WEBVTT - Episode 1: The Walk-In 0:00:15.316 --> 0:00:23.476 Pushkin Jake Alpern here Before we get started, I wanted 0:00:23.516 --> 0:00:26.276 you to know that deep Cover Season two will be 0:00:26.356 --> 0:00:31.436 dropping weekly on Mondays, but the full season is available 0:00:31.796 --> 0:00:36.356 right now ad free for Pushkin Plus subscribers. That's all 0:00:36.396 --> 0:00:40.956 ten episodes right away. Fine Pushkin Plus on the deep 0:00:40.996 --> 0:00:49.716 Cover show page in Apple Podcasts, or at Pushkin dot Fm. 0:00:49.756 --> 0:00:51.876 Here's the first thing I need to tell you about 0:00:51.956 --> 0:00:58.316 Robert Coolly. Officially, legally, he no longer exists. He's a ghost. 0:01:04.476 --> 0:01:07.876 For all intents and purposes, the man named Bob Cooley 0:01:08.076 --> 0:01:15.796 died decades but in reality, Bob, he's still very much alive. 0:01:18.156 --> 0:01:20.476 So your neighbors have no idea who you are. Oh no, 0:01:20.596 --> 0:01:25.076 certainly not. Does that work out for the best? No, 0:01:25.076 --> 0:01:27.636 no big thing either way. It's not a big thing 0:01:27.676 --> 0:01:30.116 either way. It's just that you know, and they wouldn't 0:01:30.156 --> 0:01:32.036 believe it. If you know, if I told my story, 0:01:32.076 --> 0:01:36.916 people wouldn't normally believe it. That's Bob. I've been interviewing 0:01:36.996 --> 0:01:40.596 him for the past year, mainly by zoom, but recently 0:01:40.836 --> 0:01:43.956 I visited him in person. He lives in this small 0:01:44.076 --> 0:01:47.556 ranch house at the edge of a vast desert somewhere 0:01:47.596 --> 0:01:51.116 in the American Southwest. I can't tell you the name 0:01:51.156 --> 0:01:53.956 of the town or even the state where he lives. 0:01:54.396 --> 0:02:02.916 And that's for Bob's own safety, all right. I got 0:02:02.916 --> 0:02:05.356 more on the floor than that kind in here. Bob's 0:02:05.396 --> 0:02:08.516 now in his late seventies. He has thick glasses and 0:02:08.596 --> 0:02:12.636 a strong jaw dotted with gray's stubble. When we met, 0:02:12.796 --> 0:02:15.676 he was wearing an old La Dodgers cap and a 0:02:15.676 --> 0:02:19.956 T shirt that said Parental Advisory Explicit Content, like the 0:02:20.036 --> 0:02:23.276 labels they used to put on CDs. The house where 0:02:23.316 --> 0:02:26.636 Bob lives isn't his. He just rents a room in it. 0:02:27.156 --> 0:02:30.076 I'll show you in my room beside his bed, the 0:02:30.076 --> 0:02:33.036 floor is cluttered with vats of V eight vegetable juice 0:02:33.196 --> 0:02:36.636 and cylinders of pringles. Sort of looks like he's preparing 0:02:36.636 --> 0:02:41.316 for a hurricane. Obviously, it's a very small room, but 0:02:41.756 --> 0:02:44.356 it's got a bed that's for I sleep well. So 0:02:44.476 --> 0:02:47.396 are all your worldly possessions in this room? Oh? Yeah, 0:02:47.476 --> 0:02:52.156 that's it. It wasn't always like this for Bob. Back 0:02:52.196 --> 0:02:55.716 before he vanished, before we ran for it, Bob lived 0:02:55.716 --> 0:02:58.916 a very different life. He was a big time lawyer 0:02:58.956 --> 0:03:01.876 in Chicago. I used to run around with thousands of 0:03:01.916 --> 0:03:04.916 dollars in my pocket and pick up everybody's checks and whatever. 0:03:05.356 --> 0:03:07.756 I would buy the most expensive thing, thinking it was 0:03:07.796 --> 0:03:13.356 the best. Bob drove around in a gleaming convertible, wore 0:03:13.396 --> 0:03:17.116 a hefty gold chain, partied at the nightclubs on Rush Street, 0:03:17.516 --> 0:03:20.756 gambled with the bookies, and dined out with the city's judges. 0:03:21.436 --> 0:03:25.756 But that was then. Today he survives on Social Security 0:03:26.036 --> 0:03:28.636 and lives in this tiny room at the edge of 0:03:28.636 --> 0:03:33.076 the desert, basically in hiding. Did you do you have 0:03:33.116 --> 0:03:35.556 any of your old IDs that you had under your 0:03:35.596 --> 0:03:38.596 fake names? Oh? Yeah, can you show them to me? 0:03:39.716 --> 0:03:42.516 Bob leads me over to his closet and pulls out 0:03:42.516 --> 0:03:45.916 a big stack of IDs and credit cards. It looks 0:03:45.916 --> 0:03:48.036 like what you might find at the Lost and Found 0:03:48.076 --> 0:03:51.116 at a ballpark. The name varies on each of these, 0:03:51.156 --> 0:03:54.116 but the face is the same, just a little older. 