What about the 2015 Trump Meritage, a blend of red grapes that are “sourced,” meaning trucked in from the West Coast. The label calls it “American red wine”; it sells for $30 on the Web site. My guest tasted the Meritage: “Welch’s grape jelly with alcohol. A terrible, fumy, alcoholic nose. If I served you that on an airline you’d be mad.” (A buyer at a well-known Washington wine shop I later asked to evaluate the wines—he once sold Trump vodka, produced from 2005 to 2011, because he liked it—took one sip of the Meritage, wanted no more, and said, “Grocery-store wine.”) My guest went on, “They’re lying about the alcohol on the label.” He knew this, he explained, by a strange method of marching his two front fingers down his chest after he swallowed, saying that when he could feel the alcohol down to his belly button he knew it was 14 percent alcohol, which is what the label said. But this wine pushed his fingers below the belt. He knew the Meritage was 15 percent—and a 1 percent variance, oddly, is permitted on labels. “This’ll rip you,” he said.

THE EXPERT AND I DRANK THROUGH AS MANY TRUMP WINES AS WE COULD GET.

We tried Trump Winery’s far more expensive New World Reserve, made from a similar blend of red grapes but all grown in Charlottesville. The bottle has the words “estate bottled” and “Monticello” on the front and sells for $54 on the Web site. It was better than the Meritage. A server also brought us a glass of Trump Winery’s sparkling blanc de blanc, a calling card of any Virginia winery. “It’s fine,” my friend said. “No reserve, by which I mean flavors that keep unwinding like an onion skin. It doesn’t offend. I’d get drunk on it at a wedding.” He paused. “Let’s be honest. I’d get drunk on anything at a wedding.”

I managed to engage my friend and one server in a discussion of Virginia wines, which both admitted could be decent or, in the case of a few wine-makers, much better than decent. But the server did everything possible in the course of a long meal to steer us away from Trump wines. The idea had been to impress a famous guest, and serving him products from Trump Winery was not the way to do it. “We sell these,” the server said with a theatrical eye-roll, taking in the collection of glasses that by then were crowding our table, “because we have to.”

Illustration of Donald Trump. Illustration by Barry Blitt.

Why wine—and why Charlottesville? Not because Donald Trump likes wine: he is a teetotaler. The official answer is that he was helping out an old friend in her moment of financial duress, giving new life to a dream project that had tanked just a decade after she poured into it much of her estimated $100 million divorce settlement. Patricia Kluge, raised in Iraq, the daughter of a British father and a mother who was half Chaldean and half Scottish, had married John Kluge, a self-made billionaire, in 1981, when she was 33 and he was 67. They bought up land in horsey Charlottesville, a short drive from Jefferson’s Monticello, and built a 45-room, 23,500-square-foot Georgian-style mansion where they entertained lavishly, using the golf course, the five lakes they constructed, and the game preserve they stocked. In 1990 they divorced, and nine years later, with her third husband, Patricia Kluge established a winery bearing her name. Her ambitions were simple: to make the best wine in the world.

Gabriele Rausse, the affable, Italian-born director of gardens and grounds at Monticello, worked as the Kluge wine-maker for the first 10 years, 1999 to 2009, and then consulted unpaid for an additional year and a half after Patricia Kluge went broke in the wake of the mortgage crisis. He recently recalled that when, at the outset, Kluge said she wanted to charge a stupendous $450 a bottle, “I told her, ‘If you put my name on it, you can charge $4.50. If you hire the best wine-maker in France as a consultant, you can try to charge $450.’ ” So he put her in touch with a famous wine-making friend from Champagne, and, Rausse recalls, she paid him “a crazy amount of money.” Word got out in the nascent local wine industry, which Rausse had helped build after arriving in Charlottesville, in 1976. That was a time when local wines left a lot to be desired. The first bottles he made, in 1978, he couldn’t give away: friends kept passing them along to other friends, fruitcake-style. The millions Kluge poured into her vineyard, Rausse said, made other wine-makers step up their game.

THE EXPERT SAID, “IF I SERVED YOU THAT ON AN AIRLINE YOU’D BE MAD.”

Now 72, Rausse is both frank and philosophical. “She was shooting for quality,” he says. “Her main mistake was that she wanted the best Cabernet Sauvignon in the world, but it needs four to five years to take off. She sold it right away, because she was short of money. It was a constant contradiction.” (A source close to Kluge says financial considerations played a part only after the financial crisis.) Even so, the wines, particularly the sparkling blanc de blanc, had some success, including being served at Chelsea Clinton’s wedding.