In 2007, at the ripe old age of 26, Jared Kushner made a big splash in the New York City real-estate industry when he bought 666 Fifth Avenue, for what was then a record-setting $1.8 billion. Kushner Companies, which Jared took over after his father, Charles, went to prison—for, among other things, a very classy revenge scheme that involved hiring a prostitute to seduce his brother-in-law for cooperating with a federal probe against him—invested $500 million in the property and financed the rest through debt. Even without the rapidly approaching financial crisis, which Jared failed to see coming, the deal looked crazy; with the building almost completely occupied, the revenue coming in covered just two-thirds of Kushner Cos.’s costs. When the global financial crisis did hit, the family was forced to sell the tower’s retail space for $525 million. By 2009, 666 Fifth was reportedly “making just 69 cents on rent for every $1 it owed.” By 2011, the skyscraper was “teetering near insolvency,” and almost half of the office space was sold to Vornado Trust Realty for an $80 million capital injection, with the company later acquiring more of the tower the following year. As of today, Kushner Cos. has less than two years to come up with $1.2 billion, when 666’s interest-only mortgage is due.

All in all, it’s a less than stellar set of circumstances for a deal that was supposed to demonstrate Jared’s investing genius—purportedly his primary qualification for holding one of the most powerful positions in the White House, beyond marrying the president’s daughter. It’s also particularly stressful given that Kushner Cos. was apparently this close to receiving a big bailout from a billionaire who is one of the richest, most powerful men in Qatar. Which perhaps helps to explain, in part, why the White House has taken such a curiously vengeful position toward Doha in the midst of the Qatari diplomatic crisis currently roiling the Middle East.

The Intercept’s Ben Walsh, Ryan Grim, and Clayton Swisher report that beginning in 2015, before Kushner sold his stake in 666 Fifth Avenue to work in the White House, he and his father, Charles, negotiated directly with former Qatar prime minister turned billionaire investor Sheikh Hamad bin Jassim al-Thani, a.k.a. H.B.J., to refinance the property. Of H.B.J., the former emir of Qatar once said, “I may run this country, but he owns it.” According to The Intercept, the billionaire “ultimately agreed to invest at least $500 million” through his investment firm Al Mirqab, on the condition that Kushner Companies secure additional outside refinancing. And in the wake of the election, the president’s in-laws had no shortage of people wanting to do business with them for, oh, no particular reason at all. One such party was an opaque Chinese insurance firm called Anbang, with ties to Beijing’s political elite. Unfortunately, Anbang pulled out in the wake of deafening cries of conflicts of interest, and with them, went H.B.J. All of which casts the president’s recent behavior toward Qatar—a key U.S. ally that hosts a major U.S. military base—in a somewhat troubling light.

On June 5, Saudi Arabia, the U.A.E., Egypt, and Bahrain suddenly “cut diplomatic and commercial ties with Qatar . . . accusing it of supporting terrorism, meddling in their internal affairs and advancing the agenda of regional foe Iran”—all allegations Qatar denies. The following day, Trump stunned lawmakers on both sides of the aisle by unexpectedly joining in on the Qatar-bashing. “During my recent trip to the Middle East I stated that there can no longer be funding of Radical Ideology. Leaders pointed to Qatar - look!” he tweeted. And: “So good to see the Saudi Arabia visit with the King and 50 countries already paying off. They said they would take a hard line on funding extremism, and all reference was pointing to Qatar. Perhaps this will be the beginning of the end to the horror of terrorism!”