William “Bill” Joseph Callahan, longtime employee and then owner of Woodlawn Tap, died Jan. 14. He was 78.
Mr. Callahan grew up in Hyde Park and attended Mt. Carmel High School before graduating from Loyola University Chicago with a degree in English.
After graduating from college, he taught English and math at St. Thomas the Apostle School in Hyde Park while also working part time at Woodlawn Tap, also known as Jimmy’s. He eventually became manager under the tutelage of original owner and namesake Jimmy Wilson. Mr. Callahan later owned the bar from 1999 to 2021.
The bar closed during Mr. Callahan’s first year of ownership after the city refused to renew its liquor license because it needed repairs to meet city codes. He tried for the license again and was again denied because it was too close to St. Thomas the Apostle School, said Matt Martell, who bought the bar from Mr. Callahan.
The community — including the Chicago Tribune editorial staff, writing that it was “where Nobel Prize winners rubbed shoulders with workaday South Siders, where beat poets shared the mahogany with beat cops” — then rallied around the bar, with some regulars showing up to a city appeals hearing. The license was renewed.
“It is apparent that Jimmy’s has been enriching this neighborhood as a meeting place for the community since before the middle of the last century,” the city appeals commission wrote in its March 2000 ruling. “It strikes us as a place where hard hat and lunch pail share the same bar with briefcase and Wall Street Journal, where a shot and a beer is as at home as a glass of Cabernet.”
“The busiest day we ever had was the last day we were open in 1999,” Mr. Callahan told UChicago Magazine in 2023. “And a busier day than that was when we reopened. I’d come in at seven and work till three or four in the morning. It was insane.”
Mr. Callahan met his wife, Jan, in 1967 while studying at a Chicago public library.
She sat across from him and borrowed paper and a pen and the two got to chatting.
When it was time for her to get to her part-time job at the Leo Burnett ad agency, she realized she hadn’t finished an article from a Spanish-language magazine that she needed to read for an upcoming exam.
She asked Mr. Callahan his thoughts about purloining the magazine from the library. He advised against it and offered to copy the text by hand and deliver it to her at a nearby intersection after she got off work.
It was raining at the rendezvous. They realized they were both Loyola University students and made plans to meet up again. Mr. Callahan told his mother that night that he was going to marry the girl, even though he couldn’t remember her name.
But he did remember (for the rest of his life) the first line of that Spanish-language article he copied for her.
In 2021, Mr. Callahan sold Wooldawn Tap to Martell and retired.
“I think Bill just appreciated the uniqueness of this place, where you can walk in and sit next to a construction worker or a Nobel Prize winner, it’s just such a cross-section of society,” Martell said.
He is survived by his wife of 55 years, Jan Hartley Callahan; children, Will Callahan and Kristen Callahan Alyn; four grandchildren and sister, Lauren Callahan West.
A memorial to celebrate Mr. Callahan’s life will be held Saturday, March 22, from 1 to 4 p.m. at Woodlawn Tap, 1172 E. 55th St.
Contributing: Violet Miller