Derek Caldwell is a street cat who grew up in East New York in the rough Brooklyn borough. He ran the streets from an early age, without direction, just letting the hood mentality “Do what it do” dominate his mindset and life. Due to his adventures in the game he served three prison sentences, the last one being 21 years. During his incarceration he authored several books, under various pen names, such as DC Outskirts and De Felon. His true crime memoir A Man of Substance details his change and evolving attitude on life and growth. He has an intimate knowledge on criminality and a vivid perspective on how to use street intelligence to better his life and others in mainstream society today. But don’t let us tell it, let him. Here is the Gorilla Convict exclusive –
Where did you serve time and for how long and for what offenses?
I did time in New York State, in Clinton Dannemora, that’s where Tupac was at, when he was down. I was there when he came through, he didn’t get raped (which was a fucked up rumor) he was in protective custody, because he was a celebrity. I was in Clinton three different times, Sing Sing, Greenhaven, Elmira, Comstock, Fishkill and Eastern. I served 21 years my last time down, and did two prior three year bids before this last long stretch. I had a police shooting; it was in 1991, in the Louis H. Pinkhouses. I was all over the news, being dragged out of my housing complex after the police beat the shit out of me and let a police canine bite me in the face and body several times. Two cops got shot, so I was facing a life term. I went to trial, you know rolling the dice, because the cop out was 20 years. I beat the top 24 counts and still got 20 to 40 years. For drugs and weapons offenses. The contraband was found in my house after I was arrested.
What era did you grow up in the streets? Describe the street life?
I grew up in the late 70’s and 80’s. I came out of the house young. I can remember stealing during the blackout in 77. In the early 80’s we didn’t have that much drugs in my hood. Like 81 and 82 Brooklyn, was Crooklyn, it was a stick-up state and I loved the stick up game. It was grimy, but you had to play it, if you were in the street. It was victimize or be a victim. We knuckled up with young cats from the adjoining projects everyday – Cypress Hills, Linden Plaza, Linden Houses were all around my hood. They were and still are dangerous places. You had King Tut in Cypress and my dude Drac. Linden Houses had Mark Cross, and Plaza had Kindu and is crew. I ran with one wolf, prior to linking up with Drac and some other Cypress cats. I branched out, robbing dudes all over New York. I played the Broadway shows, Midtown in the daytime, digging pockets and picking them too. Which was big back then. Then crack came and everything changed you couldn’t trust a cat in the next building, everybody was for self. I got locked up for my first bid in 1984, it probably saved my life. Because East New York had the highest murder rate in New York City. The media called the community, The Killing Zone.
Describe what you were doing on the streets and what landed you in prison?
Like I said, I never worked a job for more than a month or so, and can only remember having two of those. I robbed, picked pockets, sold drugs, played the confidence game and robbed some more. That’s what always brought me back to prison, but it was all I knew.
Describe what you went through in the criminal justice and prison system?
I had it easy my first two bids. Everybody I’d run the streets with was in jail, from Rikers to most of the Upstate prisons. So, no problems. Not even from the cats I robbed in the street. I remained the same, quiet, smart and a wolf if threatened. Facing that life sentence woke me up, however. I studied the law extensively, looking for loopholes. I found some, which the Courts didn’t respect. That gave me another perspective; I realized that criminality is a set up from the start. Through poverty I was lured into the lifestyle and being ignorant, I stayed. In prison I was classified a supermax prisoner, and had to wear chains on my feet and around my waist when brought to Court. Talk about feeling like a slave. I was a CMC max, which means they watch you more closely than prisoners in general population. I had several fights over nonsense in several jails, no big thing. I wouldn’t even classify them drama, you gotta do that shit, even when you know better, to set a tone.
Describe the gangs in prison and what other stuff went on?
There weren’t a lot of gangs in NYS when I started my bid, then the Latin Kings came, and got crazy. They were a bunch of Spanish dudes to scared to fight one on one in my opinion. So, they jumped dudes. Rat Hunters were in Clinton, then the Bloods came. I know a lot of Bloods, but didn’t join no gangs. I don’t like the idea of helping someone I don’t know personally and I don’t like dumb shit. My tolerance is real low for stupidity.
How did you feel trying to change your life around in prison and how did you deal with all the negativity?
Changing my life I did because I had no choice, the system wanted to take my life, so only I could save it. I’m well respected, for my street credibility and intelligence. I always shared info with other cons trying to win their freedom or better themselves. So the negativity around me never got to close. When it did, it wasn’t even my beef. Never, always a friends. I got down then because I’m loyal. But, I always check a friend when they are wrong. That’s just real, grown man shit! I got out of prison unscathed, so there was no real drama that I want to highlight. I liked learning, so I read, started writing and took every therapeutic class I could. Knowledge is Power.
I wrote a Man of Substance as therapy for myself first, and as a guide to help anyone else going through criminal or chemical addiction and I didn’t really think those addiction programs were clear enough, informative or giving up the real talk and solutions.
What are you doing now?
I’m still writing books, screenplays, stage plays and grinding. I write under the names DC Outskirts & De Felon as well as my actual name Derek Caldwell. I love this writing game; I am also a Prison Life Consultant for Locked up Life Line.
What do you think of all the gangs that the youth are attracted to now?
I think it’s a sad reality, because there is so much more opportunity available to the youth and everyone today. I understand the strength in unity, if it’s fostered for advancement, not bullshit. I wish I could talk to every young cat about to enter a gang and ask them. Why do you think this will make your life better? If they can’t answer that, they shouldn’t join. Point Blank.
How do you think popular culture and hip-hop affects it all?
It’s a gift and a curse. The gift is the economic opportunities hip hop and pop culture can provide to an entrepreneurial spirit. It’s global. The curse is the fact that both mediums are flooded with fools not saying or doing shit. To educate, advance anyone but themselves or give back. If the President can mention rappers then rappers can do more.
Yeah, I want to tell all the youth and street cats to slow down, it’s a thinking game today. Your life is about decision making, you can monetize your street smarts, if you think about it long and hard. Come up with a plan, and I don’t want to hear about you needing startup money. Start from where you are, there is always someone doing worse than you are. The man with no shoes didn’t think so, until he met the man with no feet! Peace!
You can order A Man of Substance from Amazon.com