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 Earning Freedom 1-13 

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Michael Santos

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Chapter Four: 1990-1992

Months 37-57

In clip 13 we start chapter 4. This 20-minute clip I share interactions with my new cellmate, Windward.

When contractors complete the remodel of B cell block, I join 600 other prisoners. We pack and carry our belongings from the old cell house to the new housing unit. It’s just across the polished corridor.

I climb the zigzagging metal staircase to the top unit. My counselor assigned me to B-3. In a few trips, I carry all of my possessions. I have sneakers, t-shirts, sweats, khakis and toiletries. I bund and tied everything up inside my blankets and sheets. I toss it over my shoulder and carry it like a hobo.

The move lifts my spirits. It’s a fresh start in a clean, new environment. Although I’m still in the same prison, somehow it feels better. The remodel has replaced the hundred-year-old decaying building with modern plumbing, working lights, and air conditioning. B cell block upgrades my life. It’s much better than I’ve known for several years. I’m learning to appreciate these incremental improvements.

In place of the old-style cages, the new housing unit features a different design. We have solid-steel doors with narrow windows instead of bars. The rooms are side-by-side, going along the outer walls of the building.

We have an open, rectangular, community area. It’s about the size of a basketball court on the mezzanine level of the housing unit. We call it “the flats.”

The freshly painted walls leave a strong chemical smell lingering in the air. Our concrete floors are bare, unfinished. Doors with cut-in windows about five feet off the ground close in six single-stall showers at the far end of the unit. We’ll have more privacy than the open showers from the old cell block.

Periodically, an annoying fire alarm starts to blast. Contractors still have some finish work to complete.

I like B cell block better, which is good because I expect to live here for several years. I’m still getting used to the mental challenges. No matter how much time passes, I’ve got to stay motivated and live with high levels of energy. I’m away from the people I love, and I’m determined to prove worthy of their support.

Prison counselors don’t offer much in the way counseling. From what I can tell, their scope of work is limited. They assign inmates to work details. They approve visitors. They assign living quarters. I don’t expect them to offer any counseling on how to cope with multiple decades in prison.

My own actions put me in here, and I have to adjust on my own. From the counselor’s list that’s posted on the wall, I see that he assigned me to cell 616. I’m on the top tier. He assigned me to share that cell with a man in his late 30s. He goes by the nickname “Windward.” It’s not really a cell we’re in, but a room because it has the steel door instead of bars. But since we’re locked in, it’s still a cell to me.

Windward is a native of Georgia. He speaks with a slow southern twang, peppered with lots of “y’alls.” After two years of being locked in the Atlanta prison, I’m more familiar with the Southern dialect. Most of the people here are from Georgia, Alabama, Tennessee, Florida, and the Carolinas.

Windward likes to say he is American by birth but Southern by the grace of God. He’s a proud man, and takes a lot of time grooming himself in the cell. Windward wears his hair in a mullet, long in the back, feathered on top, and cut short above the ears. He slopes his sideburns, calling the cut his “Georgia slant.” His mustache curves down around his mouth, and he has a habit of twirling the long ends with his fingers when he talks.

This isn’t his first time in prison. Windward told me that he was locked up in a Georgia State prison for drug trafficking a few years ago. With that conviction on his record, he couldn’t find a job. So he reverted to smuggling drugs.

The Coast Guard busted him on this case that he’s serving time for now. He steered a boat that was loaded with 300 kilograms of cocaine as it passed through the Windward channel somewhere in the Caribbean. Other inmates gave him the nickname Windward and it stuck.

Windward pleaded guilty to an importation charge and his judge sentenced him serve 20 years. Since he’s not dangerous, he makes for a good cellmate. I laugh as he tells tall tales about thousands of female conquests.

