Photo-Illustration: New York Magazine; Photos: @okbizwine/Instagram; Getty Images

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The dinner cost $7,250 a plate, but that isn’t what Krešimir Penavić remembers about the evening. What Penavić recalls is, first, the wine: four rare bottles from Domaine de la Romanée-Conti, the estate worshiped by oenophiles around the world. And, second, meeting Omar Khan, the man seated across from him, who was larger than life in every sense. “In his mass, in his voice, in his appetite, in his talk,” Penavić says. “He was sitting there buttering bread and complaining that the food was not fat enough to be served with his wine.”

The men were dining at Daniel Boulud’s flagship restaurant in February 2015, during La Paulée de New York, a weeklong celebration of the grape harvest in Burgundy. Khan, 48 years old at the time, was a familiar presence at this kind of event, where wine aficionados paid huge sums to share special vintages poured by renowned French winemakers. He wore tailored suits on a body that an acquaintance described as “perfectly spherical.” Holding court, he’d talk in a honeyed baritone about literature, business, and travel, sharing lessons he’d learned climbing Mount Fuji or waiting for a cappuccino at the Beau-Rivage in Geneva. His alluring old-world twinkle had helped him start a business hosting his own wine events, which were gaining a reputation for being some of the most extraordinary tastings in New York.

Penavić jumped at the chance to attend one. Soon he was a regular at Khan’s events, paying as much as $25,000 a seat. Penavić, who immigrated to the U.S. from Croatia in 1990 on a math scholarship, had made a fortune as one of the earliest employees at the billionaire-minting hedge fund Renaissance Technologies. He races Ferraris, spends summers aboard his 150-foot double-masted yacht, and underwrites the search for ancient shipwrecks on the floor of the Adriatic. But of all his hobbies and indulgences, it’s wine that puts a special glint in his eye. “It’s a beautiful process, to coax something like that out of a fruit,” he says, after telling me about the vineyard he owns on an Istrian hillside. “No other fruit is like that. It can be so complex. It can be so many things. It can change so much over time — hours or decades. To me, it is the most fascinating product that we get from nature.” When Khan asked Penavić to begin investing in his wine venture, he readily agreed.

Khan pitched a simple arrangement. Staging one of his dinners might cost $100,000 — to reserve a private room at Jean-Georges or another fine restaurant; to source six to ten rare bottles; to pay a sommelier. If Penavić advanced him $60,000, Khan said he would cover the rest, and they’d split the profits 50/50. The exact amounts varied according to location and size. Penavić gave Khan $75,000 for an event in London and $75,000 for another in New Jersey. He also gave $250,000 for a 37.5 percent stake in Khan’s plan to do monthly events overseas.

Penavić says his private bankers vetted Khan. But over time, he started to become suspicious. The events were postponed again and again, and when Penavić asked for updates Khan was evasive. “A month goes by, and then six months go by, and then a year goes by, and this dinner hasn’t happened yet,” Penavić says. “I’m like, ‘What’s going on? Do the dinner!’ He says, ‘Oh, this and that happened, and perhaps we’ll do it in London, and there weren’t enough people interested. We’ll see. I’m going to be in New York soon, let’s talk.’”

At some point, Penavić says, though he can’t say for sure exactly when, he realized that he’d invested some $5 million in Khan’s events and never seen a dime of profit. That’s when he started calling around to other wine people. “My hit rate was 100 percent,” he says. “Every single person I called answered the phone and said, ‘You’re calling about Omar, aren’t you?’”

In September 2019, Penavić and 12 other members of the New York wine elite sued Khan in state court, alleging that he had taken them for nearly $8.3 million. The charge was as extraordinary as it was embarrassing: For people immersed in a hobby predicated on discernment, they’d proven to be pretty easy marks. The U.S. Attorney for the Southern District of New York began investigating Khan, and in February 2020, prosecutors filed an indictment. But the authorities were unable to make an arrest. By then, Khan had fled the country.

