Going Back to Prison

When people serve time in prison, they look forward to getting out. Unfortunately, as high recidivism rates show, many people who get out once return to serve a new sentence. They don't even have to commit another crime. They can return for a technical violation of the terms of their release.

To illustrate, I'll share the story of my friend Gary. His experience serves as a lesson for all of us about the importance of educating ourselves and making informed, ethical decisions. 

Gary 

I met Gary during the later stages of my prison term. By then, I'd already served about 20 years. When I got to the Lompoc Camp, he became one of the first friends that I made. I admired Gary. He had an MBA, credentials as a CPA, and even had a law degree from UCLA. But he never practiced law. Instead, he built a successful career managing the finances of Hollywood celebrities. He wasn’t their agent but worked behind the scenes managing their spending habits, credit card payments, and travel reservations. 

Gary’s story is a prime example of how seemingly insignificant decisions can snowball into catastrophe, especially when navigating legal and financial systems.  His story reminds me of an analogy I remember reading from Benjamin Franklin:

"For want of a nail, the shoe was lost; 

for want of a shoe, the horse was lost; 

for want of a horse, the rider was lost; 

for want of a rider, the battle was lost; 

for want of a battle, the kingdom was lost, 

and all for the want of a horseshoe nail."

This analogy illustrates how one small, seemingly inconsequential detail can ultimately lead to the downfall of something much larger.

The Rise and Fall of a Successful Career 

Gary’s career took a sharp turn when one of the investments he made on behalf of his clients went south. He had placed millions of dollars into a factoring company—which provides cash to businesses with receivables. For a while, the business thrived, generating steady returns. But everything fell apart when the owner of that company caused a fatal drunk driving accident, resulting in a negligent homicide charge.

When the owner could no longer run the business, Gary found himself in a tough spot. The millions his clients had invested were at risk of complete loss. Instead of notifying the authorities or his clients immediately, Gary took over the company, determined to save his clients’ investments. That’s when things got even more complicated. 

The Gray Area of Ethics 

As Gary took control, he uncovered financial misconduct committed by the company’s prior owner. There was missing money, likely embezzled, and Gary faced a choice:

• Should he report the mismanagement to the authorities and risk his clients losing their investments and trust in him?
• Or should he cover up the losses, protect his reputation, and make the company profitable again? 

Gary decided on the latter, believing he could turn things around. He even dipped into his family's savings to stabilize the business without telling his wife. This decision, born out of good intentions, started a cascade of ethical dilemmas. When he discussed what he'd been doing with his wife, she questioned whether his actions were legal. He described them as a gray area, and she did not approve.

He decided to report the situation to the authorities. But by then, his actions amounted to fraud because he had concealed the company’s financial mismanagement from his clients and continued paying them as though everything was fine. The legal system took over, and a grand jury indicted Gary. A federal judge sentenced him to serve three years in prison. He became another headline in the Department of Justice’s press release. 

What Prison Taught Us Both 

By the time I met Gary, he was in his final months of serving his sentence. We bonded over shared interests in finance and the stock market, often talking during walks around the track. At the time, Gary looked forward to starting fresh once he got out. But Gary’s story didn’t end there. 

Like many who leave the system, Gary underestimated how challenging life on supervised release could be. One simple mistake undid everything. He failed to get proper permissions from his probation officer to travel outside his designated district. When the probation officer reviewed his credit card receipts, she found charges in nearby districts and deemed it a violation of his release terms. 

The result?

The probation officer issued a violation, which meant that Gary had to return to the judge. The judge sent him back to prison for six months. This second stint was devastating—not just for him but also for his family. His wife, who had supported him through his first incarceration, couldn’t take it anymore and filed for divorce. By the end of it all, Gary had lost his wealth, his freedom, and the support of his loved ones. 

The System is Serious 

Gary’s story reminds us that the legal and penal systems are unforgiving—even for those who think they’re making well-intentioned decisions. Many people in Gary’s situation might say, “I didn’t know it was serious,” but the system doesn't consider ignorance as an excuse. Understand the rules and seeking guidance when in doubt. Using good critical thinking skills will help you avoid complications. 

Practical Lessons from Gary’s Experience 

1. ‍ Always Understand the System: If you’re facing an indictment or navigating supervised release, take the time to educate yourself. Learn the rules, ask questions, and make sure you fully comprehend what is and isn’t allowed. ‍
2. Don't take shortcuts: Shortcuts or "gray area" decisions may seem like practical solutions at the time, but they often lead to further consequences down the road. Transparency and integrity are vital, even when the truth is inconvenient. ‍
3. Prepare for the Long Game: Understand how to live within the rules after release. From probation conditions to rebuilding your life, the more prepare, the more you advance possibilities for success.‍
4. Learn Continuously: There’s a reason I emphasize education in everything I create. Knowledge opens opportunities, whether you’re preparing for release or trying to rebuild a meaningful life after incarceration. 
5. Expect obstacles: The system is designed to receive. Expect that many people in the system will create obstructions. It's crucial to focus on success, and not get trapped by taking short cuts that can lead to catastrophe.

At Prison Professors, we’re committed to providing the resources and guidance you need to avoid the same mistakes.  Nobody can change the past, but with the right mindset and strategies, you can build a better future. 

Remember: Success doesn’t happen by accident. It happens when you take ownership of your life, educate yourself, and make intentional choices. 

Stay strong, and be cool.

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