The Transformation of a Boston Hustler

By Chuckie Brown

Chuckie Brown started selling drugs in Boston at the age of 12. He used the drug money to build an empire, starting with sneakers then moving into fast cars and faster woman; hundreds of them, resulting in several toxic relationships and the birth of his three beautiful children. Along the way he tried to help young people in his community who needed a mentor and a path to a better life. In ten short years he lost it all and was incarcerated. Luck, lawyers and the love of God helped keep him from a life in the penitentiary experienced by so many of his African brothers. A new Chuckie emerged when a judge granted him custody of his 2 sons. Today Tee a peace of mind swimming, or relaxing on some Caribbean Island.

• Language: English
• Publisher: Xlibris US
• Release date: Mar 20, 2022
• ISBN: 9781669814191

Book preview

Chapter 1

Chuckie Brown, born July 5, 19??

I first sold drugs at age twelve, was charged with attempted murder, was offered a plea (which I declined), and won in court. Went to boot camp, graduated, then fucked up—literally (I went out to find some ass and pounded it while the corrections folks were hunting for me once I had dropped off their radar). Then off to upstate prison I went.

I had a BMW at sixteen years old. I had lots of hoes and bros, made it through some rough patches and out of some tight spots. Eventually, I gave it all up.

These are my memories: my rude moments, my good deeds, the people and events that shaped my life. Some of the individuals in this book went on to be famous in the world of rap music and sports. There will be details about my first love, the trail of broken hearts, my being a husband and a father, my being a youth worker and humanitarian, dealing drugs while dealing with racism and segregation.

I will start where my story, where lives, must—at the beginning.

My first memories are of life in Boston, experiences with my friends in one of the massive housing projects that dominated large sections of the city.

I didn’t live in the projects but across the street from them. Summers were Cathedral projects spent in Florida with different relatives. I spent most of my years growing up in the. I hung with a group of five people: myself, Abdul (he loved to tell people that he started me in the drug game), Manny and Miguel, Tedro (we called him Roberto), and Orlando (we called him Lando). Abdul’s family was Muslim. They didn’t eat pork, but Abdul would sneak over to my house to eat pork. Orlando couldn’t do any wrong in his mother’s eyes, even when he was wrong. They were neighbors with Abdul, and their house was known for having roaches. Manny and Miguel lived around the corner from Abdul and Lando. Roberto lived around the corner from Manny and Miguel.

Mom hated that I hung in the projects. She came from a strict family, and she had to be strict because I was bad. My brother Earl was a square. Everybody knew my mom didn’t want me in the projects. When she couldn’t find me, she would come into the projects with a belt. I would have lookouts who would whistle when they saw my mother coming, so that I could leave a different way out the projects and make it home before my mother got back.

We used to sneak into the train station on Dover Street and sneak downtown. Once there, we would go into stores and steal action figures, especially those from the movie Star Wars. We took them out of their packages and put them into our socks. Woolworths was the easiest target. At one point, the CVS downtown sold toys, and we were friendly with the staff. We worked in teams: one of us would talk and laugh with the staff while the other would steal a toy.

One time we checked in our bags at CVS that had stolen candy in them as we went in to steal some more toys. As we went toward the toy aisle, the manager stopped us and brought us into the back room. He showed us all the empty packages from the toys we had stolen days before. He gave us a lecture about how he trusted us and then left the room to get a pen so he could write down our mothers’ phone numbers. We took off. The next day, me and Abdul went back to get our candy that we had checked at the front desk.

One day a bunch of us broke into the bus station where they parked the MBTA buses at night. Each bus had a fire extinguisher. I sprayed Manny with one of the fire extinguishers. Then his brother, Miguel, went to another bus, got an extinguisher, and sprayed me. All of a sudden, all of us were breaking into buses for more extinguishers. Pretty soon, we were all white as ghosts. I was coming around the corner with an extinguisher in my hand, and there was Manny on the ground in handcuffs, and there were police everywhere. Everybody got away except Manny, Miguel, and me.

I remember sitting in the back seat of the police car and the cops were laughing because we were all covered with fire extinguisher. They didn’t take us to jail; they took us to our parents, and I was scared as hell. They brought Manny and Miguel home first. As we pulled up in front of their house in the projects, it seemed that everyone who lived in the projects came out and surrounded the police car. It was almost like a little mini riot; there were so many people there. When they brought Manny and Miguel up to their house, they left me alone in the car. Some of the kids outside opened the door to the police car and told me to run. I thought about it, but I couldn’t because I was too scared. Somebody yelled out, Let’s go over to Shawmut Avenue, to Chuckie’s house. And the crowd started leaving toward my house.