We coordinate a schedule to keep our two-man room clean. I continue working in the factory business office, attend school, volunteer on suicide watch whenever possible, and exercise. Windward’s schedule is more relaxed. He’s a unit orderly and he works the night shift, sweeping and mopping the floors while all other prisoners in the block are locked in their cells. Except for when the prison is on lockdown, we don’t crowd each other in the tightly confined space of our closet-sized room. I have time alone to think, which is how I like it. But not everyone feels the same way.

Whenever violence rocks the penitentiary the warden orders a lockdown. Claustrophobia drives Windward stir-crazy. Sometimes the lockdowns last for a day, sometimes for weeks. Although I miss the yard, I relieve stress with pushups or running in place when I’m not working on my independent studies. We don’t have enough space for both of us to be on the floor at the same time. While I read on my rack, Windward paces four steps toward the door, peers out the window, turns, paces four steps toward the bunk, turns, and repeats this pattern over and over.

“Can’t you relax?” I ask him.

Windward snaps, telling me how he hates being cooped up in the cell. He keeps pacing.

“You know what you need? A goal,” I offer unsolicited advice. “Some self-direction, something to work toward, to fill your time.”

Windward doesn’t agree.

“All I need is a woman, a fifth a Jack Daniels, and an ounce of good weed.”

“That’s what you want,” I point out, “not what you need. There’s a difference.”

“Damn straight, and I know what I want,” he tells me. “I want a woman, some good booze, and an ounce of good weed.”

Generally, it’s best not offer unsolicited advice. But Windward and are together every day. I suggest that he work toward something that he can control, something that will make him feel productive.

He waves his hand at me. “Not again with all that dime-store psychobabble bullshit,” swatting away my suggestion as he would an annoying fly. “I told you once and I’m tellin’ you one more time. All that schoolin’ ain’t fixin’ to help you none. A convict once, Michael, a convict forever.”

“That’s giving up.”

“That’s reality, Son. Ain’t nothin’ matter here but time. Y’all can read all the books you want, but in the end ain’t nothin’ gonna matter. I done been there. You ain’t tellin’ me nothin’ I don’t know.”

Windward expresses only two possibilities for his future. Either he will seduce and marry a rich woman, or he will earn a living with drugs again after release.

Windward says I’m fooling myself with my aspirations of joining society. He’s convinced that a prison record extinguishes all possibility for a legitimate life. It’s like an echo. Wherever I turn I get the same recurring message of hopelessness. It reverberates everywhere in the penitentiary. I refuse to accept that I can’t create new opportunities and new directions for my life.

Every day I renew my commitment to work toward something better. I’m planting seeds, knowing that those seeds will take many years before they take root and blossom. When they do, they’ll provide for a better life than I’ve known, and a better life than what others tell me I can expect.

I prefer not to have contraband in the cell, but I don’t live here alone. The best I can do is get a promise from Windward. He promises that if guards find his stash during a shakedown, he’ll take the heat.

Still, I’m not deceived about the value of such promises and I worry. He assures me that he’ll never keep home-brewed wine in the cell, or drugs. Still, I know he conceals a plastic shank inside a hole he hollowed in his mattress. Windward says we need the knife for protection, and that I may thank him for it some day.

I have different perceptions on how to protect myself. I stay out of people’s way and I mind my own business. I can control my decisions, but I can’t tell anyone else how to live. I’m not going to snivel to the counselor with a request to move because I don’t like what Windward keeps in the cell. I have to roll with the realities of living inside a high-security prison.

Rolling with those realities sometimes stresses me out. I’ve made personal commitments to prepare every day. I focus on what I can do now, with the resources around me. I am going to get out successfully, and I constantly visualize the life I’ll live when I go home.

I’m not convinced that people in society agree with my prosecutor. He was biased. When he told the judge that 300 years of good deeds would not be enough to atone for my two years of selling cocaine, he was wrong. I’m going to prove it.

Redemption may be as elusive as the Fountain of Youth. Still, I’m determined to minimize exposure to problems. Problems could block my efforts to build a better future.

