Aaron Masliansky sits down with Mayor Nancy Rotering of Highland Park at City Hall for a wide-ranging conversation about leadership, housing, placemaking, and the future of one of Chicagoland’s most distinctive communities.

Mayor Rotering, now serving her fourth term, shares the story of how a neighborhood stop sign issue first brought her into public service, and how that journey eventually led to City Hall.

In this episode, we discuss:



• How a neighborhood safety issue launched Nancy Rotering’s public service journey


• What makes Highland Park unique, from Downtown to Ravinia, Braeside, and the lakefront


• Why events like Ravinia Festival and Taste of Highland Park play such an important role in community identity and economic vitality


• How Highland Park manages traffic, transit, and visitor experience during major events


• Highland Park’s long-standing commitment to inclusionary and affordable housing since 1968


• The redevelopment of the former Solo Cup site and what it means for housing supply and the city’s future


• Housing for seniors, aging in place, and why “missing middle” housing matters


• Accessibility, disability housing, and inclusive community planning


• Historic preservation versus modern housing needs


• Highland Park’s investment in sidewalks, connectivity, and public spaces


• The future of downtown Highland Park, the Ravinia District, and neighborhood investment


• Mayor Rotering’s regional work with Chicago Metropolitan Agency for Planning and broader housing policy


Memorable quotes:

“A stop sign brought me into City Hall.”

“Housing is where jobs go to sleep.”

“A community that grows is a community that’s progressing.”

Learn more:



• Highland Park


• Chicago Metropolitan Agency for Planning


• Ravinia Festival

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