At Château d’Yquem in France. Photo-Illustration: Grub Street; Photo: okbizwine/Instagram

Con men abound in fine wine. But unlike, say, Rudy Kurniawan, who famously emerged out of nowhere to dupe Burgundy fiends out of $28 million in the 2000s, Khan didn’t need to put on airs. His late father, Najmul Saqib Khan, was a Pakistani diplomat who served in Saudi Arabia; Japan; Washington, D.C.; and New York, where he was consul general — a position that allowed him to mingle with the city’s power brokers. In the 1980s, Saqib, as he was known to friends, became particularly close with the real-estate scions William Zeckendorf Jr. and Daniel Rose, who could often be found bidding up the price of rare wines at auction.

At dinners, Saqib frequently spoke with pride about his son. Omar was a student at Oxford, and something of a campus celebrity. “He knew everybody in college and everybody knew him,” says a former friend and roommate. “The whole thing was underpinned by money. Omar was, for a college student, rich. He was very generous. He would buy people rounds of drinks, he would buy people coffee, he would take people out to restaurants at a time when the rest of us always ate in the college canteen.”

Khan also gave the impression that he was an academic ace, telling stories that often ended with him confounding a professor during a lecture. That pretense was shattered at graduation when grades were released and, according to the roommate, Khan was at the bottom of the class. “It was a shock to all of us,” he says. “Then he disappeared. We did not see him after the final results were posted. We never heard from him again. He just left our lives.”

Khan enrolled at Stanford Law, but it’s not clear whether he graduated. In 1993, with partners in Karachi, he started a business, Training 2000, offering life and business coaching based on “neurolinguistic programming,” a pseudoscientific 1970s self-improvement method. The company had a few major corporate clients, according to Saleem Lodhia, an employee, but still didn’t seem to make anywhere near enough to cover Khan’s expenses. “He always lived way beyond his income,” says Lodhia. “He would go to the most expensive restaurant. He would drink the most expensive wines. He would always get chauffeured around.”

Khan married a quiet woman from Texas named Leslie Carol Freeby, and they traveled often to New York. He documented their adventures exhaustively on a blog. “Back at Per Se last night,” reads a typical entry. “I had come in possession of a Petrus ’89, a truly stunning vintage from this glittering wine-maker. Per Se adapted their evening tasting menu to locate some dishes that truly flattered the wine, and which were in turn flattered by it.” Other posts offered Gladwellian business lessons, gripes about British Airways, and praise for the works of George Bernard Shaw. He criticized service workers, chided women at a coffee shop for gossiping “with the abandon of an Athenian orator,” and described a young couple perusing the wine list at Jean-Georges as looking “adorably maladroit.”

At some point in the 2010s, Khan and Leslie moved to New York permanently. Khan continued to promote himself as an executive leadership coach under a new brand, Sensei International, marketing neurolinguistic services as “a radical software that’s installed in your mind” and touting himself as “arguably one of the best global consultants and speakers in the world.” And he reached out to his father’s old contacts, cementing his place as a regular at vintage-wine tastings. (Saqib died in 2012.)

“Every single time he brought not just far and away the best wine — but it was always the best bottle of that wine anybody had ever had,” says Dan Rosenheck, a journalist who attended numerous functions with Khan. When they met in 2013, Rosenheck had only recently started to invest in his palate and he was grateful to Khan for introducing him to wines he couldn’t afford on a journalist’s salary. “Omar was eager to share his magic potions,” Rosenheck says. “He was both my wine sherpa and my wine sugar daddy.”

Exactly how Khan could afford these wines was a mystery. His business credentials didn’t quite square with Rosenheck, who covered management consulting for The Economist. “It was very murky,” he says. “Every so often I would ask him questions about this nominal company, Sensei International, but never in great detail because he was so vague and fluffy about it.” Even though Rosenheck was a business journalist, he chose not to press. “The last thing I was going to do was throw out too many probing questions when I kept getting served these once-in-a-year wines,” he says. “Frankly, I didn’t want to kill the golden goose.”

