Why prison? Why clemency? Why look in this direction? It’d be easier to look the other way, to see prisoners as criminals who ended up behind bars for a reason, to stay as far away as I can from the issue of Mass Incarceration. For most of my life it really had nothing to do with me. But then I got lucky, I got my ass handed to me in the Waukegan Courthouse, just down the road from 120 South Genesee Street, where a few years later, both of us wearing face masks for the entire conversation, I would meet a State Representative in the middle of a global pandemic.

At this particular moment in time, there are battling pandemics, each circling the other to see who blinks first: COVID19, Racist Insanity and Mass Incarceration. All of them intersect, but this is a story about how I faced down 6 months in jail when I was charged with Indirect Criminal Contempt.

Indirect Criminal Contempt.

Why were those words flung in my direction, you might ask. What did I do to deserve it, you might wonder. Like absolutely everyone I have talked to who’s been incarcerated, this is my answer: I didn’t get a fair shake.

Those words are my bond, my reason for stepping into the darkness of things which are difficult to talk about, things only laughter can cut when the moment hangs heavy in the air.

In the 4th hour of a deposition the attorney who was questioning me insisted I read Yelp Reviews about my brother. They were less than flattering but had no basis in reality, let alone being allowed into the deposition for any other purpose besides pushing my buttons and provoking me. At the moment it felt unfair but looking back I can honestly say I have no one to blame but myself when I say this: I took the bait, exhausted and furious, calling the attorney an asshole. 

He was an asshole and I’m sure it’s not the first time he was called an asshole, but not when he’s sitting in his own office, in front of other attorneys, in front of a court reporter, in front of his client, when he’s supposed to be in charge, when he’s supposed to be sitting at the table of ultimate power where the power is clearly tilted in his favor.

He was galled by my lack of adherence to the protocol. He got under my skin with the Yelp Reviews and then I got under his skin by calling him out and so he did what attorneys do when they have an in with the judge: he took it to the next level, lying to the judge, misrepresenting the facts, telling the judge I threatened him.

The judge didn’t know anything about me, and trusting the integrity of the attorney, he felt compelled to bring in the State’s Attorney, ordering a full investigation into the allegations. This began my descent into the criminal justice system, a system designed as a trap.

I’m not going to get into the minutia of the case besides to say it was rooted in a family business, and looking back, I clearly should have listened to The 10 Crack Commandments of Biggie Smalls. Number 7: “This rule is so underrated, keep your family and business completely separated.”

You live. You learn. You go to court. You learn nothing but you pay dearly. After too many appearances to count, too many motions filed to remember, too many legal fees to calculate – without cursing my fate – one fateful day I went to the courthouse by accident, my attorney had given me the wrong date for an appearance. It turned out on that particular day, my attorney was appearing before the same judge with the same attorney who was suing me but on a different case. They didn’t know I was there and as soon as I heard the bailiff call out the wrong case number, I decided to use my anonymity to indulge a hunch, parking myself quietly in the back of the courtroom, watching how things went, taking it all in.

That single decision gave me the clarity to see what had been going on all along: the judge was friends with my attorney, the opposing attorney was friends with my attorney and the State’s Attorney was mister popularity! They were chumming it up between cases, having a great time. As my jaw tightened, I could taste the spit under my tongue as it turned to acid. 

The case ended, as the attorneys were putting the finishing touches on the paperwork to be filed and packing up their things, I quietly exited the courtroom. I waited for my attorney in the hallway, parking myself by the tarnished copper placard marked room 305.

When my attorney stepped out of the door and saw me, I watched his eyes go from easy street to busted.

“What are you doing here?” he asked me.

“You gave me the wrong date,” I said. We stood there looking at each other. I was in no hurry to cut the tension. Finally I said, “It’s a game. The whole thing is a game.”

“It’s not a game,” he said. 

“Oh yes it is,” I said. “It’s a game. I saw you. I sat in the back of the courtroom. You’re all friends, you and the judge, you and the attorney you’re pretending to be against on my case, you and the State’s Attorney, you’re all friends and you’re all getting paid and you’ve all got  your hands in my pocket. This is my life! You’re all playing a game with my life! Today the game ends, do you hear me?”

“You shouldn’t yell at your attorney,” he said. “That’s how you got in trouble in the first place.”

I stepped close enough to kiss him. “The reason I’m in trouble has nothing to do with me calling an attorney an asshole 4 hours into a deposition where I was reading Yelp Reviews for the sadistic amusement of a former family member who’s a casualty of lifestyle addiction. The reason I’m in trouble is because the attorney who was sitting to my left, who was supposed to be representing me, just so happens to be in your clique. The reason I’m in trouble is you’re all nothing more than a bunch of mean girls.”

