The only time that wine importer Victor O. Schwartz was in the same room with Donald Trump was during a lunch in the 1990s at Jean-Georges, the high-end French restaurant on the ground floor of the Trump International Hotel. Schwartz overheard a nearby table of ABC staffers — the network’s old headquarters was around the corner — ragging on the local mogul who had just left behind a mess of bankrupt casinos in Atlantic City. “A bunch of people were trash-talking him and making fun of his hair,” Schwartz says. “And then he walked by, and, of course, they’re all glad-handing him.” The moment stuck with Schwartz. “I mean, he was a laughingstock in New York, he really was,” he says. And yet when Trump entered, all mocking turned to flattery. “It’s the hypocrisy of that world.”

As a 67-year-old on the Upper West Side, Schwartz is fairly representative of the boomer class living in the city. He likes the Grateful Dead and Lucinda Williams and hates what Donald Trump has done to this country. “We were a dependable military partner, a dependable economic power. We were a country of laws, all those kinds of things,” he says. “All of that? Just with these tariffs — out the window.”

When I met Schwartz at his apartment near Riverside Park in early April, he had the New York Times headlines from the Trump indictment and conviction in Manhattan cut out and taped to the back of his front door; he called it his “Travis Bickle” collage. On the glass coffee table in the living room was an issue of Spy magazine from 1990, our current president illustrated as if he were a baby on the cover, under the headline: “WA-A-A-A-H! Little Donald—Unhappy at Last.”

As a small-business owner, Schwartz has plenty of reasons to dislike the president’s policies. For almost 40 years, Schwartz has owned and operated VOS Selections, an importer and distributor of fine wines from 16 countries. Tariffs on wine have frustrated his industry since 2018, making the already heavily taxed business of sourcing from small farms and importing bottles from abroad more expensive.

When Trump’s second-term tariffs were first announced last April, it looked like an even worse disaster for American wine importers than the first term. A blanket 20 percent on goods from Europe affected not just the wine but the cork (from Portugal and Spain) and the good barrels (France). Sake from Japan and soju from South Korea were hit with a 24 and 25 percent tax, respectively. They might as well forget about South Africa, with its 30 percent tariff. Trump called the tariff rollout “Liberation Day.” Schwartz had an alternative term: “strangulation day.”

But the tariffs were also when he realized, unlike so many frustrated by Trump, he had an opportunity to do something. The weekend after the announcement of the tax on imports, Schwartz had what he says was  a “fortuitous conversation” at a family brunch. A relative mentioned that their law professor at George Mason University, Ilya Somin, had put out a call in the libertarian monthly Reason for plaintiffs to challenge the tariffs.

“Normally when I write something, it has little to no effect,” Somin told me. But the tariff blog found a ragtag crew of small businesses who wanted to file a case against the administration: a tackle store on Lake Erie in Pennsylvania, a pipe manufacturer in Utah, a women’s cycling brand in Vermont, the maker of a banana-shaped synth in Virginia, and, eventually, Victor Schwartz and his wine-importing business. Within a few days, Somin, together with attorneys from the Liberty Justice Center, asked Schwartz to be the lead plaintiff.

The wine-importing case made sense on an Econ 101 level. Tariffs are designed to protect domestic manufacturers by making foreign products more expensive. But how could a grower in Napa re-create the exact conditions necessary to produce a heavy red from Bordeaux? Doesn’t Champagne come from only Champagne? “This is just a particularly obvious example of the more general concept of comparative advantage where it makes sense to import goods that they can produce better or more cheaply than we can,” said Somin.

Relatives were less sure the case made sense on a personal level. “This is just such a vindictive president,” warned Chloe Schwartz, Victor’s daughter who serves as vice-president at the family company. Trump had already threatened a 200 percent tariff on French wine. Why put a target on your back?

But reading the news in the first months of Trump’s second term, Victor Schwartz says he was so disappointed by the tech companies and corporate law offices and the Ivy League schools capitulating to the president’s demands that it gnawed at him. “I certainly thought that the power and money in this country would step up to the insanity from this administration,” he says. It was not some liberal “vendetta on my part against Trump,” Schwartz says of joining the case. It was what other companies failed to do: stop Trump from hurting his company. “This was a bad business decision,” he says. “This is somebody who’s been bankrupt, what, six times? I do not believe he’s a good business person.”

