Prison Friends and Ethical Choices

Ethical Choices: A Keynote Speaker’s Journey Through Prison

Reflecting on my journey, I realize that the consequences related to ethics and choices in business can shape our lives in profound ways. This includes the ones that led me to federal prison.

In our daily lives, we often make judgments about people based on their appearances, their past, or the situations they find themselves in. But life has a way of teaching us lessons that defy stereotypes, and sometimes, we discover incredible connections in the most unlikely places. I know I did.

Ethics and Choices in Business

A Connection Forged in Prison

This following story is part of my keynote presentation on ethics and choices in business. The audience almost always snickers about people who are ‘friends’ in prison. Assumptions are made with the belief of a romantic Bubba relationship between two inmates. In fact I even propagate this myth with some of the comic relief in my keynotes. I have thick skin by now.

When I Went to Prison

In the mid-90s, I was involved in a white-collar crime conspiracy. The lines had become blurry between Ethics and Choices in Business. Among other things, it led to a 21-month federal prison sentence in Yankton, South Dakota. Going in, my mind was filled with fear and prejudice. I had committed a crime, yes, but surely I was not like “them.” They were criminals, bad people — the dregs of society.

It took only a few days and a scary encounter with two of these ‘criminals’ in a dark hallway to drop my elitist attitude. I got the message — I was one of them. First lesson learned!

But yet, in this daunting place, I met a guy (not Bubba) — he has 2 college degrees; one in aviation and the other Spanish (was that a Drug Smugglers Degree?). On our first encounter we discovered we shared a similar sense of humor and intellect. With the housing on the compound, often inmates would be transferred around to different ‘rooms’ or cells and we wound up being cellmates.

prison and business ethics

Down Time: Lessons Behind Bars

Calculating our release led to a crazy coincidence in scheduling. His 36-month sentence was a result of his self-employment stemming from his college education.

He’d already been in prison for over a year. Mine was a 21-month sentence. We calculated that we’d finish our sentences at about the same time. We knew we’d be transferred to a half-way house to serve out our final 6 months. But we didn’t know exactly when that would be due to factors such as “time off for good behavior” or “space availability” at a halfway house.

Keep in mind this was also a lesson in ethics and choices in business.

We got through the next year making the best out of a host of situations. Then the news: we were scheduled for transfer to the exact same halfway house in Minneapolis, at their exact same time, on the exact same day. A sheer coincidence!

Chance had us walking the same path, but destiny had more surprises in store. This wasn’t just an unlikely friendship; it was a lifeline in the storm that lay ahead.

Halfway Home: Transitioning Back into Society

The universe seemed to conspire, keeping us together in the transition. Arriving at the halfway house, we discovered we were assigned to the same room. To call this extraordinary would be an understatement; it was almost as if the universe was conspiring to keep us together.

The odds of these coincidences were astronomically low. We were not just inmates serving time under the jurisdiction of the federal Bureau of Prisons; we were human beings; bonded, put together by the universe. And in this new environment, where freedom was just within reach, I would discover just how strong this bond would be.

Call the Doctor

A timely diagnosis revealed cancer, testing our friendship’s resilience.

The halfway house (more like a giant old house with a bunch of rooms) meant transitioning back into society. Things such as: opening a new bank account, getting a job — hopefully with health insurance, etc. But life had other plans. Just a few days before my health insurance was activated, I felt something wrong. One of my testicles had started to swell.

I called another friend, someone we called Doc. He was one of our our prison mates who was released a few months earlier (he was actually a doctor before he went to prison), and now he was my lifeline. His soft, physician-like voice told me what I feared: I needed to see a urologist, immediately.

A Timely Diagnosis: Facing Health Challenges

I went to see a urologist just after my health insurance kicked in. The diagnosis was harsh: testicular cancer that had spread into my lymphatic system. Talk about needing to overcome adversity. Cancer while serving a prison sentence. Aww, c’mon man. I was allowed to be at the hospital for the surgeries as well as a week of recovery. The remainder of my recovery was done at the halfway house, where my mobility was impaired to say the least.

Throughout this recovery and subsequent chemotherapy my cellmate was there bringing me food, medication and basically everything else I needed.

Decision to Stay in Prison

From the day any inmate begins his sentence there is the common dream of the debit being paid, and being at home with all the comforts and freedoms that go along with it. My crime relating to choices surrounding business ethics and his were lessons in drug smuggling. Me and my cellmate’s sentences would be complete on roughly the same day in March of 2021.

Home confinement was a feature whereby, with restrictions, we’d able to finish out a percentage of our total sentences at home. Since my cellmate’s sentence was 36 months and mine 21, he was going to be able go on home confinement several weeks before me.

But here’s the twist: He stayed.

The days turned into weeks, and still, he stayed. He could have left weeks earlier. But he stayed because that’s just who he was.

An Unbreakable Bond: Friendship Beyond Labels

Yes, he stayed; his selflessness strengthened our unique connection. But he was just like me; a criminal, a convicted felon and a floater at the bottom of society’s tepid pool of filth.

He stayed and on some level, it didn’t completely surprise me. I’d come to know who he was and what we were — two human beings, connected by circumstances, bound by a shared understanding of life’s complexities.

He had no motive to be kind. It wasn’t a facade put on to navigate the rough waters of prison life with some benefit on the other side. It was genuine, a part of who he was. His integrity, empathy, and selflessness were revealed not just through his actions but through the very coincidences that had brought us together.

The story of my cellmate and me is a testament to the unpredictability of life and the unbreakable bonds that can form in the unlikeliest of places. It could be a lesson on the ethical choices I made in business, but it was much more. It’s a story that continues to inspire me and the audiences I speak to, a reminder that good people can be found in the most unexpected corners of life.

My health improved, and we both went on home confinement. The year was 2001 and the bond still continues in August 2023.

Finding Good People: Humanity in Unforeseen Places

Life’s surprises taught me to find goodness in unforeseen places. You never know where you’re going to find good people. I never expected to find a friend in prison, a doctor in an inmate, or a soulmate in a fellow felon. Yet, life surprised me.

As a keynote speaker, I share this story of humanity, choices, and consequences. But more than anything, I share a tale of unexpected bonds, of finding goodness in the most unforeseen places.

May this story remind you that good people are everywhere, even where you least expect to find them.

Full Story Combining Ethics With Business Choices

I have plenty of other stories about my experiences in the business world as well as behind bars. This part however, is important and I wanted to focus on the point of meeting good people in unlikely places. For other parts of my experience you can listen to my book, Diary of a White Collar Criminal on Audible or attend one of my keynotes.

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