A Journey Through the White Collar Nightmare: Jim Clark’s Story

A St. Louis Kid Born on Third Base

I had a conversation with Jim Clark recently that took me back to our time together at Leavenworth. Jim was one of the first guys I met when I got there, and he literally helped me survive those early days. Now he’s back in Kansas City, and we talked about his journey from a successful IBM executive to federal prison and back to freedom.

Jim grew up in South St. Louis, went to the same Jesuit high school I did, and had what he calls a charmed life. “I was born on third base,” he told me. “I had a mom, dad. I have three brothers and sister, a brother and two sisters.” After college at Bradley University, he spent 13 years at IBM in Chicago before moving to Kansas City to work for Cerner Corporation. That’s where things started to shift.

The Confidence That Became a Problem

After a few years at Cerner, Jim launched his own healthcare consulting company called Swish Holding Corporation. The business took off fast, hitting $5 million in revenue. But that early success created a dangerous overconfidence. “It’s the same attitude that you want to start in your own business,” Jim explained. “That same attitude that you want to start in your own business. It’s like confidence and I can go get them and I’ll never give up. You know, there was a Trump book out there. You’ll never give up at that time. It’s the same that gives you that makes you keep digging a hole.”

Jim made what he calls fundamental business mistakes. He didn’t diversify the company enough, and then took his attention away from the core business to buy an ABA basketball team. When the market shifted and his company president had problems, everything started to unravel. The company went under, leaving Jim with a couple million dollars in debt and the IRS on his trail.

The Decision to Falsify Financials

Facing mounting pressure and debt over the $1 million IRS threshold, Jim made a choice that would cost him his freedom. He falsified financial statements to a bank. “I fully admitted what I did. I made a mistake and falsified financials, which is when you falsified financial statements to a bank, you break every banking law,” he said. “So you’re on everybody’s radar. And I was a really easy target because I wasn’t going anywhere. And I was very public.”

The publicity from owning the basketball team made Jim a perfect target for prosecutors. He became what he calls “a success story for the U.S. attorney.” Like 97% of people who get indicted, Jim decided not to fight and worked out a plea deal.

Walking Into Leavenworth

Jim was sentenced to 52 months and served 39. The night before reporting, he didn’t sleep at all. “I just laid in bed and I just I just couldn’t believe it was happening,” he remembered. “I couldn’t believe I had a priest advised me. I go, how do I even get out of the car? Yeah. You know, and I had my body say, you know, get out the way you came in.”

When he arrived at Leavenworth on August 31, 2012, Jim walked through the wrong door initially. After processing, cavity searches, and hours in holding, he finally made it to the camp. It was Memorial Day weekend, and the place smelled weird. Everyone was sleeping in the middle of the afternoon. He got put on a cot because they were “sold out” of bunks.

A guard walked up to him and said something that stuck: “Pinch your skin. Make it a hundred times thicker and you’ll be okay.”

Learning the Unwritten Rules

Jim made a conscious decision early on to learn from guys who had been down a long time, even though it was uncomfortable. Most white collar inmates, he learned, were seen as rats or conceited people who thought they were superior. But the long-timers taught him how prison really worked.

“Everything’s the opposite,” Jim explained. “So if you’ve got, there’s a saying called lay down and lick your nuts. So it’s, you know, you’ve done something wrong. Take it. Take it. Don’t sit there and complain. You did something to get you here. Take it.”

He learned that you can’t look when someone’s doing drugs next to you. You can’t say anything when guys cut in line for meals. Your whole way of thinking has to change. It took him almost a year to get “set up,” which means figuring out how to exist in that environment.

Building a Routine and Finding Purpose

By the time I arrived at Leavenworth a year later, Jim had created structure for himself. Every Saturday morning, he’d go to the mess hall with his notebook and plan his entire week. He’d manufacture goals and objectives just to have something to check off. “I come up with things I want to accomplish. I could feel like I’m checking them off,” he said.

Jim also got involved with the Catholic ministry in a way that probably hasn’t been replicated since. Through connections with his former parish in Kansas City, he brought in Father Sheber and eventually Archbishop Mark Naumann to conduct regular masses at the camp. They built what they called the Maximilian Colby Catholic parish and had 380 guys go through their programs over three and a half years.

“I would dress in my clean uniform stuff on Sunday. And I would stand out there waiting for the priest to come in. And guys would say, Hey, have you had to visit? I said, no, I’m visiting baby Jesus,” Jim told me. The ministry gave him purpose beyond himself and helped other inmates who had nothing.

Getting Close to the Door

As Jim’s release date approached, he dealt with the complex emotions that come with short time. Guys get jealous, some inmates make a big deal out of leaving, and you have to navigate those dynamics carefully. The halfway house in Leavenworth was almost worse than prison in some ways, but Jim maintained perspective: “I’m not there.”

That attitude has stayed with him. Even on bad days now, even during COVID restrictions, Jim remembers what it felt like to lose his freedom completely. “Even my worst day here. Yeah. I’m not there,” he said. “No, not having that attitude because attitudes, everything.”

Jim’s story reminds me why those early connections in prison matter so much. The guys who reach out, who share what they’ve learned, who help you find your footing when everything feels upside down. Jim did that for me, and hearing him tell his story now, I can see how he turned his worst chapter into something that taught him what really matters.