When we pulled up, that whole crowd was standing in front of my house, including my mother, who was standing there with a belt in her hand. Before the cops could even get out of the car, my mother ran over, pulled me out, and started whipping my ass all the way up the stairs to our apartment. The cops never even got a chance to speak with her. My mother, whom I love very much, would whop my ass at the drop of a dime.

When we were around eight or nine years old Abdul, Orlando, and me went downtown. It was after hours, and we had no idea our parents were driving around, looking for us. We were in the combat zone, where there were a lot of strip clubs and a lot of prostitution going on. We would open the doors of the strip clubs and watch the girls for a while until we were kicked out. As we were looking at the girls in one strip club, our mothers had pulled up in a car behind us. My mother hopped out of that car, took her shoe off, and whopped my ass right in the middle of downtown. All the prostitutes came out and were watching, and the police detectives did nothing. Some of the detectives told my mother that I was down there all the time.

There were these brothers in the projects, Chris and Allen. These two kids had everything. They were the first kids to have scooters; they called their mother by her first name, and she would let them smoke weed at an early age, maybe ten or eleven years old. Everybody thought that they were so cool. Whenever I hung around with Chris, we always got into some shit. We used to break into the flower shop on Albany Street to steal flowers, go around, and sell them. Chris’s own mother was our best customer.

One time, we broke into our own elementary school, the Blackstone, and stole all the candy that they were selling for a fundraiser. I don’t know how we got caught, but we did. Chris came up with the idea to say it was a guy named Boogaloo who stole the candy. Of course, they didn’t believe it, and our parents had to pay back the money. I can’t even remember what we did with the candy.

I can also remember this one kid named Troy who used to bully us all the time and steal our stuff. Every time we saw him, we would run.

As I got a little older, in middle school, I got introduced to sex. It’s funny, we started off playing games. My favorite was if you catch the girl and you can hump her, you still had clothes on. These games eventually led to real sex. I can’t remember the first girl I had sex with, but I remember having a lot of sex while in middle school. I used to skip school and bring girls back to the crib. A lot of girls didn’t want me to use rubbers; they wanted me to pull out when I was about to bust a nut, but I had to use a rubber because I didn’t have dick control, even to this day.

At that time, I did have a girlfriend, and I never messed with girls from the neighborhood, just from school. Everybody was sleeping with everybody; it wasn’t a big deal. I was going to Michelangelo Middle School in the North End—that’s where all the Mafia was from. Blacks weren’t really allowed to go into the North End. We were bused there to go to school. I went to school with a lot kids from different neighborhoods and local projects.

Living on Shawmut Avenue in the South End, there was a lot of Mafia around, and that’s where I was introduced to selling drugs. I started off selling joints to people in my neighborhood for two dollars each. Around this time, my sister started dating this guy named Donnie. Donnie was a real funny guy. Everybody loved him, but he had a drug problem. But he was just fun to have around. He became part of the family.

There was this white guy who used to come around looking for hash and weed. I used to get it for him and make money off the top. This was going on for a couple of months. One particular time, he wanted some hash, and my regular supplier wasn’t around. I went to this other guy I knew—his name was Ep. I went to the projects to meet Ep at his cousin’s apartment. Ep was inside the bathroom with about nine other dudes, and they were smoking something out of a pipe. The pipe was being passed around, and Ep asked if I wanted to try it. I think if there weren’t so many dudes in there, and if it wasn’t in such a scary situation, I might have tried it. I took Ep to meet with the guy who was looking to buy the hash. Ep told the guy he could get it for him. He took his money and never came back. I never saw the white dude again.

Me and Abdul remained the closest. We both went to Charlestown High School in an Irish neighborhood. The other boys here mostly hanging in the projects. I couldn’t hang out as much. My mother was too strict and definitely didn’t want me in the projects. She always wanted me home at a certain time—when the streetlights came on.

