thanks for watching. i'm john seigenthaler. msnbc takes you behind the walls of america's most notorious prisons, into a world of chaos and danger. now the scenes you've never seen. "lockup: raw." >> built in 1852 and home to california's death row, san quentin state prison is bursting at the seams due to overcrowding. when we shot our extended stay series there. but san quentin had one program designed to discourage troubled

teens. from ever joining its ranks in the future. through the squires program, selected inmates shared their experiences with teenagers who had already had run-ins with the law. >> what we need you to understand, you are in san quentin this morning. you are in a place that no kid should ever want to be in. you should be out playing somewhere in the park. you are here because of something you did. >> what's your first name? >> angel. >> angel? >> yeah. >> how old are you? >> 13. >> i'm 16. >> jonathan, i'm 16, too. >> what you want to know, that this is your life, man. you have an opportunity to leave out of this place and never come back. >> let me introduce myself to you guys. my name's david. i'm about to be 25 years old in a few more months, but i have been in prison since i was 15-years-old for murder. >> david monroe is serving a 15-year-to-life sentence after having pled guilty to second degree murder.

>> i banged before. i have been on the streets before. i'm from stockton. i done did it before, all of it. everything you guys say you did, everything you guys think that you didn't did that we ain't did, we did it. >> it's really just about us not scolding the kids. it's not a scared straight. but we try to give you the communication part like look, man, this is what i did, this is what it got me. this is the trophy that i was trying to earn. is this what you want to earn? most kids they don't. do you want to come to jail at 15 years old? do you want to come to prison and have to be on the yard? yeah. stand up. let me see how tall you are. this was me. this was me when i came to prison. >> they're 15, they look at me like oh my god, are you serious? that's usually what i get, are you serious? 15 years old, they locked you up? can they do that? >> at 15, monroe's involvement in gang violence changed his life forever. >> they say if you carry a gun, eventually you're going to use

it, and it did happen. we were with a girl. having fun, talking. i seen somebody walking by, we had a confrontation. i asked him some questions about his gang affiliation, if he had problems with my gang or my street, or the red, period, the color red, and he said yes. me trying to prove myself to my peers like okay, i'll show you that i'm down, and i reacted. i shot him six times. i ended up murdering him basically for a color. i never planned to commit a robbery, he never planned before his future to be doing a murder. he never planned for his life to be committing attempted murder. it all came about by the behavior and the lifestyle we chose. say you do a robbery, what do you think going to happen? >> if you get caught. you go to juvie. >> what about your mom? who do you think will happen to her? >> she will be sad and cry? >> and hurt. >> and you shaking your head, so you know that can happen to your mother, too? >> yeah. >> okay. that you all know this. why would you put yourself in

that situation? >> maybe you got to take a risk sometimes. >> take a risk sometimes? >> yeah. >> you don't think about it. that's the part about being a juvenile, you are not fully thinking of what you are doing. you are just trying to be cool to fit in. >> i'm real offended by what you said. i'm putting myself in your mama's shoes right now. you tell me you are willing to sell your mama out? >> it's worth it. unless you want it. you are taking a risk. >> i don't care what you say it ain't worth it. ain't nothing worth my mama to me. nothing. you guys aren't paying attention to how you hurt your mom. >> monroe never realized how his crimes would hurt his own mother until the day he was sentenced. >> when the judge actually said are you a cold blooded murderer, and i'm trying you as an adult to be sentenced to 15 years to life in prison, i heard my mom scream. and it's just -- it's horrible. it was a horrible feeling, physically, emotionally, mentally, it was just horrible. i put my head in my lap and i cried. >> the boys are given a preview

of the stark conditions they might face if they ever enter the california prison system. >> i want you guys to get a good look at this restroom. this is where you are going to use the restroom. look how they take care of this place. do you want to use this restroom? you come to prison, this is what you are putting yourself in. because you have no privacy once you are in prison. that's what you guys are coming to. >> yeah. i believe what i got out of it is i don't want to end up in jail. so i got to start watching what i'm doing. start making better choices. because one little messed up choice could ruin my whole life. >> i don't want to be here. that's about it. it ain't a good place to be. >> it has to come within you. you have to want to change. i always said this for my victim, i can't give him his life back, but i can save somebody else's life because of what i did. i hope his family knows that, you know, what happened to him, it's not in vain anymore. some people are actually being saved.

