Faces of Saint Leonard’s: Retired Executive Director, Bob Dougherty

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Saint Leonard’s Ministries has nearly 70 years of stories illustrating triumph, renewal and successes we always enjoy sharing. Today, we share the story of beloved, long-time Executive Director Bob Dougherty.

Bob Dougherty

Bob Dougherty was scanning the newspaper job ads in 1988 when he saw a post about an unidentified West Side nonprofit that was seeking an executive director.

“It was a very small and unassuming ad – and one of those things if you think another thought, you might not even have tried it,” he said.

Fortunately, he tried it. The advertisement started Dougherty’s three-decade run as the top leader at Saint Leonard’s Ministries, which celebrates its 70th anniversary in 2024.

“The mission of Saint Leonard’s has always been clear and vital,” Dougherty said. “What can we do to help people not return to prison?”

A key part of Dougherty’s legacy is the organizational pivot “from an extension of a criminal justice program to a service program designed to help people.”

“I was more focused on what we can do to make the place more reflective of sound social service,” he said. “Each resident needs many things – some of it’s education, some of it’s problem-solving, some of it’s psychological services. It’s never any one need.”

“Rehabilitation does work. It’s rebuilding, and sometimes it takes more than a second chance. If we invest in it – both money and ourselves – the results are good ones.”

This operational and culture change was necessary as the organization shifted to more appropriately refer to the participants as “residents.”

“They are people we work with and not people we were in charge of,” Dougherty said. “I’m not a particularly brilliant person. I wasn’t creative. I just responded to the needs. We have a program for men, we should have one for women,” he said, referring to the opening of Grace House which also reaches a milestone in 2024 – its 30th anniversary.

Dougherty, a South Side native who spent his career teaching after earning three master’s degrees, first began working in the justice system when he taught high school courses at Cook County Jail.

“I began to see the relationship between poverty and what it does to individuals,” he said. “And the school-to-prison pipeline became clear.”

He also served as a member of Illinois Coalition Against the Death Penalty in the 1980s to address the fact that minorities were more likely to receive capital punishment than their white counterparts.

At Saint Leonard’s, Dougherty was never interested in somebody’s criminal charge.

“I figured that isn’t my job. It was the counselors’ jobs, other people needed to know those things. I just needed the residents to know I was part of them experiencing a new beginning, a different kind of chance,” he said.

And he lived the adage that he found something he truly enjoyed, so he never worked a day in his life.

“It didn’t feel like I was going to work. It was never a job to me. It was always an opportunity to be present to people who need help. It was an opportunity to take the words we read in the Gospel and follow the Gospel mandates,” he said.

“I always felt it was a better day at Saint Leonard’s than if I hadn’t been there. It was good for me to be there.”

Today, Saint Leonard’s Ministries continues to build on the programming, housing and workforce solutions Bob put into place. As a result, Saint Leonard’s Ministries remains the leader, innovator and beacon for putting retuning citizens on the path to success. We look forward to sharing our plans in 2024 as we celebrate 70 years of service.

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