1 00:00:11,137 --> 00:00:12,262 As we've seen, 2 00:00:12,346 --> 00:00:15,391 becoming a successful mob boss requires discipline, 3 00:00:15,892 --> 00:00:17,810 an entrepreneurial mindset, 4 00:00:18,561 --> 00:00:22,940 and the willingness to do anything to protect your power. 5 00:00:25,234 --> 00:00:30,156 Put these qualities to work, and you can reap truly handsome rewards. 6 00:00:30,740 --> 00:00:35,452 However, the often inevitable fall from criminal glory can be steep. 7 00:00:35,536 --> 00:00:37,621 Most mob bosses end up dead or in jail. 8 00:00:38,915 --> 00:00:40,083 It's just the way it is. 9 00:00:43,961 --> 00:00:47,048 There is no Florida community of retired bosses. 10 00:00:48,549 --> 00:00:50,884 But you can chart a more comfortable future 11 00:00:50,968 --> 00:00:53,679 by taking care of every detail 12 00:00:53,763 --> 00:00:56,349 and always thinking two steps ahead. 13 00:00:58,476 --> 00:01:00,936 Nobody embodied these lessons more expertly 14 00:01:01,020 --> 00:01:02,980 than the master of manipulation 15 00:01:03,064 --> 00:01:07,067 who became Boston's most powerful and feared mob boss, 16 00:01:07,151 --> 00:01:09,737 James " Whitey" Bulger. 17 00:01:10,530 --> 00:01:11,822 He could be very charming 18 00:01:11,906 --> 00:01:14,867 when he wanted something from you, and then, like a snake, 19 00:01:14,951 --> 00:01:17,411 he could turn around and bite you the next second. 20 00:01:18,121 --> 00:01:19,955 It all comes back to Whitey. 21 00:01:20,039 --> 00:01:22,583 His survival, his power, his control, 22 00:01:22,667 --> 00:01:26,170 and if he feels any of that is at risk, then anything goes. 23 00:01:27,380 --> 00:01:30,925 By predicting and obliterating every threat, 24 00:01:31,717 --> 00:01:34,428 Whitey dominated Beantown's criminal underworld 25 00:01:34,512 --> 00:01:35,721 for nearly two decades. 26 00:01:35,805 --> 00:01:38,223 And when the walls started closing in, 27 00:01:38,307 --> 00:01:41,102 he performed the ultimate vanishing act. 28 00:01:41,811 --> 00:01:45,648 For the last 16 years, the notorious Boston mob boss was a ghost. 29 00:01:46,315 --> 00:01:48,984 Let Whitey show you how to go the distance 30 00:01:49,068 --> 00:01:51,821 by never getting caught unprepared. 31 00:02:08,629 --> 00:02:12,883 During Whitey Bulger's bloody reign as the head of Boston's Winter Hill Gang, 32 00:02:12,967 --> 00:02:16,178 he was suspected of ordering at least 19 murders 33 00:02:16,262 --> 00:02:19,724 while raking in an estimated 30 million in illicit cash. 34 00:02:21,642 --> 00:02:25,145 Bulger, by far, has to be the most notorious 35 00:02:25,229 --> 00:02:28,858 and I'd argue most successful criminal from Boston. 36 00:02:30,109 --> 00:02:32,444 It was all, I think, a big chess game to him. 37 00:02:32,528 --> 00:02:36,490 Creating a criminal organization that was really successful, 38 00:02:36,574 --> 00:02:39,035 and he was outwitting everyone along the way. 39 00:02:40,745 --> 00:02:44,123 To understand how Whitey charted his course to mob boss infamy 40 00:02:44,207 --> 00:02:47,835 and eventually became America's Most Wanted man, 41 00:02:47,919 --> 00:02:51,714 you first need to know a few things about this crafty killer. 42 00:02:58,971 --> 00:03:03,726 Whitey Bulger, he grew up in poverty in South Boston. 43 00:03:05,186 --> 00:03:08,981 He was the oldest of three boys. And there were three girls in the family. 44 00:03:09,482 --> 00:03:12,359 He wasn't really into school. He wasn't really into church. 45 00:03:12,443 --> 00:03:15,821 He was into kind of being wild and causing trouble. 46 00:03:16,697 --> 00:03:19,700 Billy Bulger was one of Whitey's younger siblings. 47 00:03:20,284 --> 00:03:23,036 Unlike Whitey, Billy excelled in school, 48 00:03:23,120 --> 00:03:26,374 and he went on to have a very successful career in politics. 49 00:03:27,583 --> 00:03:29,752 Bill Bulger was feared in the state house. 50 00:03:30,253 --> 00:03:33,046 If you crossed him, there would be a price to pay. 51 00:03:33,130 --> 00:03:35,966 Obviously, Whitey is a gangster and a killer. 