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The Brief and Wondrous Life of Jewberg

The Latvian American financier and quasi-counterfeit ‘Pentagon analyst’ Dan Rapoport led the kind of life that makes any cause of his recent death—assassination, suicide, or pseudocide—all equally plausible

Vladislav Davidzon
August 29, 2022
Original photo courtesy Alena Rapoport
Original photo courtesy Alena Rapoport
Original photo courtesy Alena Rapoport
Original photo courtesy Alena Rapoport
This article is part of Ukraine.
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My impossibly difficult friend Dan Rapoport played a dazzling array of roles throughout his tumultuous, colorful, and often very unhappy life. The inimitable Riga-born, Latvian American charmer was by vocation a banker, a financier, and occasional backchannel political broker—as well as an international man of mystery, an asset of multiple intelligence services, a hedonist, a stolid enemy of the Kremlin regime, a prankster internet troll, and a 32nd degree Freemason. He was also a legendary and incomparable host of bacchanals in Soho Rooms, his debauched Moscow nightclub, before being forced to return home to the United States and reinvent himself as a venture capitalist. On Aug. 14, my erstwhile pal and man-about-town in Kyiv succumbed to his injuries after a mysterious fall out of the window of his Washington, D.C., apartment. He thus joins a growing list of recently defenestrated Russian businessmen, Putin enemies, former intelligence agents, and members of the government.

Writing about Rapoport is difficult, as the facts commingle with the many myths of his own creation. Throughout the years I knew him in Kyiv, he had been mostly bored, drinking heavily and running the great multiyear scam of his alternate online identity, “David Jewberg.” In 2018, Bellingcat published a remarkable investigation of his alter ego: “‘Senior Pentagon Russia Analyst LTC David Jewberg’ maintained a popular Facebook page and was frequently quoted in Ukrainian and Russian media as a Pentagon insider related to topics concerning Ukraine and Russia. He represented himself as an actual person with the legal name ‘David Jewberg,’ not as a persona or pseudonym.” Dan spent years cultivating this bizarre identity, creating fake social security cards and military IDs for Jewberg as well as social media pages, which were “verified” by various Russia experts. Whether David Jewberg was a hilarious multiyear hoax carried out by one of the great performance artists of our time, or was actually an intelligence operation being run for or against the Russians, still remains unclear.

As a young man, Rapoport concluded his studies in finance at the University of Houston in Texas at the exact moment that the Soviet Union was dissolving. The timing, as always throughout his life, was excellent. He was promptly hired by an American bank that needed a young Russian-speaking associate to open up markets and serve as a middleman. Arriving in Russia in the autumn of 1991, he was part of the earliest wave of repatriated Western-educated professionals who would engage in piratical practices in the process of amassing tremendous fortunes. Rapoport had a knack for finding himself in historic situations. “I’ve just been a guy who was always at the right place at the right time,” he once admitted to me. He made his return to the post-Soviet world at the age of 21, he told me, via a first-class ticket to Siberia. This would set the pattern for the rest of his amusing, glorious, debased, and ultimately depressing life.

He was by all accounts a competent banker; in the ’90s, he told me, he worked for and was close to the allegedly criminal Swiss American financier Marc Rich (who died in 2013). Soho Rooms, the Moscow nightclub Rapoport co-founded in the mid-oughts, was renowned for being the most depraved, glamorous, and hard-to-access club in the capital. Anyone who was anyone in Moscow in those years would flock to it. Rapoport once bragged to me of having dined at his private table there with eight of the FBI’s 10 most-wanted fugitives of the decade—including the flamboyant gangsters who would become household names in Russia, including “Yaponchik” (Vyacheslav Ivankov) and “Taiwanchik” (Alimzhan Tokhtakhunov).

In fact, Rapoport knew literally everybody, and became an expat celebrity in his own right. He would squire around every American and British film and sports star who passed through Moscow and introduce them to women. He eventually lost control of his share of the night club, claiming to have been expropriated from his business by the partners who were in cahoots with members of the Russian security services. The same transpired with his other Russian businesses. His Soho Rooms co-founder, Sergei Tkachenko, would likewise die from a fall from a window in 2019.