0:03:54.156 --> 0:03:58.396 Each time. Bob points at one id, an old driver's license. 0:03:59.716 --> 0:04:04.716 He died about ten years ago. That's you, that's a 0:04:04.756 --> 0:04:07.036 different one. Why did he die ten years ago? He 0:04:07.076 --> 0:04:09.596 had Apparently he must have had an unfortunate an accent 0:04:09.676 --> 0:04:14.036 or something. He suddenly disappeared from the face of the earth. 0:04:14.596 --> 0:04:21.356 Here's another that's a fourth name. What happens to this guy? Yeah, 0:04:21.356 --> 0:04:23.556 he had an accident too. A lot of these guys 0:04:23.596 --> 0:04:27.116 had some very bad accents. And that's how it goes 0:04:27.156 --> 0:04:30.556 with Bob. He assumes one identity for a few years, 0:04:30.916 --> 0:04:35.156 pretending to be some guy in some random town, until 0:04:35.676 --> 0:04:40.236 Bob feels that itch like he's not safe. Then that 0:04:40.276 --> 0:04:45.076 guy dies, the id gets tossed in this pile, and 0:04:45.276 --> 0:04:49.796 Bob becomes someone else. And let me assure you, there 0:04:49.956 --> 0:04:52.916 is a reason for all of this paranoia, very good reason, 0:04:53.396 --> 0:05:02.396 a backstory that explains it all, a saga. Really. Back 0:05:02.396 --> 0:05:06.796 in his heyday, when Bob Cooley was still Bob Cooley, 0:05:06.916 --> 0:05:09.836 he was the man in Chicago. People were downtown knew 0:05:09.916 --> 0:05:13.076 him as a high priced criminal defense lawyer, but to 0:05:13.116 --> 0:05:16.676 the city's gangsters, to the mob, he was much more 0:05:16.716 --> 0:05:21.156 than this. He was their guy, their insurance policy. Sure 0:05:21.276 --> 0:05:23.876 he could argue a case well enough, but if need be, 0:05:24.396 --> 0:05:27.916 he could also fix a case, place the right bribe 0:05:27.956 --> 0:05:31.516 with just the right judge, and get precisely the right verdict. 0:05:32.076 --> 0:05:34.316 He was like a get out of jail free card, 0:05:34.796 --> 0:05:39.356 only his services weren't free. And Bob he was more 0:05:39.356 --> 0:05:41.996 than just a hired hand. He was part of an 0:05:41.996 --> 0:05:45.316 elite cadre of men. They were backed by the Mob 0:05:45.596 --> 0:05:49.156 or the Chicago Outfit as it's known. They basically ran 0:05:49.316 --> 0:05:52.836 the city of Chicago. Their powerbase was the First Ward, 0:05:53.156 --> 0:05:56.396 one of the city's most powerful districts. It was a 0:05:56.436 --> 0:06:01.076 political machine run by gangsters. They had complete control over 0:06:01.116 --> 0:06:05.596 the Sheriff's Department, the Attorney General's office, the police department, 0:06:05.796 --> 0:06:11.116 all the courts. They controlled absolutely everything. So mobsters realized 0:06:11.476 --> 0:06:14.996 if they did anything, they had absolute protection for it. 0:06:17.836 --> 0:06:20.436 Bob Cooley did the bidding of the First Ward and 0:06:20.516 --> 0:06:25.236 the Outfit for almost a decade, until one day in 0:06:25.236 --> 0:06:28.356 the spring of nineteen eighty six when he decided to 0:06:28.396 --> 0:06:33.156 betray them. He just walked into a prosecutor's office and 0:06:33.276 --> 0:06:38.956 started talking. I regret having walked into that man's office 0:06:38.996 --> 0:06:42.076 like I did, probably the worst regret of my life. 0:06:42.076 --> 0:06:44.956 But nothing I can do about that. I jumped off 0:06:44.996 --> 0:06:49.836 the building. It's a decision that, even now, thirty five 0:06:49.956 --> 0:06:53.636 years later, still baffles people. Why did he do it? 0:06:54.036 --> 0:06:57.996 People are still arguing about this, not just that there 0:06:58.036 --> 0:07:01.436 are court cases going on right now where they're