52 00:03:36,050 --> 00:03:38,719 He had a whole different toolbox to work with. 53 00:03:41,013 --> 00:03:44,266 Bulger had really good luck at committing crime 54 00:03:44,350 --> 00:03:46,978 and getting away with it from a very young age. 55 00:03:47,687 --> 00:03:52,566 He got arrested a bunch of times, but only one of the charges even stuck. 56 00:03:53,192 --> 00:03:56,945 In the 1950s, two of the men who he had robbed banks with 57 00:03:57,029 --> 00:03:58,155 ratted him out. 58 00:03:58,239 --> 00:04:03,493 So he felt deeply betrayed, but he also understood the value 59 00:04:03,577 --> 00:04:06,664 of providing information and being an informant. 60 00:04:10,293 --> 00:04:12,502 After rising through the ranks, 61 00:04:12,586 --> 00:04:17,549 Whitey made it to the top of New England's most feared Irish-American syndicate, 62 00:04:17,633 --> 00:04:18,926 the Winter Hill Gang. 63 00:04:19,427 --> 00:04:22,680 He achieved an enormous amount of power and wealth, 64 00:04:23,472 --> 00:04:25,599 but he wasn't real showy about that. 65 00:04:26,726 --> 00:04:29,811 One of the things that led to Bulger's success for so many years 66 00:04:29,895 --> 00:04:31,605 is that he preferred the shadows. 67 00:04:32,106 --> 00:04:35,609 He was more of a name that people had heard, but never really seen. 68 00:04:36,193 --> 00:04:40,364 So, even veteran investigators had never actually seen him. 69 00:04:41,115 --> 00:04:44,493 It was all part of Whitey's carefully crafted strategy 70 00:04:44,577 --> 00:04:46,495 to get away with murder. 71 00:04:48,831 --> 00:04:52,209 So, how do you make sure you stay in the game for the long haul? 72 00:04:52,293 --> 00:04:55,379 Follow along with the playbook and find out. 73 00:05:00,384 --> 00:05:02,344 If you want to endure as a mob boss, 74 00:05:02,428 --> 00:05:05,723 you need to maintain total control of your operation 75 00:05:06,682 --> 00:05:09,477 and you can't tolerate any weak links. 76 00:05:10,311 --> 00:05:13,105 Unless you have very tight control 77 00:05:13,689 --> 00:05:17,151 over the people that are running things for you on the street, 78 00:05:17,651 --> 00:05:18,694 anything could happen. 79 00:05:18,778 --> 00:05:19,611 Attention! 80 00:05:19,695 --> 00:05:21,613 And when it came to sniffing out 81 00:05:21,697 --> 00:05:23,491 potential problems in his ranks, 82 00:05:24,575 --> 00:05:26,619 Whitey Bulger was a master. 83 00:05:27,661 --> 00:05:29,788 He had a very powerful organization, 84 00:05:29,872 --> 00:05:32,541 but he ran it like a closely-held corporation. 85 00:05:33,042 --> 00:05:35,794 Bulger's group answered to no one but themselves. 86 00:05:35,878 --> 00:05:38,171 It wasn't like a Mafia organization 87 00:05:38,255 --> 00:05:40,799 where you have capos, lieutenants and all that kind of thing. 88 00:05:40,883 --> 00:05:43,802 There were very few people in his inner circle. 89 00:05:43,886 --> 00:05:46,222 His idea was this deadly power center. 90 00:05:47,515 --> 00:05:52,060 For most of Whitey's run, that center included just two key allies. 91 00:05:52,144 --> 00:05:55,314 Steve Flemmi and Johnny Martorano. 92 00:05:55,940 --> 00:05:59,026 Stevie Flemmi and Johnny Martorano grew up in Boston. 93 00:05:59,110 --> 00:06:01,486 Both have killed multiple times. 94 00:06:01,570 --> 00:06:03,196 He could trust those guys. 95 00:06:03,280 --> 00:06:06,700 And in that sense, they had the right stuff, the résumé 96 00:06:06,784 --> 00:06:08,744 to be aligned with Whitey Bulger. 97 00:06:09,703 --> 00:06:13,290 As for everyone else, to avoid Whitey's wrath, 98 00:06:13,374 --> 00:06:15,918 they had to follow very specific rules. 99 00:06:16,710 --> 00:06:22,591 It was understood that there would be no flamboyant displays of wealth. 100 00:06:23,467 --> 00:06:27,137 Don't antagonize law enforcement for unnecessary reasons. 101 00:06:27,221 --> 00:06:29,932 You don't talk your criminal business in front of others. 102 00:06:30,766 --> 00:06:34,103 And above all, don't rat anyone out. 103 00:06:34,812 --> 00:06:37,814 Any deviation from that is when Whitey would go ballistic. 104 00:06:44,447 --> 00:06:46,198 Tommy King is a longshoreman 105 00:06:47,158 --> 00:06:49,535 and an enforcer in the Winter Hill Gang. 106 00:06:51,954 --> 00:06:55,249 He was a tough, sweet guy, Tommy, and he was one of us, 107 00:06:55,958 --> 00:06:57,751 but he had a drinking problem. 