The American president has often bragged about his ability to cut deals and about how well he gets along with the Russians. The press and investigators have speculated about the extent of his connections to the Russian business and political elite. And yet, Trump never actually built anything in Moscow. When the president said, shortly after his inauguration, “I don’t have any deals in Russia,” he wasn’t wrong.

The question is why. When just about every other major hotel chain in the world was able to build in Moscow and beyond, why didn’t Trump close a deal in Russia?

The absence of Trump real estate in Russia, it turns out, is a revealing reflection of the disconnect between the image Trump projects and the reputation he and his surrogates have established in Russia.

In part it was because, as Donald Trump Jr. once said himself, Russia “really is a scary place.” In a 2008 interview with a small trade publication, Trump Jr. said that he had taken “half a dozen trips to Russia in the last 18 months” and that “several buyers have been attracted to our projects there.” But there was something getting in the way of those trips adding up to a Trump Tower Moscow. “It is definitely not an issue of being able to find a deal,” Trump Jr. said, “but an issue of ‘Will I ever see my money back out of that deal or can I actually trust the person I am doing the deal with?’ As much as we want to take our business over there, Russia is just a different world. … It is a question of who knows who, whose brother is paying off who, etc.”

Trump Jr., who did not respond to request for comment, was right: The world of Russian business is a dark and treacherous place, and Moscow real estate is one of its darkest corners. “Moscow is like New York in many ways, just way more corrupt,” says a Western real-estate developer in Russia, who asked for anonymity in order not to jeopardize local partners and ongoing business deals. “To pull a building out of the ground, you need so many permits, so many authorizations—the mind reels. And all of it is so corrupt, it’s insane.” To navigate all this, the Trump Organization would have needed a local partner that was not just a capable developer, but had the right political connections to secure all the necessary permissions. “You need a good Russian partner, otherwise there’s no way,” says Mark Stiles, an American businessman who had extensive real-estate holdings in Russia.

In 2013, Trump worked with Agalarov, who had stellar connections at the very zenith of Russian political and business life. But that deal went sour after it caused a scandal in Kyrgyzstan—long story—and after the Russian economy took a nosedive in 2014.

But at other times, Trump’s man on the ground was Felix Sater, a Russian-born wheeler and dealer from the Russian-immigrant enclaves of Brooklyn. Sater, who declined to comment on the record for this story, once served a year in an American prison on an assault conviction after he stabbed a man in the face with the stem of a broken margarita glass. Not long after he got out of jail in the mid-90s, he was charged with securities fraud. Sater struck a deal to avoid prison time by becoming an FBI informant—a role that included providing the U.S. government with Soviet-era weapons purchased from an arms dealer.