I’m familiar with executive clemency now. With the stroke of a pen, a president could grant executive clemency and commute any federal prison term. It’s rare. Presidents don’t build legacies by letting people out of prison. Still, I’m striving to build a record that proves worthy of consideration for clemency. This ambition gives me purpose, something to work toward.

“What’re you gonna do, walk on egg shells through your whole sentence?” Windward taunts, laughing at my aspirations. “Don’t you get it? No one cares what you do or what happens in here.”

“Maybe not. But what do I have to lose by trying? Even if the president doesn’t commute my sentence, if I earn real credentials, don’t you think I’ll have a better shot at success when I get out?”

“It’s just no way to serve time. Wait and see.”

As I try to advise Windward, he does the same to me. And like he dismisses the suggestions I make, I reject his advice on how to serve time.

I don’t think of serving time. Instead, I picture my life as if I’m in a hole. It’s a pit that is deep and dark. I’m doing what I can to build a ladder. I’m going to climb out. I don’t know how long it’s going to take. But I know that every step I take will make a difference in my future.

That’s why I pay close attention to Mark as I sit in those Mercer University classes. Mark is in his mid-30s. He has an athletic build, suited to his chosen sport of tennis. I never see him working out on the weight pile, where I exercise every morning. He doesn’t have tattoos and he’s one of the few prisoners in here who keeps a clean-shaven face.

Mark sits at the small desks in the same classrooms with other prisoners and me. But he’s different. His vocabulary, eloquence, and knowledge distinguish him. It doesn’t matter what course we’re studying. We could be in literature, history, or economics classes. Mark articulates his thoughts with confidence. It’s obvious our studies at Mercer are not his first university experience.

“In what ways does Jane Austen use irony in Pride and Prejudice?” Professor Higgins asks the class. Mark is the only man in the class with answers. I don’t even know what “irony” means.

“Who can help us understand the connection between the Treaty of Versailles and World War II?” Dr. Davis, our professor of history asks. He’s looking to start a class discussion. Mark is the only student capable of discussing the treaty’s influence on the morale of the German people and the subsequent rise to power of Adolf Hitler.

“How does the economic system of Marxism differ from capitalism?” The other prisoners and I shift in our seats. We stare blankly at Dr. Watkins, our economics professor. Mark’s hand shoots up. He offers an elaborate contrast between the theories of Adam Smith and Karl Marx. I’m amazed as I listen to Mark emphasize the essential influences private property, competition, and free markets had on advancing Western civilization, particularly that of the United States.

I will learn how to express myself like Mark. He speaks intelligently, and with a style that shows his understanding of the world and how it works.

Knowing that I can learn from him, I introduce myself after class one day.

“You must’ve gone to college before,” I venture a guess as I Mark and I sit to talk.

“No, I’ve only been takin’ classes in prison. I been enrollin’ here and there for the past seven years,” Mark answers.

“Seven years? And you haven’t graduated?”

He laughs. “I hardly ever finish. A year hasn’t passed when I haven’t been hauled off to the hole for something or other. Sometimes I just drop the classes. I get bored. Or I get tired of all the requirements.”

“Don’t you want to earn a degree?” He’s obviously a bright guy. I’m puzzled by his lack of ambition.

“It’s not that I don’t want a degree. I just get caught up with the day-to-day living. Can’t do much about it when I catch a shot for a dirty urine or get caught with a mug of pruno.”

“Why don’t you quit? Drugs and alcohol won’t get you anywhere.”

“You sound like my ol’ lady,” he laughs.

“You should listen to her. It seems to me that someone as smart as you would understand the importance of having a college degree.”

“If I get it, fine. If not, it doesn’t make much difference.”

“How is it that when you’re in class you sound like a lawyer. Out here you sound like you don’t care about anything?”

“When in Rome, do as the Romans,” he laughs. “Truth is, I don’t care. But in class I get tired of those professors coming in here thinking we’re all worthless.”

“They don’t see us that way,” I counter. “I’m guessing that most of us aren’t as advanced as the students they teach on campus.”

“I like letting ’em know I speak their language.”

