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The Ones Who Don't | Chapter 13

Justin Paperny

Founder White Collar Advice · October 13, 2026

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For some reason, Ray expected eighteen months in federal prison. The judge gave him sixty.

I was in the third row. Ray's wife, Alana, sat in front of me between her sister and Ray's brother. When the judge announced the sentence, Alana kept her promise to Ray and did not react.

Ray had spent the previous eighteen months preparing. He rewrote his narrative nine times, began paying restitution before his plea and volunteered with Habitat for Humanity.

Before he began volunteering, I told him to explain that he was under investigation and that a sentencing hearing was likely. No, it was a certainty. I suggested he disclose his case and confirm they would write a letter on his behalf.

Ray did not want to have the difficult conversation, so he put it off.

"I have time," he told me.

He volunteered for close to eighteen months and kept a record of the dates and what he did. When sentencing got close, he asked the director for a letter describing his contributions on Habitat for Humanity letterhead.

She simply said no. She offered to write something personally, but she reiterated that she would not use the organization's letterhead.

Ray was now paying the price for putting off the conversation. Had he asked at the beginning, he could have volunteered somewhere else and known whether the organization would document what he did.

There is nothing wrong with a win-win. Ray could help the organization, and the organization could help him. Nothing about sentencing mitigation is altruistic. Ray wanted a shorter sentence.

He reluctantly took the personal letter.

Probation recommended a guideline sentence between 63 and 78 months in prison.

The judge reviewed Ray's work and used the word "commendable." Then he talked about the loss, the victims, how long the offense went on, which was the real deal killer, and general deterrence.

Sixty months was three months below the low end of the range, yet it felt like a huge loss, in part because he had somehow conditioned himself to believe eighteen months was the magic number.

In the hallway afterward, Ray's lawyer started explaining. The judge had a reputation. The prosecutor had emphasized the number of victims. Another courtroom might have produced another result.

Ray's brother said they should have gone to trial.

Alana's sister said God had a plan.

Ray listened for a while, then looked at me.

"Can we take a walk?"

We walked about two blocks from the courthouse before he said anything.

"Eighteen months," he said. "The mornings, the narrative, Habitat, paying restitution. I did every single thing you asked me to do."

"You did."

"And I got sixty months."

I did not answer.

"Three months below the guidelines," he said. "I could have spent those eighteen months on my couch and gotten the same sentence."

"You don't know that."

"Neither do you."

He was right.

I felt the urge to do what everyone in the hallway was doing: blame the judge, the prosecutor, the number of victims; find something in the hearing that suggested the work shortened his sentence. I had tons I could say.

"You're right," I said. "I don't know."

Ray stopped walking.

"That's it?"

"That's it for right now. Sixty months is sixty months. I'm not going to stand here and tell you it's really a blessing or that it could have been worse because, in your eyes, it could have been better."

We walked back toward the courthouse.

"Everybody in that hallway has an explanation," he said. "The judge, the prosecutor, the trial we didn't have, God's plan. Everybody knows exactly why this happened."

"They're trying to help."

"I know."

"Do you want to know what helps best?" I asked.

"Let me guess. Don't be a victim. Own it."

"Sounds super cliché, but yup."

"That's easy for you to say. You're not going away for five years."

"You're right. I'm going home."

"So what am I supposed to do?"

"Today? Go home too. You walked out of the courtroom. Some guys get sentenced above the guidelines and get taken into custody immediately. They spend months in transit before they get to their prison. That did not happen to you. You have five weeks with Alana and your family."

"That's the good news?"

"It's not good news. It's what you have."

He did not look convinced. I would not have been convinced either. He expected eighteen months. I could not talk him into feeling fortunate about sixty while we were still standing near the courthouse.

Nine days later, Ray called me from his kitchen. Alana was upstairs. He would surrender in five weeks.

"Have you read the Bible?" he asked.

"No," I said.

"Do you know the story of Job?"

"I know his name."

"That's it?"

"That's it. Tell me about Job."

Ray said Job was a good man. God called him blameless and upright. Job had property, children and good health. Satan said Job was faithful only because God had given him a good life and protected him.

Then Job lost his animals, his servants and his children. After that, his health went. He ended up sitting in ashes, scraping sores from his skin.

"That's Job?" I asked.

"That's Job."

"I thought it was mostly about patience."

"That's what people say. There is a lot more to it."

Three friends came to see him. Ray said they sat on the ground with Job for seven days and seven nights without speaking because they saw how much he was suffering.

"Seven days?"

