A fence lizard clings to a velvety cluster of Cabernet Sauvignon grapes, his blood still too cold to manage much movement in the foggy Napa Valley morning. With the September sun yet to burn off the clouds, the sky is a giant soft box, bathing the vines at Chimney Rock Vineyard in a diffuse glow. The lizard shifts languidly to the backside of the grapes as a hand plucks a nearby bunch.

John Terlato pops one of the grapes, no bigger than a blueberry, into his mouth and uses his teeth to peel back the skin from the sweet flesh. John, who owns the vineyard with his father, Anthony, and brother, Bill, has flown in from their Chicago headquarters in advance of the crush, making sure these particular grapes are worthy of becoming a Terlato wine. He spits the seeds into his palm and examines them while his taste buds search out the complexities in the fruit and the nuances of the soil. They’re also straining to taste something else: greatness.

Later, as John makes his way down the hill to the vineyard’s cask storage facility, he and Doug Fletcher, his head vintner, are deep in conversation about whether 2012 will be a good year. They arrive at a Tomahawk Cabernet that was barreled last week. John plucks the stopper from the cask and uses a 50-year-old pipette to flood a wineglass with the ruby liquid. There’s a lot riding on this wine, the same way there’s a lot riding on a baseball team’s regular-season games on the way to winning the World Series. If they want to bring home the pennant, they have to do this right every single time. This is one of the wines, the family hopes, which will cement the Terlato name as one of the best in the world.

He lifts the glass to his nose and breathes.

This year marks the 75th since the family’s patriarch, Anthony Paterno (John’s maternal grandfather), opened a wine shop at Grand and Western Avenues on Chicago’s West Side during the Great Depression. Paterno’s daughter, Josephine, would later marry Anthony “Tony” Terlato, who had followed his father from the jam-packed storefronts of Brooklyn to Chicago to open a wine store of their own, Leading Liquor Marts at Clark Street and Ridge Avenue. Tony’s store was just across the border from Evanston, which had been a nexus of the temperance movement. That turned out to be a smart move; those who couldn’t get their spirits in the college town found Leading Liquor to be a handy location.

But that was just one aspect of the Terlato business savvy. At the time, the self-serve market was wide open. But the hitch was that wine wasn’t a desirable beverage in the dining realm. Coffee was the drink of the day. That would all change, thanks in part to Tony. In the evenings, he would bring home bottles of quality wine to accompany Josephine’s meals. He tasted them blindly, over and over, honing his palate. As Tony’s own appreciation was developing, so was Chicago’s. He soon left the liquor store to join his father-in-law’s distribution company, Pacific Wine Company, which had grown out of that original West Side storefront. Beginning as a suited and cuff-linked salesman, Tony first courted run-down liquor shops before shifting to restaurants and trying to teach maître d’s about the harmony between fine wine and gastronomy.

It’s a leap through 50 years of innovative business tactics, but Tony and his father-in-law grew their company from a simple bottling and distribution house to an international importer. They became one of the most influential traffickers of fine wine in the United States, and in the 1980s Tony was almost single-handedly responsible for bringing Italian Pinot Grigio to America. All the while, he was spending a considerable amount of time getting to know the great names in wine. He spent portions of his honeymoon learning from Robert Mondavi, who planted a seed in his mind about one day owning his own vineyards. He was fortuitously seated next to wine writer and entrepreneur Alexis Lichine at a dinner party in New York. Eventually, he would become close friends and partners with Michel Chapoutier of the famous Rhône family of vintners. Though his father-in-law was more interested in profit margins and supply and demand, it was as if Tony had found his way into a different echelon altogether—a world where “quality” was the secret password. Informing every decision he made was an unyielding desire for the best wines, and not just because they were nicer on the tongue. It was because he firmly believed in their business value.

“If you do business because of price, someone will come along with a better price and steal your business,” Tony says on a September afternoon, sitting in the parlor of Terlato Wine Group’s Lake Bluff headquarters, a 61-room Tudor Gothic mansion built in 1916. Empty wine bottles, signed by their famous drinkers, are arranged neatly around the estate. A picture, made with wine as the paint, depicts Tony and his smiling sons. “Quality,” he adds, “is hard to take away.”

