1 00:00:15,316 --> 00:00:23,476 Speaker 1: Pushkin Jake Alpern here Before we get started, I wanted 2 00:00:23,516 --> 00:00:26,276 Speaker 1: you to know that deep Cover Season two will be 3 00:00:26,356 --> 00:00:31,436 Speaker 1: dropping weekly on Mondays, but the full season is available 4 00:00:31,796 --> 00:00:36,356 Speaker 1: right now ad free for Pushkin Plus subscribers. That's all 5 00:00:36,396 --> 00:00:40,956 Speaker 1: ten episodes right away. Fine Pushkin Plus on the deep 6 00:00:40,996 --> 00:00:49,716 Speaker 1: Cover show page in Apple Podcasts, or at Pushkin dot Fm. 7 00:00:49,756 --> 00:00:51,876 Speaker 1: Here's the first thing I need to tell you about 8 00:00:51,956 --> 00:00:58,316 Speaker 1: Robert Coolly. Officially, legally, he no longer exists. He's a ghost. 9 00:01:04,476 --> 00:01:07,876 Speaker 1: For all intents and purposes, the man named Bob Cooley 10 00:01:08,076 --> 00:01:15,796 Speaker 1: died decades but in reality, Bob, he's still very much alive. 11 00:01:18,156 --> 00:01:20,476 Speaker 1: So your neighbors have no idea who you are. Oh no, 12 00:01:20,596 --> 00:01:25,076 Speaker 1: certainly not. Does that work out for the best? No, 13 00:01:25,076 --> 00:01:27,636 Speaker 1: no big thing either way. It's not a big thing 14 00:01:27,676 --> 00:01:30,116 Speaker 1: either way. It's just that you know, and they wouldn't 15 00:01:30,156 --> 00:01:32,036 Speaker 1: believe it. If you know, if I told my story, 16 00:01:32,076 --> 00:01:36,916 Speaker 1: people wouldn't normally believe it. That's Bob. I've been interviewing 17 00:01:36,996 --> 00:01:40,596 Speaker 1: him for the past year, mainly by zoom, but recently 18 00:01:40,836 --> 00:01:43,956 Speaker 1: I visited him in person. He lives in this small 19 00:01:44,076 --> 00:01:47,556 Speaker 1: ranch house at the edge of a vast desert somewhere 20 00:01:47,596 --> 00:01:51,116 Speaker 1: in the American Southwest. I can't tell you the name 21 00:01:51,156 --> 00:01:53,956 Speaker 1: of the town or even the state where he lives. 22 00:01:54,396 --> 00:02:02,916 Speaker 1: And that's for Bob's own safety, all right. I got 23 00:02:02,916 --> 00:02:05,356 Speaker 1: more on the floor than that kind in here. Bob's 24 00:02:05,396 --> 00:02:08,516 Speaker 1: now in his late seventies. He has thick glasses and 25 00:02:08,596 --> 00:02:12,636 Speaker 1: a strong jaw dotted with gray's stubble. When we met, 26 00:02:12,796 --> 00:02:15,676 Speaker 1: he was wearing an old La Dodgers cap and a 27 00:02:15,676 --> 00:02:19,956 Speaker 1: T shirt that said Parental Advisory Explicit Content, like the 28 00:02:20,036 --> 00:02:23,276 Speaker 1: labels they used to put on CDs. The house where 29 00:02:23,316 --> 00:02:26,636 Speaker 1: Bob lives isn't his. He just rents a room in it. 30 00:02:27,156 --> 00:02:30,076 Speaker 1: I'll show you in my room beside his bed, the 31 00:02:30,076 --> 00:02:33,036 Speaker 1: floor is cluttered with vats of V eight vegetable juice 32 00:02:33,196 --> 00:02:36,636 Speaker 1: and cylinders of pringles. Sort of looks like he's preparing 33 00:02:36,636 --> 00:02:41,316 Speaker 1: for a hurricane. Obviously, it's a very small room, but 34 00:02:41,756 --> 00:02:44,356 Speaker 1: it's got a bed that's for I sleep well. So 35 00:02:44,476 --> 00:02:47,396 Speaker 1: are all your worldly possessions in this room? Oh? Yeah, 36 00:02:47,476 --> 00:02:52,156 Speaker 1: that's it. It wasn't always like this for Bob. Back 37 00:02:52,196 --> 00:02:55,716 Speaker 1: before he vanished, before we ran for it, Bob lived 38 00:02:55,716 --> 00:02:58,916 Speaker 1: a very different life. He was a big time lawyer 39 00:02:58,956 --> 00:03:01,876 Speaker 1: in Chicago. I used to run around with thousands of 40 00:03:01,916 --> 00:03:04,916 Speaker 1: dollars in my pocket and pick up everybody's checks and whatever. 41 00:03:05,356 --> 00:03:07,756 Speaker 1: I would buy the most expensive thing, thinking it was 42 00:03:07,796 --> 00:03:13,356 Speaker 1: the best. Bob drove around in a gleaming convertible, wore 43 00:03:13,396 --> 00:03:17,116 Speaker 1: a hefty gold chain, partied at the nightclubs on Rush Street, 44 00:03:17,516 --> 00:03:20,756 Speaker 1: gambled with the bookies, and dined out with the city's judges. 45 00:03:21,436 --> 00:03:25,756 Speaker 1: But that was then. Today he survives on Social Security 46 00:03:26,036 --> 00:03:28,636 Speaker 1: and lives in this tiny room at the edge of 47 00:03:28,636 --> 00:03:33,076 Speaker 1: the desert, basically in hiding. Did you do you have 48 00:03:33,116 --> 00:03:35,556 Speaker 1: any of your old IDs that you had under your 49 00:03:35,596 --> 00:03:38,596 Speaker 1: fake names? Oh? Yeah, can you show them to me? 50 00:03:39,716 --> 00:03:42,516 Speaker 1: Bob leads me over to his closet and pulls out 51 00:03:42,516 --> 00:03:45,916 Speaker 1: a big stack of IDs and credit cards. It looks 52 00:03:45,916 --> 00:03:48,036 Speaker 1: like what you might find at the Lost and Found 53 00:03:48,076 --> 00:03:51,116 Speaker 1: at a ballpark. The name varies on each of these, 54 00:03:51,156 --> 00:03:54,116 Speaker 1: but the face is the same, just a little older. 55 00:03:54,156 --> 00:03:58,396 Speaker 1: Each time. Bob points at one id, an old driver's license. 56 00:03:59,716 --> 00:04:04,716 Speaker 1: He died about ten years ago. That's you, that's a 57 00:04:04,756 --> 00:04:07,036 Speaker 1: different one. Why did he die ten years ago? He 58 00:04:07,076 --> 00:04:09,596 Speaker 1: had Apparently he must have had an unfortunate an accent 59 00:04:09,676 --> 00:04:14,036 Speaker 1: or something. He suddenly disappeared from the face of the earth. 60 00:04:14,596 --> 00:04:21,356 Speaker 1: Here's another that's a fourth name. What happens to this guy? Yeah, 61 00:04:21,356 --> 00:04:23,556 Speaker 1: he had an accident too. A lot of these guys 62 00:04:23,596 --> 00:04:27,116 Speaker 1: had some very bad accents. And that's how it goes 63 00:04:27,156 --> 00:04:30,556 Speaker 1: with Bob. He assumes one identity for a few years, 64 00:04:30,916 --> 00:04:35,156 Speaker 1: pretending to be some guy in some random town, until 65 00:04:35,676 --> 00:04:40,236 Speaker 1: Bob feels that itch like he's not safe. Then that 66 00:04:40,276 --> 00:04:45,076 Speaker 1: guy dies, the id gets tossed in this pile, and 67 00:04:45,276 --> 00:04:49,796 Speaker 1: Bob becomes someone else. And let me assure you, there 68 00:04:49,956 --> 00:04:52,916 Speaker 1: is a reason for all of this paranoia, very good reason, 69 00:04:53,396 --> 00:05:02,396 Speaker 1: a backstory that explains it all, a saga. Really. Back 70 00:05:02,396 --> 00:05:06,796 Speaker 1: in his heyday, when Bob Cooley was still Bob Cooley, 71 00:05:06,916 --> 00:05:09,836 Speaker 1: he was the man in Chicago. People were downtown knew 72 00:05:09,916 --> 00:05:13,076 Speaker 1: him as a high priced criminal defense lawyer, but to 73 00:05:13,116 --> 00:05:16,676 Speaker 1: the city's gangsters, to the mob, he was much more 74 00:05:16,716 --> 00:05:21,156 Speaker 1: than this. He was their guy, their insurance policy. Sure 75 00:05:21,276 --> 00:05:23,876 Speaker 1: he could argue a case well enough, but if need be, 76 00:05:24,396 --> 00:05:27,916 Speaker 1: he could also fix a case, place the right bribe 77 00:05:27,956 --> 00:05:31,516 Speaker 1: with just the right judge, and get precisely the right verdict. 