How I Became “Friends” With Someone I Was About To Send To Prison

A True Story About Seeing People As People

Jonathan Greene
Jan 15 · 8 min read
Photo by k u on Unsplash

I was a prosecutor for seven years. Most days, my caseload was so overwhelming that all the names and facts blended together into a kind of alphabet soup of crime. A for Arson. B for Burglary. You get the picture.

It’s hard to look at three hundred case files and remember that each case file represents a person and an entire set of facts that have ripple effects on victims, families, and the community. People don’t like to tell you that, but they are lying. The numbers get so big that it’s hard to focus on anything but the numbers.

But every morning when I went into court, the numbers faded away and the files became those people. Where I worked in Fort Lauderdale, all of the in-custody defendants set for court appearances would be brought up early and sat in the jury box. It’s more efficient this way, but it also gives you extensive face-to-face interactions with those you are trying to send to prison.

I was an early bird when I was a prosecutor. Moreso, I was an early, early bird. I usually got to the office by 5 a.m. If I was really lazy, 6. And since I am early for everything, I was always early for court. If court started at 8:30, I would be in the courtroom with all of my files organized around 8 so I could talk to the defense attorneys before we got called.

But, just because I was always early didn’t mean anyone else was. I was often there by myself, with the bailiffs and court staff, and all of the defendants in the jury box who were dragged out of their cells at like 3 in the morning to come to court. Not always a happy bunch. And not always happy to see me, one of the toughest prosecutors in the office and the person trying to send them away for a long time.

Some days there was some gentle banter when I walked in, but I usually ignored it. I could never have direct conversations with any defendants because, of course, they were all represented by attorneys and even the appearance of impropriety would be wrong. And then there was Omar Battle (not his real name).


Omar Battle and the Rock in His Pocket

Omar’s case was as cut and dried as it could be. He was charged with Possession of Cocaine. He had like a bazillion prior drug charges. He had failed out of Drug Court twice, maybe three times. He had gotten probation. He had been to prison. Omar wasn’t new to this.

His prior record made negotiation nearly impossible. The maximum sentence for his charge, a third-degree felony, was five years in prison (sixty months). His scoresheet, based on his prior record, put the bottom of his allowed sentence at around forty-eight months. So, there was only a year of leeway for anyone to work with and with his prior record, it was highly unlikely that a Judge or a prosecutor would make a downward departure from the sentencing guidelines.

I offered him, through his attorney, the forty-eight months. It was the lowest offer I could make him. He wasn’t having it. Honestly, he didn’t have much to lose. He wanted to roll the dice and go to trial with his public defender, who was new. I couldn’t blame him.


The only problem was the facts of the case. Omar always forgot about the facts of the case. I did not. The drugs, a single rock of crack cocaine, were found in Omar’s pocket after a lawful detention, based on probable cause. Probable cause being Omar smoking crack right in front of the officer.

The defense tried to suppress the detention at some point but failed. Omar had admitted openly that he was indeed smoking crack when the officer approached. But Omar insisted the rock was not in his pocket when the officer searched him.

Cops have planted evidence before. It does happen. This was not one of those times. No one disliked Omar. All the cops knew him quite well and they probably all wished he would get off the streets and into treatment. He was the type of guy you really don’t want to arrest until he makes it impossible for you not to arrest him. By smoking crack right in front of you.


There are millions of debates we could have about the fact that Omar was about to go to prison for a single rock of cocaine. Or about how he got like that and how his entire life was a checklist of drug crimes, nothing violent. But that isn’t the point of the story.

I do not agree with filling the prisons with drug offenders. I do not agree with the disproportionate statistics of race and justice. I do not agree with a lot about how the system actually works, especially after playing a role in it for so long. But, at the point in the story where we started, my hands were tied and Omar was not the type of guy you wanted to take a risk on. But he was the type of guy you wanted to hang out with, when he wasn’t high.