In 2013, Khan founded a new company, which he called the International Business & Wine Society. Each month, members gathered for an event with three elements: a lecture, a wine tasting, and a dinner served by a world-renowned chef. Membership was $5,000 a year. Khan told people that he’d founded the society because good wine was scarce at business dinners and good conversation was rare at wine tastings. “The original meaning of the word ‘symposium’ was a drinking party where you had great conversation,” he told Forbes.

Over the next few years, the society gathered at many of the glitziest restaurants of the decade, from Eleven Madison Park to The Grill. Khan recruited a wide range of speakers. There were CEOs delivering conventional corporate talks but also figures like Elizabeth Minnich, a former assistant to Hannah Arendt; Sir Ivor Crewe, who was then the head of University College at Oxford; and J.J. French, of the heavy metal band Twisted Sister. Khan’s chosen wines got lofty themes (“An Evening of Clos de Bèze Seduction”), and he worked with god-tier chefs to create menus that complemented them.

“Omar was extremely particular about how he wanted things done,” says a sommelier who worked with Khan. “If it started at 6:30, even if you got there early, you couldn’t have a sip of Champagne until 6:30. He had his routine of how the night was going to go and adhered to it like clockwork. If you were late, he would call you out in front of everyone. He was like a nun.”

No detail was too small. Khan cut off speakers if they ran long, and seating arrangements were nonnegotiable. Once dinner was underway, Khan led general conversation; if he saw two people start a side discussion, he’d interrupt to bring them back into the group. Khan may have been an exacting host, but engineering the perfect dinner club required a passionate alchemist, and many guests thought Khan’s formula worked.

“I would drop anything to go to an Omar dinner. They were some of the most incredible vinous and culinary experiences I’ve ever had,” says Nicholas Russotto, the director of music programming at the 92nd Street Y. Khan often invited figures from the arts to attend gratis. “Omar’s great gift was that he was a really good collector of people. I work in classical music; the guy across from me was really high up in investment banks; the guy sitting next to me was a shipping magnate. We always had really interesting things to talk about,” says Russotto.

Even wine professionals, those who do tastings on a near-nightly basis, were impressed. “I found his events way more engaging than some other wine-society events that I’ve attended and belonged to,” said Jennifer Simonetti-Bryan, one of only 59 people in the country who have earned the Masters of Wine distinction. “I wish more people were as meticulous as he was.”

While Khan’s guests and clientele were enthralled, the staff working these events often were not. Waitstaff, event coordinators, and sommeliers I spoke with all described Khan as unreasonably demanding and quick to criticize. And there was often a problem when it came time to pay the bill. Khan had strange invoicing practices and checks sometimes bounced.

This is so fucking shady,” a former special-events coordinator remembers thinking at the time. “But it’s fine because he’s a weird wine guy and he’s already booked three more events with us.”

Khan’s events featured food by iconic chefs like Daniel Boulud (left of podium). Photo: Scott Heins

The value of fine wine, more than any other luxury commodity, is driven by scarcity. Every cork pulled from a rare bottle is a step toward oblivion, the extinction of that particular vintage. And as much as collectors may want to share their cellars, there’s a social calculus at play. How worthy is a given guest of a particular wine? Will they contribute money, a fine bottle of their own, a deft palate? The scene is cliquish, and no matter how rarefied a gathering is, there’s always an even more exclusive tasting on the horizon with ever-rarer elixirs. “There are groups where it’s six guys — and it’s all guys — who get together and drink $100,000 worth of wine in one night,” says the author and wine writer Jay McInerney, who crossed paths with both Saqib and Omar Khan.