78 00:05:32,076 --> 00:05:34,316 Speaker 1: He was like a get out of jail free card, 79 00:05:34,796 --> 00:05:39,356 Speaker 1: only his services weren't free. And Bob he was more 80 00:05:39,356 --> 00:05:41,996 Speaker 1: than just a hired hand. He was part of an 81 00:05:41,996 --> 00:05:45,316 Speaker 1: elite cadre of men. They were backed by the Mob 82 00:05:45,596 --> 00:05:49,156 Speaker 1: or the Chicago Outfit as it's known. They basically ran 83 00:05:49,316 --> 00:05:52,836 Speaker 1: the city of Chicago. Their powerbase was the First Ward, 84 00:05:53,156 --> 00:05:56,396 Speaker 1: one of the city's most powerful districts. It was a 85 00:05:56,436 --> 00:06:01,076 Speaker 1: political machine run by gangsters. They had complete control over 86 00:06:01,116 --> 00:06:05,596 Speaker 1: the Sheriff's Department, the Attorney General's office, the police department, 87 00:06:05,796 --> 00:06:11,116 Speaker 1: all the courts. They controlled absolutely everything. So mobsters realized 88 00:06:11,476 --> 00:06:14,996 Speaker 1: if they did anything, they had absolute protection for it. 89 00:06:17,836 --> 00:06:20,436 Speaker 1: Bob Cooley did the bidding of the First Ward and 90 00:06:20,516 --> 00:06:25,236 Speaker 1: the Outfit for almost a decade, until one day in 91 00:06:25,236 --> 00:06:28,356 Speaker 1: the spring of nineteen eighty six when he decided to 92 00:06:28,396 --> 00:06:33,156 Speaker 1: betray them. He just walked into a prosecutor's office and 93 00:06:33,276 --> 00:06:38,956 Speaker 1: started talking. I regret having walked into that man's office 94 00:06:38,996 --> 00:06:42,076 Speaker 1: like I did, probably the worst regret of my life. 95 00:06:42,076 --> 00:06:44,956 Speaker 1: But nothing I can do about that. I jumped off 96 00:06:44,996 --> 00:06:49,836 Speaker 1: the building. It's a decision that, even now, thirty five 97 00:06:49,956 --> 00:06:53,636 Speaker 1: years later, still baffles people. Why did he do it? 98 00:06:54,036 --> 00:06:57,996 Speaker 1: People are still arguing about this, not just that there 99 00:06:58,036 --> 00:07:01,436 Speaker 1: are court cases going on right now where they're discussing 100 00:07:01,436 --> 00:07:04,276 Speaker 1: what Bob did. And how old were you when the 101 00:07:04,356 --> 00:07:08,796 Speaker 1: shooting which resulted in your incarceration. Crew was eighteen years old. 102 00:07:10,556 --> 00:07:13,076 Speaker 1: There are guys in prison hoping to get out by 103 00:07:13,116 --> 00:07:19,196 Speaker 1: invoking Bob's name and the secrets he revealed. Bob's legacy 104 00:07:19,316 --> 00:07:23,156 Speaker 1: is still shrouded in controversy. But here's one thing that 105 00:07:23,236 --> 00:07:28,076 Speaker 1: most people can agree on. After Bob Cooley flipped, the 106 00:07:28,156 --> 00:07:56,036 Speaker 1: city of Chicago was never quite the same. I'm Jake 107 00:07:56,076 --> 00:08:00,876 Speaker 1: Halbern and this is Deep Cover, Season two, mob Land, 108 00:08:02,556 --> 00:08:27,116 Speaker 1: Episode one, The Walking. So I've been fascinated by mob 109 00:08:27,236 --> 00:08:29,916 Speaker 1: stories ever since I was a kid. I must have 110 00:08:29,956 --> 00:08:33,876 Speaker 1: watched The Untouchables about one hundred times. Maybe you've seen it. 111 00:08:33,876 --> 00:08:37,596 Speaker 1: It's set in nineteen thirty Chicago. Robert de Niro plays 112 00:08:37,596 --> 00:08:41,476 Speaker 1: al Capone, the villain, and Kevin Costner plays Elliott Ness, 113 00:08:41,476 --> 00:08:44,676 Speaker 1: the clean cut law man. You know, this is generally 114 00:08:44,676 --> 00:08:47,316 Speaker 1: how it goes with these films. It's the old Cops 115 00:08:47,316 --> 00:08:50,396 Speaker 1: and Robbers theme. Two sides at war with one another. 116 00:08:50,876 --> 00:08:55,116 Speaker 1: Fuck you got nothing, Yeah, because you've got nothing. You 117 00:08:55,196 --> 00:08:57,516 Speaker 1: got nothing at caught, you not got the bookkeeper, you 118 00:08:57,636 --> 00:09:01,076 Speaker 1: got nothing. From the outset, it was clear to me 119 00:09:01,156 --> 00:09:04,556 Speaker 1: that Bob Cooley's story didn't fit neatly into this genre. 120 00:09:05,236 --> 00:09:08,236 Speaker 1: From the moment that Bob walked into that prosecutor's office 121 00:09:08,276 --> 00:09:11,956 Speaker 1: that day offered to betray the mob, he was essentially 122 00:09:11,996 --> 00:09:16,076 Speaker 1: at war with himself, and in Bob's heyday, back in 123 00:09:16,116 --> 00:09:20,076 Speaker 1: the seventies and eighties, the Chicago Mob was still plenty powerful. 124 00:09:20,396 --> 00:09:22,876 Speaker 1: I heard stories about this from a whole bunch of people, 125 00:09:23,556 --> 00:09:27,516 Speaker 1: but one of them in particular stands out. A woman 126 00:09:27,596 --> 00:09:30,956 Speaker 1: named Marie Dyson told it to me. She'll eventually play 127 00:09:30,956 --> 00:09:34,476 Speaker 1: an important role in our story, but right now, all 128 00:09:34,516 --> 00:09:36,836 Speaker 1: you need to know is that back in the early eighties, 129 00:09:37,236 --> 00:09:40,916 Speaker 1: Marie was a young FBI agent based in Chicago, and 130 00:09:41,036 --> 00:09:44,676 Speaker 1: one day she got a little tutorial on how Chicago 131 00:09:45,036 --> 00:09:47,996 Speaker 1: really worked. A guy laid it all out for her, 132 00:09:48,156 --> 00:09:51,596 Speaker 1: and that lesson, she says, it came from a mob 133 00:09:51,756 --> 00:09:55,756 Speaker 1: hit man who at the time was in custody. I 134 00:09:55,796 --> 00:09:59,036 Speaker 1: remember he had real pretty eyes, and I thought, oh, 135 00:09:59,316 --> 00:10:03,636 Speaker 1: this guy's smooth as silk. You know again, I'm sitting 136 00:10:03,676 --> 00:10:05,796 Speaker 1: there thinking, you know, at any point in time, he 137 00:10:05,836 --> 00:10:09,316 Speaker 1: can come across this table and I'm a goner. This 138 00:10:09,356 --> 00:10:13,316 Speaker 1: guy had killed many, many, many people, and he just 139 00:10:13,396 --> 00:10:17,156 Speaker 1: looked at me like what is your problem. You know, 140 00:10:17,516 --> 00:10:21,276 Speaker 1: this is the way we do it. And I can 141 00:10:21,356 --> 00:10:24,196 Speaker 1: do