In high school, there was an Italian girl. Her father didn’t like me. This was in the era when blacks and whites couldn’t hang out together, but she really liked me. She was always hitting on me in school and always wanting to hang out in my neighborhood, but I wasn’t into her. One day I let her give me head in school in the library, and she wanted to come to my house so bad. Eventually, I agreed, and when she got there, my buddy Abdul and Jose and two other kids came over. They paid me, and I let all three of them have sex with her. Everything was fine. She even hung out with us after she had sex. When she realized that it was getting late, she was scared because her father would be mad. I walked her to the bus stop, and I watched her get on the bus.

The next day, when I went to school, the principal and guidance counselor was there waiting for me and Abdul. The girl had accused me, Abdul and the other two kids of rape. They had already called my mom, but I didn’t know it. We were all sitting in the office, scared as hell. Somebody announced that Mrs. Brown was here, and before I knew it, the door opened, and my mother walked in. No questions asked, she took off her shoe and started beating me in front of everybody. The girl’s father pressed charges against us, but eventually, the charges were dismissed; but we did get kicked out of school behind it. Abdul got sent to Boston High, and I got sent to English High in Roxbury, where I met my first real girlfriend, Christen (but everybody called her Munch). Munch was a really good girl. She loved me and was faithful to me, but I was a real asshole to her.

Abdul was going crazy. In and out of DYS, he had stabbed a few people on different occasions. He was a wild dude, getting into heavy drugs, sniffing dope, and hanging with a lot of drug dealers. I wasn’t into drugs like Abdul was. Abdul eventually ended up killing someone at the age of fourteen or fifteen years old. There was a black kid who was going to kill him. Abdul hid around the corner and killed the kid first. He got charged as a juvenile.

I eventually started hanging out with this kid name Mario, one of the local drug dealers. He was showing me how to sell dope and coke. I started selling drugs with Mario and sniffing a lot of cocaine. I eventually became a shooter. I was known on the streets as someone not to be fucked with. I would have a handgun or a knife on me at all times. I was known as a dangerous individual.

I loved to sniff cocaine. One time Mario dropped some coke off to me, and I sniffed it all up my nose. I was high as shit. I ducked him for two days, until the pawnshop opened up on Washington Street, and I pawned off all of my jewelry: gold chains and rings. With the money, I covered my tracks, paid Mario, and he never found out.

One day, this kid was driving by on his bike from the Lenox Street projects, and I tried to take his bike, but he ended up getting away. A few weeks later, I was in Villa Victoria, which we all called Little Puerto Rico. I was out there talking to two friends, and three dudes walked by. I knew one of them, so I said, What’s up to him.

As they walked by, I heard one of them say, That’s him. They called Mark over, one of the guys that was talking with us. They were asking Mark, Is that Chuckie? One of them pulled out a gun and started running toward me, but Mark grabbed him. When Mark grabbed him, that gave me time to run, and the other dude who was with me ran too. The dude with the gun chased me for about three blocks, shooting at me. I could hear him pulling the trigger. I guess the gun jammed. He stopped chasing me at the corner of my house.

I remember going upstairs, talking to my sister’s boyfriend, Donnie. He was asking me what was going on, and I was out of breath, explaining to him what just happened. But at the same time, I had bloody murder going on in the back of my mind. I caught two of the dudes a few weeks later down in the projects. They saw me coming. I shot at them a few times as they were running, but I couldn’t catch them. They ended up getting away.

The dude who pointed me out was named Chance. I saw him in the Villa Victoria; I was in a car and he was on foot. We chased him down Lenox Street, but he got away. I was in the mall with the Mario when I saw Chance again, with this kid name Jerry who I buy guns from. When they saw us, they ran into Wilson Suede and Leather. All I had on me was my knife, but I was so upset I was going to shank him in the mall. Jerry came out and pulled me aside to talk to me. He told me Chance was scared as shit of me. Mario told me to leave him alone; he was a pussy. So I left it alone.

Chapter 2

But life goes on. Me and Mario separated ways. He sold his drugs, and I sold mine. But we still hung out. I wasn’t making much money, though. At one point, all I had in my pocket was sixty dollars and my jewelry. I went down to Lenox by myself and bought a sixteenth of cocaine. A sixteenth was worth sixty dollars. With that sixty, I built an empire. I went from having only a sixteenth to buying a key of cocaine . . . one kilo.

Down the street from my house was a bar; the bar was called Franklin. I can’t remember who, but someone told me I would make a lot of money selling forty dollars’ worth of powdered cocaine out the bar. So I started selling drugs out this bar and I was making a lot of money ; it was like I owned the place.

