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I've ever had a guy cry when something doesn't work out. usually it's me that's crying when something doesn't work out. >> police decide to give him one more shot to set up another target in boys town, but it's got to happen fast. >> round two, he'll probably be a little more seasoned and crafty in order to try to make something like this happen. you know, he has to be. he has two days. >> while the team on the city's north side faces a setback, this team has nabbed a suspect on a minor drug offense who says he can help them find the alleged gunman we've been calling booth.

The team reconvenes later that night, while cash stays in contact with their target. an hour and a half passes until the target says he's still making deliveries to other customers. he won't make it back to his hotel, so police call it quits. >> this is the game. >> the informant made an effort. you know, he tried. but he has no control over what the target's going to do. for cash, it was his best chance to try to get his boyfriend out of jail and now it's gone. >> he's crying a little bit. he's really upset. i think this is the first time i've ever had a guy cry when something doesn't work ou...

Night, while cash stays in contact with their target. an hour and a half passes until the target says he's still making deliveries to other customers. he won't make it back to his hotel, so police call it quits. >> this is the game. >> the informant made an effort. you know, he tried. but he has no control over what the target's going to do. for cash, it was his best chance to try to get his boyfriend out of jail and now it's gone. >> he's crying a little bit. he's really upset. i think this is the first time i've ever had a guy cry when something doesn't work out. it's usually me that's cryin...

The team reconvenes later that night, while cash stays in contact with their target. an hour and a half passes until the target says he's still making deliveries to other customers. he won't make it back to his hotel, so police call it quits. >> this is the game. >> the informant made an effort. you know, he tried. but he has no control over what the target's going to do. for cash, it was his best chance to try to get his boyfriend out of jail and now it's gone. >> he's crying a little bit. he's really upset. i think this is the first time i've ever had a guy cry when something doesn't work ou...

The team reconvenes later that night while cash stays in contact with their target. an hour and a half passes until a target says he's still making delivery to other customers so he won't make it back to his hotel. so police call it quits. >> this is the game. >> the informant made an effort. you know, he tried, but he has no control what the target is going to do. >> for cash, it was his best chance to get his boyfriend out of jail and now it's gone. >> he's crying a little bit. he's really upset. >> i think this is the first time i ever had a guy cry when it doesn't work out. it's usually me...