Can One Man Transform a Struggling Chicago Neighborhood?

From education to housing to health, Chicago's Gary Comer, billionaire founder of Lands' End, invested millions into the struggling South Side neighborhood of Pocket Town in a mission to transform it into a beacon of hope for the community.

2 minute read

January 23, 2013, 6:00 AM PST

By Erica Gutiérrez


Although it was never Gary Comer's intention to see the fruits of his labor in his lifetime, from one venture to the next, he's invested $86 million into projects aiming to improve Pocket Town, the neighborhood where he grew up in Chicago's South Side. Starting with a $68,000 check to fix an electrical problem at "the two-story red brick Paul Revere Elementary School," to investing $12 million in an affordable housing program, to setting up the Comer Science and Education Foundation, Comer made sure “he would take care of [the] neighborhood” long after his passing in 2006.

Elly Fishman writes, “Comer’s hugely ambitious quest contains elements of both the Kalamazoo Promise (a Michigan philanthropist’s pledge to pay for college for all local kids who graduate from public high school) and the Harlem Children’s Zone (an urban renewal program that provides an assortment of “cradle-to-career” services for children and families in New York City’s Harlem neighborhood). The plan he eventually hit upon was to address the interconnected problems facing Pocket Town’s residents: poorly performing schools as well as issues like substandard housing and inadequate health care.”

With all that said, Fishman asks, “What results has that huge investment yielded? And what lessons are there for policymakers, philanthropists, and everyone who cares about the fate of struggling urban neighborhoods?” Comer's initiatives have yielded successes, as well as failures. His health initiatives, for example, led to the vaccination of over 700 children this year. A youth center provides recreational activities, year-round jobs and 6,000 pounds of vegetables annually via a community garden. His housing and education activities have had mixed results.

"On paper," concludes Fishman, "$86 million looks like a helluva lot of money. 'But it’s really hard to change people and communities,” says [Harvard sociologist Robert Sampson]. “We need to be realistic. . . . The social forces that permeate the South Side don’t stop at the Pocket Town boundaries.”

Thursday, January 17, 2013 in Chicago Magazine

portrait of professional woman

I love the variety of courses, many practical, and all richly illustrated. They have inspired many ideas that I've applied in practice, and in my own teaching. Mary G., Urban Planner

I love the variety of courses, many practical, and all richly illustrated. They have inspired many ideas that I've applied in practice, and in my own teaching.

Mary G., Urban Planner

Get top-rated, practical training

Close-up of "Apartment for rent" sign in red text on black background in front of blurred building

Trump Administration Could Effectively End Housing Voucher Program

Federal officials are eyeing major cuts to the Section 8 program that helps millions of low-income households pay rent.

April 21, 2025 - Housing Wire

Logo for Planetizen Federal Action Tracker with black and white image of U.S. Capitol with water ripple overlay.

Planetizen Federal Action Tracker

A weekly monitor of how Trump’s orders and actions are impacting planners and planning in America.

April 30, 2025 - Diana Ionescu

Ken Jennings stands in front of Snohomish County Community Transit bus.

Ken Jennings Launches Transit Web Series

The Jeopardy champ wants you to ride public transit.

April 20, 2025 - Streetsblog USA

Close-up of white panel at top of school bus with "100% electric" black text.

Driving Equity and Clean Air: California Invests in Greener School Transportation

California has awarded $500 million to fund 1,000 zero-emission school buses and chargers for educational agencies as part of its effort to reduce pollution, improve student health, and accelerate the transition to clean transportation.

6 hours ago - California Air Resources Board

Aerial view of Freeway Park cap park over I-5 interstate freeway in Seattle, Washington at night.

Congress Moves to End Reconnecting Communities and Related Grants

The House Transportation and Infrastructure Committee moved to rescind funding for the Neighborhood Equity and Access program, which funds highway removals, freeway caps, transit projects, pedestrian infrastructure, and more.

7 hours ago - Streetsblog USA

"No Thru Traffic - Open Streets Restaurants" sign in New York City during Covid-19 pandemic.

From Throughway to Public Space: Taking Back the American Street

How the Covid-19 pandemic taught us new ways to reclaim city streets from cars.

April 30 - Next City