Mike Zar’s family bought Daley’s Restaurant in 1918. He started working there when he was 15.

In 1892, Chicago was in a construction boom. The World's Columbian Exposition in Jackson Park was a year away. Grand structures were being built from the ground up. In nearby Woodlawn, Irishman John Daley (no relation to the future mayors) opened a lunch counter. All those workers had to eat.

More than a century later, the city’s oldest restaurant at 809 East 63rd Street is again feeding construction crews as it faces, literally, another building boom and a move into a not-quite-bigger but, by most accounts, better home across the street.

From Daley’s north-facing windows, owner Mike Zar—whose mother’s uncle, Tom Kyros, bought the place from Daley in 1918—can watch Woodlawn Station, a 15,000-square-foot building, take shape. Not that Zar does this much. On a recent morning, he was too busy packing up catering orders, stacking glasses, and filling in for a dishwasher who'd fallen ill.

By this time next year, Zar and his affable, veteran crew expect to be ensconced in their new digs on the northeast corner of 63rd and Cottage Grove, serving the same from-scratch comfort food favorites—fluffy biscuits, smothered pork chops, sweet potato pie—that have sustained generations of residents.

“We’ll pretty much lock one door and open the other,” says Zar, 37. 

Denise Williams, 57, says her favorite part of working at Daley’s is talking to customers.
Customer George Kirkendall Jr., 77, prepares to dig into his plate of mac ‘n’ cheese and biscuits.

Woodlawn Station, a $30 million, mixed-use development funded in part by a grant from the U.S. Department of Housing and Urban Development, is one of a number of revitalization projects by the nonprofit Preservation of Affordable Housing. Along with the forthcoming Obama Presidential Center and the University of Chicago’s new charter school, the development has begun changing the face of Woodlawn, which locals and business owners say has been on the decline for decades.

The ground floor of Woodlawn Station will be commercial, with 70 mixed-income apartments filling in the rest. Ain’t She Sweet Cafe, which has two other South Side locations, is the second confirmed tenant, with others to be determined in the next six months, according to Bill Eager, Preservation of Affordable Housing’s vice president for the Chicago area. 

Eager says there was never a question that Daley’s, with its well-worn walls covered in old framed photos, would be the ideal anchor for the project. “Daley’s is a local landmark. It’s just a great neighborhood restaurant. But when we first started and I’d go there to eat, I remember thinking, ‘They look like they’re due for an upgrade,’” he says.

For Zar, the prospect of a fresh start on the more visible northeast corner wasn’t a hard sell. “This building is dated. We want a fresh look. We’ll have a vintage feel with all-new plumbing, electric, a legitimately built, well-designed kitchen. It’s not too efficient right now is what I’m trying to say,” he explains. “It would be foolish of me not to move, that’s the way I look at it.”

In early September, Eager’s group closed on the sale of the building that houses Daley’s and six other businesses, including Regal Mens Fashion, another throwback to the street’s heyday as a prime commercial district.

The developer is working on plans for the property and its tenants and is in talks with artist Theaster Gates to incorporate “some kind of cultural offering, whether it’s music, fine arts, or dance” into that southeastern section of 63rd and Cottage Grove, says Eager.  A makeover of the overhanging Green Line stop into something “a little less daunting, a little less hulking” is certain, he says.

“It could be much more of a vibrant intersection,” Eager says.

Woodlawn Station (top) is being built across the street from Daley’s. Soon, it will be the restaurant’s new home, after staying in the same spot since 1892.

For many years, it was. Zar, 37, has heard the stories from his “Uncle George” Kyros, Tom Kyros’s son, now in his 90s, of the jazz clubs, dance halls, clothing and shoe stores, and soda shops that lined 63rd Street in the 1930s and '40s. This was the place to shop, dine, and boogie.

Longtime employees and customers at Daley’s tell similar stories. Flossie Williams, 84, lunching on a recent weekday with her husband, James, 87, came of age in the neighborhood. She recalls the nightclub scene in the 1950s as “lively, sophisticated, dressed well.” Daley’s was the gathering spot.

But integration prompted white flight, hastening the area’s decline and a steady population drop, from 81,279 in 1960 to 24,150 in 2015. Taverns and liquor stores multiplied while other business faltered. Buildings went vacant.

The Blackstone Rangers got their start in the neighborhood, says Stefan Howard, 64, and his brother, Michael Howard, 63. They remember this well because as kids the gang recruited Michael. The early 1970s were especially rough, violent years, says Stefan Howard, a Cook County Sheriff's officer. “It’s quite harmless around here from what it used to be like,” he says.

Customer Jerri Mathis-Davis, 76, waits at a booth.
At 33 years old and eight years at Daley’s, Quinn Richberg is one of the restaurant’s newer workers. Still, she says it feels like home.

Then, as now, Daley’s was a haven.

Where else can you get salt pork, sliced, boiled, and crisped on the flat-top, or a Belgian waffle crowned with five chicken wings that just fit on a plate, or daily specials that come with—deep breath—soup or salad, two sides, two freshly baked corn muffins, and dessert? Where can you walk in on your first or 500th time and get a “Hey, baby!” from Marilyn Poole, the cashier up front? Nowhere else, regulars say.

“When you treat people like they’re somebody, make them comfortable like they’re home, that’s what keeps them coming,” says Beverly Jamieson, 62, a Daley’s waitress for two decades.

Jamieson’s on the younger end. Poole, 77, has worked at Daley’s for 28 years, manager June Hutchinson for 27 years, waitress Rose Gillespie for 34 years.

“That lady over there. And the food,” says Jonathan Jones, 74, pointing toward Gillespie, when asked why he eats at Daley’s three times a week.

Mike Zar sits with longtime customers Carl White, 75, and Melvi Muhammad, 71.

Zar, who started working at the restaurant at age 15, says it suffered like everyone else after the 2008 financial crisis and took a big hit with the closing of Grove Parc Plaza, a swath of Section 8 housing along Cottage Grove. “They were all of our customers,” says Zar. Preservation of Affordable Housing has redeveloped the site into the mixed-income Woodlawn Park apartments.

Even at noon on a Wednesday, with just about every table taken, Zar and the others agree it’s just an average crowd, though a more diverse one than they’re used to seeing. “We get all colors in here now. That has changed,” says Hutchinson. 

Zar is bracing for higher rent across the street and the influx of crowds and traffic he’s certain the flurry of development will bring. He wants to hire more staff. He doesn’t want to raise prices. Maybe by cutting portions, he won’t have to—but he doesn’t want to do that either. Eventually, he’d like to extend the 9 p.m. closing time to stay open 24 hours a day, seven days a week. 

The thought of doing it all in a new space has him and his employees jazzed. “I might even add stuff to the breakfast menu because we'll have a bigger kitchen. Frittatas, scramblers, different kinds of pancakes, different waffles, a Greek yogurt parfait,” he says.

Customer Stefan Howard isn’t so sure that new means better, or that revitalization won’t mean displacement. “You lose some of the history when you move,” he says.

Still, he and his brother say, as their lunch of fried eggs and sausage, rice with gravy, and liver and onions appears, they won’t stop coming to Daley’s.

“As long as they keep selling the same food, I’m good,” Michael Howard says.

The Last Holdouts is an occasional series where Chicago looks at the people, institutions and groups that are sticking around while everything around them transforms. If you have ideas to pitch or submit, email holdouts@chicagomag.com.