The wine, finally, was on the move. For two weeks, a team of 14 professionals had been in the mountains, methodically transferring thousands of rare bottles from a cavernous cellar into a nondescript box truck that shuttled the cargo to a pair of tractor trailers several miles away, tucked in a private way station overseen by an armed protection detail. Even the security team didn’t know what they were guarding. All they saw were scores of black-wrapped pallets slowly filling the giant holds. When the last of the wine was finally secured and the drivers strapped in, the semis, each escorted by an armored truck, rumbled past the steel gates and then diverged, assigned to separate routes down the mountain, across more than a thousand miles and three state lines, headed for California.
In Boston, Brahm Callahan received a GPS ping every 30 minutes with the trucks’ locations and the temperatures inside the cargo bays; they were holding steady at 55 degrees. The deal had been nearly two years in the making and killed and resurrected over half a dozen times during that span. Callahan, master sommelier, 35 years old, had seen some of the most incredible wine collections in the world, but never anything like the cellar he had just bought. He knew from the moment he stepped inside it that he would never encounter another collection so miraculous, so meticulously curated, so impeccably cataloged and stored, and so impossibly stocked with unheard-of rarities. Now he and his partners were about to take possession of the entire haul. The first step of the plan was nearly complete.
The trucks would converge again at a bonded warehouse in Sonoma County, where Dan O’Brien, 40, was waiting to take possession of eight figures’ worth of wine while trying not to think about all the money they owed, or everything that needed to happen before they could pay it back. First, the wine had to show up as planned—the convoys were taking separate routes at the insistence of the insurance companies, to mitigate risks such as avalanches and hijackers—and then the designated portion, several thousand bottles of valuable rare wines, had to make its way by boat to Hong Kong in time to be received and cataloged for a Sotheby’s auction in February. The various lots needed to sell for enough to cover the money they owed to the hard-money lender who had financed the deal at terms that would make a loan shark shudder.
From his condo in Boston, Scott Leverenz ran the numbers again, out of habit. He took into account the projected auction figures, that Mafia rate of monthly interest, the roughly $700,000 they had already accrued in legal fees, the potential appreciation of the remaining portfolio, and every other variable he could think of. As usual, Leverenz, 34, was gaming out the worst-case scenario, but the numbers looked good: Even if the total from the auction came in at the low end, and even assuming it took the full 90 days to collect all the money, the three of them would hit their target: They could use the sale of the bottom two-thirds of the cellar to clear the debt and keep the most valuable top third—millions of dollars of wine—for free.
The cellar was even more impressive than advertised, unlike anything either had seen in both quality and scale.
The wine arrived in Sonoma as scheduled, where it was stored for 72 hours before being taken to Oakland and put on a container ship headed to Hong Kong, due to dock just before Christmas.
It was late November 2019 and the juice was running. The loan would reset every 30 days, the principal growing each month alongside the compounding interest in a convoluted death trap of penalties, fees, and clawbacks. Time was not on their side.
Shortly after the wine arrived, the news began reporting an unknown respiratory illness killing people in China. The country would lock down a few weeks later. Callahan, Leverenz, and O’Brien had just borrowed $12.5 million to buy a store of wine that now might as well be on the moon.
The Crew
Callahan first outlined his plan to Leverenz one morning in 2016 in the Amtrak bar car heading back to Boston from Philadelphia. They were fending off hangovers after a Guns N’ Roses concert; neither had slept. But kicking ideas back and forth across a bartop was how they had always done their best thinking, going back to when they first met as Boston sommeliers in 2009.
Callahan had made master sommelier by 30, pin number 222 of 228 in the world at the time. There is nothing achievable in the wine world above it. The final examination, administered by the Court of Master Sommeliers, is like trying to prove a physics thesis by doing backflips, meant to plumb the depth of one’s theoretical understanding, sensory abilities, and practical skills simultaneously. Callahan had lived like a monk while studying for it, forgoing shaving and taping laminated study guides throughout his apartment—on tables and mirrors, lining the cupboards, inside the shower—so there wasn’t a minute he couldn’t be learning. In the blind-tasting portion alone, candidates must correctly identify six different wines by grape variety, country of origin, district, appellation, and, finally, vintage. Not only had Callahan passed the test, he had eventually become a member of the Court.
Thousands of bottles of rare wines bound for Hong Kong left port in November 2019.