discussing 0:07:01.436 --> 0:07:04.276 what Bob did. And how old were you when the 0:07:04.356 --> 0:07:08.796 shooting which resulted in your incarceration. Crew was eighteen years old. 0:07:10.556 --> 0:07:13.076 There are guys in prison hoping to get out by 0:07:13.116 --> 0:07:19.196 invoking Bob's name and the secrets he revealed. Bob's legacy 0:07:19.316 --> 0:07:23.156 is still shrouded in controversy. But here's one thing that 0:07:23.236 --> 0:07:28.076 most people can agree on. After Bob Cooley flipped, the 0:07:28.156 --> 0:07:56.036 city of Chicago was never quite the same. I'm Jake 0:07:56.076 --> 0:08:00.876 Halbern and this is Deep Cover, Season two, mob Land, 0:08:02.556 --> 0:08:27.116 Episode one, The Walking. So I've been fascinated by mob 0:08:27.236 --> 0:08:29.916 stories ever since I was a kid. I must have 0:08:29.956 --> 0:08:33.876 watched The Untouchables about one hundred times. Maybe you've seen it. 0:08:33.876 --> 0:08:37.596 It's set in nineteen thirty Chicago. Robert de Niro plays 0:08:37.596 --> 0:08:41.476 al Capone, the villain, and Kevin Costner plays Elliott Ness, 0:08:41.476 --> 0:08:44.676 the clean cut law man. You know, this is generally 0:08:44.676 --> 0:08:47.316 how it goes with these films. It's the old Cops 0:08:47.316 --> 0:08:50.396 and Robbers theme. Two sides at war with one another. 0:08:50.876 --> 0:08:55.116 Fuck you got nothing, Yeah, because you've got nothing. You 0:08:55.196 --> 0:08:57.516 got nothing at caught, you not got the bookkeeper, you 0:08:57.636 --> 0:09:01.076 got nothing. From the outset, it was clear to me 0:09:01.156 --> 0:09:04.556 that Bob Cooley's story didn't fit neatly into this genre. 0:09:05.236 --> 0:09:08.236 From the moment that Bob walked into that prosecutor's office 0:09:08.276 --> 0:09:11.956 that day offered to betray the mob, he was essentially 0:09:11.996 --> 0:09:16.076 at war with himself, and in Bob's heyday, back in 0:09:16.116 --> 0:09:20.076 the seventies and eighties, the Chicago Mob was still plenty powerful. 0:09:20.396 --> 0:09:22.876 I heard stories about this from a whole bunch of people, 0:09:23.556 --> 0:09:27.516 but one of them in particular stands out. A woman 0:09:27.596 --> 0:09:30.956 named Marie Dyson told it to me. She'll eventually play 0:09:30.956 --> 0:09:34.476 an important role in our story, but right now, all 0:09:34.516 --> 0:09:36.836 you need to know is that back in the early eighties, 0:09:37.236 --> 0:09:40.916 Marie was a young FBI agent based in Chicago, and 0:09:41.036 --> 0:09:44.676 one day she got a little tutorial on how Chicago 0:09:45.036 --> 0:09:47.996 really worked. A guy laid it all out for her, 0:09:48.156 --> 0:09:51.596 and that lesson, she says, it came from a mob 0:09:51.756 --> 0:09:55.756 hit man who at the time was in custody. I 0:09:55.796 --> 0:09:59.036 remember he had real pretty eyes, and I thought, oh, 0:09:59.316 --> 0:10:03.636 this guy's smooth as silk. You know again, I'm sitting 0:10:03.676 --> 0:10:05.796 there thinking, you know, at any point in time, he 0:10:05.836 --> 0:10:09.316 can come across this table and I'm a goner. This 0:10:09.356 --> 0:10:13.316 guy had killed many, many, many people, and he just 0:10:13.396 --> 0:10:17.156 looked at me like what is your problem. You know, 0:10:17.516 --> 0:10:21.276 this is the way we do it. And I can 0:10:21.356 --> 0:10:24.196 do anything I want to do because I have an 0:10:24.196 --> 0:10:27.956 attorney that will pay any judge take care of every 0:10:27.996 --> 0:10:30.476 case I have, so I can kill anybody I want 0:10:30.516 --> 0:10:33.356 to kill. He was breaking. You know. This is the 0:10:33.396 --> 0:10:36.276 way it works, This is how it operates. This is 0:10:36.276 --> 0:10:39.996 how we get things done. The hitman said he had 0:10:40.316 --> 0:10:43.596 this attorney who could pay any judge to get him 0:10:43.596 --> 0:10:47.236 out of any jam. This hitman wasn't talking about Bob 0:10:47.356 --> 0:10:51.716 Cooley explicitly, but he could have been, because that's precisely 