessman Steve Witkoff. According to The Daily Beast, just before the attacks on Iran began, both men were involved in unsuccessful talks with the Iranian regime. Kushner’s deep ties to the Middle East and personal financial interests make his informal role all the more significant Wolff’s view of Kushner’s influence is based on his belief that Kushner understands Trump’s core motivation: personal benefit. “When you look at what Trump does, why he does what he does, it is always smart to look at what he can get out of it. What is the personal advantage to Donald Trump?” Wolff explained. Kushner has a track record of securing major financial deals for the Trump family, including a $2 billion investment from a Saudi fund into his private equity firm, Affinity Funds. Trump has also been expanding his circle of allies in other ways, with a controversial new addition to his Board of Peace raising fresh concerns. Kushner’s ties in the Middle East go beyond Saudi Arabia. He has long-standing relationships with UAE President Sheikh Mohamed bin Zayed and Qatari Emir Tamim bin Hamad Al Thani. Despite these personal financial interests in the region, Trump sent Kushner to meet with Iranian negotiators for denuclearization talks last month in Geneva. When Jared Kushner is engaged in talks with a foreign nation as a “diplomat,” he’s NOT representing the United States, he’s representing the Trump family. And he’ll do whatever benefits his investment firm and the Trump family business, not the American people. pic.twitter.com/jNdu6KvWNZ— Books Behind Borders (@MHTruthUltra) February 27, 2026 Wolff suggests that Trump is primarily focused on deal-making, real estate, oil, and capital, and has long seen the Persian Gulf as a major area of opportunity. This suggests that business interests may be influencing serious foreign policy decisions. Concerns are also growing outside the president’s inner circle. Trump’s former national security adviser John Bolton said he is deeply worried that Trump “hasn’t thought through the implications or laid the groundwork” for his goals in this war. The conflict has already resulted in the deaths of six U.S. troops and at least 1,000 civilians. Bolton’s warning raises serious questions about whether there is a clear and thought-out strategy behind the military action. These concerns go beyond the Iran conflict, as Trump has also shrugged off fears of new domestic terror threats at home, suggesting the administration’s approach to national security remains broadly questioned.