With money and drugs come lots of women. I was having sex like crazy, sometimes two or three chicks a night. There was one time I had sex with three girls in one night, went home, and then had sex with my girlfriend.

About this time, Abdul was getting out of DYS for murder. He was charged as a juvenile, so he didn’t get much time. The system was fucked-up back then. When Abdul got out of jail, he ended up getting his girlfriend pregnant and he soon he had a baby on the way. When he came out, he wanted to skip selling drugs and just start robbing people.

He came to me, he wanted me and him to do some robberies together. I provided the guns and the masks. I had a couple of .44 handguns lying around, and we went on a mission. We were like the gang that couldn’t shoot straight. We couldn’t get it right.

The first mission we did, we went up to Humboldt Street, and we were parked in the car with masks on and guns in hand, arguing about something; and as we were arguing, a car was coming up a one-way street. We took our masks off at the last second and came to find out it was the police. So we abandoned that mission.

The next mission one, I recruited this other kid name Rob to be our getaway driver. We all drove down to Mission Hill projects. I was driving, Abdul was in the passenger seat, and Rob was in the back. We drove up on some dudes that were selling drugs in the projects, with the lights off so they couldn’t see us. The plan was for me and Abdul to get out of the car, and rob the dudes. Rob was supposed to climb over the seat and get into the driver’s seat (this was a two-door car), but as we were approaching the dudes from behind, this asshole Rob jumped over the seat, and he fell on the horn. This alerted the drug dealers. Two of them took off, but a few stayed. We robbed them for some drugs and money, but it wasn’t much.

At this point, I came to my senses. I was making too much money selling drugs to be out here robbing people. This didn’t make any sense to me.

I came up with the idea to put Abdul down with me selling drugs. I made him a fifty-fifty partner. The plan was I would buy a couple of ounces of cocaine and show Abdul the bar scene. I’d give him half, and I’d keep half. When we were done, we would put our money back together again, and we would buy the same thing. Any money left over, we would split.

The problem with the plan was Abdul wasn’t making any money. He would have two ounces of cocaine. He could make up to four thousand dollars or even more, at a cost of eight hundred dollars per ounce. When it was time to tally up the money He would have only forty dollars. I would have to sell my coke and then go back and sell his. I was doing this over and over again, and I was still giving him half of the profit.

After a number of talks with him, I came to the decision that I couldn’t be doing this no more, because I was doing all the work. I finally sat down with him and told him this wasn’t working out. I gave him two thousand dollars cash for his pocket. I was very fair to him. I can remember him saying, Who you been talking to? You made this decision by yourself? Were you talking to Mario?

I told him, No, it was my decision.

He said he was just going to go find a job, and that’s just what he did.

After that it was back to business as usual.

I started hanging out with Rob, the getaway driver, selling drugs together. The problem with Rob was he liked to dibble and dabble with cocaine. He liked to get high. I was normally selling drugs out of the bar. But now that Rob was in the picture, I started selling in the projects again. We did mad shit together; we were having fun, living it up. There were times when I wouldn’t see Rob for a few days because he was out getting high.

There was this kid around the projects, Mike, and he hung with this kid named Mani. Now, I am not going to lie, as a kid, I was always intimidated by Mike. He was the local drug dealer, and he terrorized the projects. Mike had told Rob he couldn’t sell his drugs in the projects no more. I didn’t want any problems with Mike, so I told Rob not to sellno dope in the projects anymore, but Rob did it anyway.

I got a phone call one day. Rob was in the hospital. Mike and Mani had fucked him up for selling drugs in the projects. They fucked him up pretty bad too. They didn’t break anything, but he was in a lot of pain. I knew right there, looking at Rob, that I had no choice, I had to get payback. I recruited some dudes that night, we got some guns, and we went looking for Mike and Mani. But we couldn’t find them.

A few days after Rob got out of the hospital, we were in Villa Victoria, and who should walk by but Mani. We gave this dude a beating you wouldn’t believe. It was out in the public; everybody had seen it. Since I was known on these streets, after the first punch, I didn’t have to do no more. Everybody in the neighborhood started beating his ass.

The word was out. Mike was next. The whole South End knew that I was at war with Mike for what they did to Rob. We knew that Mike was coming back that night after what we did to Mani. So we waited in the projects. I finally got a phone call that Mike was in the projects with some of his friends. I went down to the Cathedral projects. I saw him, he saw me, and we just started shooting at each other. I took a lot of heat that night. People were calling me, females saying there were kids out there, and I was apologizing. Thank God no one was hurt.