That’s not to say it’s all about business. At the root of every boardroom decision Tony makes is a prodigious sense of taste, an unabashed passion for the way risotto plays with quail and porcini mushrooms, or the feel of a Gagliole Pecchia Rosso on the gums. Taste is such a central concept to the Terlato family that Tony even penned a memoir dedicated to it: Taste: A Life in Wine—known simply as “The Book” to his sons, employees, and friends. Each year, he hosts a legendary white-truffle dinner at $500 a plate. Nonna Giarusso, his deeply Italian grandmother, who rarely cooked from a recipe and was famous for her veal cutlet, informed Tony’s taste.

He founded a fine wine and food society that includes some of Chicago’s most influential businessmen, musicians, and surgeons. It’s called The Renaissance Club, and only 30 people are allowed membership, because that’s the number that makes for the most epic dinner party. At a recent meal, a six-course soirée at Pelago Ristorante off Michigan Avenue, Tony’s discerning palate was in full form. Chef Mauro Mafrici had just delivered a spectacular beef tenderloin in black-truffle sauce, and Tony had selected the wine: a 1997 Gaja Costa Russi. He comes alive when it hits his lips. “The wine we had before this was a very good wine,” he says, referring to the Gagliole Pecchia. “But this? This is a firecracker. You feel it up to your eyeballs!”

The same unbridled enthusiasm is so apparent in his sons that you can almost see Nonna’s wooden spoon stirring the pot through the generations. On any given evening, John might present his three children with a dozen different burger varieties and ask them to blindly rate them. During a conversation with a friend about her favorite store-bought tomato sauce, John told her: “I can do better.” He came back with his own version (again, blindly tasted against 25 supermarket brands). It was so good that he now jars the sauce and distributes it to a group of close friends by invitation only.

Now, with a third generation of Terlatos primed for the ascendancy, this renowned taste shows no signs of disappearing—and that’s exactly the way Tony wants it. If there’s one thing he prizes above his appetite and his business success, it’s his family’s legacy. When he talks about the future, it’s about how he’s going to become the modern equivalent of the old-world names that have been making storied wine for centuries. “The people we did business with talked in generations,” Tony muses. An oil painting of himself hangs above the fireplace. He pauses before adding, “In America in the 1950s, there weren’t many generations. But in Europe there were families in the wine business for 29, 30 continuous generations. You would see the portraits. And I’m thinking, how do I get to be 40 generations?”

Tony has already locked in his name as the American father of Pinot Grigio and as the visionary leader of the business empire that transformed the US wine industry. But he’s not satisfied. He wants to leave behind a significant American wine—one that stands shoulder to shoulder with the Mondavis, the Gajas, and even the Rothschilds and Contis.

His sons, Bill and John, share these dreams as they sally forth into the new era. “The legacy my dad, my brother, and I want to leave is as winemakers, in addition to what we’ve done as importers and distributors,” John says.

In an almost providential turn of events in 1996, Tony fulfilled what Mondavi had predicted 40 years before. He bought Rutherford Hill, one of the first vineyards to introduce American-grown Merlot to the marketplace. In his first meeting with his winery’s staff, Tony walked into the room with a stack of magazine covers from Wine Spectator. He had Photoshopped a bottle onto them with a headline that read “#1 Merlot in Napa Valley.” The date in the corner was five years into the future.

“I said, ‘I’ll give you five years, or you’re gone,’” Tony remembers. “They got us good numbers, but not good enough, so they were gone.” He fired and replaced his entire staff.

Over the next several years, they acquired more vineyards: Alderbrook in Sonoma, Sanford in Santa Barbara, Terlato in the Russian River Valley. But one of the jewels came in 2000 when they purchased Chimney Rock, nestled in the Stags Leap District, a narrow strip of land three miles long and a mile wide, widely acclaimed for its favorable conditions for growing Cabernet Sauvignon. In the famous Judgment of Paris in 1976, it was a wine from this region that edged out the old-world Bordeaux and clinched an American victory in a red.