0:10:51.756 --> 0:10:54.996 the kind of thing that Bob did, and did very well, 0:10:55.596 --> 0:11:03.396 that is, until he switched sides and then vanished. I 0:11:03.396 --> 0:11:05.916 should tell you I'm not the first reporter to chat 0:11:05.956 --> 0:11:08.956 with Bob. Over the years. He's done a few interviews 0:11:09.116 --> 0:11:12.356 and even written a memoir. Every once in a while, 0:11:12.476 --> 0:11:15.876 Bob Cooley just kind of pops up in Virginia or 0:11:15.916 --> 0:11:20.476 Colorado or some town in the Southwest and then vanishes again, 0:11:20.956 --> 0:11:24.676 like some kind of mystical prairie dog. Some people told 0:11:24.676 --> 0:11:27.636 me that he'd gone into the witness protection program, but 0:11:27.836 --> 0:11:32.236 that wasn't true. Bob was just really good at disappearing. 0:11:34.316 --> 0:11:37.636 This meeting is being recorded. Okay. I first connected with 0:11:37.676 --> 0:11:40.516 Bob about a year ago. In fact, before Bob and 0:11:40.596 --> 0:11:43.156 I could really get started, we had I guess you'd 0:11:43.236 --> 0:11:46.636 call it some technical difficulties. There was a dog at 0:11:46.636 --> 0:11:51.476 his house and it just would not stop barking. Hey, Bob, 0:11:51.876 --> 0:11:55.756 I'm sorry to interrupt, but is there anything we can 0:11:55.756 --> 0:11:57.556 think about with the dog, because I worry if the 0:11:57.596 --> 0:11:59.116 dog keeps up, I'm not going to be able to 0:11:59.196 --> 0:12:01.156 use some of the tape. Is there any way to 0:12:02.156 --> 0:12:03.796 get him in a different part of the house or 0:12:03.836 --> 0:12:11.516 anything like that. He wasn't being serious. Bob actually loves animals. 0:12:11.876 --> 0:12:14.436 He lives with five dogs, two cats, and he loves 0:12:14.436 --> 0:12:17.756 feeding birds to pass the time. In any case, Bob 0:12:17.796 --> 0:12:21.476 took the dog outside. We continued, and pretty soon he 0:12:21.516 --> 0:12:23.996 was telling me about that day back in March of 0:12:24.076 --> 0:12:27.276 nineteen eighty six when he made his big decision to 0:12:27.276 --> 0:12:33.636 switch sides and betray the Mob. It was a Saturday. 0:12:34.036 --> 0:12:36.876 He was out for a stroll in downtown Chicago, right 0:12:36.916 --> 0:12:40.916 by the Federal Courthouse. Yes, I remember it. I was 0:12:40.956 --> 0:12:44.276 going to get a sandwich in something. I have no 0:12:44.396 --> 0:12:47.076 idea what it was. Something just said to me, I'm 0:12:47.076 --> 0:12:48.636 going to go up there, and let's go up there 0:12:48.676 --> 0:12:51.476 and let's see who is up there. There was nobody around. 0:12:52.196 --> 0:12:55.676 When he says up there, he means the eighth floor 0:12:55.716 --> 0:12:58.276 of the Federal Courthouse that was the home of the 0:12:58.396 --> 0:13:02.436 Organized Crime Strike Force, the prosecutors who went after the mob. 0:13:03.596 --> 0:13:06.996 Bob says he walked in on an impulse, just saw 0:13:07.036 --> 0:13:10.596 the empty building and thought, do this. I went in 0:13:10.676 --> 0:13:13.236 there and went upstairs to the strike for us and 0:13:13.596 --> 0:13:15.676 you know, knock on the door, and I go in, 0:13:15.796 --> 0:13:17.916 and you know, I'd like to talk to somebody here. 0:13:18.836 --> 0:13:23.076 And that somebody was a government attorney named Gary Shapiro, 0:13:23.556 --> 0:13:26.356 and he introduced himself. You know, I'm the head of 0:13:26.436 --> 0:13:28.916 the Strike for us, and I'm sure he was shocked. 