>> you all take care, man. take care. hopefully we don't see you again, that's the hope. we don't see you again. >> san quentin is just one of numerous prisons or jails across the nation where inmates and staff provide cautionary tales for troubled youth. at the suffolk county jail in boston, massachusetts. we encountered another program jail brake. >> just remember when you are visiting here. you're going to get experience what it is to be in jail. they're going to have you empty everything out of your pockets, put into locker. make sure you take everything out of your pockets, all right? hat, you take the hat off. show some respect. take everything out of your pockets. change, quarter, nickels, anything, bus passes. >> when we film in a prison or a jail, we do do our best to be a fly on the wall. in the case of jail brake, you know, these kids came in, and, yeah, they were definitely aware of the camera. >> are you scared? >> are you scared?

how about you? >> no. >> you're not scared right now? >> no. >> there is no reason to be scared, to tell you the truth. >> at the same time i don't think it was necessarily the camera that affected them in the way that they had an attitude or they had the certain bravado. i think it was more relating to age. >> everybody stand up. come over there. >> right now, all you got to do is empty your pockets, take your jackets off. nothing should be around your wrist, in you're ears or in your pockets. everybody over there. put these uniforms on over your clothes. hurry up. >> these kids are from the boston public schools. they were suspended from school because of something that they did. >> tuck your shirts inside, guys. everybody, tuck your shirt inside. >> once they have the uniform on and i start yelling at them and start talking to them in a way that, you know, they know that i'm in control, then they don't know what to do. so they just break down.

>> you are 12-years-old, dude, you want to cut somebody. assault somebody. okay. keep on smiling like this, there is nothing funny here. >> i'm not smiling. >> keep your mouth shut. >> 16-year-old damon pope, already, recently caught with marijuana, appeared to not break down. >> you are in jail, 16, you will be 17 in a month. you have this attitude like you are too good to be in this place. you are going to run this place, are you kidding me? you think you're that cool? >> i got goals. >> tell me your goals. >> my goal is trying to entrepreneur, you know, a business, possibly take over this jail, you know, to be at home like donald trump collecting money, writing checks, possibly write you a check, you know. >> uh-huh, that sounds great. >> i tell you what your goals are, you will be in one of these units if you continue to do these things you are doing in a month. i'll give you less than that, okay, you're 17 years old. you walk through that back door and you will not leave. understand me? you will not leave.

that's what's going to happen to you. that's where you're going. everybody put your arms out. put your thumbs down. all the way out. i don't have anything. a piece of string, tie his arms together, he's not even strong enough to break that. >> these are mad tight. >> they're not made for comfort. you hear that, get used to that. >> why are you so cruel? >> get used to that. keep your mouth shut. >> what did i do to you? >> i don't like punk little kids coming into my jail and thinking it's cool. >> i didn't disrespect you. >> i don't care. i don't care because you're in my jail thinking you're tough. okay. keep your mouth shut. that's what i want you to do right now. okay. that's what i want you to do right now. pick up your feet and move. >> the boys are escorted into the jail and placed in separate cells. >> face that corner right there. are you making your mother proud? >> no. >> no? are you going to change your

ways? >> yeah. >> you know you got a friend coming, a roommate. are you ready for him? oh, you are? you're ready for him, huh? >> coming up -- >> take these off right now. get going, tough guy. >> the kids meet the inmates. >> anybody smoking weed is going to end you in jail.

>> during our extended stay shoot at the suffolk county jail in boston, three inmates pre-selected by jail staff were about to introduce themselves to four young men, participating in the jail break program. >> the 12-year-old in cell one is here for cutting his teacher. >> what's up, man?

what's up? how old are you? >> we have two fights in school. >> what are you here for? >> marijuana in three. >> and marijuana in four. >> this is a game? you think this is a game, huh? >> one in four is 16. birthday next month. he is a heartbeat away from being in here. >> stealing money and smoking weed is going to end you in jail. either or. [ bleep ] >> take your sneakers off right now, mother -- get going, tough guy. >> they always take their shoes away. this is something we know that happens in jail. we tell them, you come to jail, you will lose your shoes. >> get these sneakers off. [ bleep ] [ bleep ] >> put your hands up, are you gang banging? >> spending your mother's money on weed? what are you crying for? wipe that smile off your face. >> why are you crying now? boogies dripping down your face.

>> what does it feel like? >> i don't know. >> it didn't scare you? >> kind of. >> kind of what? >> kind of like scared and all that. just kind of. >> i saw you crying right now. >> no, i wasn't. >> was he crying? >> he did. >> why are you crying now. you weren't crying when you cut your teacher. >> you cut your teacher? >> you got him now. this is what you want to come to jail for these, a pair of these? >> this is what you come to jail for, right? a pair of these, right? i'm going to take them from you. >> whose sneakers are these? these are yours? i'm keeping them. have those. take those. you brought those, right? you can have those. >> i'm taking them. let me see you take them. yeah. that's what happens. [ bleep ] that's what happens to you. i'll take this [ bleep ] i'll take these [ bleep ] i'll take yours.