anything I want to do because I have an 142 00:10:24,196 --> 00:10:27,956 Speaker 1: attorney that will pay any judge take care of every 143 00:10:27,996 --> 00:10:30,476 Speaker 1: case I have, so I can kill anybody I want 144 00:10:30,516 --> 00:10:33,356 Speaker 1: to kill. He was breaking. You know. This is the 145 00:10:33,396 --> 00:10:36,276 Speaker 1: way it works, This is how it operates. This is 146 00:10:36,276 --> 00:10:39,996 Speaker 1: how we get things done. The hitman said he had 147 00:10:40,316 --> 00:10:43,596 Speaker 1: this attorney who could pay any judge to get him 148 00:10:43,596 --> 00:10:47,236 Speaker 1: out of any jam. This hitman wasn't talking about Bob 149 00:10:47,356 --> 00:10:51,716 Speaker 1: Cooley explicitly, but he could have been, because that's precisely 150 00:10:51,756 --> 00:10:54,996 Speaker 1: the kind of thing that Bob did, and did very well, 151 00:10:55,596 --> 00:11:03,396 Speaker 1: that is, until he switched sides and then vanished. I 152 00:11:03,396 --> 00:11:05,916 Speaker 1: should tell you I'm not the first reporter to chat 153 00:11:05,956 --> 00:11:08,956 Speaker 1: with Bob. Over the years. He's done a few interviews 154 00:11:09,116 --> 00:11:12,356 Speaker 1: and even written a memoir. Every once in a while, 155 00:11:12,476 --> 00:11:15,876 Speaker 1: Bob Cooley just kind of pops up in Virginia or 156 00:11:15,916 --> 00:11:20,476 Speaker 1: Colorado or some town in the Southwest and then vanishes again, 157 00:11:20,956 --> 00:11:24,676 Speaker 1: like some kind of mystical prairie dog. Some people told 158 00:11:24,676 --> 00:11:27,636 Speaker 1: me that he'd gone into the witness protection program, but 159 00:11:27,836 --> 00:11:32,236 Speaker 1: that wasn't true. Bob was just really good at disappearing. 160 00:11:34,316 --> 00:11:37,636 Speaker 1: This meeting is being recorded. Okay. I first connected with 161 00:11:37,676 --> 00:11:40,516 Speaker 1: Bob about a year ago. In fact, before Bob and 162 00:11:40,596 --> 00:11:43,156 Speaker 1: I could really get started, we had I guess you'd 163 00:11:43,236 --> 00:11:46,636 Speaker 1: call it some technical difficulties. There was a dog at 164 00:11:46,636 --> 00:11:51,476 Speaker 1: his house and it just would not stop barking. Hey, Bob, 165 00:11:51,876 --> 00:11:55,756 Speaker 1: I'm sorry to interrupt, but is there anything we can 166 00:11:55,756 --> 00:11:57,556 Speaker 1: think about with the dog, because I worry if the 167 00:11:57,596 --> 00:11:59,116 Speaker 1: dog keeps up, I'm not going to be able to 168 00:11:59,196 --> 00:12:01,156 Speaker 1: use some of the tape. Is there any way to 169 00:12:02,156 --> 00:12:03,796 Speaker 1: get him in a different part of the house or 170 00:12:03,836 --> 00:12:11,516 Speaker 1: anything like that. He wasn't being serious. Bob actually loves animals. 171 00:12:11,876 --> 00:12:14,436 Speaker 1: He lives with five dogs, two cats, and he loves 172 00:12:14,436 --> 00:12:17,756 Speaker 1: feeding birds to pass the time. In any case, Bob 173 00:12:17,796 --> 00:12:21,476 Speaker 1: took the dog outside. We continued, and pretty soon he 174 00:12:21,516 --> 00:12:23,996 Speaker 1: was telling me about that day back in March of 175 00:12:24,076 --> 00:12:27,276 Speaker 1: nineteen eighty six when he made his big decision to 176 00:12:27,276 --> 00:12:33,636 Speaker 1: switch sides and betray the Mob. It was a Saturday. 177 00:12:34,036 --> 00:12:36,876 Speaker 1: He was out for a stroll in downtown Chicago, right 178 00:12:36,916 --> 00:12:40,916 Speaker 1: by the Federal Courthouse. Yes, I remember it. I was 179 00:12:40,956 --> 00:12:44,276 Speaker 1: going to get a sandwich in something. I have no 180 00:12:44,396 --> 00:12:47,076 Speaker 1: idea what it was. Something just said to me, I'm 181 00:12:47,076 --> 00:12:48,636 Speaker 1: going to go up there, and let's go up there 182 00:12:48,676 --> 00:12:51,476 Speaker 1: and let's see who is up there. There was nobody around. 183 00:12:52,196 --> 00:12:55,676 Speaker 1: When he says up there, he means the eighth floor 184 00:12:55,716 --> 00:12:58,276 Speaker 1: of the Federal Courthouse that was the home of the 185 00:12:58,396 --> 00:13:02,436 Speaker 1: Organized Crime Strike Force, the prosecutors who went after the mob. 186 00:13:03,596 --> 00:13:06,996 Speaker 1: Bob says he walked in on an impulse, just saw 187 00:13:07,036 --> 00:13:10,596 Speaker 1: the empty building and thought, do this. I went in 188 00:13:10,676 --> 00:13:13,236 Speaker 1: there and went upstairs to the strike for us and 189 00:13:13,596 --> 00:13:15,676 Speaker 1: you know, knock on the door, and I go in, 190 00:13:15,796 --> 00:13:17,916 Speaker 1: and you know, I'd like to talk to somebody here. 191 00:13:18,836 --> 00:13:23,076 Speaker 1: And that somebody was a government attorney named Gary Shapiro, 192 00:13:23,556 --> 00:13:26,356 Speaker 1: and he introduced himself. You know, I'm the head of 193 00:13:26,436 --> 00:13:28,916 Speaker 1: the Strike for us, and I'm sure he was shocked. 194 00:13:29,636 --> 00:13:32,436 Speaker 1: You know, I'm sure he knew who I was. You know, 195 00:13:32,476 --> 00:13:37,396 Speaker 1: prior to that, I didn't know Bob Cooley from a 196 00:13:37,436 --> 00:13:40,676 Speaker 1: man in the moon. So when I first saw him, 197 00:13:41,596 --> 00:13:46,196 Speaker 1: I had no idea what to expect. As a prosecutor 198 00:13:46,316 --> 00:13:50,196 Speaker 1: charged exclusively with going after the mob, Gary had a really, 199 00:13:50,356 --> 00:13:53,836 Speaker 1: really hard job. It was nearly impossible to get anyone 200 00:13:53,876 --> 00:13:57,756 Speaker 1: to testify against the city's gangsters. Gary says that some 201 00:13:57,916 --> 00:14:01,316 Speaker 1: years seemed like there was a mob killing almost every week. 202 00:14:01,916 --> 00:14:05,476 Speaker 1: In fact, Gary's first big case involving the mob fell 203 00:14:05,516 --> 00:14:08,396 Speaker 1: apart when his star witness was murdered on the eve 204 00:14:08,436 --> 00:14:11,996 Speaker 1: of trial. In any case, when Bob first walked into 205 00:14:12,036 --> 00:14:17,156 Speaker 1: his office, Gary was intrigued but not exactly impressed. Well, 206 00:14:17,396 --> 00:14:19,876 Speaker 1: I hope Bob doesn't take this personally, but he's a schlub. 207 00:14:20,996 --> 00:14:25,196 Speaker 1: Bob is you know he's not. He's not impressive in 208 00:14:25,316 --> 00:14:27,876 Speaker 1: terms of the way he presents himself. I don't remember 209 00:14:27,916 --> 00:14:31,276 Speaker 1: if he was wearing his you know, his turtleneck and 210 00:14:31,476 --> 00:14:36,236 Speaker 1: gold chains, but he probably was. Turns out this was 211 00:14:36,276 --> 00:14:39,236 Speaker 1: actually a point of pride for Bob. Everybody had to 212 00:14:39,276 --> 00:14:42,836 Speaker 1: wear a tie in Chicago, every lawyer, I should say, 213 00:14:42,876 --> 00:14:46,636 Speaker 1: every lawyer except me. This super casual look was like 214 00:14:46,836 --> 00:14:50,756 Speaker 1: Bob's dress code. No fancy suit, no tie, just a 215 00:14:50,796 --> 00:14:55,276 Speaker 1: gold chain. This was all part of his branding, bling casual. 