Series I - Part 2 of 3

These evenings aren’t lectures or panels, they’re living conversations. Each session gathers a mix of historians, planners, artists, and community voices alongside everyday Clevelanders to wrestle with the questions that shape our city.

The series began in August with a near-capacity room, ages spanning from twenties to eighties, first-generation arrivals and families rooted here for over a century. What emerged was a dialogue both critical and hopeful, proof that people want more than soundbites; they want to think together about where Cleveland has been and where it’s headed.

Guided by Greg Deegan and John Perse of Teaching Cleveland, each talk blends historical insight with artwork that reimagines the familiar in vivid surreal color and composition, provoking questions, inspiring dialogue, and challenging us to think differently about our city and ourselves.

The visionaries behind Cleveland’s golden era were flawed, ambitious, and often ruthless, yet they left behind beauty and complexity that shaped generations. Together we will explore how those choices echo in our present and what it might mean to reclaim boldness without repeating their mistakes.

This is the start of an engaging conversation about creative thinking, civic imagination, and the role each of us plays in shaping what comes tomorrow.

The conversation begins here. Where it goes next is up to you.

About Teaching Cleveland

Teaching Cleveland is an educational nonprofit dedicated to connecting people with Cleveland’s history through storytelling, civic dialogue, and historical context. They help people understand where we have been so we can think more critically about where we are going.

Greg Deegan, Executive Director of Teaching Cleveland