As a candidate, Donald Trump declared it wouldn’t be hard for the United States to deal with Middle East allies that undermined our interests: we could simply seize their oil. The rally-tested notion fit into Trump’s larger campaign theme that America was being pushed around by countries that need us far more than we need them. But Trump’s evolving, uncertain response to the brutal murder of dissident journalist Jamal Khashoggi inside the Saudi consulate in Istanbul has shown little of this bravado. He’s often seemed to follow the Saudi lead, as if the U.S. needs the Saudis more than they need us. “This is one of the rare times I’ve seen Trump struggle. There’s no real leadership. It’s a disaster,” one former West Wing official told me.

According to five Republicans briefed on internal White House discussions, Trump is torn between his instincts to fight and punish and the advice he’s receiving from advisers to stick by Saudi Arabia’s 33-year-old crown prince, Mohammed bin Salman, better known by his initials, M.B.S. “Mike Pompeo is telling him this is a decision with 10-year consequences,” one source said. The most determined backstage voice pushing to not upend the relationship is that of Trump’s son-in-law, Jared Kushner, who has made M.B.S. a central node in his yet-to-be-seen Israeli-Palestinian peace plan. Speaking at a CNN forum yesterday, Kushner waved away a question about the shifting explanations Saudi Arabia has offered about Khashoggi’s disappearance. “I see things that are deceptive every day. I see them in the Middle East, I see them in Washington—and so, again, I think that we have our eyes wide open.” (The White House declined to comment.)

From the beginning of Trump’s presidency, Kushner insisted that out-of-the-box thinking was the way to find a path forward in the Middle East. He boasted to a prominent journalist with deep experience in the region that he didn’t need to read books about the Israeli-Palestinian conflict, a person briefed on the conversation recalled. It was Kushner’s belief—one shared by his father-in-law—that the conflict between Arabs and Israelis was essentially a real-estate problem, a deal to be worked out. “This was Jared’s vision,” one former West Wing official told me. Key to this dealmaking would be the creation of a new strategic alliance between Israel, Saudi Arabia, and the United Arab Emirates to counter Iran. Kushner bet big on M.B.S., encouraging Trump to make Riyadh his first trip abroad as president (it was there that Trump was photographed touching that glowing orb). The Arab face of this effort was M.B.S., a charismatic young prince who spoke the language of Silicon Valley and women’s rights. Such was Kushner’s confidence that there was West Wing talk about a Nobel Peace Prize for Trump’s work in the region, a former White House official said.

But there were warning signs early on that M.B.S. wasn’t the enlightened reformer he positioned himself to be. About a week after meeting secretly with Kushner in late October 2017, M.B.S. launched a brutal crackdown, locking up Saudi billionaires in the Riyadh Ritz-Carlton until they signed over billions to the government. As reports of instances of torture inside the Ritz circulated in the media, Trump’s national security team became alarmed. One national security official called former secretary of state Condoleezza Rice for advice. Rice’s message was that “none of these guys are perfect” and Trump should give M.B.S. a chance. “While there were some concerns about doing business with M.B.S., we really believed he was a reformer and big change, socially, was possible,” a former official said. “The real issue is, we made a deal with the devil when we aligned with the Saudis 70 years ago. We have no other options,” another former member of Trump’s national security team recalled.