216 00:14:55,436 --> 00:14:58,556 Speaker 1: I guess you could call it Gary Shapiro. He didn't 217 00:14:58,596 --> 00:15:01,196 Speaker 1: know what to make of this. He's kind of shambling 218 00:15:01,276 --> 00:15:05,756 Speaker 1: and he doesn't speak like a lawyer. You'd never think 219 00:15:05,876 --> 00:15:08,756 Speaker 1: Bob Cooley was an attorney, and that's kind of way 220 00:15:08,756 --> 00:15:11,036 Speaker 1: he present he himself. He was just this guy who 221 00:15:11,036 --> 00:15:15,796 Speaker 1: came into my office completely unimpressive, and sat down and 222 00:15:15,916 --> 00:15:18,516 Speaker 1: started telling me about the root of all evil, which 223 00:15:18,716 --> 00:15:23,076 Speaker 1: was gambling. Illegal gambling. That's what Bob had come in 224 00:15:23,116 --> 00:15:26,596 Speaker 1: to talk about initially, anyhow, and he seemed to know 225 00:15:26,716 --> 00:15:29,836 Speaker 1: an awful lot about how it all worked, how the 226 00:15:29,956 --> 00:15:33,236 Speaker 1: lion's share of the mob's profits came from illegal gambling, 227 00:15:33,596 --> 00:15:37,156 Speaker 1: and this money funded all kinds of illegal activity, including 228 00:15:37,316 --> 00:15:40,316 Speaker 1: public corruption. And look, we're not talking about a petty 229 00:15:40,356 --> 00:15:44,036 Speaker 1: bribe here and there. Back in the nineteen eighties, Chicago 230 00:15:44,156 --> 00:15:48,276 Speaker 1: was one of the most corrupt cities in America. Gary 231 00:15:48,356 --> 00:15:50,676 Speaker 1: was a mob specialist, so he knew a lot of 232 00:15:50,676 --> 00:15:54,556 Speaker 1: this already. He mainly just sat and listened and Bob 233 00:15:54,876 --> 00:15:57,596 Speaker 1: he went on to explain that he himself was a 234 00:15:57,596 --> 00:16:00,956 Speaker 1: big gambler and he was really good at it, but 235 00:16:01,436 --> 00:16:04,156 Speaker 1: he'd seen what happened to the guys who lost, how 236 00:16:04,196 --> 00:16:08,156 Speaker 1: those guys basically became slaves to the mob. You had 237 00:16:08,196 --> 00:16:13,516 Speaker 1: certain paper would have a gambling debt, Judges, politicians, others 238 00:16:14,116 --> 00:16:17,116 Speaker 1: who would gamble and lose a lot of money, and 239 00:16:17,276 --> 00:16:19,876 Speaker 1: they were in fear of being killed or being beaten 240 00:16:19,956 --> 00:16:22,836 Speaker 1: or whatever by the mob. And that's how the mob 241 00:16:22,836 --> 00:16:26,076 Speaker 1: would wind up recruiting a lot of people. That's what 242 00:16:26,156 --> 00:16:29,356 Speaker 1: I was talking to him about. Bob would tell Gary 243 00:16:29,556 --> 00:16:32,796 Speaker 1: that he knew the mob intimately, that he was connected 244 00:16:32,836 --> 00:16:37,636 Speaker 1: to corrupt elected officials, judges, and Alderman, even a state senator. 245 00:16:38,516 --> 00:16:40,476 Speaker 1: Bob claimed to be at the center of all this 246 00:16:41,316 --> 00:16:43,436 Speaker 1: and he was tired of it that he wanted to 247 00:16:43,476 --> 00:16:47,676 Speaker 1: clean up the whole system. Now here's the really weird part. 248 00:16:48,276 --> 00:16:51,516 Speaker 1: Bob was offering his services, but he didn't ask for 249 00:16:51,716 --> 00:16:55,036 Speaker 1: anything in return. In fact, he says he made just 250 00:16:55,276 --> 00:16:59,196 Speaker 1: one request. Bob wanted to confirm that he himself was 251 00:16:59,276 --> 00:17:03,556 Speaker 1: not currently under investigation. Why, Bob claimed it was to 252 00:17:03,596 --> 00:17:07,396 Speaker 1: protect his own reputation so he'd be credible if he 253 00:17:07,476 --> 00:17:10,716 Speaker 1: became a witness for the FEDS. I would never cooperate 254 00:17:10,876 --> 00:17:13,716 Speaker 1: or burn somebody taking help myself. I never would do that. 255 00:17:14,156 --> 00:17:18,676 Speaker 1: I detested stool pigeons and people that you would sell 256 00:17:18,716 --> 00:17:21,476 Speaker 1: out their friends and whatever to help themselves. I would 257 00:17:21,516 --> 00:17:24,556 Speaker 1: never have done that. Bob says he didn't want anyone 258 00:17:24,596 --> 00:17:26,916 Speaker 1: to say years from now that he was out to 259 00:17:26,916 --> 00:17:31,036 Speaker 1: save his own skin. Gary, meanwhile, wasn't sure about what 260 00:17:31,076 --> 00:17:34,076 Speaker 1: had just landed in his lap. He was a prosecutor. 261 00:17:34,476 --> 00:17:37,716 Speaker 1: When he worked with informants, it was always after the 262 00:17:37,796 --> 00:17:40,676 Speaker 1: cops or the FBI had vetted them. That was the 263 00:17:40,716 --> 00:17:44,316 Speaker 1: proper order of things. For some reason, Bob had come 264 00:17:44,476 --> 00:17:48,356 Speaker 1: directly to Gary. Why wasn't so clear, But there had 265 00:17:48,356 --> 00:17:52,356 Speaker 1: to be a reason, right. The meeting ended as it began, 266 00:17:52,796 --> 00:17:56,956 Speaker 1: rather mysteriously. Gary basically said, we'll be back in touch, 267 00:17:57,556 --> 00:18:00,796 Speaker 1: and then Bob stood up and walked out the door. 268 00:18:05,836 --> 00:18:10,476 Speaker 1: So there was Gary in his short sleeves Saturday, kind 269 00:18:10,476 --> 00:18:14,836 Speaker 1: of wondering what the hell just happened. It was intriguing, 270 00:18:14,876 --> 00:18:20,756 Speaker 1: for sure, but something seemed fishing. From my perspective, Bob 271 00:18:20,836 --> 00:18:23,716 Speaker 1: was too good to be true. And so all of 272 00:18:23,796 --> 00:18:30,436 Speaker 1: your antennae are out and you're worried about you know, 273 00:18:30,476 --> 00:18:34,476 Speaker 1: why have the gods delivered this gift to me? There's 274 00:18:34,516 --> 00:18:37,796 Speaker 1: got to be something wrong with this. I had profound 275 00:18:37,956 --> 00:18:41,916 Speaker 1: questions about his motivation, and I get it. I felt 276 00:18:41,916 --> 00:18:44,356 Speaker 1: the exact same way when Bob told me this story, 277 00:18:45,076 --> 00:18:47,956 Speaker 1: And from Gary's perspective, there were a few things about 278 00:18:47,996 --> 00:18:51,876 Speaker 1: this whole encounter that were more than a little puzzling. Obviously, 279 00:18:52,116 --> 00:18:55,436 Speaker 1: Bob knew the dangers of talking to the FEDS, so 280 00:18:55,516 --> 00:18:58,516 Speaker 1: why would Bob take the risk? I mean, he didn't 281 00:18:58,516 --> 00:19:00,716 Speaker 1: seem to be on the run from the mob, and 282 00:19:00,796 --> 00:19:02,916 Speaker 1: he didn't seem to be in trouble with the law either. 