William (Bill) Callahan, former bartender and owner of the Woodlawn Tap, passed away on January 14. He was 78 years old.

A Chicago native, Callahan spent much of his life in Hyde Park, attending St. Thomas the Apostle School and Mount Carmel High School. He eventually worked at and then operated the Woodlawn Tap, also commonly known as Jimmy’s, for 55 years. Three years ago, he retired and sold the Woodlawn Tap to his friend and colleague of 33 years, Matt Martell (A.B. ’95).

Callahan is survived by his wife, Jan Hartley Callahan, and his two children, Will Callahan and Kristen Callahan Alyn.

Those who knew Bill Callahan described him as more than just the owner of a bar.

“He always sat at the end of the bar. You just never got the sense he was the owner of the bar because there was no air of being better than anybody else,” said Will, his son. “It was almost like he was the mayor of Woodlawn Tap.”

His wife, Jan, described him as having a rare ability to connect with people from all walks of life.  “He loved being there. He loved the people who came into the bar, whether they were the professors or the construction workers or the students. I mean, he related to everybody, no matter what their position in life,” she said.

Callahan’s Renewal of the Woodlawn Tap

Founded in 1948 by Jimmy Wilson, the Woodlawn Tap is nestled in the heart of the University of Chicago community at the corner of E. 55th Street and S. Woodlawn Avenue. Callahan’s first professional job was teaching at St. Thomas the Apostle School, but he also worked part-time as a bartender at the Woodlawn Tap. Under Wilson’s mentorship, Callahan transitioned from bartender to manager, and upon Wilson’s passing in 1999, he took over as owner. For the next five decades, Callahan shaped the bar into the establishment it is today.

In the late ’90s, Callahan helped steer the Woodlawn Tap as it faced an uncertain future, Jan and Martell explained. After Wilson passed away, the city initially refused to renew the bar’s liquor license, forcing it to close for nearly a year between 1999 and 2000.

“Bill in particular saved the bar when Jimmy passed away and really went out on a limb to make sure that it didn’t go away,” Martell said. “Bill and [his brother] Jim just put their faith and their money into the bar.”

The brothers ultimately won an appeal with the city liquor control commission and were able to reopen in May of 2000.

Callahan’s Relationship with the University of Chicago Community

Martell explained that throughout his time as the Woodlawn Tap’s owner, Callahan employed over a hundred UChicago students, providing them not only with jobs but also with a sense of belonging. In this way, Callahan continued Wilson’s legacy.

“His predecessor, Jimmy Wilson, in an interview with the Maroon from maybe the 80s, said that [Wilson] had employed over 300 University of Chicago students while he owned the bar. And so, [the Woodlawn Tap] has a big impact on the neighborhood but also on the University community and the students,” Martell said.

Beyond employment, the bar became a haven for students, faculty, and alumni. “Even if you didn’t get engaged there, a lot of people around UChicago met there or dated there—or did get engaged. And it’s just a remarkable memory for so many people,” Martell said.

Jan added that Callahan made sure that the Woodlawn Tap remained a space for conversation and connection, resisting the pull of modern distractions.

“He had a hard time with the whole concept of cell phone use and the computers and the iPads and everything. He used to talk about how he would walk in the front door and everybody would be chatting with each other, and then all of a sudden came the age of all the electronics,” she said. “He finally got people to come around to have the conversations anyway.”

To many, including Martell, the Woodlawn Tap has remained largely unchanged throughout its history. “It feels almost every night like 1993 in there,” Martell said. “The nightlife, the joy, the looks on the students’ faces—it really hasn’t changed. The model is pretty much the same: a safe place where people can sit around a table, enjoy each other’s company, and talk about their lives.”

For 77 years, the bar has maintained its cash-only policy, and Callahan’s family joked about the recent switch to an electronic menu board, which Martell had installed to keep up with changing prices.

Jan shared that when Callahan took over, “The University said, ‘It’s okay if you’re running this bar, but it’s got to look exactly the same: same dark walls, same dark floors.’ But that’s what Jimmy’s has always been, and so it has to remain that way.”

Will added, “I know Matt feels the exact same way, which is why it looks the way it does today, except for the electronic menu board.”

Callahan’s Legacy

Although Callahan retired three years ago, Martell emphasized that his legacy continues to shape the Woodlawn Tap.

“Bill ran the bar with a sense of humor and kindness, and he had a really good understanding of what Jimmy’s meant to students, alumni, faculty, staff, and the neighborhood,” Martell said. “Bill’s vision, and we really talked about it quite a lot, was what people want from a bar like Jimmy’s. Whether it’s a quiet place to talk, not being overwhelmed by TVs or loud music, or having spaces for people to read or work, that was his hope, and it was my intention to keep that going.”

Kristen explained that her father wasn’t just a bar owner. “He was welcoming. People just came in and they became friends. They became like family,” Kristen said.

“I think his legacy is that the bar is still there. I think he’s going to go down as one of the last very great bar owners,” Martell said. “I’ve hung out at the bar with Bill well over a thousand times over the years. I can tell you that Bill was the kind of guy that when you walked in and he was sitting down at the end of the bar, you were really, really glad to see him.”