Reporter if it worked, he could win his freedom. If it didnt, he could lose his life. They had your back . They had my back. At least you thought. Thats what i thought. Reporter the inside man. Welcome to date line. Everyone. Im lester holt. Why would anyone volunteer to spend time behind bars in a prison for the criminally insane . It was a chance to escape a tenyear sentence and walking out of prison a freeman. Before he would be sprung he had a job to do and that special and especially dangerous prison. Getting it it turns out, was the easy part. Getting out alive was much harder. Reporter two enemies who didnt trust each other faced off across a table. One of them in handcuffs was a clever con named jimmy keene. The other, a hardcharging prosecutor. In court, he called me the john gotti of kankakee. Reporter the prisoner was worried sick. The prosecutor, who had just convicted keene and put him behind bars, suddenly wanted to talk. A topsecret meeting, no less. What more could he do to jimmy . He was the last person i expected to hear from. He was my biggest fear. Reporter but keenes fears went off the charts when the prosecutor, Larry Beaumont, slid an accordion file in his direction. On top was a grisly photo of a dead girl. And i flip to the next page, and heres another young, dead, mutilated girl. And im thinking whoa, wait a second. Hes probably thinking at this point that youre about to charge him with something else. Yeah, because, you know, i had been pretty rough on him in the initial prosecution. Reporter jimmy was in the dark. He had no idea the crazy scheme beaumont had in mind. He says, jimmy listen. He goes, this is something that we have another person on. He has killed many, many young women. And i personally think youre the one that can help us with this. Reporter this turned out to be an investigation to try and catch a suspected serial killer. Beaumont, an outsidethebox thinker, believed this convict, jimmy keene, was the one who could somehow crack the case, taking on a unique and deadly mission. I realized how serious it was. I realized the danger of it. Reporter but what he couldnt know was how such a Daring Mission would change his world and the person he was forever. If this all seems fodder for a hollywood movie, brad pitt would agree. The megastar who was benjamin button, then moneyballs billy beene was interested in playing none other than jimmy keene. Brad pitt likes the fact that this guy jimmy keene risked his life to try and find what he could find. Reporter clearly, this guy is one of a kind. Charismatic, conceited, courageous and complicated. From an early age, he had the personality, charm and cockiness that made him dream that a Hollywood Star might, one day, want to play him in the movies. His first big brush with fame came on the football field. I heard they called you the assassin in football. That was a good thing, i take it. Yes. I was taught by my dad at a young age. He said, son, if you dont hit that guy first, hes gonna hit you and hurt you first. Reporter a superstar athlete and mr. Popularity in high school, jimmy seemed to have it all as a big fish in the river city of kankakee, illinois, a bluecollar town south of chicago. I was most valuable player. I was captain of the Team Every Year i played. Reporter jimmy grew up in the shadow of his father, big jim, a giant of a man who was a cop, fireman and hero to his son. Hes my best friend. He was my backbone in pretty much everything i did. Reporter but all keenes grand potential would be put in peril by a terrible choice he made. As a teenager, he began selling drugs. He started small, peddling bags of marijuana here in this kankakee park. Then he expanded to cocaine and, at the tender age of 17, he moved to chicago, where the business and profits exploded. He was now a big fish in a bigger pond, lake michigan, to be exact. He was his own in crowd. Fast cars. Faster women. And supedup living. All the hot stops, all the big nightclubs, all the owners i was in tight with. I would come in there and have Carte Blanche in every place that i went to. Were you feeling invincible . Yeah, there was a certain point where i would say there was an invincible feeling. Did your pop know what you were doing . Did he suspect . He didnt suspect it until much, much later. Reporter it would be a rude awakening for both his dad and jimmy the day in 1996, when jimmy was just relaxing at one of his chicago homes. All of a sudden, kaboom. The whole door just blew off the hinges and come flying into the house. And all of these dea, fbi and locals all came in, in single file line. With their automatic weapons pointed at me. Freeze, get on the ground, get on the ground. Reporter he had been caught in a drug sting, spearheaded by that hardnosed federal prosecutor, Larry Beaumont. We scooped him up in an operation that i ran called, we called it operation snow plow. Reporter and in court, beaumont showed keene no mercy. He was coming at you on all fours, though, wasnt he . Oh, yeah. He was. He was a bulldog. Reporter jimmy was convicted and slapped with a 10year sentence. It was a pretty stiff sentence. And i knew he didnt expect to get 10 years in that case. Your father was in the courtroom. Right. I knew id let him down in probably one of the biggest ways you can let somebody down. Reporter keenes future was bleak. He faced 10 years away from his glamorous life, the fast women, the fancy cars, the big bucks. But in 1998, just when all hope seemed lost, his old nemesis, beaumont, came to him with an offer of freedom attached to that accordion file hed slid across the table. In return, keene would have to agree to risk everything and become an undercover informant in one of the roughest prisons in the country, the maximum security lockup in springfield, missouri. It was a psychiatric prison with both hardcore killers and the criminally insane. These people all have life sentences. Theyre all in there, and theyre crazy loons, and they have Nothing Better to do but to try to hurt you or kill you just for some fun. Reporter if he accepted beaumonts