283 00:19:03,476 --> 00:19:07,436 Speaker 1: So was Bob for real? I thought the more realistic 284 00:19:07,476 --> 00:19:12,356 Speaker 1: possibility that this was another job who had a Messiah clomplex. 285 00:19:13,276 --> 00:19:15,636 Speaker 1: And yet, I mean, I'm not going to turn down 286 00:19:15,876 --> 00:19:35,036 Speaker 1: the Messiah. I'm not going to say no to the Messiah. 287 00:19:44,116 --> 00:19:47,076 Speaker 1: Bob walked out of Gary's office under the streets of 288 00:19:47,116 --> 00:19:50,796 Speaker 1: downtown Chicago and began to take stock of the situation. 289 00:19:51,396 --> 00:19:54,836 Speaker 1: Once I made the step, I could not undo that. 290 00:19:56,036 --> 00:19:59,356 Speaker 1: And you know, as I said, in an hour, after 291 00:19:59,596 --> 00:20:03,076 Speaker 1: a minute, probably after I started talking to Gary, I 292 00:20:03,556 --> 00:20:07,076 Speaker 1: regretted doing what I did. I regretted coming in there. 293 00:20:07,676 --> 00:20:10,996 Speaker 1: I was mad at myself again, and you know again, 294 00:20:11,076 --> 00:20:14,756 Speaker 1: couldn't understand why I did it. You know, I just couldn't. 295 00:20:15,156 --> 00:20:18,356 Speaker 1: He felt like he'd thrown it all away. Everything he'd 296 00:20:18,396 --> 00:20:21,636 Speaker 1: worked for. Bob had started off as a cop walking 297 00:20:21,676 --> 00:20:24,876 Speaker 1: the beat, scraped his way through law school, slowly built 298 00:20:24,956 --> 00:20:28,516 Speaker 1: up a successful practice as a criminal defense lawyer. He 299 00:20:28,676 --> 00:20:32,036 Speaker 1: was known throughout the city no tie, gold chain Bob. 300 00:20:32,396 --> 00:20:34,836 Speaker 1: He drove around in a big Chrysler that looked a 301 00:20:34,836 --> 00:20:37,596 Speaker 1: bit like a Limo. For a few years, he owned 302 00:20:37,596 --> 00:20:40,196 Speaker 1: a health club and was also part owner of an 303 00:20:40,196 --> 00:20:44,196 Speaker 1: Italian restaurant called Greco's. He'd worked hard to gain the 304 00:20:44,236 --> 00:20:49,076 Speaker 1: confidence of many powerful men, from respected judges to mob captains, 305 00:20:50,036 --> 00:20:53,236 Speaker 1: so why risk all of that now? Suddenly it seemed 306 00:20:53,356 --> 00:20:57,676 Speaker 1: rash crazy. Even Bob began to hope that maybe Gary 307 00:20:57,676 --> 00:21:01,596 Speaker 1: Shapiro would see it this way too. I'm hoping this 308 00:21:01,636 --> 00:21:04,556 Speaker 1: guy thought I was some kind of a nut and 309 00:21:04,676 --> 00:21:06,756 Speaker 1: I wasn't going to call him. I was not going 310 00:21:06,796 --> 00:21:08,836 Speaker 1: to call him or talk to him, or stop in 311 00:21:08,916 --> 00:21:12,116 Speaker 1: to see him. And I'm hoping that nobody comes, you know, 312 00:21:12,276 --> 00:21:16,396 Speaker 1: nobody comes to see me. And I'm even thinking, initially, well, 313 00:21:16,716 --> 00:21:19,036 Speaker 1: if somebody comes, I'm gonna tell him. I changed my mind. 314 00:21:19,596 --> 00:21:22,156 Speaker 1: Bob just hoped that Gary didn't talk to anyone with 315 00:21:22,236 --> 00:21:26,916 Speaker 1: loose lips. The trick now was acting normal, just go 316 00:21:26,996 --> 00:21:29,796 Speaker 1: about with my life and hoping that I wouldn't suddenly 317 00:21:29,836 --> 00:21:31,636 Speaker 1: have somebody come up and shoot me in the back 318 00:21:31,676 --> 00:21:34,676 Speaker 1: of the head. The one person who may have picked 319 00:21:34,756 --> 00:21:39,316 Speaker 1: up on Bob's jitters was Judy d'angelus, Bob's secretary slash 320 00:21:39,356 --> 00:21:43,196 Speaker 1: paralegal slash office manager. She was in her twenties, young 321 00:21:43,316 --> 00:21:46,836 Speaker 1: and wide eyed. Judy she knew Bob about as well 322 00:21:46,836 --> 00:21:49,676 Speaker 1: as anyone did. We were friends. I mean, I was 323 00:21:49,796 --> 00:21:52,196 Speaker 1: never a girlfriend of his. I think I was the 324 00:21:52,196 --> 00:21:58,636 Speaker 1: only secretary to say. And he'll admit that. Judy and 325 00:21:58,676 --> 00:22:01,876 Speaker 1: Bob had a kind of instant synergy. Bob says that 326 00:22:01,916 --> 00:22:04,236 Speaker 1: he trusted her from the moment he first met her. 327 00:22:04,596 --> 00:22:07,236 Speaker 1: I met Judy when she was in a grocery store, 328 00:22:07,676 --> 00:22:10,316 Speaker 1: just in talking to her like a very sharp girl. 329 00:22:11,156 --> 00:22:13,956 Speaker 1: So I suggested, you would you want to come to 330 00:22:14,036 --> 00:22:17,876 Speaker 1: work for me? And you know, oh yeah, sure, I'd 331 00:22:17,876 --> 00:22:21,116 Speaker 1: love it. Whatever I mean. She had obviously no experience 332 00:22:21,116 --> 00:22:24,356 Speaker 1: in the legal field, nothing like that, and I put 333 00:22:24,356 --> 00:22:26,596 Speaker 1: her in charge of my whole office. Wait, what made 334 00:22:26,596 --> 00:22:28,316 Speaker 1: you think, Like you met this random woman at a 335 00:22:28,316 --> 00:22:30,236 Speaker 1: grocery store, Like, what makes you what made you think 336 00:22:30,276 --> 00:22:32,956 Speaker 1: that she would be the right to run your whole office? 337 00:22:33,596 --> 00:22:36,676 Speaker 1: I have no idea take, I don't know why, it 338 00:22:36,316 --> 00:22:39,116 Speaker 1: just it just came to me. Judy knew that Bob 339 00:22:39,196 --> 00:22:42,356 Speaker 1: was a big gambler. Bob bet on sports games mainly. 340 00:22:42,756 --> 00:22:45,716 Speaker 1: He used a bunch of different bookies and these guys 341 00:22:46,076 --> 00:22:48,236 Speaker 1: you had to pay or work out some kind of 342 00:22:48,356 --> 00:22:51,876 Speaker 1: arrangement because almost all of them were backed by the mob, 343 00:22:52,276 --> 00:22:54,396 Speaker 1: so you didn't want to get too deep in the hole. 344 00:22:55,076 --> 00:22:57,916 Speaker 1: But for Bob, gambling was a way of life. I 345 00:22:57,956 --> 00:23:02,676 Speaker 1: think he loved the the actual act of gambling and 346 00:23:02,836 --> 00:23:05,916 Speaker 1: you know, getting it right. I think Bob will tell 347 00:23:05,956 --> 00:23:09,276 Speaker 1: you the same thing that he was not motivated by me, 348 00:23:09,356 --> 00:23:11,436 Speaker 1: but boy, if he had it, he spent it, and 349 00:23:11,476 --> 00:23:13,036 Speaker 1: then if he didn't have it, he'd go out and 350 00:23:13,036 --> 00:23:16,276 Speaker 1: find more. This is part of what made Bob such 351 00:23:16,316 --> 00:23:19,916 Speaker 1: an exciting guy to know. He was a whirlwind of activity, 352 00:23:20,436 --> 00:23:23,476 Speaker 1: and sometimes Judy loved getting swept up in it all. 353 00:23:23,836 --> 00:23:27,196 Speaker 1: So did her then