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Covered. >> many of the best informants begin their careers while locked up at chicago's cook county jail. detainees here are ripe for recruitment, most are accused, not convicted of crimes, and are being held awaiting trial. those who flip and cooperate with authorities can get reduced sentences. some of them will continue working for money after they get out. that's exactly what one former inmate who grew up hustling drugs on the city's west side is doing. >> basically his entire life has been in the business. at one time he was probably more successful than he is now. he had a nice car and ...

>> nothing to be mad about. it's still a hit. you've still got illegal ammunition. >> in order to nab the target red-handed, they'll need help from an inside source again. >> it's going to be real hard unless we can get somebody else to work. wouldn't want to use the same guy. try to get somebody new. try to find somebody new in the area. >> protecting confidential sources is just part of the job for any investigator, but there are limits. their lead informant roosevelt lands right back where he started. the chicago p.d. and fbi busted him as part of their sweep. he faces various drug-related ...

The dope hustlers are getting suspicious because he's not buying or selling anything, investigators call him off the block with. >> everyone head back. we'll debrief. >> one undercover unit takes a quick drive pass the target on their way out. >> there's our guy right there with the burgundy hat on, burgundy hoodie. >> did they ask him if he wanted to work? they asked him if he was ready to work? >> you ready, you want to work? he said yeah, later on. he said they flagged him like, man what are you doing out here? they don't want guys just to hang out. >> while authorities weigh their options,...

Alley. i believe he's looking to see. this block, this area here, this dope line, these guys are out early in the morning. >> here is one of your fiends right in front of us. >> white guy definitely does not live in this area. he's out looking or he already copped. heroin addicts get up early. they need that as soon as they get up. it's like coffee for them. this is time kids should be walking to school. going to have a mixture of foot traffic. unfortunately, it's going to be kids and dope finds. >> as surveillance teams continue circling the area, their informant phones in updates over the ne...

Game. i'll be tempted. you can make $50 real quick. but i'll sit back and i think that $50 can cost me five years. >> how about tomorrow morning, 7:00 a.m. you're on the block? >> great. >> being on the block for roosevelt though means playing a role. he's got to pretend that he's still in the game without breaking the law.ç >> wonder why i'm not on the block? >> it's a fine line for him to walk. one false move could get him killed. >> it could change with one bullet. it could chaenge in a heart bea. >> coming up -- >> there is sbog this informant. >> you got to sell her today. sell my guy. ...