To access higher tiers of wine appreciation — and money — Khan turned to people like Krešimir Penavić. Any concerns Penavić might have had about Khan’s trustworthiness were allayed whenever he saw Khan move through the fine-wine scene. A year and a half after they met, in the fall of 2016, Khan organized a dinner for eight in a small cupola on the roof of the Nomad hotel. One of the guests was Pierre Lurton, a luminous figure who made wine for both Château d’Yquem and Cheval Blanc. According to Penavić, before leaving to catch a flight to Paris, Lurton invited the group to visit him in Bordeaux. Penavić assumed Lurton was just being polite, but a few months later, Khan sent an email: “So, who is going?”

In Bordeaux, Lurton personally hosted Khan, Penavić, and their wives at Château Cheval Blanc, showing them the cellar and vineyards. After lunch, the group was chauffeured to d’Yquem, where they again toured the vineyard and ate, then retired to rooms on the estate. Penavić could not believe he was getting to experience these places so intimately. The next morning, Khan offhandedly suggested they drop by Château Pétrus, perhaps the most esteemed estate in the world, and see its chief, Olivier Berrouet. To Penavić, this was akin to popping into the Vatican and saying hi to the pope. Somehow, Khan delivered. “We just drove up and the winemaker himself was there. He let us in, he walked us through the vineyard, he tasted his wine with us, he showed us the wine,” says Penavić. “I was agog. These people don’t receive. They don’t have tastings!”

When they got back from France, Khan approached Penavić about more investments, including a tasting in London that would double as a fundraiser for his alma mater, Oxford, and a series of dinners to honor Daniel Rose, who was by then in his late 80s. Penavić wired Khan $396,000. Most of the investments were handshake agreements, and after a number of the events seemed to stall out, with vague promises to get them back on track, Penavić shifted the terms. He continued to make investments with Khan, but only if he agreed to sign promissory notes covering the prior deals. Looking back, Penavić compares the tactic to an attempt to get out of quicksand.

At the pinnacle of the wine market, fraud often goes unreported because victims would rather eat a loss than take legal action and risk publicly damaging their reputations. It’s a form of omertà among the 0.01 percent. “One element certainly is that these guys spend an awful lot of money on wine and they don’t necessarily want to advertise just how much they spend,” McInerney says. Penavić claims that he knows at least a half-dozen wealthy acquaintances who were ripped off by Khan but choose to remain silent. “They don’t want their names coming out. One guy is about to be elected to the board of a publicly traded company,” he says. “It’s a small price to pay. You lost $100,000 or $200,000, but you are now going to lose millions if it comes out.”

Penavić didn’t mind going public. In 2019, he hired Rob Seiden, a former prosecutor the New York Times once called “a Wall Street bounty hunter,” to look into Khan. The lawsuit Seiden eventually filed against Khan also named Leslie, accusing her of assisting his scheme and benefitting from it. (Leslie did not respond to requests for comment. When I approached her in person recently, a lawyer shooed me away.) Seiden also fed evidence to the FBI, including emails that he says show Khan impersonating his attorney, that he thought would make for a good criminal case. But it was far from clear, especially as COVID set in, whether prosecutors would prioritize a wine caper featuring a group of victims who spent so much money on Burgundy.

At various times in his life, Khan had called Sri Lanka home. At the end of 2019, Lodhia, Khan’s former business partner, told me that friends had spotted Omar and Leslie in the country. Over the next couple of years, Khan popped up there — offering his expertise as a global consultant at a conference in Colombo, or voicing skepticism over COVID vaccines in a column for a Sri Lankan news site. At one point, Seiden told me that the Khans were living at the Hilton residences in Colombo. When I called and asked for Khan’s room, an operator patched me through, but no one picked up.

U.S. prosecutors were in fact interested in the case. After indicting Khan under seal in early 2020, the Department of Justice eventually petitioned Sri Lanka for Khan’s extradition. According to the government, he was ultimately deported for overstaying his visa. In late February 2024, he was put on a plane to New York and arrested at JFK. The next morning, Khan pleaded not guilty to charges of fraud and identity theft. “Mr. Khan looks forward to resolving the allegations against him and believes that the place to do so is in a court of law, not the court of public opinion,” his attorney, Andrew Dalack, said in an emailed statement.

