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The end nears for Jake's Dilemma. What about other Upper West Side shops?
By
Willow Higgins
Published Sep 30, 2026
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Willow Higgins/Gothamist
By
Willow Higgins
Published Sep 30, 2026
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For decades, the sports bar Jake’s Dilemma has been a go-to for all walks of life on the Upper West Side, according to longtime employee Michael Staff. That includes college students watching football, dads needing a beer after a long day at the nearby children’s museum, and neighborhood locals looking to bump into a familiar face.
But after 32 years in business, the Amsterdam Avenue watering hole recently announced that it lost its lease, and will close in October.
“It's like losing a limb,” said Staff, the managing partner of Jake’s Dilemma and the Gin Mill, a sister bar several doors down.
Jake’s Dilemma is one of at least five longtime Upper West Side businesses to announce closure plans in recent months. The list includes long-serving Broadway grocery Barzini’s as well as Good Enough to Eat on Columbus Avenue, long known for wait lines that snaked outside the building.
Businesses come and go all the time in the neighborhood, as they do elsewhere in the city, but the loss of so many venerable storefronts in a short span, the long duration of some vacancies, as well as the plethora of vacancies of all sorts have been jarring to some business and government leaders, who are weighing fixes.
Remnants of another Upper West Side business, where empty storefronts abound.
Willow Higgins/Gothamist
Parts of the Upper West Side rank among the city neighborhoods with the highest shares of what a city comptroller's report calls deep, structural vacancies: storefronts that have remained empty for extended periods of time.
The same report notes that “storefront vacancy remains a significant feature of New York City’s post-pandemic economic landscape.” But it also notes that small businesses “continue to thrive and have resisted being overtaken by chains.”
Across the five boroughs, nearly 12,700 small businesses that were operating in 2020 are now vacant storefronts, according to the report. At the same time, “an almost comparable” 10,700 storefronts that were vacant in 2019 are now operating as new small businesses, according to the findings.
Remnants of another Upper West Side business, where empty storefronts abound.
Willow Higgins/Gothamist
What to do about those neighborhoods and business categories that continue to struggle? The report urges policymakers and stakeholders considering “future interventions” to develop a “comprehensive understanding of the drivers, duration, and localized impacts of” the vacant storefronts in their midst.
City Councilmember Gale Brewer, who represents much of the Upper West Side and lived in the neighborhood for more than 50 years, is already investigating solutions.
“ It's very, very difficult running a small business,” Brewer said. But, she added, “they are the DNA of our neighborhood.”
Remnants of another Upper West Side business, where empty storefronts abound.
Willow Higgins/Gothamist
Brewer is the sponsor of one remedy before the City Council, the Storefront Bill of Rights.
It would require a written lease for storefronts with tenancies longer than one year. Brewer said she’s encountered many businesses without official leases – only a handshake deal. “When the rent goes up 500%, they have nothing to fight with,” Brewer said.
Leases would also be required to be translated in languages other than English, and provide relevant information about the building.
Remnants of another Upper West Side business, where empty storefronts abound.
Willow Higgins/Gothamist
Another provision would require that commercial renters have the option to automatically renew their lease for up to one year, with the rent increase capped at no more than 10% of the current rate.
Jessica Walker, the president and CEO of the Manhattan Chamber of Commerce, told Gothamist she is concerned the provision could backfire by disincentivizing landlords from renting to small businesses that could be seen as less reliable tenants.
Brewer said she knows that there are concerns about that particular provision and she is open to amending it.
Another remedy comes from Councilmember Virginia Maloney, who represents the Upper East Side and adjoining neighborhoods.
She is the sponsor of a bill that specifically targets legacy businesses. The legislation would establish a registry of qualifying businesses – nominated by a city official – that have been operating for at least 20 years. Maloney said in a statement to Gothamist that the bill would “give the city a tool to help keep them there.”
The bill would come with a “preservation fund” – a new city grant program – that would help registered businesses confront rising costs and incentivize landlords to offer long-term leases, Maloney said in the statement. The size of the fund or the grants have yet to be floated, according to a spokesperson for Maloney.
Businesses that have served a community for 20, 30 or even 50 years become part of a neighborhood’s identity and history, Maloney said. “Some of the first conversations I had while running for office were about empty storefronts and the neighborhood institutions New Yorkers were watching disappear,” she added.
Brewer said she likes Maloney’s idea, but said the funding piece is “where you're gonna run into a problem.”