Illustrated by Matthew Woodson
Leverenz had a head for numbers. He and Callahan had both passed through Grill 23 & Bar, a revered Boston steak house that operated as a sort of elite boot camp for those forging a career in wine. Unlike most restaurants with encyclopedic wine lists, Grill 23 actually moved the juice, and opportunities to taste rare and notable vintages were frequent. Leverenz went on to become a somm and wine director for some of Boston’s top restaurants before managing national sales for major importers; he also traded in rare and fine wines. Having experience in both buying and selling had stripped away the varnish of romance that dazzled so many people into ostensibly bad business decisions: Leverenz liked to say that the best way to end up with a million-dollar winery was to start with a $2 million winery. He loved the industry and wasn’t immune to the glamour, of course—he just preferred to understand it for what it was, and to make a profit off of it when he could.
Like Callahan and Leverenz, O’Brien had cut his teeth at Grill 23 and had a natural allergy to all of the stupid money sloshing around the wine industry, though unlike the other two, he wasn’t much for sitting on appreciating assets for the sake of a tidy profit down the line—he’d rather drink a Dujac Grand Cru immediately after buying it, maybe with a burger. With his beard and glasses and easygoing grin, the onetime Boston somm now looked the part of an affable San Francisco garage winemaker, but there were few areas of the industry he hadn’t touched, from developing wine programs for luxury hotel groups to producing blends for private-label clients to revamping a historic Calistoga vineyard as COO. He had extensive experience buying, storing, and transporting wine—easier said than done given that alcohol is a highly regulated substance, which makes moving it across state lines a costly, time-consuming, and tediously complicated bureaucratic process. He had the bonded storage, insurance premiums, and drawers full of licenses and permits to attest to that.
Callahan had worked with both separately, but despite all being Grill 23 alums, the trio had never worked together until now. They sealed their partnership over omelets and coffee at a grungy diner down the street from an impound lot.
The Plan
What Callahan pitched was this: Raise enough money to buy a white whale of a cellar, a highly secretive monster collection somewhere in the Rocky Mountains—one of those murmured opportunities that surface from time to time in the tight, clubby world of master somms and elite collectors. It supposedly contained vast quantities of vanishingly rare wine, the kinds of bottles that simply didn’t come to market anymore or were never supposed to have existed in the first place: unheard-of large-format Burgundies; decades of Hermitage; massive stores of cult Champagne. The collector had started acquiring in the ’80s, back when you could just show up in Vosne-Romanée, knock on the door of some family producer that had been making Burgundy in the region for hundreds of years, and walk off with however many cases you felt like shipping home. Provenance and documentation were said to be perfect.
And yet the cellar had been quietly on the market for some time, with no takers. Why? First, the asking price, a vast sum even in the voracious world of high-stakes wine collecting, kept rising—first $8 million, then $10 million, now likely more—the longer the collection sat and the more the wines inside kept appreciating. More challengingly, it had to be all in one go, to one buyer: no cherry-picking, no allocation, a single check for the entire lot, non-negotiable. The seller didn’t need the money and seemed in no rush to part with the wine.
Normally, anyone walking into a cellar with an eight-figure check is going to expect to set some of the terms of the deal, so the sheer ego slap delivered by the take-it-or-leave-it nature of the offer cleared a host of private buyers from the table. Resellers are more pragmatic, but it was still a huge amount of cash, and a significant chunk of the inventory wouldn’t reach peak profitability for years; gray-market prospectors rarely buy and hold, preferring to flip bottles for quick profit rather than leave capital tied up in a basement.
Callahan figured he had a way to leverage the volume of the cellar. A collection of that size and caliber would otherwise take decades to procure, and this one was said to be composed of some of the best-performing wines on the market, heavily over-indexing for Burgundy, Northern Rhônes, and Champagne. If you could price the inventory correctly, acquire it at reasonable value, then engage an auction house to move the most immediately profitable tranches of wine in one push, you could repay the loan plus interest while holding on to the best long-term investments. Essentially, between loan, acquisition, and auction, you could triangulate an extremely small aperture through which it would be possible to come into a few million bucks’ worth of unbelievable rare wine, for free—but if you miss the window, don’t bother preparing for impact.
Taking on the whole thing at once meant they could play the long game. The cellar had such vast stores of specific vintages that you could effectively corner the market, taking advantage of short-term price fluctuations by strategically liquidating bottles at their most lucrative while continuing to accrue yearly appreciation on the rest. The remaining top slice of inventory, the cream of a once-in-a-lifetime crop, could be used as the basis for a wine-backed investment fund, or a high-end wine retailer. Or, put the profits into a négociant winery, buying grapes or juice and bottling under their own brand, and for private labels. Or, depending on how the auction went, all three.
