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    Jake’s Dilemma, Popular Upper West Side Bar, Will Close After 32 Years

    September 8, 2026 | 8:39 PM - Updated on September 9, 2026 | 12:41 PM
    in NEWS, OPEN/CLOSED
    37
    The inside of Jake’s Dilemma. Photo courtesy of Mark Bollettieri.

    By Gus Saltonstall

    Jake’s Dilemma, the incredibly popular Upper West Side bar at 430 Amsterdam Avenue, will close next month after more than three decades of business, the restaurant announced Tuesday on its Instagram.

    “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 bar wrote. “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.”

    The bar, located on Amsterdam Avenue, between West 80th and 81st streets, describes itself as “an old school pub vibe mixed with a downtown bar atmosphere boasting an outdoor café.” It was known for its late-night hours, sports-watching options, and dance floor.

    “We still have a little time left, so come have One Last Round with us before October 18,” the watering hole added on its social media post.

    Jake’s Dilemma is under the same ownership as The Gin Mill, which is located nearby at 442 Amsterdam Avenue. “And while Jake’s is closing, the party isn’t. You’ll still find us right next door at The Gin Mill, waiting with open arms.”

     

    View this post on Instagram

     

    A post shared by Jake’s Dilemma (@jakesdilemmanyc)

    Comments on the bar’s closing announcement immediately flooded in.

    “’Heartbreak’ doesn’t even feel adequate. 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 commenter penned, “Wow! A staple of the UWS and the BEST stretch of Amsterdam Avenue. Thank you for it All!”

    West Side Rag will update this story if we can find specifics on what happened with the lease.

    Subscribe to West Side Rag’s FREE email newsletter here. And you can Support the Rag here.

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    Please limit comments to 150 words and keep them civil and relevant to the article at hand. Comments are closed after six days. Our primary goal is to create a safe and respectful space where a broad spectrum of voices can be heard. We welcome diverse viewpoints and encourage readers to engage critically with one another’s ideas, but never at the expense of civility. Disagreement is expected—even encouraged—but it must be expressed with care and consideration. Comments that take cheap shots, escalate conflict, or veer into ideological warfare detract from the constructive spirit we aim to cultivate. A detailed statement on comments and WSR policy can be read here.

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    37 Comments
    Mike
    Mike
    5 days ago

    So sad to see this

    I haven’t been myself in many years but it is a neighborhood staple and will be missed!

    19
    Reply
    Lll
    Lll
    5 days ago

    Sorry, how the hell are landlords letting businesses lose their leases? Places are starting vacant for years. So sad to see another business close

    36
    Reply
    An Actual Scientist
    An Actual Scientist
    4 days ago
    Reply to  Lll

    Retail space mortgages often have debt service coverage ratio covenants that will force a lessor into technical default if the rent falls below a certain threshold relative to monthly payments.

    Rates are going up. Monthly payments are going up. Landlords *have* to raise rents.

    2
    Reply
    Sherri Rosen
    Sherri Rosen
    4 days ago
    Reply to  Lll

    Greed of landlords. They couldn’t care less about putting restaurants out of business or people out of work.

    4
    Reply
    julia davis
    julia davis
    5 days ago
    Reply to  Lll

    Wouldn’t it be more likely that landlords are CAUSING businesses to lose their leases? When they raise the rent too steeply at one go, the businesses have lfew options except to close.

    18
    Reply
    Morocco
    Morocco
    5 days ago

    The bar and lounge is great the owner is amazing we had parties from the largest part of Manhattan in New York City there in Jake dilemma … but some ladies hunters there that take free drinks movebadly in bar and that makes clients never come back again. Please check the invoice of regular and bartender friends we can’t be charged like the other staying there all evening and night paying a dims we see all

    0
    Reply
    Waddy what?
    Waddy what?
    5 days ago
    Reply to  Morocco

    Once more— this time in English, please

    22
    Reply
    Jake's bigger dilemma
    Jake's bigger dilemma
    4 days ago
    Reply to  Waddy what?

    Morocco should explain it in Darija!

    0
    Reply
    LongtimeUWSer
    LongtimeUWSer
    5 days ago

    Jake’s didn’t lose their lease. 430 Amsterdam Partners, which shares the same managing partners as Jake’s, sold the building in May.

    15
    Reply
    Anonymous
    Anonymous
    5 days ago
    Reply to  LongtimeUWSer

    ? Why do you think this means they didn’t lose their lease? Maybe the new building owner didn’t renew the lease, or asked for an exorbitantly larger rent. I don’t even see how these two things contradict each other

    16
    Reply
    72RSD
    72RSD
    5 days ago
    Reply to  LongtimeUWSer

    This is a great bit of information, and explains why the number of years in business isn’t a round number corresponding to a typical lease term.

    Yet another business deciding to close after a good run, but falsely blaming “the landlord”. Which, in this case, was themselves for decades!

    13
    Reply
    5 cent comments
    5 cent comments
    4 days ago
    Reply to  72RSD

    Yeah, I’m guessing that they also tried to negotiate a lease into the sale but the new owner saw it as a low-ball offer. Possibly didn’t cover the costs and loan payments required to make the purchase possible. At that point, 430 had a choice to sell the building or to keep it and continue to run Jake’s. They decided to sell. This is a business decision freely entered into by both parties and yet some people just blindly blame “greedy landlords” because it conforms to their world view.