A few weeks after the shootout, I was in Villa Victoria, playing ball. I was a little nervous after the shootout with Mike. I didn’t have a gun or weapon on me. I was worried that Mike might come out while I was playing ball, just incase mike showed up I wanted him to believe that I had a weapon on me so I picked up a stick and put it in a paper bag and put it across from me, where I could easily grab it if he did show up.

About an hour and a half later, someone gave the signal that Mike had pulled up. When Mike got out of his truck, he was looking to see if I was on the court. I saw him looking at me. I grabbed the paper bag and pointed it athim as if I had a gun. He immediately started, ducking behind cars. Everyone was running to get out of the way. I took off, he took off. It worked out perfectly.

The very next day, I was in the car with Rob we was stopped at the lightsand Mike pulls up beside us, not knowing we were there. When I saw him, I started to panic. I reached under my seat. Rob leans back, and I pull out the gun and started shooting at Mike. He takes off, and I took off after him. He was in an SUV, and I was in a little-ass Hyundai. We were on a high-speed chase through Mission Hill, projects but we lost him.

I was rushing home to put the gun away, but before I could even get to my house, my phone was ringing. It was Mario. He was telling me, to Leave Mike alone. That dude doesn’t want any problems with you. He said Mike was saying, Tell Tee, I’m sorry, man. He was even talking about going to the police.

I was shocked I thought Mike was a G . . . a gangster. After that I never saw Mike or Mani again. The Word on the street was that Mike and Mani was both gay and they was fucking each other there was even rumors that Mike started snitching.

When I got out of high school, everybody was still cool; but we were doing our own things. But Rob was still hanging with me, and still getting high . . . using drugs periodically. One particular day, I got into it with this kid named Ski. I can’t remember what the altercation was about. Ski was from the Circle, and he used to bully all the people in his part of the neighborhood.

Me and Rob went looking for Ski. I had a shank on me, and Rob had a .32. The plan was that I was going to stab Ski instead of shooting him so it wouldn’t make any noise. We went walking through the Circle looking for Ski and we bump into a few people that we knew, we asked them if they had seen Ski no one had seen him. I walked away from Rob and went to take a piss. While I am pissing, Ski comes around the corner on a bike. We caught eye contact at the same time. I ran over to him and pulled out the knife, but as I was trying to shank him, I tripped and fell; and when I fell, Ski pulled out a gun and aimed it at me and that’s when. Rob came out of nowhere, blasting away at Ski. Ski dropped his bike and started running, shooting back at us. All the people sitting around started running, hiding and getting in cars. Me and Rob took off. I always felt that Rob saved my life that day, and I owed him.

As time went on, my friend Mario told me to stop hanging with Rob because he gets high too much. But like I said, he saved my life, and I owed him. One night a bunch of us went out to the bar that I hustled at. Everyone was buying drinks in my name putting on my Tab. Rob gets up and he leaves the bar.

Later on that night, Donnie came into the bar, asking me, What’s going on with your mother? She’s all upset. Turns out, Rob went to my house. He knew where my coke was stashed—in the closet downstairs, in the pocket of one of my sister’s old coats that she didn’t wear anymore. He took the drugs and told my mother, who was always on my case, Ms. Brown, I’m worried about Chuckie. He’s selling drugs. Here’s the drugs.

He wanted me to think that my mother had found the drugs, not that he gave them to her, so I wouldn’t be after him. I must have had about three or four ounces of cocaine, worth about eight thousand dollars. He gave her less than two hundred dollars’ worth of coke. So my mother was bitching and moaning about it, cussing me out.

Rob disappeared after that. I hadn’t seen him in months. Mario was asking me, was I going to kill him? I didn’t want to because I always said that he saved my life.

I was back to business as usual, back to selling drugs, making money.

One day we all went out drinking—my brother, his wife, the neighbors, my girlfriend. We were having a good time. I’m not much of a drinker, but I was fucked-up on this day. We were all leaving the bar, and everybody was drunk, laughing, and having a good time.

When we was leaving the bar Me and Donnie were walking in front of everybody, laughing and cracking jokes. As we got to the corner of my house, who should come around the corner but Rob, carrying a case of beer. I immediately took a swing at him. I was so drunk I just fell into his arms. Rob dropped the case of beer. Bottles were rolling everywhere, and we started fighting.

While we were fighting, rolling