They were 3 men, but to my eyes, in that exact moment, they were mean girls. His eyes turned from remorseful to hatred. I fed on the anger, thrilled by the rush of awareness.

“I’m breaking up the clique,” I said. “I’m ending the popularity contest. I want it over. Tomorrow. Today. Right now. Yesterday. Got me? Are we clear? It ends or I’m taking you all down and you know I’ll do it. I’m giving you an out, Counselor. I’m tired of you, I’m tired of your games. I’m offering you a one-time one-day-only deal. Here’s the deal. I’ll happily pay my legal fees to never see your asshole face again. Asshole. You have 12 hours to sort things out with the other assholes or I’m taking my legal fees somewhere else. Got it? Asshole!”

He winced, looking down like a cornered bitch.

“Got it.”

George Moore took a moment to gather his thoughts, letting my story sink in before he smiled. “Okay, now, since we’re having this real dialog and conversation,” he said, “let’s just have it. No way a black man could do that.” 

He took a long pause. We both looked at each other, sitting there in the uncomfortableness. Then he said, “As I’m hearing you say it, it’s like the elephant in the room that I didn’t want to address. Let me clarify, a black man should do that but what I’m saying is that life holds a different kind of weight when you’re a person of color.” Then he thought better of it, looking at me, sizing me up, looking for a way to bring me into the predicament, “And you’re a person of color too.”

“Ish,” I said.

He laughed. I laughed. We laughed together and then to cut the tension I said, “I’m soft cappuccino. You’re moca. And Oscar is chocolate deliciousness.”

The laughter ran its course and then George brought things back to where they belonged, which is one of his many gifts. “The lighter you are,” he said, “in this country, the more privilege you earn. Not to go too deep into it but I would probably have more privilege than Oscar.”

Who’s Oscar, you might ask. What does Oscar have to do with this, you might wonder. Oscar is the reason I was talking to George. They call him Smiley and when you meet him, it’s no wonder. If a whole body could occupy a smile, that would be Smiley. His eyes smile. His laugh smiles. The sound of his voice when he talks lights up the room. And yet he spent 30 years doing a bit.

I had to ask: “What’s a bit?”

“My time,” he said. “Sometimes I still slip up and call my plate my tray and I call my bed my bunk. I get mad when I do that but my wife says you’ve been locked up 30 years, what do you expect?”

He did time in Pontiac. He did time in Menard. He did time in Stateville. Those places held Smiley but they will not define him which is to say of course they will define him because how can you spend time in a place and not take a part of that place with you? Now Smiley works at Legacy Reentry Foundation with George.

“I still struggle with enabling people,” George said. “I don’t want to, some people tug on my heart strings, it doesn’t happen often but I have this thing with being not judgmental. I don’t care who you are, I don’t care if you murdered someone yesterday, I’ll still sit down and have a conversation with you because I know what it’s like to be judged. So I think I went extreme – it’s this PTSD thing – but we try to talk about it and teach everyone here, and I’m even learning in some ways, you can enable somebody without knowing and tough love is the best love and finding out when to administer tough love is a level of discernment that most people don’t have.”

What is tough love? We hear it all the time. Are you supposed to shut someone down when they’re hurting themself with drugs or dating people where the chemistry has a spark of domestic abuse set on fire by both sides before one side strikes the match of combustibility and the problem is suddenly there for everyone to see as a bruise? Once you take a dark turn, how do you find your way back to the light? Can you get back without the help of people around you, without family, without a sense of community where you can stretch your potential beyond the haunting memories of things you should have gotten right to begin with but were too caught up in something that wouldn’t appeal to you now, even if it was presented as a winning lottery ticket with all of the taxes paid and all of your friends signing a reverse promissory note to never hit you up for cash. Short cuts never end well and neither does tough love.

Rita Mayfield is the State Representative in the 60th Legislative District of Waukegan. She has an office at 120 South Genesee Street. The parking meters along the block were frozen but they still had no problem swallowing my coins, funny how some things always work. As soon as I walked in the door, I noticed an artist rendering in her office of Tupac Shakur. Above him was another rapper. I asked Rita if she knew who it was. She didn’t, which made me feel better about not recognizing the face.

I know Tupac, Jay-Z, Biggie Smalls, the usual suspects. I was hoping it might be someone who’s name I’d remember once I heard it so that we could share a moment and it would give us something to create a false sense of bonding. It was a cold day in the middle of a global pandemic, we were both wearing masks and keeping our distance and so instinctively I felt the desire to reach for something easy we could have in common, like a room filled with strangers in a karaoke dive bar singing along to Big Poppa back when gathering together wasn’t something we even noticed, it was something we took for granted.