108 00:06:59,336 --> 00:07:01,964 Whitey and Tommy never quite hit it off. 109 00:07:04,008 --> 00:07:05,467 Both of you go to hell! 110 00:07:05,551 --> 00:07:08,345 And Whitey sees Tommy's increasingly erratic behavior 111 00:07:08,429 --> 00:07:09,429 as a threat. 112 00:07:16,312 --> 00:07:21,274 So one day, Whitey invites Tommy to come along as backup on a hunting trip 113 00:07:21,358 --> 00:07:23,360 to take out a rival gangster. 114 00:07:24,320 --> 00:07:27,281 Steve Flemmi and John Martorano join in as well. 115 00:07:28,824 --> 00:07:33,162 As they head out of town, Tommy shows off his new bulletproof vest 116 00:07:33,746 --> 00:07:37,708 and jokes that if they don't find their target, they can try it out. 117 00:07:39,502 --> 00:07:41,504 Whitey has a different plan. 118 00:07:45,883 --> 00:07:47,717 The hit was a success, 119 00:07:47,801 --> 00:07:51,180 but Whitey knows he'll likely be suspected in Tommy's disappearance. 120 00:07:51,680 --> 00:07:55,392 So he spreads the story of suggesting Tommy committed a murder himself 121 00:07:56,018 --> 00:07:57,727 and left town to hide. 122 00:07:57,811 --> 00:08:00,272 Whitey gets behind a propaganda machine. 123 00:08:00,356 --> 00:08:03,067 He's good at this too. Selling a story. 124 00:08:03,776 --> 00:08:06,153 Whether his people believe it or not, 125 00:08:06,237 --> 00:08:09,323 they know better than to ask too many questions. 126 00:08:10,699 --> 00:08:16,663 Bulger had little patience for people he viewed as a liability to him, 127 00:08:16,747 --> 00:08:19,124 and he didn't hesitate to have them killed. 128 00:08:20,626 --> 00:08:23,087 And that's what kept his gang in line. 129 00:08:23,712 --> 00:08:24,671 No need to get tough. 130 00:08:24,755 --> 00:08:25,881 They were afraid of him. 131 00:08:28,300 --> 00:08:32,221 Running a tight ship will keep your long-term plan in good health. 132 00:08:32,972 --> 00:08:37,434 But when murder is your medicine, you need to watch out for side effects. 133 00:08:38,018 --> 00:08:40,145 How do you make sure your rising body count 134 00:08:40,229 --> 00:08:41,313 doesn't trip you up? 135 00:08:47,278 --> 00:08:48,737 Let's be honest. 136 00:08:49,238 --> 00:08:53,826 All mob bosses need to cut loose threads from time to time. 137 00:08:54,326 --> 00:08:58,789 But if you don't want to end your days behind bars, every detail counts. 138 00:08:59,290 --> 00:09:02,375 Any crime you commit, you wanna get rid of evidence, 139 00:09:02,459 --> 00:09:03,585 so you don't go to jail. 140 00:09:03,669 --> 00:09:04,837 It's as simple as that. 141 00:09:08,007 --> 00:09:10,800 And that often means going the extra mile. 142 00:09:10,884 --> 00:09:14,971 You burn the clothes, throw the guns right in the ocean. 143 00:09:15,055 --> 00:09:16,473 Get rid of everything. 144 00:09:16,557 --> 00:09:19,476 There should be no car. There should be no DNA. 145 00:09:20,352 --> 00:09:21,979 If there's no body, there's no murder. 146 00:09:22,563 --> 00:09:25,065 Little wonder why all the best bosses 147 00:09:25,149 --> 00:09:27,276 know the value of a good cover-up. 148 00:09:29,778 --> 00:09:32,906 When Pablo Escobar wanted to get rid of a pair of disloyal underlings 149 00:09:32,990 --> 00:09:34,574 he thought were cheating him, 150 00:09:34,658 --> 00:09:37,536 he allegedly invited them to his private prison 151 00:09:37,620 --> 00:09:39,330 and had them incinerated. 152 00:09:41,624 --> 00:09:43,667 When former Gambino boss, 153 00:09:43,751 --> 00:09:47,128 Paul Castellano, needed a rival disappeared, 154 00:09:47,212 --> 00:09:49,422 he relied on hitman Roy DeMeo 155 00:09:49,506 --> 00:09:53,885 and his Gemini method, named after DeMeo's favorite hangout. 156 00:09:53,969 --> 00:09:56,805 It involved fully draining a corpse of blood 157 00:09:56,889 --> 00:10:00,976 to minimize mess before cutting it into tiny pieces. 158 00:10:01,977 --> 00:10:05,188 While Salvatore Riina eliminated his problems using a practice 159 00:10:05,272 --> 00:10:07,482 known as lupara bianca , 160 00:10:07,566 --> 00:10:10,027 which could involve dissolving victims in acid, 161 00:10:10,611 --> 00:10:11,820 feeding them to hogs, 162 00:10:11,904 --> 00:10:14,531 or even throwing them into a steel smelter. 