The Richmonder 25: Jim Bailey helps prisoners make the most of their fresh start

When Jim Bailey decided he wanted to give back to the community, he didn’t simply want to volunteer somewhere.

“It had to be something gritty,” he said. “Something with some hair on it.” 

That’s how the corporate attorney at Williams Mullen came to serve in prison ministry, teaching regular classes at State Farm Correctional Center in Goochland. 

“I love my job,” he said of his legal work. “I’ve been here for 13 years. After I felt like I was on solid ground, I wanted to find a way to do something meaningful outside of work.”

A friend suggested he consider prison ministry. He came along to one session where he witnessed a young convict give what Bailey described as “the most passionate speech I’d ever heard” about crime and turning one’s life around. 

“He talked about how he made a mistake he’s regretted every day since, but all he could do is do everything possible to make his mother and grandmother proud,” Bailey said.  “I thought, ‘Sign me up.’ I’ve been teaching a weekly class ever since.” 

Bailey’s class has two components. The first is an hour of what he described as “very, very basic” Bible study. 

“Everybody in prison needs hope,” he said. “In the class there are guys who are very spiritual, devout Christians, and there are others who have never read the Bible and are interested in learning more. It’s great to have that very broad strip of guys in class.” 

The second part of the class is “one hour of life skills,” he said. 

“Often it’s financial skills,” he said. “I can apply a little of my day job as a lawyer to these lessons.” 

Among the things he teaches: “Don’t sign a lease jointly with your girlfriend you’ve known less than a month,” he said with a laugh. 

“We also learn what a credit score is. We talk about mortgages. We really discuss anything financial that you or I were taught from college or parents. It’s really sort of the basics of personal finance.”

“The point is to be practical,” he said. “I tell the guys, when you get out of prison, you have to jump a series of hurdles, and it’s important that you don’t make a mistake simply because you don’t understand something.”

For Bailey, the classes represent a chance to teach prisoners about redemption in a variety of forms. 

“It’s about second chances,” he said. “But it’s also about third chances, fourth chances, fifth chances. It’s about empowerment. You can leave this place and be empowered to have a successful life without having to come back here.”

He described the environment of the classes as “supercharged.” There are strict attendance and homework rules to the course, he said; the high expectations lead the prisoners to police themselves effectively, resulting in a cohesive and impactful classroom. 

In addition to his work teaching the class, Bailey is also the chair of GraceInside, a nonprofit that contracts with the government to provide chaplains to the state correctional facilities. 

“The chaplains do so much to help men and women [in prison] with rehabilitative needs and moral support,” he said. “But they also help the correctional officers, too.” The nonprofit was on the verge of bankruptcy several years ago before Bailey and several others turned it around. 

Bailey described the experience in the prison classroom as “an ongoing dialogue, the complete opposite of a monologue.”

“I tell the guys every week: I get more out of that class than they do, for sure,” he said. “They give so much back to me. They’re very receptive to the work, to what I’m teaching. It’s just a great environment.”

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