0:13:29.636 --> 0:13:32.436 You know, I'm sure he knew who I was. You know, 0:13:32.476 --> 0:13:37.396 prior to that, I didn't know Bob Cooley from a 0:13:37.436 --> 0:13:40.676 man in the moon. So when I first saw him, 0:13:41.596 --> 0:13:46.196 I had no idea what to expect. As a prosecutor 0:13:46.316 --> 0:13:50.196 charged exclusively with going after the mob, Gary had a really, 0:13:50.356 --> 0:13:53.836 really hard job. It was nearly impossible to get anyone 0:13:53.876 --> 0:13:57.756 to testify against the city's gangsters. Gary says that some 0:13:57.916 --> 0:14:01.316 years seemed like there was a mob killing almost every week. 0:14:01.916 --> 0:14:05.476 In fact, Gary's first big case involving the mob fell 0:14:05.516 --> 0:14:08.396 apart when his star witness was murdered on the eve 0:14:08.436 --> 0:14:11.996 of trial. In any case, when Bob first walked into 0:14:12.036 --> 0:14:17.156 his office, Gary was intrigued but not exactly impressed. Well, 0:14:17.396 --> 0:14:19.876 I hope Bob doesn't take this personally, but he's a schlub. 0:14:20.996 --> 0:14:25.196 Bob is you know he's not. He's not impressive in 0:14:25.316 --> 0:14:27.876 terms of the way he presents himself. I don't remember 0:14:27.916 --> 0:14:31.276 if he was wearing his you know, his turtleneck and 0:14:31.476 --> 0:14:36.236 gold chains, but he probably was. Turns out this was 0:14:36.276 --> 0:14:39.236 actually a point of pride for Bob. Everybody had to 0:14:39.276 --> 0:14:42.836 wear a tie in Chicago, every lawyer, I should say, 0:14:42.876 --> 0:14:46.636 every lawyer except me. This super casual look was like 0:14:46.836 --> 0:14:50.756 Bob's dress code. No fancy suit, no tie, just a 0:14:50.796 --> 0:14:55.276 gold chain. This was all part of his branding, bling casual. 0:14:55.436 --> 0:14:58.556 I guess you could call it Gary Shapiro. He didn't 0:14:58.596 --> 0:15:01.196 know what to make of this. He's kind of shambling 0:15:01.276 --> 0:15:05.756 and he doesn't speak like a lawyer. You'd never think 0:15:05.876 --> 0:15:08.756 Bob Cooley was an attorney, and that's kind of way 0:15:08.756 --> 0:15:11.036 he present he himself. He was just this guy who 0:15:11.036 --> 0:15:15.796 came into my office completely unimpressive, and sat down and 0:15:15.916 --> 0:15:18.516 started telling me about the root of all evil, which 0:15:18.716 --> 0:15:23.076 was gambling. Illegal gambling. That's what Bob had come in 0:15:23.116 --> 0:15:26.596 to talk about initially, anyhow, and he seemed to know 0:15:26.716 --> 0:15:29.836 an awful lot about how it all worked, how the 0:15:29.956 --> 0:15:33.236 lion's share of the mob's profits came from illegal gambling, 0:15:33.596 --> 0:15:37.156 and this money funded all kinds of illegal activity, including 0:15:37.316 --> 0:15:40.316 public corruption. And look, we're not talking about a petty 0:15:40.356 --> 0:15:44.036 bribe here and there. Back in the nineteen eighties, Chicago 0:15:44.156 --> 0:15:48.276 was one of the most corrupt cities in America. Gary 0:15:48.356 --> 0:15:50.676 was a mob specialist, so he knew a lot of 0:15:50.676 --> 0:15:54.556 this already. He mainly just sat and listened and Bob 0:15:54.876 --> 0:15:57.596 he went on to explain that he himself was a 0:15:57.596 --> 0:16:00.956 big gambler and he was really good at it, but 0:16:01.436 --> 0:16:04.156 he'd seen what happened to the guys who lost, how 0:16:04.196 --> 0:16:08.156 those guys basically became slaves to the mob. You had 0:16:08.196 --> 0:16:13.516 certain paper would have a gambling debt, Judges, politicians, others 0:16:14.116 --> 0:16:17.116 who would gamble and lose a lot of money, and 0:16:17.276 --> 0:16:19.876 they were in fear of being killed or being beaten 0:16:19.956 --> 0:16:22.836 or whatever by the mob. And that's how the mob 0:16:22.836 --> 0:16:26.076 would wind up recruiting a lot of people. That's what 0:16:26.156 --> 0:16:29.356 I was talking to him about. Bob would tell Gary 0:16:29.556 --> 0:16:32.796 that he knew the mob intimately, that he was connected 0:16:32.836 --> 0:16:37.636 to corrupt elected officials, judges, and Alderman, even a state senator. 