The end of Jake’s Dilemma
Staff said Jake’s Dilemma occupied property long owned by the eatery’s owner.
When the property was sold, that spelled doom for Jake’s Dilemma, according to Staff. The real estate agency now advertises the space as “ideal for upscale sit-down dining or premium healthy concepts” — a far cry from a bar whose menu includes “nachos grande” for $13.99.
They were given 60 days to close up shop, Staff said.
In the mid-90s, when Staff first started working at the bar, he said “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,” Staff said. “I would put an A-frame out in front of the bar with our specials out every day, and there was a guy out there that I would have to chase away that was selling drugs.”
About 10 years into their business, Staff said, it became “more and more family-oriented” – dads with their infants in Baby Bjorns started to show up to watch college football. These days, he said, there is an influx of young people, which he said might have boosted business if it weren’t already too late.
The dimly lit sports bar with a pool table and a tin ceiling made an impact on the neighborhood during its long run. An Instagram post announcing the bar's closure has more than 1,000 comments – most are from regulars who say they will sorely miss it.
“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 commenter wrote.
Others were less nostalgic. “Oh good, now we can get yet another Blank Street Coffee, Joe & the Juice, or maybe Pret A Manger,” wrote another.
The West Side Rag, a community newspaper, has chronicled many of the goings, including the end of Good Enough to Eat after a 45-year run due to declining business and a disagreement over the lease; and Cheesy Pizza, which closed after more than three decades.
ILovetheUpperWestSide, another community newspaper, announced the closures of Edgar’s Cafe, named after poet and Upper West Side resident Edgar Allen Poe, after nearly 40 years in business.
The old school grocery Barzini’s, which was dinged for health code violations, shuttered this summer after falling nearly $1 million behind on rent, according to a court record.
A Broadway problem
Alex Bell, the chair of the community board on the Upper West Side, also grew up in the neighborhood. He pointed out that Columbus and Amsterdam avenues feel much more lively than Broadway, where, he said, “you can feel the empty stores.”
Bell is part of the steering committee to create the Upper Broadway Business Improvement District, which could add things like supplemental street cleaning and additional security to the neighborhood – cleanliness and feeling safe were the two biggest concerns of the more than 1,600 surveyed community members.
Community members also highlighted the importance of filling vacancies.
“Empty storefronts kill the UWS and need vibrant, creative interim solutions,” one survey responder said.
Walker, from the Manhattan Chamber of Commerce, agreed that the vacancies in the Upper West Side is primarily a problem on Broadway, where nearly 40% of the neighborhood’s empty storefronts are, according to data the agency obtained from a storefront tracker called Live XYZ.
Walker, Brewer and Bell all pointed out that this is likely to do with the storefronts themselves on the street, which are larger, often designed for offices or retail stores that struggle to compete against the conveniences of online shopping.
“ If you have like a big pharmacy or a large bank, it becomes very hard for another tenant to wanna take that over,” Walker said. “ Those are the ones that sit vacant for a long time.”
But across the board, Walker said, “the ramifications of tariffs and inflation have hit small businesses particularly hard,” especially restaurants.
“How much can you charge for a bowl of spaghetti? You know, at some point that becomes a problem,” Walker said.
On the Upper West Side, Walker also has concerns about a lack of succession planning for business owners who, after running their storefront for decades, eventually want to retire.
Especially when times get tough, without a plan to either sell the business or put a family member in charge, Walker said, “they're gonna close.”
'Saviors in the neighborhood'
Jake's Dilemma is hosting three, back-to-back going away parties on Oct. 16, 17 and 18. The business is inviting all patrons, new and old, to have one last glass with them.
“Jake’s has been so much more than a bar,” read an encased poster next to the building’s wooden French doors. “It’s been late nights, gamedays, first dates, bad decisions, lifelong friendships, incredible staff, and more stories than we could ever fit into one poster.”
But the party isn’t over yet: Jake's sister bar The Gin Mill, located just across the street, “is waiting with open arms,” the farewell poster advertises.
For Brewer, small local businesses are worth fighting for.
“That is an ongoing appreciation for them every single day,” Brewer said. “They are our saviors in the neighborhood.”
Tagged
economy
new york city
Willow Higgins
Willow Higgins covers changes in New York City neighborhoods for WNYC and Gothamist. She has previously reported on wrongful convictions, corruption in district attorney offices and Texas' child welfare system.
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Gothamist is funded by sponsors and member donations
Gothamist is funded by sponsors and member donations
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