Prison Camp: Last Hope
A White-Collar Journal forum for criminal justice, lived experience, and the personal search for redemption
This week’s post precedes my incarceration, before justice ever enters the picture. Last Hope is about that moment, when denial becomes its own form of imprisonment, and the quiet failure to tell the truth sets the stage for everything that follows.
LAST HOPE
During that period when my business was unravelling, I would routinely wake up in the middle of the night, review all the crises that lurked, the tipping points that had been missed, and try to conjure up one last strategy, one last reorganization that would resolve the morass our portfolio had become. Occasionally, an idea would emerge, once or twice, compelling enough that I would get up and write it down. But when I woke up—usually several hours later in a bath of perspiration—and reviewed these notes, they were only scribblings at best. Every now and then, in my most intense moments of desperation, I would resolve to confide in someone about the actual status of our company. Someone in the industry who was not directly connected to the company, might come up with the miracle I was looking for.
My best friend, Tom Gray, was in the real estate business, very successful, and a confidante for more than 40 years. We became friends as young marrieds, watched our kids grow up together, vacationed together, and regularly met for dinner, just the two of us, almost every month. He was the most likely person to confide in. He understood the business, knew me, my partners, and the story of our company. He had always encouraged me. He was the one who convinced me to leave the family construction business and enter the real estate industry. Before every meeting, I would consider opening up to him, but I could never pull the trigger. But after the turn-down from the private equity group, I committed to confiding in him the true status of my company and the nefarious activities I had implemented to deal with its issues.
Tom usually reached out to me. However, after being rejected by private equity, I called him the next day and invited him to dinner. Recently, we had been meeting at a small but highly regarded Italian restaurant in Westport. It was a high-energy place, a small but busy bar, with fresh pizzas pouring out of the open kitchen right next to it, and a long line of tables for two along the windows. I always arrived first. Recently, I had made it a policy to arrive early for every meeting. It was as if there was some formula, or magic, or behavior that would turn everything around. I’d usually have a drink at the bar while a table was being prepared. The bartender always seemed busy, shaking a colorful cocktail while working the crowd at the bar without missing a step. The positive, celebratory energy always lifted me up. In fact, it lifted me up too much. It created a false sense of optimism that often led me to ignore conversations about my business problems with Tom.
But on this evening, I was committed to telling all to Tom. He was knowledgeable, he had been in terrible straits and survived them, and I knew that he wouldn’t judge me.
I finished my drink—my favorite, a Negroni straight up—a perfectly cut orange peel clinging to the side of the glass. It was probably not a good choice, as it’s accompanied by a sudden rush of an undeserved good feeling. I waited for him at a table along the windows, spaced enough apart to make it comfortable to speak. And because it was a noisy place, the background noise made it easier for me to talk about the truth.
Tom looked and lived younger than his years. Although we were the same age, he was always in great shape. Lean and athletic, he had won 14 club championships in golf. It was through golf that we met, over 40 years ago. His wife was nutritionally extreme, fostering a macrobiotic diet, which Tom embraced. He had always been disciplined: working out, keeping to a restricted diet, and limiting his alcohol. But when we had dinner, he would break from his routine and almost always ordered whatever I was having. I seemed to be an excuse for him to break from his regimen. We’d even share a bottle of wine. A rare occurrence for him. An occasional beer was the lone departure from that regimen.
It was easy to pick him out, as he was always dressed in a perfectly tailored, crisp suit and an equally perfectly cut mustache. Wearing a big smile, he walked in, looked around, and recognized me, smiling and almost laughing as he made his way to the table. I got up and we hugged. I could feel, like always, how happy he was to be out to dinner. It always felt like a vacation when we got together for dinner—like playing hooky from school, or a break from all responsibilities, family, business, and the kids. By the time we sat down, I was already losing resolve.
A waitress arrived at our table almost the minute he sat down. An attractive thirty-something, in a crisp white blouse—the uniform of all the servers—a blond ponytail, and a big, smile. A welcome distraction to postpone the ominous revelations I had committed to reveal.
“Bottled water or tap,” she asked, rubbing her hands together.
There’s a surprising bias in my social group to disdain the bottled water. It’s perceived as a kind of high jinks to increase the bill. Tom immediately waved off the bottled water option and asked me to order some wine.
I looked out the window. It was surprisingly dark out. It was early November, and the days were losing daylight day by day, so it took you by surprise that, this early in the evening, it was already dark. There was a slight mist on the window, and I could see the wind from the street circling some leaves. A pall briefly came over me. But I recovered and asked about a white wine.
‘Do you have a vermintino you’d recommend?”
“Absolutely, we have—,”
“I’m sure it’s fine,” I interrupted. “We’ll try it.”
After she left, Tom patted me on my arm. Smiling, almost laughing.
“So, how’s your deal going?’
The deal he was referring to was the deal to sell or recapitalize the company, the history and narrative which I’d been sharing with him for the past year. But, all of it communicated to him without proper context, so that he was really in the dark and unable to understand what was going on, and therefore unable to provide effective counsel, as I had always redacted the true complexity of the company’s situation. But here, without even me trying, without any leadin or uncomfortable preparation, he handed me the opportunity at the outset. This was the time. Just do what my wife once said to our kids. “Pick up your fear and do it anyway.”
There was a sudden commotion behind us. Someone dropped a plate or a tray. I couldn’t tell. Only that it was so loud that the entire restaurant momentarily became silent. I didn’t turn around, but I could hear several people scurrying. Then, after a few minutes, the din in the restaurant returned. And then at the exact moment, the waitress returned with our wine, smiling like nothing had happened. She poured a small amount into my glass to sample it. The wine was cold, cutting, but in a good way. I could feel the rush. I motioned to her my approval, and as she proceeded to fill Tom’s glass, I could feel the courage seeping out of me. By the time she began to fill mine, I was overcome by the moment, and I knew it was not going to happen.
We shared a plate of the pasta special, followed by a dessert, chosen by Tom. We talked about golf, our kids, our friends, the state of Connecticut’s fiscal crisis, and anything else that didn’t relate to my business crisis.
It was pouring rain as we left.
“Johnny D, I love you, pal,” Tom said at the door after a big hug and then ran to his car.
“I love you too, pal,” I said, but pausing before I also made a dash for my car, on the other side of parking lot from where Tom had parked.
I was feeling the booze as I drove up the ramp of I-95 heading home. My wife was in New York for the evening. I was looking forward to an empty house. There was a pit the size of an elephant in my stomach.
Thank you for reading White-Collar Journal. Subscribing is free, and I hope you’ll continue with me as I explore stories of incarceration, justice, and redemption.
If this piece resonated with you, consider sharing it or leaving a comment. To support this work and help spread awareness about justice reform for white-collar defendants, subscribe to White-Collar Journal and stay connected. John DiMenna is a member of the White Collar Support Group.
To leave a comment, Substack may ask you to verify your email address (a one-time step to prevent spam). You don’t need to subscribe or create an account. Just check your inbox for a one-time link.