Schwartz’s case — V.O.S. Selections, Inc. v. United States — was filed the next week in the Court of International Trade. After it was bumped up to the federal court of appeals, it appeared before the Supreme Court this past November. He was in the room to hear the case along with famous faces like Treasury Secretary Scott Bessent, Commerce Secretary Howard Lutnick, and actor John Mulaney — a friend of Liberty Justice Center attorney Neal Katyal.

In February, when the 6-3 decision came down that Trump had overstepped his authority, Schwartz tells me he was at home with his daughter. They started “jumping around dancing,” he says. To celebrate, they opened a 2015 blend of Grenache and Syrah grapes from the Châteauneuf-Du-Pape appellation in the Rhône Valley, unfiltered and aged in oak barrels. (That’s a red, by the way.)

Schwartz was quick to explain that his win at the Supreme Court was not the end of the fight. The decision launched a process to return over $160 billion in refunds; VOS Selections is looking at a low-six-figure payment, Schwartz says, plus 6 percent interest. But he expects delays in the process to return the illegal import tax, given the blundering nature of the administration’s paperwork so far. Trump has already weaponized this process, saying on April 21 that he would “remember” any companies that do not fill out the simple application for a refund. Meanwhile, the president has applied a blanket 10 percent tariff on all imports — a tax that could be overturned by another small business in New York, this time a spice importer in Jackson Heights.

Having spent a year of his life thinking about this, Schwartz has developed a grand theory of how the tariffs represent all things Trump. The president has been “hell bent” on this outdated policy for decades and was able to apply them only “because everyone let him do it.” “It’s very much out of the Roy Cohn playbook,” he said. “We’re just going to do it until we get caught.”

The tariffs are only the latest in a long line of downturns and unexpected challenges since Schwartz initially got into the wine business 40 years ago after leaving his first real job: commercial lending at Union Bank in San Francisco. He says he quit because they would not let him wear “fun ties.” Half a lifetime later he still favors paisley and small-flower patterns, like the white-and-blue pedals on his oxford the afternoon in early April we chatted.

Starting up in New York in the 1980s, he had to worry about the mob, which had a stake in alcohol dating back to the Prohibition era. “You were not in the wine business,” he says, “it was the booze business.” But the larger barrier to entry was cross-continental communication. “You didn’t have any of this technology,” he says, referring to a phone with GPS. “You had to go from this little village to that little village. You had to ask people questions.” Email and a globalized economy brought more competition in the 1990s but also made the job easier for Schwartz. Now, with President Trump’s tariffs and rocketing energy and fertilizer costs and generally skeptical trade partners across the board, he says his work — sourcing from small growers on five continents — is like a “canary in the coal mine” of a de-globalizing world. “We really are on the front edge of this, the frontier of it,” he says.

But the real challenge for the next decade is not on the supply side. You may have heard that people in their 20s are drinking less than they used to — a piece of information that sounds like an op-ed writer may have heard it from a taxi driver. But it is true: The industry is preparing for what analyst Rob McMillan calls the “sunsetting of the boomer.” McMillan is the founder of Silicon Valley Bank’s wine division and he has been warning about this trend since at least 2018, when it became obvious to him that when the most powerful consumer generation “gets to a certain age, they just can’t drink like they’re 30,” he says. “Our largest issue is demand.”

The Schwartzes are fighting this decline, too. “You want to develop a generation of people who want to enjoy a glass of wine with dinner,” says Chloe. “But if they can’t afford that, then that’s not what they’re reaching for and that culture doesn’t happen.”

Still, Schwartz is confident that he can find a way past the current tariffs and the generational time bomb ticking in the distance. Mostly, as we speak, he seems eager to get out of the apartment. A few weeks after the Supreme Court decision, Schwartz underwent surgery to replace his left hip. Other than the cane he favors to walk around the apartment, it doesn’t seem to slow him down much. An acquaintance in the wine world said he was a “pistol,” a word I’d never heard used to describe a man.

At home over the past few weeks, he has been tinkering with an elaborate wood puzzle shaped like a map of North America, which sits on a side table in the dining room. (The long banquet table in the middle of the room is covered with half-empty bottles of American Pinot Noir, which he was showing to a producer from Burgundy the night before.) Next to the puzzle is a fish spatula, which seems to me to be out of place. With his cane in one hand, Schwartz explains that it is for putting pieces together and moving them “wholesale” to their place on the map. “It’s a technique,” he says, to help make sense of this puzzle of our world. “Otherwise it’ll fall apart.”

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