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LESSON: When slammed by extreme adversity, we enter a world where up may be down, and wrong may be right, but all we can do is give maximum effort in what we believe is the path of truth.  The universe will throw us curve after curve, but we cannot give up.


The below lesson is an excerpt from my recently released book, When Not If: A CEO's Guide to Overcoming Adversity, Forbes Books, January 16, 2024. 


Despite the fact that ninety-nine times out of a hundred, the motions I filed on behalf of my fellow inmates and myself were summarily denied, or never received a response, I filed literally thousands of motions, petitions, and letters over the eleven years I was a federal prisoner. What other option did I have to help these prisoners, and maybe help myself?


It was a numbers game akin to the financial advisory business, what we earlier termed the theory of “n,” referencing it’s all just mathematical equations. My cold calling “n” had been “89,” which meant I had to dial 89 numbers from the phone book in order to get one prospective client to agree to a meeting. I noted the irony of how closely this number matched my dismal success ratio presenting motions to the court.


Then, every once in a great while, I would experience a small victory, such as when a US Supreme Court case would set a new precedent with which I could file a novel petition to apply these interpretations to an inmate’s case and get some relief. A few cases redefined what constituted certain acts adding mandatory minimum sentences.


Consider the case of an inmate I’ll call Sammy. A bunkie in my twelve-man room at FCI Ft. Dix, I got to know Sammy well. His was a typical story of drug-addict parents abandoning him, raised by his grandmother in Ohio, a boxing background, and his six-foot, eight-inch frame made him an incredible basketball player on our team. I knew he could probably have had a big-time Division I college career if he had simply experienced a middle-class upbringing like my own.


He was serving a twenty-year sentence for brandishing a firearm during an altercation at a bar. Every one of my bunkies had firearms on their list of charges. It was simply a way of life. It would be incomprehensible for them to think about not carrying a firearm.


The dichotomy of life experiences always struck me in dealing with these cases. Knowing my own competitive nature and love of leadership, I always thought of how, given different circumstances, I would have very likely been the top gang leader and top drug salesperson for my city. Luckily for me, I had so many more options.


Gary, a fellow prison law clerk much smarter than me, took the lead on Sammy’s case. He spent innumerable hours researching and writing while I did my best to add value and draft a compelling narrative. It worked. After many months we received notice that Sammy would be heading to a minimum-security camp and then be released ten years early. We were in shock and delighted by the radical impact our efforts had on Sammy’s life.


That evening in my room of twelve metal bunks, Sammy got into an argument with Alex the store guy. The store guy is normally an inmate with access to funds who buys extra commissary—drinks, packs of tuna fish, oatmeal, peanut butter—and then sells it at a markup. Just like on the outside, people are willing to pay extra for convenience. We were allowed to go to the commissary but once a week, so most of us were willing to pay a little more for items without waiting. But not everyone.


Sammy didn’t like the high markup Alex was currently charging, and Alex, a man of small stature from Guatemala, made the mistake of commenting on the virtue of Sammy’s mother. Respect is very important in prison and must be maintained. Disrespect in prison can lead to extremely violent situations. So it was in this moment.


Sammy hit Alex over and over, and Alex dove into Sammy’s knees and held on for dear life, a tactic the smaller inmates used when faced with sure destruction. Sammy didn’t enjoy hitting Alex on top of his head, so he began to violently choke him. I don’t know what compelled me, but I ran across the room and, literally, jumped on Sammy’s brawny back, grabbed him around the neck, and screamed, “Stop! You’re going to a camp! You’re going home! Don’t destroy it all now over a packet of tuna!”


Sammy released Alex, turned to me with a stare looking deep off into something, said “Thanks,” and walked back to his bunk. For Sammy, it was over as quickly as it started. Not so for me. That evening, I sat up most of the night in my top bunk vibrating with the adrenaline the episode released. Eventually, I relaxed and contemplated what we had done. Was it a victory Sammy was being released, or was it a terrible mistake that would befall some other store owner in Ohio?


I hated the system. I hated the universe. I hated my life.


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