163 00:10:16,492 --> 00:10:20,245 But none of these masters covered their tracks as painstakingly 164 00:10:20,329 --> 00:10:21,372 as Whitey Bulger. 165 00:10:22,081 --> 00:10:24,874 A lot of gangland slayings, 166 00:10:24,958 --> 00:10:27,419 bodies would be just left in trunks of cars. 167 00:10:28,629 --> 00:10:31,215 Or sometimes just left on the street. 168 00:10:31,799 --> 00:10:37,763 Bulger and his crew went out of their way to hide bodies. 169 00:10:38,681 --> 00:10:40,390 Really far out of their way 170 00:10:40,474 --> 00:10:44,561 to make sure the bodies were buried where nobody would ever find them. 171 00:10:45,813 --> 00:10:50,025 In case the body was discovered, he'd cut fingers off, pull out their teeth 172 00:10:50,109 --> 00:10:53,904 because someone's identity could be revealed through their dental records. 173 00:10:55,489 --> 00:10:58,951 So that was the technique, if you had the stomach for it. 174 00:10:59,743 --> 00:11:02,370 But when you're trying to win the long game, 175 00:11:02,454 --> 00:11:05,123 you need to make sure that proof of your handiwork 176 00:11:05,207 --> 00:11:07,834 stays hidden permanently. 177 00:11:07,918 --> 00:11:09,294 Goodbye, Dr. Farb. 178 00:11:09,378 --> 00:11:12,005 You may have been a crummy dentist, but you were a nice fella. 179 00:11:15,801 --> 00:11:17,469 Whitey has a few go-to spots 180 00:11:17,553 --> 00:11:20,681 that he returns to to conduct his business. 181 00:11:22,307 --> 00:11:25,728 One of the locations was right in South Boston 182 00:11:26,311 --> 00:11:27,813 on one of the main streets. 183 00:11:28,313 --> 00:11:31,107 It was an older home that had a dirt basement. 184 00:11:32,526 --> 00:11:33,485 No! 185 00:11:33,569 --> 00:11:36,154 It soon earns a nickname, the Haunty... 186 00:11:38,365 --> 00:11:40,742 ...where after his bloody work is complete, 187 00:11:40,826 --> 00:11:44,121 Whitey makes good use of the home's unfinished basement. 188 00:11:46,331 --> 00:11:48,792 But one day, there's a problem. 189 00:11:49,668 --> 00:11:51,920 The Haunty goes up for sale. 190 00:11:53,714 --> 00:11:56,383 Whitey has a troubling vision of the future. 191 00:11:58,177 --> 00:12:00,053 He needs to move. 192 00:12:00,137 --> 00:12:03,849 So, Whitey picks an appropriate night for his ghoulish plan... 193 00:12:07,019 --> 00:12:09,396 and brings along an associate to help. 194 00:12:13,275 --> 00:12:17,737 They load the bodies into a station wagon and drive them across town 195 00:12:17,821 --> 00:12:20,783 to a field beside a fireman's union hall. 196 00:12:22,159 --> 00:12:26,580 Ever the planner, Whitey already had new resting places prepared. 197 00:12:28,957 --> 00:12:32,752 Ensuring that neither Whitey nor the Haunty's new owners 198 00:12:32,836 --> 00:12:35,881 end up with an unpleasant surprise. 199 00:12:37,674 --> 00:12:39,426 Happy Halloween. 200 00:12:40,427 --> 00:12:42,179 He was a cunning strategist. 201 00:12:43,347 --> 00:12:46,475 He was a very clever and very dangerous guy. 202 00:12:47,976 --> 00:12:53,607 And that's why many of his murders were, in fact, left unsolved for many years. 203 00:12:54,817 --> 00:12:56,484 A solid body disposal program 204 00:12:56,568 --> 00:12:59,363 will help keep murder detectives off your trail, 205 00:12:59,947 --> 00:13:03,742 but there's an even better way to stay ahead of every potential problem. 206 00:13:04,660 --> 00:13:06,870 All it takes is the right hookup. 207 00:13:12,251 --> 00:13:15,587 As a mob boss, you can use creative means 208 00:13:15,671 --> 00:13:17,881 to keep cops out of your business. 209 00:13:17,965 --> 00:13:23,470 But to achieve real staying power, you should pursue a deeper relationship. 210 00:13:24,263 --> 00:13:25,805 If you want a long shelf life, 211 00:13:25,889 --> 00:13:29,225 find a way to get someone on the inside of law enforcement, 212 00:13:29,309 --> 00:13:31,812 as high up as you can, to watch your back. 213 00:13:32,479 --> 00:13:33,438 That is huge. 214 00:13:33,522 --> 00:13:38,694 And that is so much of what made Whitey Bulger the mob boss that he was. 215 00:13:40,571 --> 00:13:45,617 Bulger had a lot of local contacts in the state police, Boston police, 216 00:13:45,701 --> 00:13:50,455 and he would pay off law enforcement officials, 217 00:13:50,539 --> 00:13:51,956 especially around Christmas. 