About Me

Fighting for the City I Love

Hi, I’m Leo Fiascone. I believe Chicago is the greatest and most loyal city on earth. In some ways it is among the messiest as well.  The right way to approach the messy parts is to embrace Chicago communities as unique and valuable with ideas that restore but don’t replace its grit and personality.  That is my goal. My connection to its grit was tested on May 19, 2022, when a mass shooting outside my school left nine people shot and two dead. Later, another shooting struck outside of my sister’s preschool in the pick-up line. My family reached a breaking point, joining Chicago’s middle-class exodus to the Hinsdale Central school district in the suburbs.

Suddenly, I was a city kid displaced from my home.  I was driving a 161k-mile 2013 Ford Flex in a student parking lot of brand-new Broncos and Range Rovers. Refusing to let my zip code change my DNA, I self-taught AI (UPenn) and Urban Planning (Johns Hopkins) on Coursera because my new school didn’t offer these classes.  I wanted to learn the core material to help slow, and hopefully reverse, the middle class exodus that Chicago has experienced where 50% of the city was once middle class and today that number is 16%. 

Since January of 2024, I have spent hundreds of hours researching "kitchen table" issues affecting Chicagoans and developing practical, implementable ways to improve them. Through outreach and communications with over 65 experts, I’ve been writing detailed policy analysis and proposed solutions from Public Safety, to Education, Economic and Fiscal concerns, Community and Health, and Infrastructure & Housing.  Several of my plans have been published, and I’m continuing to advance these ideas with a goal of improving the city I love.

I have made many mistakes along the way, and I have a lot to learn, but I am doing my small part. Through policy analysis, AI tools, and civic action, my hope is this project turns exit into repair by building systems that help more Chicagoans thrive.

Welcome to my work.