"Yes."

"I would be uncomfortable after seven minutes."

"They should have stopped there."

Once the friends started talking, they tried to explain why Job was suffering. Maybe he had sinned. Maybe his children had done something wrong. Maybe God was punishing him or correcting him. Ray walked me through what each friend believed, although I could not have told you their names five minutes after he said them.

"The more Job argued, the more they told him he must have done something," Ray said. "They could not accept that he might be telling the truth."

"The hallway," I said.

"That is what made me think about it. My lawyer blamed the judge. My brother blamed the decision not to go to trial. Alana's sister called it God's plan."

"And you blamed the eighteen months."

"I said they were worthless."

"Do you still believe that?"

"I don't know. Some days."

Ray continued with Job. Job told his friends they were wrong. He knew he had not done what they were accusing him of doing. He also wanted God to answer him.

"Does God answer?" I asked.

"Eventually."

"What does He say?"

"God asks Job a bunch of questions. Where were you when I made the earth? Can you control the weather? Can you understand how all of this works? Things like that."

"Does He tell Job why He let it happen?"

"No. He never gives Job that answer."

"That would annoy me."

"It annoyed Job."

Ray said God later became angry with the friends because what they said about Him was not true. Job recovered and lived for many more years, but that did not erase what happened to his children or explain why it happened.

"So Job never gets the answer he wanted," I said.

"No."

Ray paused.

"But Job was innocent. I'm not. I committed a crime. People got hurt. I cannot pretend this just happened to me."

I had never read Job. Ray was explaining it to me nine days after he stood outside the courthouse blaming the previous eighteen months for not producing the sentence he expected.

"Then tell me what I do with the eighteen months," he said.

"I don't know if the work moved your sentence one month. I also don't know what would have happened if you had spent eighteen months on your couch."

"So what did I get?"

I knew what he wanted me to say. He wanted something he could measure against the additional forty-two months he had not expected. I did not have it.

He did not rewrite his narrative nine times because he wanted to become a better writer. He wanted eighteen months. He did not begin paying restitution early only because it was the right thing to do. He wanted the judge to see it. He volunteered at Habitat because he wanted to help, but he also wanted a letter.

That was sentencing mitigation. Nothing wrong with admitting it.

"Your kids read the ninth draft," I said. "Alana did too."

"That was awful."

"I know."

In the early drafts, Ray spent pages explaining what other people had done, what the government got wrong and why his conduct was not as bad as it looked. I would send the drafts back. He would rewrite them and then find another way to avoid saying the part his family needed to read.

By the ninth draft, he said it.

His children read what he did in his words. Alana did too.

"That doesn't give me the forty-two months back," he said.

"No."

"It doesn't give me anything with the judge. Sentencing is over."

"Yes."

"So you still haven't answered me."

"I don't have an answer that makes sixty months feel better."

Ray did not respond.

I was tempted to tell him the narrative changed him, that restitution proved something or that Habitat had been worth every Saturday even without the letterhead. Some of that was probably true. I also knew he would hear it as me defending the work I had encouraged him to do.

He had five weeks before surrender. I did not need to convince him of anything that afternoon.

"What am I supposed to do tomorrow?" he asked.

"You have five weeks. Spend them with your family. Handle what you need to handle in the business."

"No more Habitat?"

"Do you want to go?"

"No."

"Then don't."

During those five weeks, Ray concentrated on his family and his business. There was no longer a judge who might see what he did on Saturday. Ray was not ready to start thinking about a case manager who might help him get home earlier or a probation officer who could give him more freedom after prison.

After eighteen months of relentless work, he needed to decompress.

Then he surrendered.

For two months, Ray disappeared.

There was no blog, nothing to review. He called Alana once a week and sounded depressed, sad, like this would never end. I wrote to him twice and received no response.

During his third month in prison, a message arrived through CorrLinks.

Day one again. Don't make it a thing.

I replied:

Missed you, buddy. Since I heard from you last, you are sixty days closer to home!

Chapter 13 Reflection Journal

Ray expected eighteen months. What sentence are you expecting, and who gave you that number?

The people in the hallway cared about Ray. How are the people who care about you explaining what happened?

Ray said he could have spent eighteen months on his couch. If your judge never mentions what you are doing, which parts will you wish you had done anyway?

Ray delayed the conversation with Habitat. What conversation are you putting off?

After two months of silence, Ray wrote, "Day one again. Don't make it a thing." What have you stopped doing?

Written by

Justin Paperny

Founder White Collar Advice