“I didn’t even know we didn’t have parole in Illinois. We got invited to this debate. It was myself and other legislators,” Rita said. “They were talking about bringing back parole and we were like, what do you mean? Bring back parole? We have parole! We didn’t realize that certain individuals never even had the opportunity to have parole. So it was very educational. It was interesting because each of the individuals who were doing the debates, they got up there and did their spiel, but they also told a little bit about their story. So Oscar, when he told his story, he talked about the fact that he was offered a plea deal and had he accepted the plea deal he would be out but because he didn’t take the plea deal they basically threw the book at him. I heard what he said and it bothered me. But you hear so many cases, so many people, I get letters, I get maybe 10 inmate letters a week, so you get all these letters and everybody is saying, you know, I didn’t get a fair shake.”

I Didn’t Get A Fair Shake.

That’s how it feels on the inside when it’s happening to you which makes it frustrating to get across especially when it’s easy for emotion to overtake language when you’re in the middle of expressing the unfairness and before you know it you’re pushing someone away when you’re trying desperately to bring them in but it takes time to develop the gift of having patience within the unfairness to express yourself in a manner suited to building camaraderie but it underscores an advantage unique to Smiley: what is a bit, afterall, besides time?

“We have this imaginary image of what will happen when we get out,” George said. “One thing I tell people is the worst thing they could give you is time because when you get time you have time to think it over, time to think about it, time to really consider what’s going on in your life. One thing I messed up when I was coming out, I could have got my degree because I thought I had time and everybody always thinks they have time but you don’t. You gotta take advantage of the time you have. Prepare yourself.”

Generally speaking, you wouldn’t describe a cookie as a component of preparation, maybe a snack, maybe a treat, but a mechanism for preparation? Preparation is something that works to your advantage. So tell me, what would you say about 4 cookies?

This is the story of how Oscar, otherwise known as Smiley, got from Menard to Stateville where he ended up being on The Debate Team where, over time, he would hone the skills necessary to express himself like a smile underscoring purpose so that when a group of State Legislators, including Rita Mayfield, came calling at Stateville, the bells of clemency began to ring in the  Kingdom Of Heaven and the gates cracked open just enough for a sliver of light to break free.

“I’m a relationship guy. I’m not a religion guy,” Smiley said. “Religion is man made. Relationship is about you and God. I look at the 4 cookies as God. Let me show you how God worked with me. But I had to get caught. They never shake down, right? But this one day they decided to shake down. Everybody stole. I never stole but this is the one time. So if there hadn’t been a shake down at Menard, I never would have been moved to Stateville. If I wouldn’t have been at Stateville, I wouldn’t have been in the education program. If I wouldn’t have been in the education program, I wouldn’t have been on The Debate Team. If I wouldn’t have been on The Debate team, I wouldn’t have known how to tell my story. All this because of 4 cookies.”

When Rita Mayfield heard the story, it didn’t sit right, not the words, the words were perfect, not the emotion, the emotion caught her off guard, it was the circumstances Smiley described in his story that were pressing down on Rita’s conscience, chipping away at her ability to put the unfairness out of her mind.

“So I wanted more information,” Rita said. “I called down to the prison and told them I wanted to meet with The Debate Team again. I didn’t say anyone specifically, I said the team, because I wanted to make sure I heard what I heard. I didn’t want to provide any false hope.”

What’s the difference between hope and false hope, you might wonder. How can you tell the difference, you might ask. False hope is the subtext of every story ever rapped by Biggie Smalls and yet he finessed the bravado into ambition, willing himself out of circumstances no one should ever have to face. Biggie Smalls was at the top of his game, 24 years old, when he was shot dead. He touched greatness, had it taken from him and for what? For nothing. Smiley went to prison as a young man, on a 30 year bit, holding it together, turning setbacks into challenges, navigating 3 prisons, earning a nickname born out of optimism in the Hellfire of Mass Incarceration.

“I’m gonna say 2 things,” George said, “since we’re talking real talk. I don’t want this to be taken the wrong way but I’m just gonna say it, not everybody is meant to make it, not everybody is meant to come out. And so, going back to enablement, I learned the hard way, still learning, not everybody is ready and if you take that, if you paint that broad brush and say…We Need Everybody To Be Out Of Jail! Defund The Police! No Jail At All! We Don’t Want Prisons! I don’t agree with The Department Of Corrections methods but I can tell you, having been in there, some of those people are not ready to be out. Now could that be part of the fact we’ve created this society that profiles and puts them in a predicament, and then we can go into poverty, we can go all the way back into slavery, we could really deal with it, the origin. Not everybody will love me for saying it, but not everybody is ready to come out.”

Defund The Police was born on the streets at the moment of ultimate heartbreak, having watched George Floyd being murdered by a sadistic police officer while his partners all passively stood around, shuffling government shoes with their hands in their pockets. I recently heard Barack Obama take a shot at the slogan, Defund The Police, talking about how it put people off and I couldn’t help thinking what put people off was saying Yes We Can, winning 2 terms in the White House, and then governing under the philosophy of Maybe We Shouldn’t.