offer, keenes target would be the suspected serial killer. A mysterious maninavan. Coming up every picture tells a story. When i put the picture reporter several years before jimmy keenes arrest and conviction, his drug business was booming and his personal life, as he tells it, was nonstop fun and games. There were a lot of hot clubs here. In the 90s. This was the place you were doing business, as well . Lived, worked and played right here, yes. It was a good time. Reporter back then, he had no idea about the danger lurking 150 miles south and a lifestyle away that would change his life forever. Rural, tranquil georgetown, illinois, was where terry roach and her husband, loren, were raising their 15yearold daughter jessie and two other children, far removed from bigcity crime. Everybody knew who everybody was. So they were more conscious of what was going on, usually. You could count on somebody to get after your kids, if they needed it. [ laughter ] reporter in 1993, jessie was a high school sophomore, devoted to home and family. Jessie was really a very much of a homebody. So one bike ride up the road and back, she was done. And then she would be watching gone with the wind. Reporter one monday in september, jessie went out for a bike ride. But just minutes later, her sister noticed jessies beloved bike down on its side, in the middle of the road. Not on the side of the road, middle of the road. Yeah. She would have put the kickstand down and stood the bicycle up. She would never lay the bicycle down. And i immediately went down there, and theres the bicycle. And its like i knew somethin was wrong. Reporter Deputy Sheriff gary miller was dispatched to the scene. The more we learned about the family and and the girls background, we just didnt feel that she was staying away by choice. Reporter the haunting image of a bike, tipped over and abandoned, terrified all the investigators and, of course, jessies family. I mean, you never lose the hope for them not to come walking in. You still hope that. I mean, we knew she was not just gonna walk away. Reporter after six weeks, jessies parents worst fears were realized. Her body, beaten and sexually violated, was discovered in a cornfield. It can never be easy telling telling a parent that their child is dead. No, it wasnt. But at least we were able to tell them, this is her, shes gone. We were able to erase all doubts. Reporter gary miller had a murder case to solve and it was now a federal case involving prosecutor Larry Beaumont as well, since jessies body actually had been found across the Illinois State line. For the next year, miller did lots of legwork but to no avail. Every day you get up, are you thinkin about this case . Oh, every day. What have what have i missed . Exactly. I know this case really shook him from the beginning. And he would check any and all leads that would involve young girls and kind of run em down. Reporter then, in late 1994, millers persistence finally paid off a man in a van had been reported chasing two teenage girls in jessies hometown of georgetown. Miller traced the van to a man named larry hall from wabash, indiana, a threehours drive from georgetown. Is your heartbeat starting to pick up a little bit . Yeah, yeah, yeah. Im thinking, this has gotta be checked out. Reporter miller learned that hall was a gungho civil war reenacter, a pretend Union Soldier who traveled the midwest to fight fantasy battles. Miller immediately drove to wabash to interview hall, who wasnt saying much. So miller showed him a photo of jessie roach. When i put the picture down he he flinched, raised his arm up and turned in his chair and refused to look at the picture. Reporter convinced larry hall was hiding something, miller became obsessed with making a case against him. Days later, back in illinois, miller turned up a huge lead. He found witnesses who vividly remembered hall from a revolutionary war reenactment in the georgetown area the very weekend before jessie was abducted. To them, hall stood out for his bushy muttonchop sideburns. But also for playing a soldier who was fighting the wrong war. He was wearing a civil war uniform, and he had a civil war hat. At a revolutionary war reenanctment. Exactly. Reporter armed with this new information, Deputy Sheriff miller returned to wabash for a second crack at hall. This time, he pressed his suspect harder, stressing that halls fellow reenacters had seen him near georgetown. He came along to the point where he said, well, you know, i go to so many reenactments, i could have been there and i just dont remember because i go to a lot of them. Hes giving a little more ground. Right. Yeah. Reporter miller seized the opening and kept at it. Finally, he said, hall came clean and confessed that he abducted, sexually violated and strangled jessie roach to death. How much detail did he give you about the killing of Jessica Roach . Very good detail what he actually did and what took place. Reporter not only that, miller says larry hall confessed to other killings, including a coed from Indiana Wesleyan University in nearby marion, indiana, named Tricia Reitler. He did say he was involved in reitler. Reporter Deputy Sheriff miller didnt know much about tricia, so he called on the local Indiana Police whod been handling that case. But when marion detective jay kay and other indiana cops arrived, hall was suddenly telling a much different story. He denied confessing to any killing including jessies and tricias. Whats more, he claimed it was all a misunderstanding about disturbing dreams he had. He takes us out to a location where, in my dreams, i strangled her here and left her to lay here. We searched the woods, we searched the area. And never really found anything. Reporter the indiana cops, who were familiar with hall, were not at all surprised by his actions. Some of them, like jay kay, thought hall might be a wannabe a pretender who gets his kicks from confessing to crimes he didnt commit. Is it possible hes simply obsessed with these cases . But but not involved . Theres no doubt in my mind that he does follow these cases, that