During my interview on Scandal, I was asked how long Sean Combs might spend in federal prison. I didn’t answer with a number. That wasn’t the point. I told the host what I’ve seen too many people ignore: guessing sentences is a distraction. The focus should be on the one person who controls the first and most important document the judge will read—the probation officer.

The judge will make the final decision. But the person influencing that decision most right now is not the prosecutor, not the defense attorney, and not the media. It’s the probation officer.

The First Question Judges Ask

At sentencing, judges don’t open with emotional statements or long monologues. They begin with something basic: “Have you read the probation report?” Then, “Did you review it with your lawyers?”

They don’t ask that out of formality. They ask because the report influences the sentence and they value the opinion of the probation officer writing it. Judges rely on it. They study it. And when the report is done well—when it’s honest, thorough, and backed by actions—it can be the difference between a shorter and longer federal prison sentence.

I’ve seen people spend years trying to undo damage from a weak report. That’s why I said Diddy’s obsession shouldn’t be about predictions. It should be about what’s in that report.

Judges Expect You to Earn Leniency

Some people assume a high-profile defendant will get special treatment. Others assume the opposite. Both views miss the real question: what has the defendant done to earn leniency?

On the show, I said plainly that the judge isn’t going to hand down time served because a lawyer gives a passionate closing or files a thick memo. Judges don’t need lawyers to tell them a defendant is a good father or a changed man. They’ve seen it all before. They know when someone is trying to sell them something.

And they’re not buying.

They want to know what the defendant has done—not what he claims to believe, not what he promises for later, but what he’s already done. Has he made progress? Can it be verified? Did it take place over time, or did it all start right before sentencing?

That’s what earns a downward departure. That’s what earns early release. That’s what proves the defendant is not the same person who committed the crime.

Judges Discount Lawyers—and Prosecutors Too

One of the most important things I said during the interview was this: the judge knows the lawyer is paid to say certain things. The judge knows the prosecutor has their own interest—maybe a future political campaign or some press coverage.

So while both sides will present arguments, most judges don’t rely heavily on either one.

They rely on what they can see. They rely on the defendant’s record of behavior. They rely on what the probation officer observed. And they rely on the tone, detail, and credibility of the probation report.

Judges Remember What You Do in Custody

The judge kept Diddy in custody despite some charges being dropped. That tells you everything you need to know about where things stand. The burden is on him to prove that he’s changed—and that he’s not likely to offend again.

If he’s using his time inside to teach others, document change, and create a measurable record, that should be reflected in the report. If he’s sitting back and waiting for the lawyers to “handle it,” the judge will see right through it.

Judges are used to excuses. They’ve heard it all—trauma, addiction, loss. Most won’t accept those explanations unless they’re paired with real effort. Many people go through pain without committing a crime. Judges see that contrast. They expect you to see it too.

Judges Expect Consistency After Sentencing

Even after sentencing, most people still want something—early release, home confinement, compassionate release, early termination of supervised release. If the judge only hears from you when you’re asking for something, it will damage your credibility.

I’ve heard judges say, “They told me they’d stay in therapy. I haven’t heard from them since sentencing.”

If you say something on sentencing day, follow through. Prove it. Send updates. Keep the commitment. Otherwise, the court has no reason to take your next request seriously.

Judges Are Watching What You Do—Not What You Say

It doesn’t matter what your legal team says you’ve learned. It doesn’t matter how polished your memorandum is. It doesn’t matter how long you’ve been in custody unless you’ve used that time to produce something concrete.

Every judge is asking the same thing: What has this person done, day after day, that proves you’re different than the government’s version of events?

You don’t need a perfect message. You need a consistent one.

What are you doing today that your judge will believe—and your probation officer can document?

→ Join our webinar or schedule a call if you’re ready to build a record that speaks louder than your lawyer ever could.

Best,

Justin Paperny