The Most Influential Failed Bar

With its molecular leanings and misfit chef-bartender duo, New York’s Tailor was daring, eccentric and 10 years too early.

Tailor opened in September of 2007, one year before the Great Recession took New York City by the scruff of the neck and shook it like a dog that peed on the carpet. The chef, Sam Mason, former pastry chef of Wylie Dufresne’s wd-50, was a poète maudit in the kitchen. The mixologist—a term not yet rendered annoying —was Eben Freeman, a bookish, analytical fellow who resembled a shorter Stephen Merchant and wore his hair with an almost Zack Morris-ian flip. Like Mason, Freeman had worked at wd-50 [and nearly every other iconic bar in New York—from the divey (Mona’s, Sophie’s, the Shark Bar, Muggs) to the tony (Palladin at The Time hotel).]

From the jump, the narrow, bilevel space on Broome Street had Icarian ambition. For a full year leading up to its opening, the local internet was abuzz with anticipation, and when the space was finally revealed, Mason and Freeman’s obsessive labor seemed to reward the scrutiny. The sartorial theme manifested in a wall upholstered with pinstripe fabric; a giant textile bolt rested against another wall, and a garment rack hung out in the dining room. The servers themselves wore bespoke handstitched waistcoats by Lord Willy over dress shirts.

But it was Mason’s menu and Freeman’s drinks that drove the food world to unprecedented distraction. Bifurcated into “sweet” and “savory,” Mason’s menu appeared an edible exquisite corpse: “Foie gras terrine, cocoa dust, peanut soil, pear paper” or “Pork belly, butterscotch miso sauce, green apple stick.” Though the pared-down syntax wasn’t anomalous at the time, the verve with which Mason collided strange things into stranger things and the molecular formality with which he did so—Tailor’s menu was peak foam—was unusual. Momofuku Ssäm took off that year, the dawning of a Dionysian era of ugly delicious, and Tailor was nothing if not pretty.

In the more informal subterranean lounge, dominated by a wide marble bar and kept louchely dark, Freeman explored the hinterlands of cocktails, producing works like the Bazooka (a bubble gum–infused vodka riff on the -tini trend) and the Waylon, named after Waylon Jennings, which included cherry- and alder wood–smoked Coca-Cola. There was the Yerba Mate Sour, a Masala Mai Tai spiked with garam masala, a Mushroom Margarita, a Beet Sangria, a Violet Fizz with a rare crème de violette smuggled back from Europe. Freeman was known for his profusion of infusions, including Scotch with pumpernickel-raisin bread and bourbon with cigars, as well as his Gin-and-Tonic jellies and solid Rum-and-Cokes. One didn’t get tight on the booze at Tailor’s bar. One went sideways with wonder.

At the time, New York was intoxicated with the re-creation of the speakeasy. It was the year of PDT, a moment when the arch-traditionalists of Pegu Club and Employees Only reigned supreme, a time when Manhattans and Old-Fashioneds were everything. And into this solemn, rule-ridden, dress-up game came Freeman, slinging hot pink Appletini variations and smoking Coke like Hunter S. Thompson on a bad day. With his double-breasted vest and rolled-up sleeves, he looked like every other craft cocktail Stan, but he was an agent provocateur.

Mason, meanwhile, was just provocative. He was the apotheosis of bad boy chefs of that era. Lustrous was his goatee, inked were his arms, smoldering was his stare and tousled was his bouffant. At one time, he had a show on IFC called Dinner with the Band, a sort of “Tiny Desk Concert” meets Barefoot Contessa for the Pitchfork crowd. Long before LCD Soundsystem’s James Murphy opened a wine bar and Beastie Boy Mike D became a somm, Mason was making black olive cobbler for Les Savy Fav and jerk pheasant for Matt + Kim. Downstairs, particularly late at night, when Freeman was in the flow and the bar was crowded with off-shift industry folk, cocktail geeks and a few of Mason’s rock star friends, there was that rare New York-y feeling—an atmospheric magic akin to a mash-up of Fluxus and a Todd P party and a Larry Tee party, with a touch of Elaine’s.

Now I have to admit, at Tailor’s height, I was but a whippersnapper. The place was spendy, around $800 for four people. I hardly knew four people, let alone anyone who had that kind of dough. I have hazy memories of the bar downstairs, but mostly recall rolling in the whitewater of breathless Eater and Grubstreet reports, and catching the wake of eGullet posts left by DocSkonz and Ulterior Epicure. “I think what Tailor did for me,” wrote Ulterior Epicure, “that no other American restaurant has done to date, is successfully made me reconceptualize / reposition / reorient / revolutionize the way I perceive and understand the roles of savoriness (i.e. saltiness) and sweetness in a “traditional” (American) meal,” wrote the still then anonymous Epicure in September There are more than 12 pages of comments on this thread.

But from the start, Tailor was plagued by its ambition. Its beauty and danger were hidden in its name all along. It is perhaps telling Mason didn’t call the place Mason. A mason is someone who builds. A tailor is someone who alters. Was it a noun or a verb? And if a verb, who or what was being tailored? Was Mason building a restaurant to suit the world or was he attempting to alter the world to suit his idea of what a restaurant should be?

By late 2007, eGullet posts had taken on a funereal air: “Was surprised that the dining room wasn’t full when we arrived at 8:45, and I don’t think it filled up while we were there, either.” A middling New York Times review appeared in November: “Food’s the center of a meal, the stuff of survival, so you expect a final balance of basic satisfaction,” wrote critic Frank Bruni, “And like some of his envelope-pushing peers, Mr. Mason may be too invested in his mind games to attend to that.” In November 2009, after a brief stint in Chapter 11, Tailor closed. The world it left was vastly different. Sobered and chastened, Tailor’s exuberance was already out of style.

A test balloon for just how far a chef and a bartender could lure customers, Tailor’s brief and brilliant stint on this earth left an indelible afterimage. Fat-washing and smoked drinks entered the cocktail lexicon, while, post-Recession, many ambitious chefs scampered to fast casual. Tailor was as bold a proposal as a planned city in the jungle or baseball diamond in the middle of a cornfield. But, alas, they didn’t come. Twelve years later, Mason is making ice cream and runs a dive bar called Lady Jay’s. Freeman directs the beverage program for AvroKo, a large restaurant group. And though both men seemed to have learned that a tailor must suit the needs of man more than man needs a tailor-made suit, I rue a bit the heady days of pork and butterscotch, bubble gum–infused vodka and smoked Coke.

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Joshua David Stein is a cookbook author and editor who lives in Brooklyn. He is the co-author of Notes from a Young Black Chef with Kwame Onwuachi; the author of the children’s books Can I Eat That?; What’s Cooking?; Brick: Who Found Herself in Architecture; Can You Eat and the forthcoming Book of Balls. He is the editor-at-large at Fatherly and host of the Fatherly podcast.