    10
    Reply
    Anonymous
    Anonymous
    5 days ago
    Reply to  72RSD

    But it’s not a great piece of information. It has a new owner; maybe the new owner didn’t renew the lease.

    6
    Reply
    72RSD
    72RSD
    5 days ago
    Reply to  Anonymous

    If you are selling the building and you also lease the commercial space from yourself, typically you also negotiate the commercial rent before you sell the building.

    4
    Reply
    rick
    rick
    4 days ago
    Reply to  72RSD

    I suspect (but do not know) that since the lease was originally negotiated between an owner and tenant who were the same that it was not at market levels. The new buyer could be expect to flag that and say “I’m happy to have the bar stay but only at a market-equivalent rent”. So as part of the purchase the seller would agree to end the lease. One assumes that the seller is good at math and that the deal was, all in, to its satisfaction.

    5
    Reply
    Erica
    Erica
    4 days ago
    Reply to  rick

    Spot on, no way they were paying themselves a market rent. They decided to sell the building, cash out what was likely a great investment over time.

    1
    Reply
    72RSD
    72RSD
    4 days ago
    Reply to  rick

    I agree, Rick.

    Which is why I think saying that they “lost our lease” is potentially a disingenuous explanation compared to “we sold the building” (assuming that’s what happened here).

    4
    Reply
    5 cent comments
    5 cent comments
    5 days ago

    Definitely important to have relatively inexpensive, fun bars in the neighborhood but I sadly aged out of the Jake’s demographic many years ago.

    10
    Reply
    Dino Vercotti
    Dino Vercotti
    5 days ago
    Reply to  5 cent comments

    Drink at home.

    0
    Reply
    Glen
    Glen
    5 days ago
    Reply to  5 cent comments

    No you didn’t 🙂

    4
    Reply
    Greg K
    Greg K
    4 days ago

    My literal home for over 10 years (I was a resident of 430 Amsterdam Ave), very sad to be losing it. Can confirm that 430 Amsterdam Partners owned the building and the bar, so makes sense that selling the bar preceeded this. They were the best landlords I ever had – I moved in during the 2009 recession and they only raised my rent when they finally had to. Very nice folks as well

    10
    Reply
    julia davis
    julia davis
    4 days ago
    Reply to  Greg K

    Can you clone them?

    2
    Reply
    Joe Margiotta
    Joe Margiotta
    4 days ago

    They had two UWS locations, maybe time to open a location outside Manhattan.

    1
    Reply
    Jose A Torres
    Jose A Torres
    4 days ago

    I celebrated my 21st birthday at this place back in July 2001, and it was a nice atmosphere. The people there were easy going and the place was well kept and it had a good variety of music being played that night. I passed by this bar many times after my first visit and I never got a chance to go back in

    1
    Reply
    Dan V.
    Dan V.
    4 days ago

    Fine landlords who let storefronts go vacant for lengthy periods.

    1
    Reply
    Sherri Rosen
    Sherri Rosen
    4 days ago

    This city is going to be nothing but bike lanes, pot shops and oversized apartment buildings. No more neighborhoods. Sad.

    4
    Reply
    julia davis
    julia davis
    4 days ago
    Reply to  Sherri Rosen

    And the herds of nail salons.

    3
    Reply
    Kate
    Kate
    3 days ago
    Reply to  julia davis

    Like some commenters say — everything in moderation! ENJOY!

    0
    Reply
    Kate
    Kate
    4 days ago

    My dilemma is — why are people still drinking alcohol when the science says just one drink harms your liver? Please inform.

    0
    Reply
    WakeMeWhenItsOver
    WakeMeWhenItsOver
    3 days ago
    Reply to  Kate

    Why are people still not taking action to stop rapid climate change when science clearly says action is necessary? Why do people not do anything they “should” be doing? Because human, that’s why. Are you one?

    1
    Reply
    5 cent comments
    5 cent comments
    3 days ago
    Reply to  Kate

    ugh… these kids. Absolutely no perspective

    Last edited 3 days ago by 5 cent comments
    1
    Reply
    Pat Choulli
    Pat Choulli
    4 days ago
    Reply to  Kate

    It’s called living Katy. Everything in moderation. Salt is bad, sugar is bad, alcohol is bad, caffeine is bad, the air is bad. We can’t all lock ourselves in a closet and survive on celery. Besides, if it weren’t for the “social lubricant” that alcohol provides, half the population would never have sex. Lol! Lighten up, have a cocktail once in a while. Enjoy your life. Peace.

    7
    Reply
    Jo wase
    Jo wase
    4 days ago
    Reply to  Kate

    Is everything you consume good for you?

    3
    Reply
    Kate
    Kate
    4 days ago
    Reply to  Jo wase

    I don’t go out of my way to harm myself.

    0
    Reply
    Mark Lilien
    Mark Lilien
    4 days ago

    Retail businesses live forever only if they own their real estate.

    3
    Reply
    Lawrence
    Lawrence
    3 days ago
    Reply to  Mark Lilien

    I.e. – Zabars

    2
    Reply
    Hameed
    Hameed
    3 days ago

    Jacky will be missed and some of Friday goers too. Central Park will be always there bars moves and bartenders are the best like Jacky

    0
    Reply

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