Ninety-hour workweeks, huge fortunes in the balance, cutthroat competition: it’s no wonder Wall Street drinks. The lap of global wealth and economic power, densely concentrated at the lower tip of Manhattan, has always had a relationship with the bottle, dating back to 1860s when cocktail legend Jerry Thomas operated a saloon there and nearby bars created a jigger tailor-made for bankers who wanted to pop in and out for a light nip.

These days, the archetypal vodka-guzzling, coke-snorting Master of the Universe, mythologized in films like The Wolf of Wall Street and American Psycho, is a familiar one. But with banking still under a harsh post-crash spotlight and Silicon Valley poaching many of the top brains that used to beeline for J.P. Morgan and company, the stereotype is also an increasingly inaccurate one. Wine, Wall Street’s urbane drink of choice throughout the past 25 years, offers a subtler lens to examine how the culture of decadence has evolved.

Beginning in the late ’80s and early ’90s, America took a new interest in the wine, thanks in large part to a burgeoning domestic wine market in California and a famous 1991 segment of CBS’s 60 Minutes on the phenomenon of “the French paradox.” On the program, researchers argued that the French had a lower incidence of coronary heart disease than Americans thanks in part to their steady consumption of red wine. Studies showed a 39 percent increase in U.S. sales of red table wine the following year. And it wasn’t just table wine that was picking up: between 1991 and 1999, cases sold of ultrapremium wine in the U.S. jumped from 2.4 million to 10.1 million, a trend that was mirrored on Wall Street, which was quick to embrace it as a new symbol of status.

Jeff Zacharia, president of Westchester, NY-based Zachys, considered one of the best wine shops in the country, joined the company in 1983. He recalls seeing an influx of interest from bankers who, while bearing mixed degrees of knowledge, were eager shoppers and fast learners.

“High-end wine really had a cachet at the time, in a way that beer and cocktails didn’t,” says Zacharia. “It was about quality of life—showing you had an appreciation for the good things.” Bordeaux and California reds—increasingly influenced by a “more is more” approach to winemaking—became best-sellers. While for some, they were gateways to more vast and varied world of wine, by and large these wines came to define Wall Street’s tastes in the ’90s and early aughts: big, bold and brash—a kind of liquid corollary of Wall Street’s own hedonistic tendencies.

With its countless regions and micro-regions, vintages, producers and grape varieties, wine provided an endlessly complex hierarchal system in which enthusiasts could constantly resituate themselves based on knowledge and wealth. For meritocratic bankers accustomed to comparing bonuses as a measure of self-worth, the subtle—and sometimes not so subtle—one-upmanship of wine came quite naturally.

In retrospect, it was a perfect marriage. Wine was a social lubricant and finance was an eminently social field of work, in which some of the most important conversations and deals could happen over an Upper East Side dinner table or on a Hamptons back porch. It conveyed European sophistication and aesthetic refinement: the fine art of drinking. Moreover, with its countless regions and micro-regions, vintages, producers and grape varieties, wine provided an endlessly complex hierarchal system in which enthusiasts could constantly resituate themselves based on knowledge and wealth. For meritocratic bankers accustomed to comparing bonuses as a measure of self-worth, the subtle—and sometimes not so subtle—one-upmanship of wine came quite naturally.

“Robert Parker is definitely a piece of the puzzle,” says Zacharia, of the role Parker’s The Wine Advocate played in stoking the flames of the new obsession. Parker, a former assistant general counsel for Farm Credit Banks of Baltimore, was an everyman Wall Street could relate to. In the bimonthly publication, Parker spoke a frank, unadorned and—most importantly—quantitative language that bankers understood. His occasionally controversial 100-point ranking system simplified the vast and confusing selection of wine to a vertical scale recognizable from high school math tests.

His tastes proved so influential that industry watchers coined the term “Parkerization”: a theory that posited that vintners were producing more of the wines that he (and many bankers) preferred: high-alcohol, rich, bombastic. Concomitantly, The Wine Spectator proved successful at lassoing in the other accouterments of the good life—fast cars, Rolexes, decadent meals—further pushing the market towards a swaggering style reminiscent of the Wall Street attitude. As a media culture began to grow up around the industry, wine became a baked-in aspect of the banker lifestyle.