“What’s happening in Napa right now is what happened in Burgundy,” explains Fletcher. “People are recognizing that not every spot is great for every wine.” The Terlatos are reverential when they talk about the volcanic soil of this hallowed ground. They nod to the terroir, a French expression for the role land plays in the taste of its produce. For Chimney Rock, this is especially pronounced in its Tomahawk Cabernet, which is grown on just one plot of eight acres out of the vineyard’s 130 and deemed so good that it shouldn’t be mixed with grapes from anywhere else. “You can drill down into California, then Napa, then the Stags Leap District, then the specific vineyard,” John explains. “With Tomahawk, it’s like you’re on the head of a pin.”

So far, it isn’t just the Terlatos blowing smoke. When Robert Parker, the man with the million-dollar nose, tasted the 2007 Tomahawk, he gave it 91 points and wrote in his tasting notes that it was “a quintessential Stags Leap Cabernet to drink over the next 10 to 15 years.” That’s not the only Terlato wine to catch Parker’s nose: He scored their 2007 Ganymede as a 92 and praised its silkiness and notes of “beef blood, crushed rocks, and earth.”

The Terlatos have also zeroed in on a key demographic: young millennials, who obsess over the story behind what they consume like no generation before them. The family have become regular guests on Bravo’s hit series Top Chef, and of the show’s 3 million viewers, 80 percent are under age 35. “That tells you who’s interested in food and wine,” says Bill, who judged the season finale in 2010. “What you wear, what you drive, what you eat, where you go—they all reflect lifestyle choices. They’re seeking authentic experiences.”

High-end Terlato wines (like their headlining Episode and Galaxy blends) are regulars in the retail division of Hart Davis Hart Wine Co., an upmarket auction house in Chicago. There and elsewhere, there’s a marked sense of admiration for the family’s ambition. “I just tasted the ’08 Cabernet from Chimney Rock, and it’s a very good example of what the Terlato family is trying to do,” chairman John Hart says, though he hesitates to rank any wine without a blind tasting. “I respect them very much, and at our end of the business, at the very top end, I can’t say that about too many people.”

If simply wanting to be the best made it so, the Terlatos would be home free. Plenty of people aspire to carve their names in history. What makes wine an especially challenging arena is the crowd of grape-stompers who are all vying for legend status. In a field where the gates were once shut except to aristocrats—people like the Prince of Conti and the Rothschilds, who own “the king’s wine”—the doors have been blown open, and there are now more wines on the market than ever.

Indicators like the score (on a 100-point scale) and price (cult wines like Screaming Eagle can command thousands per bottle) don’t always tell the full story. The opinions of critics, too, can be brutally subjective. “I really think the only difference between a 96-, 97-, 98-, 99-, and 100-point wine is the emotion of the moment,” Parker told the Naples Daily News in 2007.

But Fletcher, the head vintner, isn’t worried. If the Terlatos are willing to fire one of their previous teams, that means they’re willing to outfit their current staff with whatever tools they require to succeed. “The Terlatos have given us a carte-blanche mandate [to] produce world-class wines,” he says.

So Fletcher balances the vines with his pruning shears, sparing only the grapes that will get the most efficient hydration from the stem. He clocks the drip-irrigation, and when the time comes for barreling, he uses subtler French oak instead of the cheaper American. He and his team have taken apart every piece in the process like an engine, examining each piston and gasket to see if it’s good enough. An example: At Chimney Rock, they spent a chunk of time exploring equipment that would mimic an ancient basket press. The process isn’t the most efficient, but it’s gentle. Modern machinery that smashes the skins to the max could yield 10 to 12 percent more juice, but, like squeezing a tea bag, it would also release astringent flavors that would lower the quality of the wine. “‘This is the way we’ve always done it’ is not a good enough answer,” Fletcher says.

Back at Chimney Rock, in the Napa Valley morning, John Terlato is twirling the Tomahawk Cabernet, splashing it high on the sides of the glass. He inhales its aromas: hints of flowers, black currants, maybe a little cedar. Finally he takes a sip, spreading it around his mouth and letting it coat his palate.

As John swallows, Fletcher looks him in the eye: “Not half bad, is it?”

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