he does read and is attracted to cases all over the country. So the question does come, you know, is he a wannabe . Reporter Deputy Sheriff miller and prosecutor beaumont, however, felt certain they had a real killer on their hands, a serial killer with a unique m. O. He would drive crosscountry to reenanctments where hed play fantasy soldier, then prey on young women and kill for real. The fbi started discovering girls that were in fact missing at these various areas at the time larry hall wouldve been there. Reporter but the only case for which prosecutors had sufficient evidence was jessie roachs. Larry hall was arrested in connection with her death, even though he denied making that confession to miller. Hall went on trial in 1995. As a prosecutor, whats the best card youre holding . We had his statement. His confession. Said he did it. Reporter beaumont called Deputy Sheriff miller to the stand to testify that hall had indeed admitted that he abducted and killed jessie after he spotted her with her bicycle. She was walking her bike at that point. Reporter miller testified that, in his confession, hall gave him a detail that only the killer would know that jessie was not riding her bike but walking it a safety precaution the roaches insisted she follow when she was on their narrow road. That was never in the press that she was walking her bike that day. Right. When you heard that, did that give more credence to his story . That just sealed it for me. I knew. I knew that he was the one. Reporter a jury unanimously agreed. It took just three hours to convict larry hall. But prosecutor beaumont believed this was just the tip of the iceberg. He felt certain hall was a serial killer, and now he had to find a way to prove it. So he began investigating Tricia Reitlers abduction a case that wasnt his, for a family he didnt even know. I cant imagine sending my daughter off to school and never seeing her again. Reporter and he came up with an outsidethebox scheme to get hall, which would risk the life of that charismatic convict he had just put away for dealing drug jimmy keene. What happens when ive gotta deal with all these crazy killers and stuff . What if i get shanked . What if i get killed . I mean, am i gonna survive this . Coming up a get out of jail people typically dont admit murders, sexual assaults and murders, to Police Officers unless in fact they probably have done it. So it was clear we felt he was responsible for the Tricia Reitler disapperance. She had such a zest for life. And shed walk in the room, and and everybody knew she was there. Reporter Tricia Reitler, a 19yearold psych major at Indiana Wesleyan University, was on her way to becoming a family counselor. Her goal was to be able to put families back together again. Reporter then, in march, 1993, donna and Garry Reitler received that latenight phone call every parent dreads. A cop from marion, indiana was on the line. He said, do you know where tricia is . In my heart, you know, i knew that something was drastically wrong. Tricia had walked to an offcampus supermarket and never returned to her dorm. Now more than 20 year later, her parents are still waiting. You purchased a cemetery plot. Yes. No headstone . No, not until no. Not until we find her. And we have no answers. Thats what eats at me. Somebody out there has that answer for us. Reporter Tricia Reitler wasnt even prosecutor beaumonts case but he was deeply moved by her parents. It was always a horrible crime to me. I knew about the facts of the case, and i knew about the family. I never met em, but i read all the the newspaper articles, and the accounts of them, you know, asking for help. Beaumont felt certain that suspected serial killer larry hall was responsible. Not only did the hall live 25 minutes from indiana wesleyan, hed been identified chasing two coeds there, just a week after tricia went missing. So in the summer of 1995, a month after convicting hall for jessie roachs murder, beaumont was leading a search for tricia. It was in those same indiana backwoods where hall had told indiana authorities he dreamt he killed and buried tricia. I wanted to feel like i did everything i could to see if we could find her body. Reporter but after two days searching in sweltering heat and humidity, tricias body didnt turn up. We couldnt find anything. Doesnt mean it wasnt there. Reporter then, beaumont decided to try something completely different. I came up with the idea of putting somebody in the prison cell with him to see if we can get him to tell us what he did with Tricia Reitler. Did they all think you were crazy . Most people did think i was crazy, yeah. But i was able to convince them we should do it anyway. Reporter enter jimmy keene, the drugdealer beaumont had just convicted and sent to a lowsecurity prison. Why did he stick out in your mind . Because i knew he was kind of a con man. He was smart. If anybody could pull it off, he would probably be the one to be able to pull it off. He says, youve been trained in martial arts. He goes, you can go into a dangerous environment where a lot of people cant. You can maintain and protect yourself in in an environment like that. Reporter in return, beaumont offered jimmy freedom. But first, jimmy would have to exact more than a confession. I told him that, unless we found the body, he would get no credit. No body, you get nothing. Reporter jimmy was skeptical. He was a drug dealer, not a criminal profiler. And he knew that this was a mission impossible. He said no. But then fate intervened. Jimmys dad suffered a stroke. Weeks later, frail and sickly, he came to visit jimmy. My dad was in a wheelchair. Now, this is big jim, the guy that had been superman to me whole my entire life. We cried through the window to each other, and we talked for a while, and he didnt even know about the offer. Nobody knew about it. Reporter jimmy now realized that he had a onetimeonly opportunity to fix the mess hed made for himself and get out while his dad was still alive. As soon as we were done with the visit i called my lawyer and i said, tell beaumont, im g