Even White-Collar Criminals Can Get Screwed Over by the Prison System

During the 26 years that I served in federal lockups, I kept myself productive by writing about the prison experience. Besides tallying my own experiences, I interviewed people from every background. While in high-security penitentiaries, I rubbed elbows gang leaders; when I transitioned to minimum-security camps, I befriended men were convicted of white-collar crimes.

There are many different paths through incarceration and beyond, but without exception, people face challenges when they return to society, regardless of background. Gary, a former inmate who had a law degree and an MBA and was a certified public accountant (CPA), made that clear.

I met Gary the first day that i walked onto the yard of a minimum-security California camp after my transfer from a prison in Colorado. He was raking leaves and stopped when he saw me approach. "Welcome to Lompoc," he said. He wore freshly pressed green khakis and he had a purpose about his step.

I guessed that Gary was in his early 60s. He wore stylish glasses and clearly devoted a lot of time to fitness. "Where'd you roll in from?" he asked.

"I was in Florence."

"Why'd they transfer you here?"

Gary's questioning and demeanor told me a lot. If he changed from prison khakis to suit and tie, he could have been a CEO. In higher-security prisons, like the ones where I began serving my sentence, the men projected fiercer images; instead of making nice, they kept to themselves and were standoffish to newcomers. In an instant, I reasoned that Gary had served all of his time in minimum-security settings.

"I'm a writer. Staff don't like inmates who write," I explained. "This is the sixth time I've been transferred and it probably won't be the last."

Gary told me that he was 69 years old; he had a law degree from Berkeley and an MBA from Stanford. He'd built a career managing resources for celebrities in Hollywood. When an investment deal went bad, he accepted a plea agreement of five years for wire fraud. Although I sensed that smiles and an easy disposition always characterized his life, Gary was especially jubilant when I met him. He'd come to the end of his term, and was just days away from his transfer to a halfway house. He told me that he had secured a job in an accounting firm.

Three years later, authorities locked me in solitary and charged me with a disciplinary infraction for "running a business." They didn't like that I wrote books from prison. After being held in solitary for two months, I succeeded in reversing the disciplinary infraction, but administrators transferred me to a different camp. After locking me in chains, they drove me to the federal prison in the city of Taft.

I wasn't there for long when I saw Gary walking the track. I recognized him right away.

"Gary? What's up dude? What are you doing here?"

I frequently encountered people who served time with me previously, but I never expected to see Gary again after his release from prison. His shoulders sagged and he shook his head. "You're never going to believe what happened."

We walked side by side as Gary told me his story. From the day he went to the halfway house, he had problems. Rules prohibited him from accepting the job he had arranged. The case manager overseeing his case didn't approve of the "professional" job in the accounting firm—she told him that he had too much liberty in that position. He said that she preferred for him to work in a job with more structure and without so much discretion. Gary explained that he was only working as a clerk, but the case manager wasn't having it. Since he wasn't able to find a job that satisfied her, he had to spend all of his time in the halfway house. While there, he worked as a janitor.

When Gary finished his obligation to the Bureau of Prisons (BOP) and the halfway house, he transitioned to federal probation. A probation officer would oversee him for a three-year term of "supervised release."

Gary said the probation officer made life hard on him too—it was almost worse than being in prison. Since he had a prior relationship with the owner of the firm that was going to hire him, he was never going to be allowed to work there. And despite being nearly 70 years old, Gary was subjected to all kinds of weird hassles. For example, he had to participate in anger-management and drug classes—and had to pay for them. His probation officer kept on him about finding a job, but only the type of job that fit her description of what was suitable. Like his case manager, she didn't want him working anywhere that resembled "management" and insisted that he find something more "appropriate."

Gary was released during the Great Recession, and jobs weren't exactly plentiful—especially for felons. "I told her that I didn't need to work, that I could live off retirement savings and my wife's income," Gary told me. "The probation officer said that if I didn't find work, she'd consider me noncompliant. From the start, I knew there were going to be challenges. It was as if she envied or resented the success of my previous career."

I told Gary that I heard a lot of stories about people facing employment challenges while on supervised release. "But why did she violate you, why did she send you back here?" I asked.

Gary explained that while on supervised release, his probation officer required that he request permission for travel. He was released to the Central District of California, a judicial district that included the greater Los Angeles area. If he wanted to travel anywhere outside of that general area, he'd need to submit a request to his PO and wait for approval.

"A close friend passed away while I was serving my sentence," Gary explained. "His daughter was getting married in San Diego and she asked that I attend the wedding to give her away at the altar. I'd known her all her life. I submitted a request to attend the wedding more than two months in advance. My probation officer never responded and I missed the wedding. After that, I decided that I'd never ask again."

About two months before his three years of supervised release came to an end, Gary's probation officer called him in and she asked that he bring all credit card receipts for the past year. When she saw that receipts for gasoline and hotels in districts that were outside of the Central District, she asked for an explanation, reminding him that she hadn't authorized his travel. As a consequence of those travels, she "violated" Gary, charging that he did not comply with the conditions of his release. A federal judge sentenced Gary to serve another year in prison.

When he concluded the year, Gary said, he would have to begin his term of supervised release all over again. Worse, his wife of more than 40 years came to visit him; she told him that she had gone through the prison system once with him, but couldn't do it again. She had filed for divorce.

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Gary's story captures how broken the system is. It is designed to receive and not to release. Even people who do not need supervision are made to endure challenges out of sync with their danger to society.

I face the same challenge. Despite my stability in society, I'm scheduled to remain on "supervised" status until 2035. The more time probation officers waste supervising me, the less time they have to focus on people who truly need to be watched.

These days, judges and prosecutors seem to go pretty easy on elite criminals; convictions for white-collar crime are at a 20-year low. But when I saw men like Gary returning to prison—not for breaking the law, but for ridiculous technical violations like not asking for permission to travel—I became more convinced than ever that we needed both sentencing and prison reform in America.

Follow Michael Santos on Twitter and check out his website here.