The loss of his club was only the start of the crackdown against Rapoport, who had become increasingly committed to the Russian opposition—the part of his character I most respected and admired—and deeply involved in Russian diaspora opposition circles. According to Bill Browder, CEO of Hermitage Capital Management, Rapoport was one of the first Moscow-based financiers who publicly supported Alexei Navalny.

Rapoport was later summarily kicked out of Russia under murky circumstances. A British intelligence official of my acquaintance, also a Freemason, once informed me over lunch that Rapoport had been given advance warning by other Freemasons inside the FSB that he would soon be arrested. He was told to leave the same night, which he did. Rapoport then spent several fruitless years attempting to get back at the Russians—but the best he could do was to get one of the security service agents who dispossessed him placed on a no-fly list within Russia for outstanding debts. (In other words, the guy had to drive to Minsk in order to get on a plane out of Belarus if he wanted to go to Europe—back when planes still flew to Minsk.) That is the sort of man he was: obsessive, honor-oriented, restless.

Rapoport was also emotionally cagey: oversensitive and high-strung, depressive and deeply proud. After immigrating from Soviet Latvia to Texas in 1980, he had attended some very poor schools. A gangly and bespectacled Jewish 10-year-old with an Eastern European accent among predominately African American classmates, he was badly bullied. In his graceful moments of disarming honesty, he would open up about the years in which he was beaten up every day after school. That may very well have been one source of his internal anguish: At parties he would alternate between imperious hauteur and touching, overly transparent sensitivity worthy of an emo kid listening to the latest Fall Out Boy album. He craved respect and would lash out if he thought it was not forthcoming. I once had to storm out of a dinner with him after he had insulted me, wrongly thinking that I was interrupting him in the midst of one of his monologues. Yet he was much too fantastical a figure, too fascinating, too fun, too well connected, and too full of excellent political gossip to be displeased with for long.

After leaving Moscow, he reluctantly moved to Washington, D.C.—that grayest, most formal, and least hedonistic of cities—where he was a neighbor of my family in the upscale Kalorama neighborhood. My relatives would visit him for tea in the stately house that he occupied before he was forced to sell it to Ivanka Trump and Jared Kushner in the wake of his financially disastrous divorce from a Russian model. My relatives were alternately charmed, fascinated, and repulsed by him, his lifestyle, and his tall tales of 1990s Moscow. “I did not like his stories about flying around on private airplanes and picking out good-looking girls from a queue along with his oligarch pals like Oleg Deripaska and Mikhail Prokhorov,” explained my aunt. “But beneath this vulgar nouveau riche ‘new Russian’ game-playing exterior he was a wounded and very sensitive Jewish boy with a strong attachment to his family. He once spent several hours showing me pictures of his childhood and of his parents on his cellphone. He spoke in the most sweet and sensitive manner about his ancestors. I still do not know why he opened up to us.”

The last time Dan and I had dinner was on February 23rd, the night before the Russian bombing commenced.

Rapoport would confess to me years later that he had been sitting in the garden of that house in Kalorama—after he had sold it to the first daughter of the United States—when he contemplated killing himself. He said he had put one of the many guns from his collection—he grew up in Texas, after all—into his mouth in order to play Russian roulette. But at that precise moment, he said, he received a call from an investor who wanted him to relocate to Kyiv to look after an investment fund there. Rapoport promptly took the gun out of his mouth and accepted the offer.

In Kyiv, he quickly distinguished himself: A larger-than-life character even in the historic, revolutionary atmosphere of post-Maidan Kyiv, a town full of such figures. After a while he met his next wife, a doctor, quit drinking, and had another child. He would spend his days playing the stock market and pretending to be Jewberg online. His nights were spent playing high-stakes poker with Ukrainian businessmen, oligarchs, and government ministers, one of whom insisted (on condition of anonymity) that he was “a degenerate gambler who had made disastrous gas and oil decisions for the country based on his gambling addiction.” A highly placed member of the Ukrainian government revealed to me during dinner in London last year that Rapoport had an admirable amount of self-control during those evenings.