0:16:38.516 --> 0:16:40.476 Bob claimed to be at the center of all this 0:16:41.316 --> 0:16:43.436 and he was tired of it that he wanted to 0:16:43.476 --> 0:16:47.676 clean up the whole system. Now here's the really weird part. 0:16:48.276 --> 0:16:51.516 Bob was offering his services, but he didn't ask for 0:16:51.716 --> 0:16:55.036 anything in return. In fact, he says he made just 0:16:55.276 --> 0:16:59.196 one request. Bob wanted to confirm that he himself was 0:16:59.276 --> 0:17:03.556 not currently under investigation. Why, Bob claimed it was to 0:17:03.596 --> 0:17:07.396 protect his own reputation so he'd be credible if he 0:17:07.476 --> 0:17:10.716 became a witness for the FEDS. I would never cooperate 0:17:10.876 --> 0:17:13.716 or burn somebody taking help myself. I never would do that. 0:17:14.156 --> 0:17:18.676 I detested stool pigeons and people that you would sell 0:17:18.716 --> 0:17:21.476 out their friends and whatever to help themselves. I would 0:17:21.516 --> 0:17:24.556 never have done that. Bob says he didn't want anyone 0:17:24.596 --> 0:17:26.916 to say years from now that he was out to 0:17:26.916 --> 0:17:31.036 save his own skin. Gary, meanwhile, wasn't sure about what 0:17:31.076 --> 0:17:34.076 had just landed in his lap. He was a prosecutor. 0:17:34.476 --> 0:17:37.716 When he worked with informants, it was always after the 0:17:37.796 --> 0:17:40.676 cops or the FBI had vetted them. That was the 0:17:40.716 --> 0:17:44.316 proper order of things. For some reason, Bob had come 0:17:44.476 --> 0:17:48.356 directly to Gary. Why wasn't so clear, But there had 0:17:48.356 --> 0:17:52.356 to be a reason, right. The meeting ended as it began, 0:17:52.796 --> 0:17:56.956 rather mysteriously. Gary basically said, we'll be back in touch, 0:17:57.556 --> 0:18:00.796 and then Bob stood up and walked out the door. 0:18:05.836 --> 0:18:10.476 So there was Gary in his short sleeves Saturday, kind 0:18:10.476 --> 0:18:14.836 of wondering what the hell just happened. It was intriguing, 0:18:14.876 --> 0:18:20.756 for sure, but something seemed fishing. From my perspective, Bob 0:18:20.836 --> 0:18:23.716 was too good to be true. And so all of 0:18:23.796 --> 0:18:30.436 your antennae are out and you're worried about you know, 0:18:30.476 --> 0:18:34.476 why have the gods delivered this gift to me? There's 0:18:34.516 --> 0:18:37.796 got to be something wrong with this. I had profound 0:18:37.956 --> 0:18:41.916 questions about his motivation, and I get it. I felt 0:18:41.916 --> 0:18:44.356 the exact same way when Bob told me this story, 0:18:45.076 --> 0:18:47.956 And from Gary's perspective, there were a few things about 0:18:47.996 --> 0:18:51.876 this whole encounter that were more than a little puzzling. Obviously, 0:18:52.116 --> 0:18:55.436 Bob knew the dangers of talking to the FEDS, so 0:18:55.516 --> 0:18:58.516 why would Bob take the risk? I mean, he didn't 0:18:58.516 --> 0:19:00.716 seem to be on the run from the mob, and 0:19:00.796 --> 0:19:02.916 he didn't seem to be in trouble with the law either. 0:19:03.476 --> 0:19:07.436 So was Bob for real? I thought the more realistic 0:19:07.476 --> 0:19:12.356 possibility that this was another job who had a Messiah clomplex. 0:19:13.276 --> 0:19:15.636 And yet, I mean, I'm not going to turn down 0:19:15.876 --> 0:19:35.036 the Messiah. I'm not going to say no to the Messiah. 0:19:44.116 --> 0:19:47.076 Bob walked out of Gary's office under the streets of 0:19:47.116 --> 0:19:50.796 downtown Chicago and began to take stock of the situation. 0:19:51.396 --> 0:19:54.836 Once I made the step, I could not undo that. 0:19:56.036 --> 0:19:59.356 And you know, as I said, in an hour, after 0:19:59.596 --> 0:20:03.076 a minute, probably after I started talking to Gary, I 0:20:03.556 --> 0:20:07.076 regretted doing what I did. I regretted coming in there. 