But first they needed to get their hands on a whole lot of cash.
The Money
You can’t just walk into a bank and ask for, say, $10 million to buy a bunch of fine wine—or Picassos or vintage Ferraris or ancient Sumerian manuscripts—even if everyone knows they’re going to appreciate. It’s just not what banks are set up for, which mostly is to deal in simple, stable assets like homes and cars and small businesses. So Callahan went to Dave S. instead.
Callahan first met Dave S. over a magic trick of sorts at Grill 23. A bearded, broad-shouldered hedge-fund type, he had ordered a beguiling 1998 Bordeaux, a great Right Bank vintage—enough to pique Callahan’s interest. Either this guy made a lucky guess, he thought, or he knew something about wine. Dave S. knew enough to see an opportunity to stump the somm. He pulled out his phone and flashed a picture of himself from a recent shooting weekend, barely hoisting a gargantuan Nebuchadnezzar of ’67 Château d’Yquem—had Callahan ever seen a bottle like that in person? Callahan said he had, and then did Dave S. one better: He told him where the picture had been taken. The hedge funder, who was a professional magician in his youth, felt the hairs go up on the back of his neck—now that was a magic trick. Callahan explained that he knew the total number of bottles of ’67 Yquem in the 15-liter format in existence, plus who owned them around the world—including a certain prominent billionaire with three in his New Jersey cellar, which is where Dave S. was standing in the picture. He and Callahan became fast friends after that.
Yet despite his decades allocating capital and executing complex financial deals, Dave S. wasn’t the one to finance this play—but he knew who was. The guy who connects the pipes that make the money flow. The man they called the Plumber.
When the federal government needs to underwrite some sprawling, unprecedented, staggeringly complex program—say, a nationwide rebate for used-vehicle trade-ins, with all the labyrinthine financing that entails—the secretary of the Treasury picks up the phone and calls the Plumber. A math whiz since his teens, he was legendary in New York banking for never assuming risk and always making money, a deal-structuring genius who could put 28 hooks into you without your ever realizing, until God forbid something bad happened and suddenly your pecuniary guts were sliding all over the floor. The Plumber had a sideline in exotic investment plays—heady, esoteric, out-of-the-box stuff. Like backing the acquisition of a multimillion-dollar wine cellar for an unprecedented flip.
The planned sale in Sotheby’s auction room slammed into the realities of Covid.
Illustrated by Matthew Woodson
Dave S. didn’t mince words: The numbers would have to work, down to the penny. These people didn’t care about wine except insofar as it represented collateral for the deal—and as a regulated substance it made for complicated surety. The path of custody would need to be rigorously established and precisely controlled, and execution would have to be flawless or the various frictions would eat them alive: First, the buyer needed to assess and document over 12,000 bottles of wine, checking fill rates and bottle stamps and backtracking the ownership trail, then take and retain legal control of it through several stages of storage and transport across state lines and national borders—a notorious minefield of red tape—all while insurance, taxation, fees, governmental regulation, and the rest gnawed away at the bottom line from all angles. Every shipment, every transaction, every license, every insurance policy, every fee—thousands of variables—had to be accounted for, across all conceivable scenarios, until the sale was complete, the money collected and transacted, and everyone repaid.
Normally, anyone walking into a cellar with an eight-figure check is going to expect to set some terms of the deal.
And the three of them were going to be put through their paces. The Plumber’s people needed to understand who they were giving their millions of dollars to. Did they have a grasp of the details? Could they problem-solve under pressure? Were their industry contacts as solid as they claimed? The Plumber only dealt with people vibrating at the highest frequency, Dave S. said, and his crew would mess with them—changing deadlines at the last minute or giving them 24 hours to turn around a half dozen pages of analysis for no reason—just to see how they reacted to stress. The deal would come down to numbers, sure, but it wasn’t the only consideration. The Plumber wanted to know: How badly did they want it?