In Kyiv, where a particular kind of intellectual Anglophone camaraderie is not easy to find, we gravitated toward one another after he moved there in 2016. He was widely and eclectically learned—a prodigious reader with countless quirky character traits and baroque habits. (He refused to eat chicken, for example, because it had once been a little dinosaur and he had “a thing about eating dinosaurs.”) In between his attempts to recruit me to join the Freemasons, we would spend hours arguing about the history of linguistics, Greek politics, anthropology, the history of Judaism, evolutionary biology, and the internecine internal politics of the French Revolution. He once read a hundred books on the history of neurobiology over the course of two months in order to prove a point.

He intended to move his young family to a house in Ternopil in western Ukraine and then, eventually, to Denmark. Out of a sense of survivor’s guilt, he would attempt to return to the capital after the battle of Kyiv ended in April of this year—but there was no business in Ukraine for him, and so he reluctantly returned to America, to what seemed to be mounting debts.

We had spoken by phone over the last few months, and he had been manic—if also generous—about offering me business advice. He had occasionally called me over the previous half-decade when he was looking out for capital for some business plan (on one occasion he wanted to invest in Ukrainian grain elevators). Over the last several months, he was reported to have been stiffed out of a payment by a Russian venture capital firm and was in a dour mood. After he died a couple weeks ago, the Daily Mail reported that he had separated from his wife and that the former editor of the Russian Tatler had seen “Rapoport back in May at London’s swanky Connaught Bar, alleging that he was there ‘in the company of young girls.’” The Russian news outlet RBC reported that his widow has shut down all speculation of these rumors and others. “There were no suicide notes, no suicide, no trip to London, no breakup,” she said, adding that Rapoport’s death was being investigated by the authorities.

The last time Dan and I had dinner, it was in an upscale restaurant full of surreal anxiety in Kyiv. It was February 23rd, the night before the Russian bombing commenced. The restaurant was full of Ukrainian elites anxiously discussing what was about to happen. Dan regaled me for the umpteenth time with one of his favorite tall tales—about the time he allegedly seduced a young Britney Spears in exchange for a bag of cocaine, which I highly doubt was true. He marveled at how little money journalists make in comparison to venture capitalists and bankers, and also bitterly complained about the fact that his many enemies were now using “Jewberg” to try to ruin his life. At around 11 p.m., dessert was served and the evening reached its denouement. We both suddenly began receiving cascades of frantic phone calls from our sources telling us that the Russian bombing was about to begin and that Russian airborne paratroopers were about to land in northern Kyiv. We hugged goodbye—something I had never done with him before—and we told each other to take care in the war to come.

In the days before his death, Rapoport posted a picture on Facebook of Marlon Brando as Colonel Kurtz in Apocalypse Now, with the words, “The horror, the horror.” It is impossible to know whether it was the Russians or his own demons that got him in the end. Perhaps, as some of his innumerable friends and acquaintances continue to hope, Dan is still with us somehow, in the VIP section of a nightclub in the sky. His history of close escapes, pranks, and over-the-top schemes, both real and fake, leaves room for hope that perhaps he absconded from whatever creditors or Russian hitmen were after him, got plastic surgery, and disappeared to South America with a plane full of money. Dan Rapoport was an original—and there can be no higher praise. Wherever you are, soldier of fortune and my brother, I owe you dinner for having picked up the check the night before the war.

Vladislav Davidzon is Tablet’s European culture correspondent and a Ukrainian American writer, translator, and critic. He is the Chief Editor of The Odessa Review and a Non-Resident Fellow at the Atlantic Council. He was born in Tashkent, Uzbekistan, and lives in Paris.