Omar would always be in the box when I got to court on his court days. He loved telling his attorney to get him a continuance. Honestly, no one really cared. His case was locked. He could spend the time awaiting trial in the County Jail or he could plea and go to prison. Omar was going to make it take as long as possible before going to trial. And I always thought he would eventually plea, but he didn’t.

A few court hearing before the trial, Omar started talking to me when I was there early and no one was around. “Hey, Mr. Greene. Throw me 30 months. Come on.” At first, I ignored him, but then he started going in with some flattery. “I see how you do your job. You take this sh*t seriously. Good job. But still, can you make it 30 months?”

He eventually wore me down with a taunt. “Mr. Greene, you know you can’t win this trial.” Them was talking words. My table was about six feet from where he was when I finally entertained him. “Battle, the rock was in your pocket.” You’ve never seen a smile like the one Omar laid on me then.


After that day, each time his case came up and he was in the jury box early in the morning, we traded barbs, jokes, and life lessons. Sometimes the other defendants in the box with him felt like he was a traitor talking to me, but eventually, more of them wanted a little dialogue to ease the boredom.

When you are in the system as a defendant, you are treated like a subhuman. And don’t get me wrong, some defendants have more than earned that right based on their crimes, but some have not. And no one likes being treated like a subhuman day in and day out.

I have to admit that there were plenty of times I wasn’t looking at those people in the box as fellow humans. I was looking at them as criminals. I thought I was better than them. It wasn’t until I left the law that I started to think about all the Sliding Doors moments in someone’s life that could have changed the trajectory of it.

Most of us, at some point in our lives, were just a slip or a turn away from sitting in that box. Even if you think you weren’t, you were. Any time in your life that you drove drunk, you could have killed someone and you would have been in felony court. In the jury box. With Omar.

Those pills you got from a friend, the ones you had too many of. So you planned to sell a couple to a friend. That’s Possession with Intent to Distribute. None of us are that clean and none of us were always as far away from sitting in that box as we like to think.


I’d say Omar and I became “friends.” I wasn’t going to look him up when he got out, but some days I would dap him up, while he was handcuffed to the chair. Omar made the whole day more interesting. And when it came time for trial, Omar took it to another level.

The day before trial at Calendar Call, he said to me, “Mr. Greene, come on, you really going to take this to trial?” I looked at him and said, “Battle, are you really going to take this to trial?” We both said yes. I reminded him about the rock in his pocket again. He smiled that smile again.

Some might interpret this dialogue as demeaning or inappropriate. All I can say is that you had to be there and you had to do the job. I liked Omar. I didn’t want him to go to prison, but my hands were tied. The Judge’s hands were tied. Based on his record, he was definitely going to get the full boat, sixty months, after trial. Omar was just taking his time to get to an inevitable conclusion. And he was having some fun along the way.


Seeing People as People

Omar changed the way I did my job. I stopped looking at files as numbers and numbers as a representation of another criminal in the system. I started looking at those files as people and I started looking those people in the eyes when I saw them. Even the ones I was scared of.

Justice is a moshpit. It’s sweaty, messy, things get broken, and some people make it out unscathed. But when you are in it, you are doing your best to survive. Omar’s trial went about as well as expected. It was all done in about three hours. The jury was out for less than a couple of minutes. And Omar got sixty months in the can.

I felt bad for Omar. But Omar also had like twenty prior convictions, mostly drug offenses and minor crimes committed to get money to buy drugs. He flunked out of treatment when repeatedly given another stay. He had his chances. But he was still a person. And I was glad that I learned to see him, and everyone else in the system, as just that.


Jonathan Greene

Written by

Father, writer, poet, real estate investor, certified life coach, podcaster, sociable introvert. Curating a meaningful life. IG: trustgreene | trustgreene.com

Welcome to a place where words matter. On Medium, smart voices and original ideas take center stage - with no ads in sight. Watch
Follow all the topics you care about, and we’ll deliver the best stories for you to your homepage and inbox. Explore
Get unlimited access to the best stories on Medium — and support writers while you’re at it. Just $5/month. Upgrade