Tonight, somewhere between West 80th and 81st Streets, a great many people in their forties will discover that they can still do a shot of Tullamore Dew, and a great many people in their twenties will discover that their parents were once fun. Tomorrow, Sunday, Oct. 18, Jake’s Dilemma, the Upper West Side sports bar at 430 Amsterdam Avenue, pours its last round after 32 years.
The bar announced the closing on Instagram in September, as West Side Rag reported. “After 32 years on the Upper West Side, we’re heartbroken to share that we lost our lease, and Jake’s Dilemma will close its doors on October 18,” the post read. “Jake’s has been so much more than a bar. It’s been late nights, game days, first dates, bad decisions, lifelong friendships, incredible staff, and more stories than we could ever fit into one post.” It is the rare closing notice that doubles as a fairly complete sociology of Amsterdam Avenue.
The three-night wake
Jake’s, which opened in September 1994, per Hoodline, is going out with three back-to-back farewell parties, Oct. 16, 17 and 18, Gothamist reported, inviting patrons new and old to have one last glass.
They will be saying goodbye to a particular kind of room: dim, tin-ceilinged, with a pool table, televisions tuned to every game, beer pong and foosball, 19 draft beers, and a downstairs party room, the Oak Cellar, with stone archways and stained glass that Hoodline describes as European in style. The menu runs to wings, sliders and, per Gothamist, “nachos grande” at $13.99, a price that may itself qualify for landmark status.
The Instagram post drew more than 1,000 comments. “Jake’s is significantly responsible for the life I have today: including numerous lifelong friendships, a happy marriage, and my unwavering ability to throw back a shot of Tully,” one patron wrote. Another, less sentimental: “Oh good, now we can get yet another Blank Street Coffee, Joe & the Juice, or maybe Pret A Manger.”
The wild west, then the Baby Björns
Michael Staff, the managing partner of Jake’s and its sister bar, gave Gothamist a short oral history. “It’s like losing a limb,” he said. When he started in the mid-1990s, “it was like the wild west up here. We used to have a cop that walked the beat, and you were glad to see him.” He recalled chasing a drug dealer away from the A-frame sign out front.
About a decade in, the crowd turned “more and more family-oriented,” Staff said: dads with infants in carriers came to watch college football. Lately there has been an influx of young people again. The bar, in other words, has tracked the Upper West Side itself, from frontier to stroller row to whatever it is becoming now.
What actually happened to the lease
The phrase “lost our lease” carries a lot of weight in New York, and here it carries a twist. Staff told Gothamist that the bar occupied property long owned by its owners. Hoodline, citing transaction records reviewed by Traded, reported that the five-story mixed-use building, with 20 apartments over the bar, sold in April for $7.825 million to SL Property Group. After the sale, Staff said, the bar was given 60 days to close.
Readers of West Side Rag’s comments section, never shy, were quick to point out the irony that the bar’s own landlords had sold the building out from under it. The commercial space is now being marketed, Gothamist and Hoodline report, as “ideal for upscale sit-down dining or premium healthy concepts.” That is broker-speak for “no beer pong,” and a fairly exact description of the direction of Amsterdam Avenue.
A wider vacancy problem
Jake’s is not an isolated case. Gothamist counted at least five longtime Upper West Side businesses announcing closures in recent months, among them Good Enough to Eat, the Columbus Avenue brunch institution, and Barzini’s, the Broadway grocer. A city comptroller report, Gothamist noted, found parts of the Upper West Side among the neighborhoods with the highest shares of long-term storefront vacancy.
Council Member Gale Brewer, who represents much of the neighborhood, is pushing a Storefront Bill of Rights that would require written leases for longer tenancies and give commercial tenants an option to renew, with increases capped at 10 percent. Jessica Walker, president of the Manhattan Chamber of Commerce, told Gothamist she fears the cap could discourage landlords from renting to small businesses; Brewer said she’s open to amending it. Council Member Virginia Maloney has proposed a registry and preservation fund for legacy businesses of 20 years or more. “They are the DNA of our neighborhood,” Brewer said of small businesses.
None of which would likely have saved Jake’s, where the owners sold their own building. But the bills are an attempt to answer a question every New Yorker eventually asks while standing in front of a papered-over window: where did my place go?
The Gin Mill, a few doors up
The good news, if there is any, is that the party is moving rather than ending. Jake’s shares ownership with The Gin Mill, at 442 Amsterdam, a few doors up the block. “And while Jake’s is closing, the party isn’t,” the bar wrote. “You’ll still find us right next door at The Gin Mill, waiting with open arms.”
So tonight, go. Order the nachos grande while they’re still $13.99. Do the shot of Tully. Tell the bartender your first-date story; they have heard it before, and they will listen anyway. Then, on Monday, walk a few doors up Amsterdam and start the next 32 years.
The City Politic has reached out to Jake’s Dilemma and Council Member Gale Brewer’s office for comment and will update this story with any response.
Photo: Amsterdam Avenue at West 89th Street on the Upper West Side. Deansfa / Wikimedia Commons, CC BY-SA 4.0.


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