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Restaurateur Bruce Cooper is big on dates. He opened Jake’s in Manayunk on Oct. 19, 1987 — Black Monday, the day the stock market crashed.

He’ll close it on Oct. 19, 2026, the start of its 40th year on Main Street.

In between was another financial crisis, an expansion that reflected changing tastes, a devastating flood, a pandemic — and nearly four decades in which Jake’s evolved along with Manayunk itself.

Cooper, 72, is selling the side-by-side Main Street properties that house what is now Jake’s & Cooper’s Wine Bar. Before the final night, he plans to turn the wind-down into a reunion. Past employees will get a 50% discount on Sundays and Mondays, and the restaurant will extend its September restaurant week (Sept. 14-20) pricing through the final day. On Oct. 19, a party will empty the bar and kitchen, with proceeds going to a local charity.

“I just wanted to get to [the start of] 40 years,” said Cooper. “I wanted to get out two years ago.”

When Cooper arrived in Manayunk, Main Street hardly looked like the retail and restaurant district it would become.

Cooper, a Culinary Institute of America graduate from Upstate New York, had spent a decade as executive chef at Lankenau Hospital before deciding that he wanted a restaurant of his own. He took business courses at Community College of Philadelphia and St. Joseph’s University and spent years looking at properties before a real estate agent showed him a former print shop in Manayunk in early 1987.

Cooper didn’t commission traffic studies. While walking along Main Street, he noticed Jaguars and other expensive cars rolling up to a posh restaurant called Jamey’s, which had opened a year and a half before. Otherwise, as he remembers it, “there were practically tumbleweeds floating down the street. You could find parking on a Saturday.”

That spring, Cooper bought 4365 Main St. and assembled a group of investors to open Jake’s, his then-wife Helena’s nickname.

Jake’s was conspicuously ambitious: white tablecloths, contemporary artwork, an extensive wine list, and Cooper’s refined cooking, including pastas from scratch. Dishes included crab cakes with raspberry butter, scallops with red pepper and papaya sauces, and duck breast with tangerine sauce.

The restaurant’s whimsical facade depicted an oversize table setting, with food spilling from a plate and wine pouring into a glass, surrounded by flowers, flatware, linen, and crystal — designed to suggest both fine dining and a sense of fun.

Many early customers came from the Main Line, crossing the Schuylkill over the Green Lane Bridge into the former mill town.

Business grew quickly. When Cooper had put together his business plan, his accountant told him his projected sales were impossible for a 65-seat restaurant. Jake’s reached the projection in its second year, Cooper said.

By the 1990s, Main Street was crowded with boutiques and similarly high-aiming restaurants like Sonoma and Kansas City Prime.

In a 1998 review, Inquirer restaurant critic Craig LaBan described a room of cushioned banquettes, contemporary design, and a stylish but unstuffy clientele. He called out the veal dumplings with caramelized ginger, seared tuna with sticky rice, foie gras with grilled mango, and the barbecued salmon — a signature.

And then there were the mashed potatoes. One version paired Yukon gold potatoes with buttermilk and roasted corn. Another, served beneath medallions of veal, was infused with lobster and cream. Patrons, LaBan reported, had taken to calling the latter “sex on a plate.”

LaBan awarded Jake’s three out of four Liberty Bells, the rating system he used at the time. “That’s when it really started to take off,” Cooper said.

Manayunk’s overall success brought its own problems. Friction between residents and the expanding restaurant and bar scene in the late 1990s led then-City Councilmember Michael Nutter to push for a five-year moratorium on new restaurants in the district.

Cooper, who later served as president of the Manayunk Development Corp., believes that the moratorium lasted too long and helped push Main Street toward nightlife. He later helped develop agreements among restaurateurs, landlords, the business association, and neighborhood groups that placed operating restrictions on new restaurants.

Meanwhile, the style of dining that had made Jake’s successful was changing. White tablecloths were giving way to small-plate menus.

Which leads to another consequential date: March 14, 2008, on the eve of another financial crisis, when Cooper bought the former clothing store next door at 4367 Main St. and opened Cooper’s Brick Oven Wine Bar. Cooper’s is a markedly different restaurant, drawing a younger crowd and serving pizza, small plates, craft beer, and less expensive wines.

The dividing line quickly blurred, Cooper said. Customers at Cooper’s wanted food from Jake’s, and Jake’s customers wanted dishes from Cooper’s. The restaurants shared a kitchen, and Cooper eventually merged their menus and identities as Jake’s & Cooper’s Wine Bar.

Then came July 17, 2016.

Cooper got a middle-of-the-night phone call that a city water main had ruptured outside the restaurant, sending water through the building and destroying the kitchen and the apartments above. He gutted and rebuilt, with business-interruption insurance helping carry the restaurant through a six-month closure.

The experience changed the way Cooper thought about the business.

“When you stop a business and then restart it, there are people who had been coming every week, and then they stopped,” he said. “They got into another routine. They went elsewhere.”

Even months after Jake’s reopened, Cooper said, customers would walk in surprised to discover it had reopened. “That’s when I started looking at things differently,” he said.

Cooper considered selling, but a real estate adviser urged him to wait as residential development accelerated in Manayunk and Roxborough. Three years later came the pandemic. His extended time at home spoiled him, he said.

Three years ago, Cooper moved to Delaware. His son, Bruce Joseph Cooper II, 37, now manages the restaurant day to day, while the senior Cooper comes north once or twice a week to handle scheduling, wine orders, and other duties.

In June, Cooper put the properties, including four upper-level apartments, on the market for an undisclosed asking price. Cooper said he wants a clean break rather than passing the restaurant to his son, though neither rules out working together on another project someday.

The closing will end one of the longest remaining restaurant runs from the era that transformed Manayunk. Pitchers Pub (1987) and Zesty’s (1993) are still at it; U.S. Hotel Bar & Grill has been open irregularly since Bill Green, the former mayor and congressman, reopened it in 1986.

For Cooper, that history encompasses more than the people who ate there. “When you look back, you think about the generations of customers — in a lot of cases, we’re talking about three generations,” he said. “But it’s not just the customers. It’s all the people behind the scenes: the banker, the produce person, all those people who helped you get through things.”

Cooper’s son grew up at Jake’s, handing out cookies at holiday meals his father helped organize through North Light Community Center. He joined the restaurant full-time during the pandemic, starting as a food runner and eventually taking over management.

Purveyors and other restaurateurs have approached Cooper Jr. with potential job offers, he said, and he would consider working with whoever buys the properties. He once imagined taking over Jake’s himself but is no longer certain that is what he wants.

His father understands.

The restaurant business, the senior Cooper said, demands long hours and constant attention. One lesson he would give a new restaurateur is the one that helped him survive both the flood and the pandemic: Own the real estate if you can.

“If I didn’t own this real estate during COVID, I would have owed the landlord,” he said.

Cooper has begun informally advising other restaurateurs about the economics of getting into, staying in, and getting out of the business. After nearly four decades, he said, he is ready to find out what comes next.

His son thinks about Jake’s in more personal terms.

“Even in my almost five years working as a manager here, I’ve seen kids go from being in the womb to toddlers, and they know me as Uncle Bruce,” the younger Cooper said. “That’s one of the greatest feelings in the world — being able to say, ‘I knew you before you were born, little one.’”