boyfriend now husband. They both told 354 00:23:27,236 --> 00:23:31,396 Speaker 1: me Bob treated them like family. He would buy them dinner, 355 00:23:31,596 --> 00:23:33,676 Speaker 1: take them out for nights on the town, get their 356 00:23:33,676 --> 00:23:38,196 Speaker 1: parking tickets fixed. Bob was like their mobbed up fairy godfather, 357 00:23:38,516 --> 00:23:44,036 Speaker 1: sprinkling magic dust wherever they went. But there were other 358 00:23:44,116 --> 00:23:48,076 Speaker 1: moments when they caught glimpses of Bob's darker dealings. They 359 00:23:48,076 --> 00:23:51,596 Speaker 1: didn't ask too many questions, but they understood the lurking 360 00:23:51,676 --> 00:23:55,276 Speaker 1: dangers and this particular week, even though Judy didn't know 361 00:23:55,596 --> 00:23:57,756 Speaker 1: all the details of what was going on with Bob, 362 00:23:58,396 --> 00:24:03,156 Speaker 1: she knew enough to worry. I was spiritful for Bob's life. 363 00:24:03,996 --> 00:24:06,996 Speaker 1: I would come into the office in the morning, and 364 00:24:07,036 --> 00:24:10,516 Speaker 1: if he didn't call me right away, I didn't know 365 00:24:10,716 --> 00:24:16,476 Speaker 1: if he was in a trunk somewhere dead. And I 366 00:24:16,596 --> 00:24:20,436 Speaker 1: was careful about his gambling. I used to spend hours 367 00:24:20,436 --> 00:24:25,516 Speaker 1: and hours checking different things, checking odds, checking numbers, checking 368 00:24:26,116 --> 00:24:29,316 Speaker 1: power ratings, checking all these things. I didn't do it 369 00:24:29,356 --> 00:24:32,956 Speaker 1: that week. That week, he means, the week he visited Gary, 370 00:24:33,356 --> 00:24:36,916 Speaker 1: the week his life started to unravel. That week, he says, 371 00:24:36,916 --> 00:24:41,396 Speaker 1: he dispensed with his usual precautions, gambled recklessly, placed several 372 00:24:41,436 --> 00:24:46,676 Speaker 1: impulsive bets, and ultimately lost man. I had three or 373 00:24:46,716 --> 00:24:49,516 Speaker 1: four of the worst days of my life gambling. Everything 374 00:24:49,556 --> 00:24:52,996 Speaker 1: I'm doing is wrong. I'm losing I'm losing this, I'm 375 00:24:53,036 --> 00:24:58,116 Speaker 1: losing that. And by now later in the week, I 376 00:24:58,276 --> 00:25:01,276 Speaker 1: realized I go like one hundred and it was like 377 00:25:01,316 --> 00:25:05,516 Speaker 1: one hundred ten, one hundred and twenty thousand dollars. You 378 00:25:05,516 --> 00:25:08,796 Speaker 1: you kind of lost your cool a little bit, Oh, 379 00:25:08,876 --> 00:25:13,476 Speaker 1: no question about it. Bob's concerns about his debts were 380 00:25:13,476 --> 00:25:16,476 Speaker 1: compounded by his gnawing feeling that he hadn't seen the 381 00:25:16,596 --> 00:25:20,556 Speaker 1: last of Gary Shapiro, that by walking into Gary's office, 382 00:25:20,596 --> 00:25:25,596 Speaker 1: he'd put something much bigger into motion, thinking what did 383 00:25:25,636 --> 00:25:28,756 Speaker 1: I do? You know? What did I do? And again 384 00:25:28,836 --> 00:25:34,196 Speaker 1: I was hoping against hope that okay, that'll be the 385 00:25:34,316 --> 00:25:36,596 Speaker 1: end of it. But I knew that wasn't going to 386 00:25:36,676 --> 00:25:39,076 Speaker 1: be the case. I mean, I knew I'd be getting 387 00:25:39,116 --> 00:25:41,836 Speaker 1: a visit. I didn't know when, but I knew I'd 388 00:25:41,876 --> 00:25:47,196 Speaker 1: be getting a visit. Then one morning it happened. I 389 00:25:47,276 --> 00:25:50,956 Speaker 1: walked into the office and that Judy was behind the desks, 390 00:25:51,756 --> 00:25:55,316 Speaker 1: and Judy said to me, I think there's some FBI 391 00:25:55,396 --> 00:25:59,076 Speaker 1: agents here to see you. In the moment she said 392 00:25:59,116 --> 00:26:02,636 Speaker 1: that I knew exactly what it was. It was the 393 00:26:02,756 --> 00:26:06,156 Speaker 1: thing he'd been dreading, the very thing he himself had 394 00:26:06,156 --> 00:26:09,996 Speaker 1: set in motion coming right back at him for FBI 395 00:26:10,076 --> 00:26:36,196 Speaker 1: agents on his doorstep, and they had questions. One of 396 00:26:36,236 --> 00:26:39,716 Speaker 1: the FBI agents to visit Bob that day was Marie Dyson. 397 00:26:40,156 --> 00:26:43,436 Speaker 1: Marie was in some ways an unlikely agent. She joined 398 00:26:43,476 --> 00:26:45,996 Speaker 1: the bureau kind of on a whim after her dad 399 00:26:46,076 --> 00:26:50,636 Speaker 1: suggested that she apply, and that began the process. And 400 00:26:50,676 --> 00:26:53,516 Speaker 1: then I went to Quantico like everybody else for four 401 00:26:53,596 --> 00:26:57,916 Speaker 1: months training, had no idea what I was getting myself into. 402 00:26:58,836 --> 00:27:01,356 Speaker 1: Marie didn't want to mess this up. She was a 403 00:27:01,396 --> 00:27:04,876 Speaker 1: young woman, a real rarity in the bureau. Around the 404 00:27:04,876 --> 00:27:08,596 Speaker 1: time that she joined, only two percent of FBI agents 405 00:27:08,596 --> 00:27:13,196 Speaker 1: were women, and Marie she felt that, Wow, you've entered 406 00:27:13,196 --> 00:27:16,396 Speaker 1: a man's world. You know, we can make mistakes, we 407 00:27:16,476 --> 00:27:19,556 Speaker 1: can screw up. Everybody laughs about it, but y'all don't 408 00:27:19,596 --> 00:27:22,596 Speaker 1: have that luxury. You know you cannot make a mistake. 409 00:27:23,476 --> 00:27:26,876 Speaker 1: And I will speak personally for myself, but I think 410 00:27:27,196 --> 00:27:28,836 Speaker 1: I kind of felt like, well, we need to prove 411 00:27:28,876 --> 00:27:32,676 Speaker 1: ourselves that we can do the job. She was sent 412 00:27:32,676 --> 00:27:35,516 Speaker 1: to Chicago in nineteen eighty one, where she was assigned 413 00:27:35,516 --> 00:27:38,796 Speaker 1: to the public Corruption squad, and she quickly learned the 414 00:27:38,836 --> 00:27:42,156 Speaker 1: mob playbook. The evidence is going to get tainted or 415 00:27:42,196 --> 00:27:46,556 Speaker 1: thrown away. Any eyewitnesses will take care of them, you know, 416 00:27:46,676 --> 00:27:49,876 Speaker 1: they'll be eradicated, and then the judge will be taken 417 00:27:49,956 --> 00:27:53,116 Speaker 1: care of. And it was a way of life, It's 418 00:27:53,116 --> 00:27:58,436 Speaker 1: how it operated. The mob was teflon. So Marie shows 419 00:27:58,516 --> 00:28:01,356 Speaker 1: up at Bob's office with three other agents, all of 420 00:28:01,396 --> 00:28:04,556 Speaker 1: them guys. We walked in and set in Bob's office, 421 00:28:04,596 --> 00:28:08,356 Speaker 1: and he was not very happy about this. And he 422 00:28:08,516 --> 00:28:11,236 Speaker 1: looked around and he said, you all look like FBI 423 00:28:11,356 --> 00:28:15,556 Speaker 1: agents except for the girl. And he always said that 424 00:28:15,716 --> 00:28:19,396 Speaker 1: he would say that, you know, thereafter, because I don't 425 00:28:19,436 --> 00:28:22,916 Speaker 1: know what an FBI agent female was supposed to look like. 426 00:28:22,996 --> 00:28:25,676 Speaker 1: But he didn't think I look like one, which seemed 427 00:28:25,716 --> 00:28:28,956 Speaker 1: to relieve him a little bit. Marie and these other 428 00:28:28,996 --> 00:28:32,396 Speaker 1: agents had managed to piece together some limited info on 429 00:28:32,436 --> 00:28:35,716 Speaker 1: who Bob was. They knew, for example, that he wasn't 430 00:28:35,716 --> 00:28:39,196 Speaker 1: the target of any ongoing investigations, so he was in 431 00:28:39,276 --> 00:28:43,916 Speaker 1: no imminent legal trouble, which raised the question why had 432 00:28:43,956 --> 00:28:48,356 Speaker 1: Bob come in? It was not commonplace. It was very suspicious. 