In the summer of 2010, Jack Silverstein was chatting with friends at a Wicker Park bar when the subject turned to his writing.
That March, he had published a book, “Our President,” a series of essays about Barack Obama. He was covering the Chicago music scene heavily for several outlets. But two of his buddies offered a suggestion.
They told Silverstein that he should write about sports. They acknowledged his writing chops but said he reached another level when he wrote about sports.
“I thought sports was too easy,” Silverstein said this week. “Maybe in a sense I was looking down on it. It came so naturally to me that I thought nothing this easy can be worthwhile. What I found was, I was terribly wrong.”
Silverstein loved sports, especially Chicago sports. He grew up on the North Shore in the 1980s, when the Bears and Bulls were rising to power and the Cubs were returning to relevance. Sportswriting might have come easy for him, but there was a way to make it challenging and make his work stand out — become Chicago’s sports historian.
“That’s a self-applied title,” Silverstein said. “My father always said, ‘Let them put you in a box,’ meaning help people know who you are. I love history, I love sports. I thought that was good branding. I thought ‘Chicago sports historian’ was crisp and gave me something it live up to.”
Which he has. Silverstein, 44, has broken news retroactively. In 2019, when the Bears had Kyle Fuller and Tarik Cohen model 1936 throwback uniforms, Silverstein discovered they were the first Black players to wear them because the NFL had banned Black players from 1934 to ’45. His research drew not just the Bears’ attention, but the late Jesse Jackson’s, and the story was picked up by ESPN, Fox and even the BBC.
In 2021, Silverstein led the Bears to correct their record book, making “Chuckin’ ” Charlie O’Rourke the then-record holder for touchdown passes by a rookie with 11 in 1942. When Caleb Williams broke it with 20 in 2024, O’Rourke received his long-overdue recognition.
Silverstein has appeared on Chicago radio, TV and podcasts. His work appears on the website Windy City Gridiron and his own site, A Shot On Ehlo, named in honor of Michael Jordan’s buzzer-beating, playoff-series-winning shot over the Cavaliers’ Craig Ehlo in 1989. Late Bulls radio voice Jim Durham said the words “a shot on Ehlo” on his call.
Silverstein’s Bulls research has led to his 2016 e-book “How the GOAT Was Built: 6 Life Lessons From the 1996 Chicago Bulls,” and the series of posts on his website are leading to his book, “6 Rings: The Bulls, The City, and the Dynasty that Changed the Game.”
“[‘How the GOAT Was Built’] was really important because it formalized my position as a sports historian,” Silverstein said, “and it gave me something I could do shows on.”
All of this work isn’t even Silverstein’s job. By day, he’s the director of content at WTWH Media, where he covers the business of senior living. By night, he’s researching and writing about sports.
“I just write a lot. I have a gear,” said Silverstein, who’s married with two kids. “There’s no good way to explain it. I have a gear that just goes. If I didn’t get these stories out, I would break down.”
Former Sun-Times columnist Rick Telander noticed that gear early. As a sophomore at New Trier, Silverstein hosted a radio show and asked Telander to be a guest. Telander appeared and then invited Silverstein to sit in on a recording of the beloved show “The Sportswriters on TV.”
“He had this enthusiasm that kind of cracked me up,” Telander said. “He knew all kinds of stuff about Chicago sports. He was deadly serious about this stuff.
“I realized he had some writing skills. He had a book on Obama, I remember reading that. The enthusiasm affected me. There was a whole lot of optimism. And then he turned that same enthusiasm into writing about sports.”
That enthusiasm runs through his most recent book, “Why We Root: The Mad Obsessions of a Chicago Sports Fan.” It’s 500 pages of Silverstein’s work as he rides a roller coaster of emotions that began in childhood. He explored not just big events, but their place in our shared culture.
His current research project is on Paul Patterson, the Bears’ first full-time Black employee. Silverstein said the Bears hired Patterson in 1967 but he wasn’t in the team’s media guide until 1969. He held titles of “player relations” and “traveling secretary” before being lost to history.
“I love to write, love to research, love to learn and love to figure out a way to tell stories that don’t exist,” Silverstein said.
Said Telander: “He found something no one’s doing. Doing research, journalism work, interviewing people, being persistent. Other people don’t want to do the work.”