0:20:07.676 --> 0:20:10.996 I was mad at myself again, and you know again, 0:20:11.076 --> 0:20:14.756 couldn't understand why I did it. You know, I just couldn't. 0:20:15.156 --> 0:20:18.356 He felt like he'd thrown it all away. Everything he'd 0:20:18.396 --> 0:20:21.636 worked for. Bob had started off as a cop walking 0:20:21.676 --> 0:20:24.876 the beat, scraped his way through law school, slowly built 0:20:24.956 --> 0:20:28.516 up a successful practice as a criminal defense lawyer. He 0:20:28.676 --> 0:20:32.036 was known throughout the city no tie, gold chain Bob. 0:20:32.396 --> 0:20:34.836 He drove around in a big Chrysler that looked a 0:20:34.836 --> 0:20:37.596 bit like a Limo. For a few years, he owned 0:20:37.596 --> 0:20:40.196 a health club and was also part owner of an 0:20:40.196 --> 0:20:44.196 Italian restaurant called Greco's. He'd worked hard to gain the 0:20:44.236 --> 0:20:49.076 confidence of many powerful men, from respected judges to mob captains, 0:20:50.036 --> 0:20:53.236 so why risk all of that now? Suddenly it seemed 0:20:53.356 --> 0:20:57.676 rash crazy. Even Bob began to hope that maybe Gary 0:20:57.676 --> 0:21:01.596 Shapiro would see it this way too. I'm hoping this 0:21:01.636 --> 0:21:04.556 guy thought I was some kind of a nut and 0:21:04.676 --> 0:21:06.756 I wasn't going to call him. I was not going 0:21:06.796 --> 0:21:08.836 to call him or talk to him, or stop in 0:21:08.916 --> 0:21:12.116 to see him. And I'm hoping that nobody comes, you know, 0:21:12.276 --> 0:21:16.396 nobody comes to see me. And I'm even thinking, initially, well, 0:21:16.716 --> 0:21:19.036 if somebody comes, I'm gonna tell him. I changed my mind. 0:21:19.596 --> 0:21:22.156 Bob just hoped that Gary didn't talk to anyone with 0:21:22.236 --> 0:21:26.916 loose lips. The trick now was acting normal, just go 0:21:26.996 --> 0:21:29.796 about with my life and hoping that I wouldn't suddenly 0:21:29.836 --> 0:21:31.636 have somebody come up and shoot me in the back 0:21:31.676 --> 0:21:34.676 of the head. The one person who may have picked 0:21:34.756 --> 0:21:39.316 up on Bob's jitters was Judy d'angelus, Bob's secretary slash 0:21:39.356 --> 0:21:43.196 paralegal slash office manager. She was in her twenties, young 0:21:43.316 --> 0:21:46.836 and wide eyed. Judy she knew Bob about as well 0:21:46.836 --> 0:21:49.676 as anyone did. We were friends. I mean, I was 0:21:49.796 --> 0:21:52.196 never a girlfriend of his. I think I was the 0:21:52.196 --> 0:21:58.636 only secretary to say. And he'll admit that. Judy and 0:21:58.676 --> 0:22:01.876 Bob had a kind of instant synergy. Bob says that 0:22:01.916 --> 0:22:04.236 he trusted her from the moment he first met her. 0:22:04.596 --> 0:22:07.236 I met Judy when she was in a grocery store, 0:22:07.676 --> 0:22:10.316 just in talking to her like a very sharp girl. 0:22:11.156 --> 0:22:13.956 So I suggested, you would you want to come to 0:22:14.036 --> 0:22:17.876 work for me? And you know, oh yeah, sure, I'd 0:22:17.876 --> 0:22:21.116 love it. Whatever I mean. She had obviously no experience 0:22:21.116 --> 0:22:24.356 in the legal field, nothing like that, and I put 0:22:24.356 --> 0:22:26.596 her in charge of my whole office. Wait, what made 0:22:26.596 --> 0:22:28.316 you think, Like you met this random woman at a 0:22:28.316 --> 0:22:30.236 grocery store, Like, what makes you what made you think 0:22:30.276 --> 0:22:32.956 that she would be the right to run your whole office? 0:22:33.596 --> 0:22:36.676 I have no idea take, I don't know why, it 0:22:36.316 --> 0:22:39.116 just it just came to me. Judy knew that Bob 0:22:39.196 --> 0:22:42.356 was a big gambler. Bob bet on sports games mainly. 0:22:42.756 --> 0:22:45.716 He used a bunch of different bookies and these guys 0:22:46.076 --> 0:22:48.236 you had to pay or work out some kind of 0:22:48.356 --> 0:22:51.876 arrangement because almost all of them were backed by the mob, 0:22:52.276 --> 0:22:54.396 so you didn't want to get too deep in the hole. 0:22:55.076 --> 0:22:57.916 But for Bob, gambling was a way of life. I 0:22:57.956 --> 0:23:02.676 think he loved the the actual act of gambling and 0:23:02.836 --> 0:23:05.916 you know, getting it right. I think Bob will tell 0:23:05.956 --> 0:23:09.276 you the same thing that he was not motivated by me, 0:23:09.356 --> 0:23:11.436 but boy, if he had it, he spent it, and 0:23:11.476 --> 0:23:13.036 then if he didn't have it, he'd go out and 0:23:13.036 --> 0:23:16.276 find more. This is part of what made Bob such 0:23:16.316 --> 0:23:19.916 an exciting guy to know. He was a whirlwind of