433 00:28:49,116 --> 00:28:52,636 Speaker 1: That's how we looked at it in the beginning. Marie's colleague, 434 00:28:52,676 --> 00:28:56,356 Speaker 1: Steve Bowen, shared her skepticism. He was there that day too. 435 00:28:56,756 --> 00:28:59,476 Speaker 1: Marie and Steve were pretty close. They actually drove to 436 00:28:59,516 --> 00:29:03,236 Speaker 1: work together. Yeah, they were carpool buddies. Steve was a 437 00:29:03,276 --> 00:29:06,356 Speaker 1: former cop from Indianapolis who had entered the FBI at 438 00:29:06,356 --> 00:29:09,716 Speaker 1: thirty five, which was the cutoff for joining, and that 439 00:29:09,796 --> 00:29:12,036 Speaker 1: must have made him just about the oldest rookie in 440 00:29:12,076 --> 00:29:16,036 Speaker 1: the bureau. So in a way, Steven streetwise, but in 441 00:29:16,116 --> 00:29:19,356 Speaker 1: other important ways he was very green. I've only been 442 00:29:19,436 --> 00:29:24,796 Speaker 1: an agent two years. I've got no Chicago Mob background. 443 00:29:25,276 --> 00:29:28,356 Speaker 1: I don't know who the players are. They dropped names 444 00:29:28,436 --> 00:29:31,716 Speaker 1: that would mean absolutely netting to me. He might have 445 00:29:31,756 --> 00:29:34,956 Speaker 1: been green, but he knew enough to realize just how 446 00:29:35,076 --> 00:29:37,716 Speaker 1: rare it was to have a guy like Bob Cooley 447 00:29:37,756 --> 00:29:44,236 Speaker 1: show up and offer to help. Started kidding me unheard of. 448 00:29:44,916 --> 00:29:48,836 Speaker 1: It just doesn't happen for someone just to walk in 449 00:29:48,876 --> 00:29:52,876 Speaker 1: out of the blue. Why is he doing this? I mean, 450 00:29:52,916 --> 00:29:56,716 Speaker 1: he's literally putting his life on the line, and I honestly, 451 00:29:56,756 --> 00:29:58,756 Speaker 1: I think it caught everybody with their pants down. We 452 00:29:58,756 --> 00:30:01,276 Speaker 1: didn't know how to handle it at first, and that's 453 00:30:01,356 --> 00:30:04,596 Speaker 1: really why Steve and Marie visited Bob that day to 454 00:30:04,676 --> 00:30:07,876 Speaker 1: get a handle on things. You've got an attorney that 455 00:30:07,956 --> 00:30:11,076 Speaker 1: we really wan't familiar with. We didn't know how high 456 00:30:11,156 --> 00:30:15,956 Speaker 1: up in the mob he was, if he was at all, 457 00:30:16,876 --> 00:30:20,516 Speaker 1: So we just had to start setting up meetings with 458 00:30:20,596 --> 00:30:23,356 Speaker 1: him and talk to him and trying to get a 459 00:30:23,396 --> 00:30:26,756 Speaker 1: feel for what he's doing, where is coming from, what's 460 00:30:26,756 --> 00:30:31,036 Speaker 1: wrong with him? If anything? Is he a plan? Is 461 00:30:31,036 --> 00:30:35,276 Speaker 1: he a double age. What is he? You couldn't really 462 00:30:35,276 --> 00:30:37,916 Speaker 1: figure out a guy like Bob and just one sitting 463 00:30:38,436 --> 00:30:41,356 Speaker 1: or even three for that matter. So this was actually 464 00:30:41,356 --> 00:30:44,076 Speaker 1: the first of many meetings that Steve and Marie had 465 00:30:44,076 --> 00:30:46,916 Speaker 1: with Bob. They had to vet him, much the way 466 00:30:46,956 --> 00:30:49,516 Speaker 1: the CIA would have to vet a Soviet defector who 467 00:30:49,556 --> 00:30:53,076 Speaker 1: just walked in off the street. And Bob he understood 468 00:30:53,116 --> 00:30:56,716 Speaker 1: this Steve and those others for a long time after 469 00:30:56,756 --> 00:30:59,756 Speaker 1: I came in, I knew they didn't believe me, and 470 00:30:59,876 --> 00:31:01,916 Speaker 1: I knew that they were waiting. You know, they felt 471 00:31:01,916 --> 00:31:04,956 Speaker 1: there something wrong. But you know what was I to say? 472 00:31:05,036 --> 00:31:08,036 Speaker 1: I mean, I knew that just based on certain reactions 473 00:31:08,076 --> 00:31:10,956 Speaker 1: from them, and the best of it. After that first 474 00:31:10,996 --> 00:31:14,236 Speaker 1: meeting at Bob's office, they met elsewhere at a hotel 475 00:31:14,516 --> 00:31:16,236 Speaker 1: where no one would see what they were up to, 476 00:31:16,956 --> 00:31:20,636 Speaker 1: and gradually, over a series of meetings, Bob started talking, 477 00:31:21,036 --> 00:31:24,716 Speaker 1: and once he did, he didn't stop. Bob could give 478 00:31:24,796 --> 00:31:30,796 Speaker 1: us judges, lawyers, police officers, court personnel, politicians, He could 479 00:31:30,836 --> 00:31:34,636 Speaker 1: give us those people. It was like, after having all 480 00:31:34,636 --> 00:31:37,676 Speaker 1: those jitters, he just leaped into the deep end, no 481 00:31:37,796 --> 00:31:40,916 Speaker 1: looking back. He started laying out the details of his 482 00:31:41,036 --> 00:31:45,236 Speaker 1: story that he was a powerbroker for the city's notorious 483 00:31:45,316 --> 00:31:48,956 Speaker 1: First Ward. Technically, the First Ward was just one of 484 00:31:49,036 --> 00:31:52,476 Speaker 1: Chicago's fifty legislative districts, but it was one of the 485 00:31:52,556 --> 00:31:55,716 Speaker 1: most powerful and rumored to be among the most corrupt. 486 00:31:56,516 --> 00:32:00,676 Speaker 1: A political machine run by gangsters, and Bob claimed to 487 00:32:00,716 --> 00:32:07,076 Speaker 1: be their lawyer, their fixer, a trusted confidant. We controlled 488 00:32:07,116 --> 00:32:10,076 Speaker 1: the courts, We controlled the States Attorneys Office, We control 489 00:32:10,196 --> 00:32:16,996 Speaker 1: the police Department. We controlled that absolutely everything. Okay, so 490 00:32:17,196 --> 00:32:21,236 Speaker 1: he's bragging a bit. They didn't control absolutely everything, but 491 00:32:21,676 --> 00:32:25,676 Speaker 1: they controlled an awful lot. Bob was and still is 492 00:32:25,956 --> 00:32:29,756 Speaker 1: a natural storyteller, and he presented himself as the good guy, 493 00:32:29,996 --> 00:32:32,916 Speaker 1: the hero who'd fallen in with the wrong crowd and 494 00:32:32,996 --> 00:32:36,276 Speaker 1: now wanted to make amends. He had a whole mythology 495 00:32:36,316 --> 00:32:39,036 Speaker 1: about himself. Most of it was to put himself in 496 00:32:39,076 --> 00:32:41,796 Speaker 1: a good light and to protect himself. He was street savvy. 