The case of a Greenwich, CT-based hedge fund manager named John (whose real name has been changed) is instructive. Introduced to wine by his older brother who was also in finance, John took an active interest in wine from an early age, even signing up for tasting classes through his college’s hospitality program. After graduating in the early ’90s and taking his first hedge fund job, he noticed that when he got to tag along on dinners with senior staff, they would easily spend 40 minutes talking about wine. “I would be blocked out of it, but I would listen and pay attention,” he says. “I wanted to be an insider as well.”

Now a serious collector with 3,000-4,000 bottles to his name, John says he can easily spend an entire dinner discussing the subject with fellow wine lovers, a skill which has proved to be vitally important in bonding with clients. “You’re showing you’re personable,” he says. “I can say, ‘Hey, remember two weeks ago when we had dinner and we were talking about that ’85 Rayas? I finally got to try it.’ You get the conversation going without just calling someone up two weeks later and asking, what were you saying about Boeing?”

John and his ilk weren’t taking clients out to wine bars—restaurants were their preferred arena for consumption, and the city was beginning to take note. Where wine lovers once had to sniff out the odd spot that happened to boast a decent wine list, restaurants in New York City began catering to the moneyed, newly enthusiastic suits from the Financial District. Nowhere was this more true than at Veritas, which opened in Flatiron in 1999, boasting an incredible wine collection that combined the private cellars of its two founders, Park Smith and Steve Verlin.

“Veritas is an early clue to a new direction, a sign that restaurants may be changing…because at Veritas, the wine is more important than the food,” wrote New York Times restaurant critic Ruth Reichl in her three-star review. “It is in fact so important that it could be called a wine cellar with a restaurant attached.” Four years later, Cru opened in Greenwich Village with a collection of no less than 65,000 bottles; each table was afforded two phone-book-sized leather-bound volumes, one for reds and one for whites. Both restaurants became regular stops on bankers’ wining and dining circuits, places where they could impress clients and colleagues by blowing expense account funds on a bottle of Screaming Eagle or Pétrus.

And both restaurants, perhaps tellingly, are now closed. According to Robert Dentice, head of healthcare investing at Cantor Fitzgerald, wine buying and drinking are much different in post-2008 Wall Street, where the optics of lavish spending are a liability for banks. And thanks in part to the demand that Wall Street originally helped create, wine prices have risen in the past two decades.

“In the late 80s and early 90s, you bought Bordeaux and Burgundy,” says Dentice. “Nowadays, if you walk into a store and say, I want to buy a case of first growth and you’re a junior banker, it would be like $15,000. Back then, you could get a case of first growth for $4,000 or $5,000 and you were much more wealthy on a relative and absolute basis. Bankers have almost been priced out of wine.” Now, Dentice says, its successful entrepreneurs who can write their own checks that are dropping $10 or $15 million dollars at an auction for wine. Global demand, especially from China, has also driven up prices for wine, leading to phenomena like the Bordeaux bubble of 2011, in which cases were going for as much as $23,000.

But Wall Street’s taste in wine has changed along with the market. “Now it’s more about showing you’re hip,” says John. “That means you can put something on the table that isn’t difficult to acquire simply because of price. If you can introduce someone to a wine and they really like it and then they go and try to find it and can’t, you feel cool about it.”

Dentice’s noticed that even bankers—with their predilections for stress, cholesterol-clogging steaks and cigars—are more health conscious than they used to be and their evolving tastes in wine seem to reflect this.

“People are gravitating towards lower alcohol, more balanced wines,” he says. He’s taken over 30 clients to Rouge Tomate, the sustainably focused, Upper East Side Michelin-starred restaurant. It’s a choice that also reflects a changing, modern definition of luxury, in which provenance matters as much as prestige. It seems that even bankers can’t escape the Brooklynization of New York. “I’m not picking the 98 Parker-rated wine that’s sold out everywhere,” says Dentice. “I’m picking wines that have a story—this wine is small production, I visited the winery, this is the background.”

Just as Wall Street’s elders once passed their infatuation onto finance’s younger generation, so the current generation has begun molding the class below them in their own image. As luxury companies reach into company lore to bolster their image as heritage brands, tastes in wine are increasingly tending towards the small-batch, organic and esoteric. Dentice has already started taking his junior group out for some early introductions. “One of my coworkers here, I’ve turned him onto orange wines and that’s all he talks about now,” he says. “I don’t think he even realizes that orange wines are extremely geeky. He just likes them.”