Come on, man!

It’s easy pulling apart slogans, debating words, it’s hard stepping into the moment, crafting policies to lift people up, reshaping our future so the obstacles of unfairness are exposed and more people coming up have a fair shot at a good life. Maybe they won’t touch greatness, probably they won’t touch greatness, but so what? Hope is for everyone. False hope is the broad brush of celebrity and after four years of a celebrity president, I think it’s fair to say we all deserve a break today.

“So you come out of jail,” I said. “Where’s the first place you want to eat?”

“McDonalds,” Smiley said, laughing until he couldn’t breathe. “And it was awful. But McDonalds was always my place because when I was a kid, my dad had his own landscaping business out there in Lake Forest and Highland Park. He used to take me with him and I remember that was our lunch, McDonalds. That was always our food place, so when I came out, I ate a Big Mac and man it was terrible!”

You need family. You need love, lots of love. You need to go with your dad to work. You need to go with your mom to work. You need friends to knock you down, to give you a hard time, to have your back when you step in the wrong direction, to show up for you, to chase fun, to beatbox your raps, to take chances, to forgive you when you can’t forgive yourself, that’s the secret sauce. It’s hard, life is hard. When he came out, Smiley had people waiting for him, people who loved him, people who have loved him all of his life, who stood by him. I remember one night while I was at home, he called me. It was late and I was sitting on the couch with my wife after a long day when I noticed I had missed the call. So I called him right back.

“Sorry Greg,” he said. “That was a butt dial.”

“No problem,” I said. “Wanted to make sure I called you back as soon as I got it.”

“I appreciate that,” he said.

I didn’t know it at the time, but looking back I could see I was becoming aware that if Smiley was out in the world, and I was going to be part of doing more than telling his story, if I was going to become part of him succeeding on the outside, I was going to have to make myself available, not to become an enabler, but to take his call, or at the very least, get back to him soon enough to let him know that even though I was busy, even though I had things I was working on and a life of my own to lead, he was important, him finding a way to make it on his first year out of prison was important to me.

“The second part is we have to have empathy,” George said, “we have to have mercy. We have to allow for the fact that this is a process. You have to be able to get hurt. We’re a society where we don’t want to get hurt. We don’t want to take risks. You take risks every day! But you don’t want to take a risk on people? We take a risk on teachers, we take a risk on pastors, we take a risk on police, we trust them and you know the vast majority are going to screw up. They’re people. So why is this group of people different? We have to be okay with knowing this is a process, with knowing you’re going to get hurt.”

This is what makes Rita Mayfield so unusual, when is the last time you heard of a politician sticking their neck out?

“I did, I put my neck out,” she said. “I stepped out on the line for him.”

We’ve successfully turned the word politician into an eye roll, no one expects anything from them besides doing whatever they can to stay in power. So what’s the point of power besides staying in power and if staying in power is the only game in town, what are you there for in the first place? But Rita took a chance on Smiley, who she still calls Oscar, she connected the dots between his journey through darkness toward freedom and the sliver of light known as clemency.

“In this particular case, he’s lucky. Oscar comes from a caring family, you know. They wrapped their arms around him while he was in prison and they wrapped their arms around him when he came out. He reconnected with the mother of his children, they got married, you know. Everybody doesn’t have that success story. Everybody doesn’t have those support systems. Oscar is going to be fine, you know. I don’t ever think we’ll ever have to worry about Oscar going back in after what he’s been through. But for the person who doesn’t have family, we have to make sure the community is wrapping their arms around them.”

My family didn’t know how to wrap their arms around me, but the truth is we were raised to go for the win and even though I can’t forgive what they did to me, dangling 6 months in a Waukegan Jail on a bogus charge at the beginning of what would become a global pandemic, in a place where social distancing is a myth, despite all that I have to admit sometimes in a moment of weakness I see myself going for the win in my own marriage, risking everything I hold dear for the need to be right. What is that? DNA? Or arrogance…

“Don’t get up from the table because somebody calls you an ex-offender, don’t get up from the table because somebody calls you a jailbird,” George said. “I go to a church in Libertyville. I’m different when I walk in the room, I have to conduct myself in a certain way. If we could just have a conversation, if we could just talk, I’m not what you think I am. Gimme a chance.”

Nobody gets a fair shake but every now and then, you get a second chance. You can spend time beating your head against the unfairness of it all or you can smuggle 4 cookies through the darkness of purgatory, searching for a sliver of hope.

“This is the mindset I came out with,” Smiley said. “It’s bigger than me. It’s bigger than you. Get in position to catch a blessing.”