due to mature subject matter, viewer discretion is advised. msnbc takes you behind the walls into a world of danger. now the scenes you've never seen. the scenes you've never seen. home to california's death row, san quentguin quentin state pri bursting at the seams. san quentin had one program

designed to discourage troubled teens from every joining its ranks in the future. through the squires program, selected inmates share their experiences with teenagers who had already run ins with the law. you're in a place that no kid should ever want to be in. you should be out playing in a park. >> when is your birthday? >> how would are you? i'm 16. >> i'm 16, too. >> this is your life, man. you have an opportunity to leave out of many place and never come back. let me introduce myself i'm david. about to be 25. i've been in prison since i was 15 for murder. >> david monroe serving a

15-year to life sentence after having plead guilty to second-degree murder. >> i banged before. i've been on the streets before. i'm from stockton. everything you think you did we did it. we try to give you the communication look this is what i did and this is what it got me. this was the trophy i was trying to earn. most kids they don't. do you want to come to prison and have to be on the yard stand up. let me see how tall you are. this was me. this was me when i came to prison. >> they're 15 and they look like me oh, my god. i usually get are you serious. 15 they locked you up. can they do that?

his involvement? gang violation. we had a conversation and i asked about gang afghanistan if he had problems with my gang or the color red and he said yes. he tried to prove myself to my peers and i reacted. and i shot him six times. i ended up murdering him for basically a color. >> i never planned to commit a robbery. he never planned for his future to be doing a murder. he never planned for his life to be committing attempted murder.

if you know this you -- >> you have to take a risk sometimes. you adopt think about it. that's the part of being a juvenile. you're not fully thinking of what you're doing. you're trying to be cool. i'm offended by what you said. you telling me you're willing to sell your momma think it is what you needed. >> it was worth it. i was taking risk to do it. >> i don't care what you said was worth it. ain't nothing worth my momma to me. you're not paying attention to how you are hurting your mom. >> monroe never realized how his crimes would hurt his own mother until the day he was sentenced. >> the judge said you're a cold-blooded and sentenced me to life in prison. i heard my mom scream. it's -- it was a horrible feeling and physically and emotionally and mentally it was

horrible. i put my head in my lap and i cried. the boys are also given a preview of the stark conditions they might face if they ever enter the california prison system. >> i want you to get a good look at the restroom. this is where you use the restroom you have no privacy once you're in prison. that's what you're coming to. i don't want to end up in jail. i have to start watching what i'm doing and make better choices. one messed up choice could ruin my life. >> i don't want to be here. it's not a good place to be. >> you have to want to change. >> i said this is for my victim. i can't give him his life back but i can save somebody else's

life because of what i did. and i hope his family knows. hopefully we don't see you again. >> san quentin is one of numerous prisons and 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 called jailbreak. >> when you visit you experience what it's like to be in jail. empty everything out of your pockets. take the hat off and show respect. take everything out of your pockets. when we film in a prison or jail, we do our best to be a fly on the wall. in the case of jailbreak, you know, these kids came in and, yeah they were aware they were

aware of the cam perhaps. >> kblour not scared now? >> no. there's no reason to be scared. they tell you the truth. >> at the same time i don't think it was necessarily the camera that affected them in the way they had an attitude or they had the certain bravado. i think it was relating to age. empty your your products. nothing should be in your ears or in your pockets. everybody over there. put the uniforms on. these kids are from the public schools in boston. they were suspended from school because of something they did. once they have the unit format on and i yell at them and talking to them in a way that,

you know, they know i'm in control then they don't know what to do. they break down. you want to cut somebody. you're smiling like something is funny. keep your mouth shut. 16-year-old who had been recently caught with marijuana peered determine to not break down. >> you're in jail now 16. you'll be 17 in a month. you have this attitude like you're too good to be in this place. you're going to run this place. are you kidding me? are you kidding me? you think i was like donald trump writing checks possibly writing you a check. >> that sounds great. >> you'll be one of these if you continue to do the things you're doing. i'm give you less than that.

17 years old. you walk in the back door and you will not leave. you understand sne you will not leave. that's what is going to happen to you. everybody put your arms out and your thunderstorms down. tie his arms together. he's not even strong enough to break that. >> these are too tight. >> they're not made for comfort. >> why are you so -- >> what did i do to you? >> keep your mouth shut. >> i don't like to talk to no kids coming into my jail thinking it's cool. i don't care. you're in my jail thinking you're tough. keep your mouth shut. that's what i want you to do right now. move. the boys are escorted into the jail and placed in separate

cells. >> are you making your mother proud? >> no. >> are you going to change your ways? >> yes. >> you know you have a roommate coming. are you ready? >> you are. >> are you ready? >> coming up. tough guy. the kids meet the inmates. >> smoking weed is going to get you in jail. security. it's how you stay connected to each other and to your customers. with centurylink you get advanced technology solutions, including an industry leading broadband network, and cloud and hosting services - all with dedicated, responsive support. with centurylink as your trusted technology partner, you're free to focus on growing your business. centurylink. your link to what's next.