218 00:13:53,584 --> 00:13:56,461 But Whitey wanted the ultimate inside track, 219 00:13:57,337 --> 00:13:59,339 and he knew just how to get it... 220 00:14:01,258 --> 00:14:02,718 through an old friend. 221 00:14:04,845 --> 00:14:08,932 John Connolly grew up in South Boston, and he idolized Whitey. 222 00:14:09,808 --> 00:14:12,477 Connolly was younger than Whitey Bulger. 223 00:14:12,561 --> 00:14:17,440 Bulger protected him from some fistfight years ago, and as a result, 224 00:14:17,524 --> 00:14:21,153 Connolly always felt some sort of, uh, loyalty to Bulger. 225 00:14:21,778 --> 00:14:24,907 And Whitey had a plan to collect on that debt. 226 00:14:27,117 --> 00:14:32,163 Throughout 1974, Whitey begins meeting covertly with Connolly 227 00:14:32,247 --> 00:14:35,250 to discuss rekindling the relationship. 228 00:14:36,126 --> 00:14:38,795 Connolly's convinced that getting an in with the gangster 229 00:14:38,879 --> 00:14:43,383 would transform his career, while Whitey has his own agenda, 230 00:14:43,467 --> 00:14:46,219 VIP treatment from the local FBI. 231 00:14:47,262 --> 00:14:49,180 He begins feeding Connolly tips 232 00:14:49,264 --> 00:14:51,892 on his rivals inside the Boston underworld, 233 00:14:53,018 --> 00:14:56,396 so federal agents can do his dirty work for him. 234 00:14:59,733 --> 00:15:04,320 Whitey is credited with helping the feds nab their most coveted prize, 235 00:15:04,404 --> 00:15:07,824 the head of Boston's Italian Mafia, Jerry Angiulo... 236 00:15:09,201 --> 00:15:12,287 ...by securing inside information about Angiulo's headquarters, 237 00:15:12,371 --> 00:15:14,748 which they used to set up wiretaps. 238 00:15:16,375 --> 00:15:20,670 It leads to a successful takedown of the entire Angiulo crime family. 239 00:15:21,672 --> 00:15:26,301 With the Mafia sidelined, Whitey becomes even more powerful. 240 00:15:27,386 --> 00:15:31,556 Connolly also keeps Whitey's name off of official FBI reports 241 00:15:31,640 --> 00:15:33,767 and tips him off about investigations. 242 00:15:35,268 --> 00:15:38,063 It's a profitable relationship all around. 243 00:15:39,564 --> 00:15:42,818 And as the line between criminal and cop begins to blur, 244 00:15:43,318 --> 00:15:46,863 Whitey himself becomes nearly untouchable. 245 00:15:47,656 --> 00:15:50,533 I don't think in the history of American crime 246 00:15:50,617 --> 00:15:54,162 there's anyone who achieved what Whitey Bulger achieved 247 00:15:54,246 --> 00:15:56,956 when it came to having corrupt law enforcement 248 00:15:57,040 --> 00:15:59,042 feeding you valuable intel. 249 00:16:00,377 --> 00:16:03,338 So many people in law enforcement were going crazy 250 00:16:03,422 --> 00:16:05,757 trying to get Bulger on something. 251 00:16:07,009 --> 00:16:10,428 Everybody wondered, "How does he know? It seems like he knows what we're doing." 252 00:16:10,512 --> 00:16:12,431 Sometimes that's 'cause he did. 253 00:16:13,807 --> 00:16:17,644 But while sharing secrets with the feds can preserve your freedom, 254 00:16:17,728 --> 00:16:21,273 it's not going to win many friends among your peers. 255 00:16:22,024 --> 00:16:23,942 No one likes a rat. 256 00:16:24,818 --> 00:16:27,738 How do you keep your dirty secret from coming out? 257 00:16:33,618 --> 00:16:37,330 Whitey had a reputation as the ultimate stand-up guy. 258 00:16:37,414 --> 00:16:40,249 Someone who doesn't talk to the authorities. 259 00:16:40,333 --> 00:16:41,834 Doesn't give anybody up. 260 00:16:41,918 --> 00:16:45,254 Doesn't give any information, no matter what the circumstances, 261 00:16:45,338 --> 00:16:47,966 no matter what the threat, no matter what the pressure. 262 00:16:48,050 --> 00:16:50,135 You stand up and say nothing. 263 00:16:50,802 --> 00:16:52,929 Of course, Whitey's actual relationship 264 00:16:53,013 --> 00:16:55,766 with law enforcement was more complicated. 265 00:16:56,808 --> 00:16:58,768 Whitey always had to be on his guard, 266 00:16:58,852 --> 00:17:01,605 always, 'cause he was living a double life. 267 00:17:03,190 --> 00:17:06,610 The underworld had no idea he was a rat. 268 00:17:07,444 --> 00:17:11,823 So, he was always living with that. He knew what would happen if we found out. 269 00:17:13,366 --> 00:17:14,659 Need more proof? 