How Jack Silverstein became Chicago's sports historian

February 19, 2026 - 22:38

The title "Chicago sports historian" carries a certain weight, evoking images of official archives and academic credentials. For Jack Silverstein, however, it began as a simple act of self-branding, a fusion of his two great passions. “That’s a self-applied title,” Silverstein admits. “I love history, I love sports. I thought that was good branding. I thought ‘Chicago sports historian’ was crisp and gave me something to live up to.”

And live up to it he has. Through relentless research, captivating storytelling, and deep-dive interviews, Silverstein has carved out a unique niche. He doesn't just recount scores and statistics; he excavates the cultural and human moments that define the city's athletic legacy. His work spans from the dynasties of Michael Jordan's Bulls to the forgotten sandlots where neighborhood legends were born, connecting generations of fans to the soul of Chicago sports.

By embracing his self-appointed role, Silverstein has become an essential voice, transforming from a passionate fan into a dedicated preservationist. He ensures that the narratives beyond the headlines—the personal struggles, the community impact, and the sheer drama—are not lost to time, proving that sometimes the most authentic historian is the one who appoints themselves to the task.