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

fireworks in school. marijuana in three. >> [ expletive ]. >> and marijuana in four. >> this is funny, huh? >> this is a game, huh? >> the one boy is 16 roughly next month. he's a heart beat away from being here. >> smoking weed is going to end you in jail. either/or. >> take his sneakers off right now. tough guy. >> they take their shoes away because it's something they know happens in jail. if you come to jail you're going lose your shoes. >> take your sneakers off. take your sneakers off. >> why you crying? what you crying for? >> take that smile off your face. >> why you crying now, huh?

>> i don't know. >> did it scare you? >> kind of. >> kind of like scared and all that. just kind of. >> i saw you crying. >> no, i wasn't. >> did you cry? >> he did. >> why you crying now? you wasn't crying when you cut your teacher. >> you cut your teacher. >> whose sleeves are these. >> these are yours? >> i'm keeping them. you ain't going to have them. you can have those. these are mine. you want them. come take them. let me see you take them. yeah. that's what happens in here. that's what happens. i'll take his [ expletive ] i'll take yours. i'll take yours. 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 you see all the inmates, you know, working together toward a common cause. once the kids were brought into the unit you could tell everyone was there to put the fear inside them. [ yelling ] while the three younger boys seem shake at times, 16-year-old damon maintained his attitude. >> give me my sneakers. >> what did i tell you. i don't give a [ expletive ] how much you paid. you're in jail. you're in jail.

okay. welcome to jail. your back to the wall. >> we followed the kids up to one of the housing units where they could see one of their next bedrooms could be if they continued on the path. i think that was probably one of the scariest parts being locked up inside a cell and the idea of it. >> welcome home. there's only two beds. you have to share beds. have a seat. make yourself comfortable. that's where you're going to be. >> you want to cut people? >> go on now. i'm going put you in there. i'm going put you in there. he's going in. yeah. do you want to go in there. huh, let's go.

>> this is it. that's your bed. >> you have to stay in one room the whole time for every day of the year for how long you're here for? that's crazy. >> everybody out. let's go! everybody out. that way. merry christmas. get out of here. >> if they'll keep doing what i'm doing, yeah. >> yeah. >> you are going in the bathroom and take the uniforms off, fold them nice and neat, and bring

them out to me. everybody understands, right? >> yes. keep on making the noises. because you walk in out the front door doesn't mean you won't see me again. you'll be back in this place. >> no. >> three weeks. remember that. remember that. he's going end up in this place if he really doesn't change. he's really going to end up in here. he's so close to being 17. and 17 you will end up in this place. he doesn't understand that. he thinks everything is a joke and he thinks he could do this. >> you're a good dude, you know that, right? >> hopefully i adopt have to do my job with you. >> the other three i think they learned their lesson. >> he might have as well. nearly a year after our shoot, he hasn't returned to the suffolk county jail. ♪ coming up --

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depending on the inmate, doing time can result in endless boredom or inspire new heights of creativity. >> that's a v-twin motor. >> this inmate who asked only to be identified by his nickname lucky used his time in san quentin to create intricate models from open, soil, and paper. >> that's the tread of the tire made out of salt. it takes a long time. i've been doing it for, like, six years, and it keeps me from being depressed and angry and everything else. >> what do the bikes mean to you?

what do they represent? >> i guess freedom. you have to be free to ride them. >> lucky's models were more than just a hobby. he made a special bike as a gift to his daughter whom she had never met. >> she never had a dad. i don't know what to give her. i want to give her something she don't have. ♪ in some cases, the prison sentence allows an inmate to discover a talent he might never had known he had. ♪ for clay lomez in california state prison doing time lead him to the harmonica. >> i'm almost 50 years old, i'll be over 50 when i get out. 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 as a street musician if i'm sober, i think i'll do okay.

♪ you can play what you feel without reading music, and i've tried to play guitar, piano -- all kinds of stuff and i never went anywhere not that i'm going anywhere with this, but i know a few songs. mostly h lly gospel songs. it just expresses me. >> he was serving a 20 year sentence on 27 counts of burglary. >> i wanted to do something for the lifers to kind of express them. i can sing you the last verse to speak for itself. it goes

♪ ain't done no wrong since the days of old out in california ♪ ♪ ain't no -- carry away in the cold someone tell the warden to please ship me to the dixieland ♪ ♪ because the only way they get out is when, well, when the angels come down and pick them up and take them home. ♪ making a fist

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