“I’ve noticed. Someday I hope to know as much as you.”

“None of it’s new. This stuff was drilled into me night after night at the dinner table growing up. Got turned off of education when the parents beat me over the head with it. They kept talking about how crucial school was to my future. Fuck it. Started getting high instead, rockin’ out with Led Zeppelin and Hendrix and the Stones.”

“I wish I knew so much that I could simply turn my educational level on and off at will. It takes everything I have just to keep up with the class.” I explain to Mark that I consider an education essential to my future. I describe how I’ve structured my time inside to avoid the obstacles that block so many others.

“Doesn’t that get old?” he asks.


“All that goody-two-shoes bullshit, the rigidity, that structure. I mean, Dude, we’ve got enough people telling us how to live in here. I can’t see how you’d want to put even more demands on your time. I mean, let’s be real. You’ve got enough on your plate. It wouldn’t hurt nothin’ to let up a little.”

“Yeah, I don’t see it that way. I’ve got an opportunity to earn a degree right now. Who knows whether I’ll have it tomorrow? I’ve got to seize the moment, then create something from it.”

“Big deal. Let’s say you finish all your classes and get your degree. What’s next? You’ve still got more than 20 years to go.”

“One step at a time. With a degree, I know I’ll be able to open new opportunities. Maybe I can go to law school. I’ll find something and I know the degree will help, especially if I can learn how to express myself as well as you. How did you build such an extensive vocabulary?” I ask.

Mark laughs. “You mean my ‘grown up talk?’ All you need to know in here is ‘motherfucker.’ Learn to use that word as an adjective, noun, and verb. Drop as many motherfuckers as you can into every sentence. Drop it into the middle of words and you’ll fit right in. Like I fuckin’ said. When in Rome, fuck everyone else. Do as the motherfuckin’ Romans.” He laughs.

“I’m not trying to fit in here. This isn’t my life. It’ll never be my life. I’m serious. How did you develop such an impressive vocabulary?”

“I don’t know. How did you learn the word window?”

“Really, I’m serious.”

“I’m serious too. I learned the language that my parents spoke at home. When I write home or to people outside, I communicate one way. When I’m in here I use the language of the pen.”

From my pocket, I pull out a stack of index cards. I always carry them with me and I want to show Mark how I learn. On one side I’ve written a word that I came across in a book. On the other side, I write the definition, the part of speech, and an example of the word in a sentence. “This is how I train myself to learn new words,” I tell him. “It’s a strategy I picked up after reading The Autobiography of Malcolm X. Whenever I’m waiting in line or whenever I have down time, I work through the flash cards. Test me.” I toss Mark the stack.

“You’re kidding. Man, you’re fuckin’ obsessed, intense!” He starts shuffling through the cards, looking at the words. “Immutable?”

“I-m-m-u-t-a-b-l-e.” I spell it. “Not capable of being moved or changed.”

“Okay, that’s pretty close. How about truculent?”

“Mean, a bad attitude, a truculent person is one who always wants to fight or battle.”

“A lot of that in here. I don’t even know this one. Tenebrous.”

“Dark and gloomy.”

“See, your vocabulary’s good, just as good as mine.” He passes the stack back to me. “Just keep reading.”

“It’s not the same. I’m learning the words and I’m able to use them in writing when I concentrate. But they don’t come easily to me. The words don’t roll off my tongue naturally when I’m trying to express myself. That’s what I want to learn.”


You’ve just listened to a free audio clip from Earning Freedom: Conquering a 45-Year Prison Term. I’m Michael Santos. Visit Prison We help people prepare for success through prosecution, sentencing, and prison. Our digital products bring value to prison systems, schools, and corporate training. Visit Prison to learn more, or find us on YouTube. Learn how my partner Shon Hopwood and I can help you. Stay tuned for the next free audio clip. We invite you to subscribe to our podcast. Please share and leave an honest review, wherever possible. If you’d like to engage in the discussion, please leave a comment.

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