activity, 0:23:20.436 --> 0:23:23.476 and sometimes Judy loved getting swept up in it all. 0:23:23.836 --> 0:23:27.196 So did her then boyfriend now husband. They both told 0:23:27.236 --> 0:23:31.396 me Bob treated them like family. He would buy them dinner, 0:23:31.596 --> 0:23:33.676 take them out for nights on the town, get their 0:23:33.676 --> 0:23:38.196 parking tickets fixed. Bob was like their mobbed up fairy godfather, 0:23:38.516 --> 0:23:44.036 sprinkling magic dust wherever they went. But there were other 0:23:44.116 --> 0:23:48.076 moments when they caught glimpses of Bob's darker dealings. They 0:23:48.076 --> 0:23:51.596 didn't ask too many questions, but they understood the lurking 0:23:51.676 --> 0:23:55.276 dangers and this particular week, even though Judy didn't know 0:23:55.596 --> 0:23:57.756 all the details of what was going on with Bob, 0:23:58.396 --> 0:24:03.156 she knew enough to worry. I was spiritful for Bob's life. 0:24:03.996 --> 0:24:06.996 I would come into the office in the morning, and 0:24:07.036 --> 0:24:10.516 if he didn't call me right away, I didn't know 0:24:10.716 --> 0:24:16.476 if he was in a trunk somewhere dead. And I 0:24:16.596 --> 0:24:20.436 was careful about his gambling. I used to spend hours 0:24:20.436 --> 0:24:25.516 and hours checking different things, checking odds, checking numbers, checking 0:24:26.116 --> 0:24:29.316 power ratings, checking all these things. I didn't do it 0:24:29.356 --> 0:24:32.956 that week. That week, he means, the week he visited Gary, 0:24:33.356 --> 0:24:36.916 the week his life started to unravel. That week, he says, 0:24:36.916 --> 0:24:41.396 he dispensed with his usual precautions, gambled recklessly, placed several 0:24:41.436 --> 0:24:46.676 impulsive bets, and ultimately lost man. I had three or 0:24:46.716 --> 0:24:49.516 four of the worst days of my life gambling. Everything 0:24:49.556 --> 0:24:52.996 I'm doing is wrong. I'm losing I'm losing this, I'm 0:24:53.036 --> 0:24:58.116 losing that. And by now later in the week, I 0:24:58.276 --> 0:25:01.276 realized I go like one hundred and it was like 0:25:01.316 --> 0:25:05.516 one hundred ten, one hundred and twenty thousand dollars. You 0:25:05.516 --> 0:25:08.796 you kind of lost your cool a little bit, Oh, 0:25:08.876 --> 0:25:13.476 no question about it. Bob's concerns about his debts were 0:25:13.476 --> 0:25:16.476 compounded by his gnawing feeling that he hadn't seen the 0:25:16.596 --> 0:25:20.556 last of Gary Shapiro, that by walking into Gary's office, 0:25:20.596 --> 0:25:25.596 he'd put something much bigger into motion, thinking what did 0:25:25.636 --> 0:25:28.756 I do? You know? What did I do? And again 0:25:28.836 --> 0:25:34.196 I was hoping against hope that okay, that'll be the 0:25:34.316 --> 0:25:36.596 end of it. But I knew that wasn't going to 0:25:36.676 --> 0:25:39.076 be the case. I mean, I knew I'd be getting 0:25:39.116 --> 0:25:41.836 a visit. I didn't know when, but I knew I'd 0:25:41.876 --> 0:25:47.196 be getting a visit. Then one morning it happened. I 0:25:47.276 --> 0:25:50.956 walked into the office and that Judy was behind the desks, 0:25:51.756 --> 0:25:55.316 and Judy said to me, I think there's some FBI 0:25:55.396 --> 0:25:59.076 agents here to see you. In the moment she said 0:25:59.116 --> 0:26:02.636 that I knew exactly what it was. It was the 0:26:02.756 --> 0:26:06.156 thing he'd been dreading, the very thing he himself had 0:26:06.156 --> 0:26:09.996 set in motion coming right back at him for FBI 0:26:10.076 --> 0:26:36.196 agents on his doorstep, and they had questions. One of 0:26:36.236 --> 0:26:39.716 the FBI agents to visit Bob that day was Marie Dyson. 0:26:40.156 --> 0:26:43.436 Marie was in some ways an unlikely agent. She joined 0:26:43.476 --> 0:26:45.996 the bureau kind of on a whim after her dad 0:26:46.076 --> 0:26:50.636 suggested that she apply, and that began the process. And 0:26:50.676 --> 0:26:53.516 then I went to Quantico like everybody else for four 0:26:53.596 --> 0:26:57.916