Which meant, even as Callahan and Leverenz were cautiously wooing the seller with polite correspondence and the occasional highly orchestrated visit, and O’Brien was laying the groundwork for the eventual possession and transport, they were simultaneously being put through rigorous crash courses in debt financing and tax law. The seller, meanwhile, was rarely available and seemed to have a knack for going dark the moment they felt any momentum begin to build. The deal was always under threat of collapsing from one end or the other—either because the seller had walked away or because the loan-to-value ratio had tipped a cent into the red and the money did. At one point, the deal hinged on whether Callahan could procure luxury portable toilets on short notice; at another, the cost of an overlooked California permit—the difference of maybe a few thousand dollars in a deal worth millions—was enough to get the Plumber’s people to start packing up, until O’Brien realized he had the necessary paperwork via another company he owned. This dragged on for months. Then a year. Then longer.
The motivation to press on, reenergized every time Callahan and Leverenz were able to inspect the wine, was that the cellar was even more impressive than advertised, unlike anything either had seen in both quality and scale, in fundamentally pristine condition. The attrition rate of unsellable bottles due to oxidation, lack of proper documentation, breakage, or improper storage was basically nil; even the small percentage of bottles they couldn’t send to auction—say, due to a detached label—they knew to be genuine.
And then, just like that, a switch flipped and it was go time. The seller agreed to the terms; in response, they wired $1 million into an escrow account as a sign of good faith. A short time later, a cashier’s check in the low eight figures was delivered by hand to the seller’s lawyer; there was the flurry of planes and trucks and boats; and the plan for a massive 90-day flip was in motion at last—until Covid reared its head and the entire world came screeching to a halt.
The Auction
The early days of pandemic lockdown for Callahan, Leverenz, and O’Brien were pretty much the same as for everyone else—awkwardly wiping down groceries, uncertain about whether you were supposed to buy masks or not buy masks because medical personnel needed them. Without its normal daily punctuations, time became a run-on—except for that charged moment every month when they recalculated what they owed to the Plumber. That always had a way of standing out. The monthly interest alone, which had started around $110,000, had jumped to $115,000, then to over $125,000, then to $130,000.
The months dragged on. February came and went. Then March, then April, then May, then June, the debt ballooning. Dave S. kept the mood up: Keep finessing the numbers, keep working the plan, these are just obstacles, you’ll find your way around. The Sotheby’s people pushed the auction, then pushed it again, then said they weren’t quite sure when it would take place despite being very upbeat that it would, in fact, happen; they were storing a gargantuan haul of wine they weren’t selling and so were as desperate as anyone to see it all across the auction block. Finally, the dates were set—a two-day affair, July 5 and 6, 2020. There was only one problem: Online auctions were still a fairly new format, and a remote wine sale of this size was unprecedented.
Hong Kong is 13 hours ahead of the east coast of the U.S. and 16 hours ahead of the west, which meant that it was July 4, America’s Independence Day, when the Summit: A Complete Cellar auction kicked off in Asia. O’Brien was at a backyard cookout in California wine country; Callahan and Leverenz were at a party at Dave S.’s house in Massachusetts. Everything they had done to this point, work now measured in years, hinged on these results. Had their proprietary valuation system—based on an intricate matrix of scarcity, reputation, current and future market interest, time to peak drinkability, and profit potential—priced the wine correctly? Difficult enough to gauge under normal circumstances, but this situation was sui generis. There was literally nothing to compare it to.
As it turned out, it was a perfect storm. The stir-craziness of isolation, collector appetite bottled up to bursting, and a global customer base newly comfortable with spending serious cash over the internet meant that the entire wine world was watching—and desperate to bid. It was a frenzy from the opening hammer.
The guys streamed the action on laptops, O’Brien holed up in a TV room as the party carried on outside, Leverenz and Callahan roaming the halls of Dave S.’s sprawling house and dipping into his pool in between calculating conversion rates. The numbers exploded from the jump and never relented, with world records shattering one after the other. In the six-liter format alone, a 1989 Ramonet Montrachet hammered for over $61,000, a 1999 La Tâche for over $90,000, and a 1990 Domaine de la Romanée-Conti Richebourg for over $154,000. The final sale clocked in over $15.6 million; they would clear $3.1 million in profit, minus some additional friction, while still holding what they considered to be the most valuable third of the original cellar, calculated to be worth between $3.5 million and $4 million.
Of course, they couldn’t actually get their hands on the money yet, which would be collected in dribs and drabs by the auction house over the next 90 days and deposited into a Hong Kong bank, in Hong Kong dollars. That currency is pegged to the U.S. dollar and therefore reliably stable—unless the President of the United States starts antagonizing China by threatening to decouple the HKD, as then-President Trump did later that month.
