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Someone scheduled a call. I called. The first thing he said was, dude, I'm not buying what you're selling.
I said, I haven't said anything yet. What's the problem?
He told me there was no value in trying to prepare for a shorter sentence, because his attorney said to him, you have a really difficult judge who doesn't go outside the guidelines.
I said, well, maybe. Try to build a record. Maybe you'll influence him.
He said, well, it might not work.
I said, that's true.
What about building a record that could persuade a case manager to give you more time if you go to prison?
He said, yeah, but there's a chance it doesn't work.
I said, that's absolutely true.
What about building a record so when you go to the halfway house, you go to home confinement sooner? Your probation officer gives you more liberty on supervision. Maybe you get off probation earlier.
He said, yeah, but it might not work.
I said, yeah, that's absolutely true as well.
I agreed with him every time
He was right on the facts. Building a record might not move his judge. It might not move a case manager. It might not shorten his time on supervision.
Where we split is what he does with that.
He takes "it might not work" and turns it into a reason to do nothing. Nine months later, he sits in a probation interview with nothing to hand over, and the only version of him in the room is the one in the plea agreement and the press release.
The sentencing hearing is one decision, not the only decision
His lawyer may be right about the judge. Lawyers who appear in front of the same judge for years know things I don't.
Here is what that reasoning leaves out. There are several people ahead of him who make decisions about his liberty, and they make those decisions at different times, on different records.
The judge. Guidelines are advisory. At sentencing the court still has to weigh the defendant's history and characteristics along with the other factors in 18 U.S.C. § 3553(a). A judge who rarely departs is still reading something. What he reads is partly up to the defendant.
The case manager. If he goes to prison, prerelease custody is a Bureau of Prisons decision. 18 U.S.C. § 3624(c) allows up to 12 months in a halfway house, with home confinement capped separately, and earned time credits under the First Step Act can also go toward prerelease custody. How much any one person gets varies by facility, by staff, and by conduct. Case managers hear "I want to get home to my family" every week. They do not hear it with documents attached very often.
The probation officer. After release, the officer decides what to approve: the job, the travel, the business. That is a judgment call about a person, and officers form that judgment from a file.
The judge again. Under 18 U.S.C. § 3583(e)(1), a court may terminate supervised release after one year if it finds that warranted by the defendant's conduct and the interest of justice. That motion is a request with a record behind it, or a request with nothing behind it.
Four decisions. He was ready to concede all four because of what one lawyer told him about one of them.
Michael Santos did not know either
Imagine Michael Santos, who served a quarter century in prison, saying I'm only going to build this record and educate myself and strive to educate others if I someday run a nonprofit that influences millions of people in prison.
It doesn't work that way.
He wrote for 26 years without any assurance of what it would produce. The nonprofit came later. The Prison Professors work in federal and state facilities came much later. None of it was promised to him on the day he started.
You try regardless. You don't know what's going to happen.
The plague I want to fix
So this plague in my industry that I want to fix is speaking in absolutes. Convincing yourself that nothing is going to matter.
The result of that is you don't try. You don't start.
I sat in that seat. I wasted three and a half years waiting, hiding, and hoping my case would go away, and I started writing on October 12, 2008, after I was already in federal prison. Nobody told me a handwritten blog would get my probation officer to approve me to work with people who had felony convictions. That came four years later.
If you want somewhere to start this week, it is small and boring:
- Write 300 words today about how you got here and what you have done since. Date it.
- Do it again tomorrow.
- Show it to your lawyer before your probation interview, and ask him what he would add.
That's it. It might not work. Do it anyway.
Do not speak in absolutes. You can't predict the future. You never know what's going to happen.
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Written by
Justin Paperny
Founder White Collar Advice