i'll take yours. and you won't do nothing about it. you understand? you understand me? >> yes. >> i can't hear you. do you understand me? >> yes! >> all right, guys. >> hurry up. let's go. >> it's not often that you see all the inmates, you know, working to the sort of a common cause. and once those kids were brought up into that unit you could tell that everyone was there, to put the fear inside them. >> get them sneakers. >> they're gone already. >> you in there? >> bring them in here. bring them in here. >> bring them in here. >> you and me going to play, right? >> while the three younger boys seem shaken at times. 16-year-old damon pope maintained his nonchalant attitude. >> can you give me the time? >> you have somewhere to go? >> i'm going somewhere. >> keep your mouth shut. what i tell you? i don't care how much -- you're in jail. you're in jail. okay? welcome to nashua street jail.

step to the back of the wall. >> we followed the kids up to one of the housing units so they could see where one of their next bedrooms could be if they continued on this path. i think it was probably one of the scariest parts for the kids, the idea of being actually locked up inside of a cell. >> get in there. welcome home. oh, there is only two beds. you got to share beds, have a seat. make yourself comfortable. that's where you're going to be. [ bleep ] >> you want to cut people. you want to cut people. >> they can't let you out the door when you want to go home now! i'm going to put you in there. >> let him in there. >> yeah, he's going in.

you want to go in there? huh? let's go. >> you got a bed for him? >> oh, no, he ain't sleeping on the bed with me. that's my bed. >> when one person is using the bathroom? what is the other one going to do? this is it. you be right here. it's steel. it's not -- that's your home. that's your bed. >> you got to stay in one room the whole time for every day of the year for how long you are here for? that's crazy. >> everybody is out, let's go, down here. everybody else go that way. >> they're his now. ask him if you can have your sneakers back? you don't want to ask him? >> grab your shoes, merry christmas. get out of here. >> are you scared you will end up here? >> if i keep doing the things i'm doing, yeah. >> you will go in the bathroom. you will take those uniforms off, fold them nice and neat and

bring them out to me. everybody understand, right? keep on making those noises. >> i'm not doing nothing. >> just because you are walking out the front door doesn't mean you won't see me again and won't be back in this place. >> i won't be back. >> remember that. google me. you can check me up in the computer when you get here. >> he will end up in this place if he doesn't change. he's really going to end up in here. he's so close to being 17 and at 17, you will end up in this place. he doesn't understand that. he thinks everything is a joke. he thinks he could do this. >> you are a good dude, no lie. you do your job well. >> hopefully, i don't have to do my job with you. >> the other three, i think they learned their lesson.

>> pope might have as well. nearly a year after our shoot, he had not returned to the suffolk county jail. [ music playing ] >> coming up. ♪ ain't done no wrong >> inmates who use their time to hone their talents. ♪ out in california

depending on the inmate, doing time can result in endless boredom or inspire new heights of creativity. >> this is a twin motor. >> this inmate who asked to only be identified by his nickname "lucky" used his time at san quentin state prison to create intricate models from soap, oil and paper. >> i carve it out. it's the tread of the tire made out of soap. it takes a long time. i have been doing it for like six years. it keeps me from being depressed and angry and everything else. >> what do these bikes mean to you? what do they represent?

>> i don't know. i guess freedom. you got to be free to actually ride them. >> lucky's models were more than just a hobby. he made one special bike as a gift to his daughter whom he had never met. >> she's 9 years old. she's never had her dad and i don't know how to be a father. so i really don't know what to give her. i want to give her something she don't have. ♪ >> in some cases, a prison sentence allows an inmate to discover a talent he might never have known he had. for clay lopez, the california state prison corcoran, doing time led him to the harmonica. >> i'm almost 50 years old. and i'll be over 50 when i get out. so i don't have a career or anything, so i thought, well, you know, if i learn to play the harmonica, i can at least pay my own rent when i get out as a street musician or if i'm sober, i think i'll do okay. ♪

>> you can play what you feel without reading music and i have tried to play guitar, piano. all kind of stuff and i never would anywhere. not that i'm going anywhere with this. but i know a few songs, mostly hymnals in hymnals and gospel songs. a few of my own. it just expresses me. >> lopez was serving a 20-year sentence on 27 counts of burglary, but it was his exposure to inmates serving life terms that inspired him to pay them tribute through his songs. >> i just wanted to do something for the lifers, to kind of

express them. what i can sing in the last verse and speak for itself goes, ♪ ain't done no wrong ♪ since the days of old out in california ain't no other road ♪ ♪ when i'm carried away in the coroner's car ♪ ♪ someone tell the warden to please ship me to the dixie land ♪ that's the only way they're going to get out is when, well, when the angels come down and pick them up and take them home. that's why it's got that train sound. see. ♪

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