It was a new emergency: If Trump carried out his threat, the stroke of a pen would catastrophically evaporate their profits—meaning that, despite an auction bonanza far beyond their most optimistic projections, which set scores of world records, the three would still find themselves deeply in the red. The bulk of the wine was gone, they were out of money and had paid off virtually none of the debt—which was still accruing all sorts of replicating interest and spring-loaded fees. Even the inventory they had held back was out of reach: Until he got his money back, everything belonged to the Plumber.
This was the point at which O’Brien tapped out. Whatever happened between now and the end, he said to Callahan and Leverenz, whether it all worked out or everything collapsed, he didn’t need to know. He would be in California. Wake him when it was all over.
Coda
On a warm Boston night this past May at Grill 23 & Bar, I sat with the three cofounders of Faucet Wine—CEO Brahm Callahan, CFO Scott Leverenz, and COO Dan O’Brien—as they recalled the party they threw when the dust finally settled. Callahan and Leverenz had gone back to the Plumber asking for a $1 million hedge against the currency decoupling, and he was only too happy to oblige: The move further protected his investment, and the interest charged on the extra million would net him even more profit. In the end, Trump moved on from poking China, all of the auction money was collected, a check was issued from the Hong Kong bank and converted to U.S. dollars. All outstanding bills were paid. The Plumber was made whole. For the first time, some four years after Callahan had initially launched his scheme on the train, they were money good. They even wound up making a tidy six-figure profit from the hedge thanks to all the volatility.
The victory party took place in November 2020, still at the height of Covid, when congregating in person required nasal swabs and temperature checks and weeks of negotiation. A small group gathered at O’Brien’s house. The celebration was wine-country casual—tiki torches, a sprawling deck overlooking a creek, dogs clambering up and down stairs, a rap-heavy playlist bumping in the background—though few if any Sonoma Valley cookouts before or since have poured a magnum of 1990 Bâtard-Montrachet alongside a 1949 Musigny from Camille Giroud. Or a dream-haunting 1974 Ramonet Chassagne-Montrachet “Les Ruchottes.” And these were just some of many astonishing and wondrous vintages. They were the best of the authentic but unsellable stock, plus a small number of bottles they had held back for themselves, even if it sliced into the profit margin. The three had survived a long swim with some of the biggest sharks in the financial world, but they were ultimately all wine geeks at heart: If now wasn’t the time to finally taste your greatest-hits list of once-in-a-lifetime vintages, when would be?
O’Brien in particular relished the chance to share these treasures with his friends and neighbors—farmers and blenders and small winemakers who otherwise might never get the chance to experience a 1971 Domaine de la Romanée-Conti Romanée-St.-Vivant or a 1991 Chave “Cuvée Cathelin.” As he watched the fall sun inch below the horizon, sitting with friends and contemplating some of the greatest wines ever made, all seemed right with the world. They were in the black. He could exhale at last. And now, finally, they could get to work. Securing the auction money wasn’t the end of things, after all, but the beginning. They still had a company to build.
From left: Leverenz, Callahan, and O’Brien toast to a heroic success that almost wasn’t.
Illustrated by Matthew Woodson
The profit from the sale eventually produced Faucet, a wine-focused venture-capital fund with a portfolio of proprietary businesses, from négociant winery Where With All to investments in rare bottles to the Sonoma Valley producer Gail Wines. There’s even a fine-wine purveyor, Berkeley and Stuart, named after the intersection where Grill 23 sits, and where each of the partners got his start in the industry. Where, in some sense, it all began.
Few if any Sonoma Valley cookouts before or since have poured a magnum of 1990 Bâtard-Montrachet alongside a 1949 musigny from Camille Giroud.
Callahan is now an investor in that restaurant and stores some of the group’s wine there. After dinner, he walked me through the cellar, showing off various bottles. One label stood out, faded yellow and black, with an image like an Art Deco clamshell opening over a twinkling cosmos. It read: “25th Anniversary, Windows on the World, 1976–2001,” part of a store Faucet had acquired of custom Veuve Clicquot produced for the famous restaurant that once straddled the 106th and 107th floors atop the North Tower of the World Trade Center, which collapsed into rubble along with everything else on September 11, 2001. Another marvel in a seemingly never-ending saga of them.
As I walked down the steak-house steps into a humid late-spring evening, passing under the lamplit street signs, a snippet from the auction catalog popped into my head: “Put simply,” wrote Serena Sutcliffe, honorary chairman of Sotheby’s Wine, “it would be beyond comprehension if it did not exist in reality.” Exactly so.