In early March, a U.S. Marshal escorted Khan into a mostly empty federal courtroom in lower Manhattan. He was in a wheelchair, which his lawyer attributed to “injuries he suffered while he was unfairly detained in Sri Lanka in dangerous and unsanitary conditions.” A few rows back, Leslie sat quietly while a prosecutor summarized the government’s case against her husband, claiming Khan scammed about a dozen victims for a total of $9.5 million. The hearing was thin on details. At one point, the judge seemed confused. “You’re investing in someone else having dinner?” he asked.

A bond hearing is scheduled for early April. In the meantime, Khan will be held at a rehab and nursing facility in Queens.

Exactly who the government’s victims are is unclear. In 2022, ruling on the civil case, a judge ordered the Khans to pay Penavić and his co-plaintiffs more than $8 million, with the vast majority going to Penavić. Many others are also trying to get their money back. Khan has yet to pay a $630,587.15 judgment in favor of Jean-Claude Bernard, the owner of Hôtel Le Cep in Beaune, France, who says Khan tricked him into investing in events in Burgundy and London that never happened; a $125,000 judgment to David Sinegal, the heir to the Costco fortune, who claims that Khan solicited money for rare wines that he failed to deliver; a $337,591.44 judgment to Ben Wallace, who invested in Khan’s dinners and also provided rare wines; and a $2,955,306 judgment to Jack and Lorena Broesamle, a Philadelphia couple who loaned money to Khan. The Beau-Rivage hotel in Geneva has an open case against Khan as it tries to collect an allegedly outstanding bill of $72,347. Rose, now 94, has filed a $59,210 lien against him. (Still others say the cost of filing a lawsuit against Khan is too great. I spoke to Cathy Corison, a Napa winemaker, who says Khan never paid her for some expensive bottles, and a sommelier who says she’s still waiting on an unpaid tab of $5,000.)

More than once, I asked Penavić why he continued giving Khan so much money when he repeatedly failed to deliver. He offered a number of answers. For one, even a person with his fortune couldn’t resist the allure of a seemingly quick and easy profit. He blamed Khan’s “pressure tactics”: The window of opportunity to taste, and invest in, a certain bottle was always about to close, and once shut it would be gone forever. In hindsight, Penavić noticed that Khan’s tightly choreographed dinners meant investors never had time to speak privately and perhaps share their frustrations or suspicions with each other. He also blamed his own naïveté. At Renaissance Technologies, he’d written sophisticated algorithms to detect hidden patterns and outsmart the market. But that was no use to him here. “The models I worked on count on the herd behavior of various individuals,” he said. “They’re not applicable to one single individual.” Ultimately, Penavić says, he was just too enticed by the wine — and by Khan’s genuinely entertaining company.

James Finkel, a senior adviser at Kroll who dined with Khan often, compares him to Curnonsky, the pen name of a French food and wine critic in the first half of the 20th century. A conspicuously large man, Curnonsky dined out every night and rarely reached for the check. “It is better not to pay than to have complications,” he was fond of saying. To Finkel, both gastronomers had an exuberance that enriched a table’s food, drink, and conversation alike. “At banquets, seated at the head table, solemnly appraising the food and wine brought before him, he could always be counted upon for some Gallic witticisms, reminiscent reveries, and a few reverberating words on the glory of la cuisine française,” The Atlantic wrote of Curnonsky in 1958, a description that could just as easily apply to Khan a few years ago. When Khan’s alleged frauds came to light at the end of 2019, Finkel was working on a translation of a long-lost Curnonsky interview. He had planned to dedicate it to Khan.

“In a funny way, I’ll miss him,” Finkel says. “I love those Curnonsky types. We don’t really have them anymore.”