270 00:17:14,743 --> 00:17:17,245 See what happened to these other chatty dons. 271 00:17:19,748 --> 00:17:23,418 Big Jack Zelig, boss of Manhattan's Eastman Gang, 272 00:17:23,502 --> 00:17:25,294 got knocked off in 1912 273 00:17:25,378 --> 00:17:28,715 while riding the Second Avenue trolley after his people learned 274 00:17:28,799 --> 00:17:31,718 he was in the pocket of a corrupt NYPD lieutenant. 275 00:17:32,511 --> 00:17:36,347 Chicago crime boss James Ragen was ambushed and shot after exposing 276 00:17:36,431 --> 00:17:39,184 the top echelon of the Chicago mob to the feds. 277 00:17:39,810 --> 00:17:43,062 While recovering in the hospital, he identified the gunman 278 00:17:43,146 --> 00:17:46,108 and was summarily murdered via mercury poisoning. 279 00:17:46,858 --> 00:17:49,527 And Bonanno family captain, Dominick Napolitano, 280 00:17:49,611 --> 00:17:53,281 got whacked for allowing FBI agent Joseph Pistone , 281 00:17:53,365 --> 00:17:56,868 aka Donnie Brasco, to infiltrate the family. 282 00:17:57,452 --> 00:17:59,579 He was ultimately found with his hands cut off, 283 00:17:59,663 --> 00:18:02,999 a traditional penalty for divulging Mafia secrets. 284 00:18:07,546 --> 00:18:11,382 When it came to protecting Whitey Bulger's stand-up image, 285 00:18:11,466 --> 00:18:14,177 his homicidal reputation came in handy. 286 00:18:14,261 --> 00:18:15,887 No one suspected someone 287 00:18:15,971 --> 00:18:19,974 as dangerous as him to be a top FBI informant, 288 00:18:20,058 --> 00:18:21,768 basically ratting on other people 289 00:18:21,852 --> 00:18:24,395 to enhance his position, increase his power. 290 00:18:24,479 --> 00:18:27,774 There had been rumors, but most people scoffed at the rumors 291 00:18:27,858 --> 00:18:29,693 because it was too ridiculous. 292 00:18:30,694 --> 00:18:35,157 To keep it that way, nothing and no one was off-limits. 293 00:18:38,660 --> 00:18:43,415 Debra Davis is the longtime mistress of Steve Flemmi, Whitey's right-hand man. 294 00:18:43,999 --> 00:18:46,585 Generally, Whitey doesn't pay her much mind 295 00:18:47,502 --> 00:18:50,254 until she catches wind of Whitey's secret 296 00:18:50,338 --> 00:18:53,008 that he's been working with the FBI for years. 297 00:18:53,633 --> 00:18:57,011 Flemmi, who has developed his own FBI connection, 298 00:18:57,095 --> 00:19:00,473 tells Whitey everything's under control. 299 00:19:01,099 --> 00:19:02,976 Whitey isn't convinced. 300 00:19:03,560 --> 00:19:07,355 And when Flemmi and Debra's relationship starts to hit the rocks, 301 00:19:07,439 --> 00:19:09,441 the risk becomes untenable. 302 00:19:12,444 --> 00:19:14,654 Whitey has Flemmi set a trap, 303 00:19:14,738 --> 00:19:18,742 telling Debra he wants to show her a house he wants to buy for her. 304 00:19:19,784 --> 00:19:21,828 But when Flemmi gives her a tour, 305 00:19:22,454 --> 00:19:25,290 she ends up with a different sort of closing. 306 00:19:31,755 --> 00:19:33,131 Cleanup is quick 307 00:19:33,965 --> 00:19:34,883 and thorough. 308 00:19:37,677 --> 00:19:40,639 They bury Debra next to Tommy King on Tenean Beach. 309 00:19:42,349 --> 00:19:45,852 And just like that, Whitey's secret stays hidden. 310 00:19:46,853 --> 00:19:50,231 This guy had no empathy for anybody, only for himself. 311 00:19:50,315 --> 00:19:52,150 He didn't care for no one, this guy. 312 00:19:52,234 --> 00:19:53,568 They killed women. 313 00:19:54,194 --> 00:19:55,820 They killed innocent people. 314 00:19:55,904 --> 00:19:58,239 It was amazing, the things he was capable of doing 315 00:19:58,323 --> 00:20:02,118 in the name of his security and his freedom. 316 00:20:02,786 --> 00:20:04,955 But even if you take all the right precautions 317 00:20:05,664 --> 00:20:07,957 and have all the right protection, 318 00:20:08,041 --> 00:20:10,335 no one stays untouchable forever. 319 00:20:10,835 --> 00:20:13,672 When the tide turns, you need to be ready. 320 00:20:14,256 --> 00:20:16,299 Let the playbook show you the way. 321 00:20:21,888 --> 00:20:24,516 When a mob boss wants to evade justice, 322 00:20:25,100 --> 00:20:28,061 many of them have to eventually go on the run. 323 00:20:30,480 --> 00:20:33,942 But that's difficult to do if you're not disciplined. 