497 00:32:41,876 --> 00:32:44,916 Speaker 1: He was a survivor. You understood that. I mean, you 498 00:32:45,276 --> 00:32:47,476 Speaker 1: just can't be a real straight up on his guy 499 00:32:48,036 --> 00:32:51,196 Speaker 1: and survived with this. Bob knew how to keep himself alive, 500 00:32:51,756 --> 00:32:54,996 Speaker 1: and he could excuse me bullshit with the best. It 501 00:32:55,076 --> 00:32:58,396 Speaker 1: all came down to the old bullshit meter. I asked 502 00:32:58,396 --> 00:33:01,716 Speaker 1: Steve Bowen about this, Did you have a gut feeling 503 00:33:01,756 --> 00:33:07,356 Speaker 1: about him? No, and that's what was disturbing. I didn't 504 00:33:07,876 --> 00:33:11,316 Speaker 1: see your tone is all this and you want nothing 505 00:33:11,396 --> 00:33:14,316 Speaker 1: for it. You're not really looking for anything. You're looking 506 00:33:14,356 --> 00:33:16,596 Speaker 1: for money. We tried to get a figure out. I mean, 507 00:33:16,676 --> 00:33:19,876 Speaker 1: what do you want? What are you doing? He says, 508 00:33:20,036 --> 00:33:22,596 Speaker 1: I'm just tired of it. I'm just I don't know 509 00:33:22,596 --> 00:33:26,276 Speaker 1: what happened to change his mind to bring him forward, 510 00:33:26,596 --> 00:33:29,516 Speaker 1: and to this day, I still don't. Bob did want 511 00:33:29,716 --> 00:33:33,876 Speaker 1: one thing. He made one request. I had asked the agents, 512 00:33:34,676 --> 00:33:37,636 Speaker 1: I'm asking you to do me one favor. What's that 513 00:33:38,196 --> 00:33:41,796 Speaker 1: If I get killed, you let everybody know. I wasn't 514 00:33:41,836 --> 00:33:44,476 Speaker 1: doing it because out of fear of the mob or 515 00:33:44,956 --> 00:33:48,116 Speaker 1: or as basically as a stool pigeon. I had come 516 00:33:48,196 --> 00:33:50,156 Speaker 1: forward and I was doing the right thing to clean 517 00:33:50,236 --> 00:33:53,436 Speaker 1: up the system. I asked a couple of the agents that, oh, 518 00:33:53,516 --> 00:33:56,316 Speaker 1: certainly I was. I was scared stiff, but I had 519 00:33:56,316 --> 00:34:08,516 Speaker 1: a mission. Was this was my mission. I've spent the 520 00:34:08,596 --> 00:34:12,356 Speaker 1: last year digging deep into Bob's story, talking to people 521 00:34:12,396 --> 00:34:14,836 Speaker 1: who knew him back in the day, which was a 522 00:34:14,916 --> 00:34:18,876 Speaker 1: whole cast of characters. Because Bob rubbed shoulders with just 523 00:34:18,996 --> 00:34:25,756 Speaker 1: about everybody. Judges, politicians, bookies, gangsters, cops, and hitmen. They 524 00:34:25,876 --> 00:34:29,636 Speaker 1: all confided in him. Bob was a keeper of their secrets. 525 00:34:30,276 --> 00:34:34,196 Speaker 1: Secrets had implicated not just a few powerful men, but 526 00:34:34,316 --> 00:34:38,756 Speaker 1: a whole shadowy realm, a black market of corruption where 527 00:34:38,796 --> 00:34:43,196 Speaker 1: politicians were bought and justice was sold, where for the 528 00:34:43,276 --> 00:34:48,196 Speaker 1: right price, even murderers could walk free. Bob was privy 529 00:34:48,236 --> 00:34:50,556 Speaker 1: to all of it, and he kept it under wraps 530 00:34:50,996 --> 00:34:54,476 Speaker 1: until the spring of nineteen eighty six, when he started 531 00:34:54,476 --> 00:35:12,356 Speaker 1: to talk up on season two of Deep Cover. For 532 00:35:12,516 --> 00:35:16,636 Speaker 1: approximately five years, a Chicago lawyer has been a government informant, 533 00:35:16,716 --> 00:35:20,756 Speaker 1: secretly recording conversations with some of this city's movers and shakers. 534 00:35:20,916 --> 00:35:23,396 Speaker 1: The identity of this informant will come as a shock 535 00:35:23,516 --> 00:35:26,556 Speaker 1: to some powerful people. I can say with all certainty, 536 00:35:26,636 --> 00:35:28,716 Speaker 1: I think he's a hero because he didn't have to 537 00:35:28,716 --> 00:35:30,796 Speaker 1: do what he did, and he did it anyway. Well, 538 00:35:30,796 --> 00:35:33,636 Speaker 1: I can see how people would think that, Yeah, because 539 00:35:33,716 --> 00:35:37,396 Speaker 1: Cooley is very manipulate too. But he just sort of 540 00:35:37,396 --> 00:35:41,036 Speaker 1: got away with murder and he said, don't ever tell 541 00:35:41,116 --> 00:35:43,916 Speaker 1: us what to do. He said, nobody wears a wire 542 00:35:43,956 --> 00:35:59,236 Speaker 1: in US and lives to talk about it. Deep Cover 543 00:35:59,396 --> 00:36:02,796 Speaker 1: is produced by Jacob Smith and Amy Gaines and edited 544 00:36:02,836 --> 00:36:07,156 Speaker 1: by Karen Shakerji. Our senior editor is Jan Guera. Original 545 00:36:07,236 --> 00:36:09,836 Speaker 1: music in our theme was composed by Louis Gara and 546 00:36:09,916 --> 00:36:13,076 Speaker 1: Fawn Williams as our engineer. Our art this season was 547 00:36:13,156 --> 00:36:16,636 Speaker 1: drawn by Cheryl Cook and designed by Sean Carney Mia 548 00:36:16,716 --> 00:36:20,556 Speaker 1: Lobell as our executive producer. Special thanks to Heather Fame, 549 00:36:20,916 --> 00:36:25,956 Speaker 1: John Schnars, Carl Mcliori, Maya Caning, Christina Sullivan, Eric Sandler, 550 00:36:26,116 --> 00:36:31,076 Speaker 1: Mary Beth Smith, Brant Haynes, Maggie Taylor, Nicole Morano, Megan Larson, 551 00:36:31,276 --> 00:36:36,316 Speaker 1: Royston Baserve, Lucy Sullivan, Edith Russlo, Riley Sullivan, Jason Gambrell, 552 00:36:36,556 --> 00:36:51,036 Speaker 1: Martin Gonzalez, and Jacob Weissberg. I'm Jake Halbern. Pleasure Us. 553 00:37:21,156 --> 00:37:23,676 Speaker 1: If you want to learn more about Bob Cooley's story, 554 00:37:23,876 --> 00:37:26,316 Speaker 1: you can check out his memoir, published in two thousand 555 00:37:26,396 --> 00:37:30,516 Speaker 1: and four. It's called When Corruption Was King. Bob co 556 00:37:30,636 --> 00:37:34,076 Speaker 1: wrote it with Hill l Levin. Subscribe to pushkin Plus 557 00:37:34,116 --> 00:37:36,596 Speaker 1: and you can binge the rest of the season right now. 558 00:37:36,876 --> 00:37:40,156 Speaker 1: Adds free. Find pushkin Plus on the deep Cover Show 559 00:37:40,196 --> 00:37:44,716 Speaker 1: page in Apple Podcasts or at pushkin dot fm. To 560 00:37:44,756 --> 00:37:50,276 Speaker 1: find more Pushkin podcasts, listen on the iHeartRadio app, Apple Podcasts, 561 00:37:50,756 --> 00:37:52,636 Speaker 1: or wherever you listen to podcasts.