How Reilly’s Daughter Survived 50 Years To Become A Hub Of South Side Irish Pride

OAK LAWN — When James “Boz” O’Brien opened Reilly’s Daughter on the Southwest border of Chicago a half-century ago, the tavern quickly became the go-to bar for folks from Mount Greenwood and around the area to gather.

Reilly’s Daughter — which is named after an Irish folk song — became so popular that celebrities and politicians used to drop by: Chicago Bears quarterback Jim McMahon was a regular and hosted a TV show there, as did former Notre Dame coach Lou Holtz. Mayor Richard M. Daley also made appearances.

The bar, which sits on the Oak Lawn side of the city border at 4010 W. 111th St., had become a household name on the Far Southwest Side by the time O’Brien sold it in 2002 to focus on a newly opened location in Midway Airport.

In the O’Brien family’s absence, the bar went through various incarnations, including stints as Quigley’s South Side Irish Pub and Hops and Helmets.

But in 2015, the bar went back up for sale, and O’Brien’s son Brendan said he couldn’t pass up the chance to bring Reilly’s Daughter back to its original location.

“I wanted to do it,” Brendan O’Brien said. “I just love it. I love the people in the neighborhood, the sense of community. We have tons of events and fundraisers, and it’s just a really great sense of community that you don’t find at the airport location.”

Last month, Reilly’s Daughter held a 50th anniversary celebration; it had originally opened on June 16, 1976. For the family that owns the establishment — and for the many patrons and employees who are now part of the Reilly’s Daughter extended family — the celebration was a long time coming.

“It’s rare when a bar or restaurant of any fashion makes it five years, let alone 50. We are definitely proud of it,” O’Brien said. 

A Family Affair

As a kid, O’Brien, now 43, often spent his nights there doing his homework.

“I started cleaning up there when I was a small kid. I would get picked up from school by bartenders and waitresses,” he said. 

O’Brien said his father always liked being around people — that was part of what sparked his interest in starting Reilly’s Daughter 50 years ago. When the business started, he said his father viewed it as a side business, but it just kept expanding — much like the O’Brien family. 

O’Brien’s parents met the night the bar opened. Several of his aunts and uncles met their spouses while working at the bar, he said.

“A good chunk of my family is a product of the bar opening,” he said. 

Looking back on his favorite memories at Reilly’s Daughter, O’Brien told Block Club it is hard to pick just one, but the memories often involved a large crowd in the bar. 

“[As a kid] I loved when it was busy, and there were tons of people around, and it’s still very true to this day because now it generates into dollars. The more people around, the more money you are making typically,” O’Brien said with a laugh. 

“I just love being around people, so anytime we had a large crowd I was happy, even as a child. So maybe that was a sign that I was meant to do this,” he said. 

Boz O’Brien died in January at the age of 75. A post on the bar’s Facebook page announcing the founder’s death garnered over 600 comments; he was remembered for his ability to strike up a conversation with anyone and his love of entertaining. 

The anniversary was something the father and son often discussed before his death, O’Brien said.

The 50th anniversary celebration featured a live performance from the Dancing Noodles and other festivities throughout the day. The business was packed with familiar faces, longtime employee Bill Mallo said.

“The whole day, a lot of people came in, people who used to work there years ago,” he said. “It was just phenomenal. It was probably one of the best times I have ever had up there.” 

Mallo, who started working at Reilly’s Daughter about 40 years ago, said the bar has remained relatively the same over the years. 

“It’s a place where people can come up and enjoy. We have good bands up there. It’s just a friendly place to meet people,” he said

Throwing Bricks At TVs

Terry O’Reilly first went to Reilly’s Daughter when it opened in 1976. His weekend softball team was one of the first — of many — to be sponsored by the bar.

“We used to hang out there on Saturday nights, and then we played in the Brother Rice Alumni League on Sunday mornings. We would get up, go play softball in the morning and then head back up to Reilly’s for the rest of Sunday,” he said. 

Reilly’s Daughter was the spot to hang out, O’Reilly said. That was especially true around St. Patrick’s Day, when patrons would hear Terry McEldowney sing his legendary neighborhood anthem, “South Side Irish.”

Mary Meade has been going to Reilly’s Daughter since the bar’s early years, celebrating holidays like St. Patrick’s Day and New Year’s Eve and everything in between.

“You knew everybody, and we are still friends to this day,” Meade said. “It was just a comfortable place to go. You have your local bar you want to go to because you’re gonna know everybody there and feel welcome.
That’s it. That’s Reilly’s.” 

Mount Greenwood neighbor Kevin O’Ryan lives within walking distance to Reilly’s Daughter, and he used to be at the bar every week. O’Ryan said Boz O’Brien was a big draw.

“He was always very jovial, always with a handshake and always had something to say. Of course, he would always do the usual, ‘Do you know so and so, and so and so, and so and so?’ and he kept doing that until you hit a link and now you are connected. He would do that with everyone,” O’Ryan said. 

Reilly’s Daughter was a fun spot both for the patrons who sat along the bar and for those behind the counter. Beverly resident Willie Winters started working at Reilly’s Daughter as a bartender in 1976 and later as a manager. 

“It was the most successful bar anywhere on the South Side. I don’t think any place came really close in volume and the amount of people that came in and out the door and the amount of barrels of beer that we went through,” Winters said. 

Winters said he learned a lot during his nine years working there. 

“It was a very creative place to work. We were always coming up with these crazy promotions and ideas, and they would say, ‘Yeah, let’s just do it,’” Winters said. 

Some of those promotional ideas included a Thanksgiving raffle of a live turkey and a raffle during “Monday Night Football” in which the winner was given a brick to throw at a TV when broadcaster Howard Cosell was featured. It was so popular the bar put up bleachers to watch.

“As soon as Howard Cosell came on after halftime, the raffle winner would throw a brick, and if the first guy missed, the second guy would throw. We did it the whole season,” Winters said. “We went through a lot of TVs.”

Reilly’s also used to rent an “L” train car and threw a party as it traveled through the city, Winters said. 

Meade recalled a day of drinking and singing as the bar went mobile throughout the city. 

“It was so much fun,” Meade said.

Stepping Up For The Community

Reilly’s Daughter sold hats and T-shirts to mark its 50th, with 100 percent of the proceeds donated to Matt Knight, a Chicago firefighter battling cancer. Knight is the son of former Chicago Police Officer John Knight, who was killed in the line of duty in 1999.

This past year, the bar has held multiple fundraisers for first responders killed in the line of duty, including for Chicago Firefighter/EMT Michael “Mickey” Altman, a Mount Greenwood resident who died while battling a Rogers Park fire in March. 

“When somebody from the community you live in needs help or needs assistance in any fashion, you step up,” O’Brien said. 

Helping the community is part of running a neighborhood business, O’Brien said. That has been Reilly’s Daughter’s motto through its 50 years and under both generations of ownership, Mallo said.

“Brendan just goes above and beyond, and Boz always did too. Brendan takes after Boz; I keep telling him, ‘You are just like your dad,’” Mallo said.