324 00:20:34,734 --> 00:20:35,985 But as we've seen... 325 00:20:36,069 --> 00:20:37,069 Need a little grass? 326 00:20:37,153 --> 00:20:39,488 ...discipline was Whitey's middle name. 327 00:20:39,572 --> 00:20:40,448 No, thanks. 328 00:20:41,950 --> 00:20:45,661 Whitey was always in full control of his environment. 329 00:20:45,745 --> 00:20:47,122 I've never seen him drink. 330 00:20:47,622 --> 00:20:50,333 He never socialized. He didn't mix with people. 331 00:20:51,001 --> 00:20:53,628 That's a vulnerability if you're doing the wrong thing. 332 00:20:54,671 --> 00:20:57,548 He was often thinking about, "Well, what if I do get charged?" 333 00:20:57,632 --> 00:20:58,842 "I should be prepared." 334 00:21:01,553 --> 00:21:05,890 Whitey had been planning for years for the curtain to fall on his show. 335 00:21:06,975 --> 00:21:09,435 He had a well-planned escape route 336 00:21:09,519 --> 00:21:12,647 where he could completely drop off the face of the Earth. 337 00:21:14,983 --> 00:21:17,443 The Whitey Bulger method for getting out of Dodge 338 00:21:17,527 --> 00:21:20,989 consists of a few key steps that any outlaw can follow. 339 00:21:21,489 --> 00:21:23,950 Step one, start saving early. 340 00:21:24,784 --> 00:21:29,831 Stash cash, jewelry, and fake passports in safe deposit boxes all over the globe. 341 00:21:30,582 --> 00:21:33,084 Step two, build aliases. 342 00:21:34,336 --> 00:21:36,921 Pay top dollar for fake IDs, birth certificates, 343 00:21:37,005 --> 00:21:38,757 and credit cards in various names, 344 00:21:39,591 --> 00:21:42,427 then use new identities to open bank accounts. 345 00:21:43,595 --> 00:21:46,765 Step three, find the perfect hiding place. 346 00:21:47,432 --> 00:21:50,142 Choose somewhere you can easily blend in, 347 00:21:50,226 --> 00:21:53,063 some place with turnover and tourism. 348 00:21:54,397 --> 00:21:57,817 Outsiders will be less likely to take note of your quirks. 349 00:21:59,277 --> 00:22:02,697 Once you've found your new hometown, it's onto the next step. 350 00:22:03,698 --> 00:22:08,411 Tell no one when, where, or how you're leaving. 351 00:22:09,412 --> 00:22:12,415 You'd be surprised how many people forget this one. 352 00:22:13,333 --> 00:22:15,794 Finally, it's time to make your getaway. 353 00:22:17,045 --> 00:22:18,004 But when you do, 354 00:22:18,088 --> 00:22:21,925 don't forget the most important rule of all for going underground, 355 00:22:22,425 --> 00:22:24,052 be ready for anything. 356 00:22:27,430 --> 00:22:30,224 For 20 years, Whitey's guardian angel and the FBI 357 00:22:30,308 --> 00:22:32,643 had kept him safe from prosecution. 358 00:22:32,727 --> 00:22:37,273 But by the early 1990s, Whitey's luck was starting to run out. 359 00:22:39,943 --> 00:22:45,698 In the early 1990s, we began an investigation of Bulger and his group. 360 00:22:46,282 --> 00:22:51,037 Ultimately, we had enough evidence to charge him with racketeering, 361 00:22:51,121 --> 00:22:52,830 along with several other individuals. 362 00:22:52,914 --> 00:22:55,959 The FBI, of course, knew we were seeking the indictment. 363 00:22:57,335 --> 00:23:00,505 Whitey's top ally, Steve Flemmi, is quickly arrested. 364 00:23:01,464 --> 00:23:05,927 It is a state trooper and a DEA agent who captured Flemmi. 365 00:23:06,678 --> 00:23:11,682 And then the others went over to South Boston trying to find Whitey, 366 00:23:11,766 --> 00:23:13,351 but it was to no avail. 367 00:23:13,435 --> 00:23:14,686 He was long gone. 368 00:23:15,603 --> 00:23:17,939 Now, how do you think that happened? 369 00:23:19,149 --> 00:23:21,025 Bulger was tipped off by Connolly, 370 00:23:22,110 --> 00:23:25,405 and he was able to take off before the indictment came down. 371 00:23:29,117 --> 00:23:31,869 It was enormously frustrating to work on a case 372 00:23:31,953 --> 00:23:35,122 which the main target disappears into the mist. 373 00:23:35,206 --> 00:23:36,707 So, the strong message is 374 00:23:36,791 --> 00:23:40,461 that law enforcement will continue the effort until we get him. 375 00:23:40,545 --> 00:23:43,047 And while his whereabouts are a mystery, 376 00:23:43,131 --> 00:23:46,509 Whitey Bulger's victims have been turning up all over Boston. 377 00:23:47,260 --> 00:23:49,470 My thoughts were, they're not gonna find him. 378 00:23:49,554 --> 00:23:51,139 I know how he prepares. 379 00:23:52,015 --> 00:23:54,392 It's one thing to make a clean getaway. 380 00:23:55,435 --> 00:23:59,647 Staying safe for the long haul will take genius-level execution. 381 00:24:00,148 --> 00:24:01,691 So, follow the master. 382 00:24:10,033 --> 00:24:14,245 When you've made a name for yourself as one of history's top mob bosses, 383 00:24:14,329 --> 00:24:17,832 authorities won't be so quick to let you just disappear. 384 00:24:18,374 --> 00:24:21,043 So much about being a mob boss is being somebody. 385 00:24:21,127 --> 00:24:23,379 You have to be at ease 386 00:24:23,463 --> 00:24:27,508 and make a transition to being unrecognized and unacknowledged, 387 00:24:27,592 --> 00:24:28,968 to being a nobody. 388 00:24:29,761 --> 00:24:32,388 Whitey Bulger, a known master of disguise, 389 00:24:32,472 --> 00:24:35,057 has not been seen in six years. 390 00:24:35,141 --> 00:24:39,228 The trail is cold, even though there's a one million dollar reward out 391 00:24:39,312 --> 00:24:41,731 for information leading to his arrest. 392 00:24:43,191 --> 00:24:45,192 Even members of law enforcement in Boston 393 00:24:45,276 --> 00:24:46,861 couldn't tell you what he looked like. 394 00:24:48,154 --> 00:24:51,741 In fact, he probably looked like half the people at Fenway Park. 395 00:24:53,618 --> 00:24:55,995 But even if people don't know your face, 396 00:24:56,538 --> 00:24:59,749 keeping yourself off the radar will be a full-time job. 397 00:25:00,250 --> 00:25:03,586 Whitey excelled at this second career as well. 398 00:25:06,172 --> 00:25:07,798 After crossing the country, 399 00:25:07,882 --> 00:25:12,553 Whitey and his longtime girlfriend, Catherine Greig, settle in Santa Monica, 400 00:25:12,637 --> 00:25:15,640 where they take the names Charlie and Carol Gasko. 401 00:25:16,558 --> 00:25:19,477 Just a harmless retiree and his loving wife, 402 00:25:19,561 --> 00:25:23,481 living in a rent-stabilized apartment building near the Pacific Ocean. 403 00:25:24,148 --> 00:25:28,444 They were your typical snowbirds from the East Coast, 404 00:25:28,528 --> 00:25:30,029 living in a warm climate, 405 00:25:30,113 --> 00:25:33,199 and, you know, not causing any problems for anyone. 406 00:25:35,243 --> 00:25:37,161 Tenants in their building are friendly, 407 00:25:37,245 --> 00:25:39,872 but the Gaskos choose to keep their distance, 408 00:25:40,415 --> 00:25:42,166 especially Charlie. 409 00:25:43,626 --> 00:25:48,214 However, there are some people he makes a point of seeking out. 410 00:25:48,798 --> 00:25:51,967 Bulger would befriend homeless people 411 00:25:52,051 --> 00:25:56,680 or people really in desperate situations, and he would pay them for their ID. 412 00:25:56,764 --> 00:25:58,474 For Bulger, it was like gold. 413 00:25:58,975 --> 00:26:02,102 Whitey would tell them he's an illegal immigrant from Canada 414 00:26:02,186 --> 00:26:03,605 in need of medical help 415 00:26:04,147 --> 00:26:06,148 and offer to pay hundreds of dollars 416 00:26:06,232 --> 00:26:09,360 for their driver's license and social security number. 417 00:26:10,612 --> 00:26:11,696 Most agree. 418 00:26:13,615 --> 00:26:15,032 To avoid being tracked, 419 00:26:15,116 --> 00:26:19,162 Whitey and Catherine rotate identities at dental and medical appointments. 420 00:26:20,121 --> 00:26:24,542 And when they cross into Tijuana to buy Whitey's heart medication, 421 00:26:25,126 --> 00:26:27,211 authorities pay no mind. 422 00:26:28,713 --> 00:26:31,131 Everybody just sees Charlie and Carol Gasko 423 00:26:31,215 --> 00:26:34,719 enjoying their golden years by the California coast. 424 00:26:36,304 --> 00:26:40,016 The perfect cover for the perfect couple. 425 00:26:44,145 --> 00:26:47,731 For 16 sun-soaked years, Charlie... 426 00:26:47,815 --> 00:26:51,402 I mean, Whitey, lived his best life 427 00:26:51,486 --> 00:26:55,114 as authorities continued their efforts to track him down. 428 00:26:55,198 --> 00:26:57,450 The greatest escape in mob history. 429 00:26:58,368 --> 00:26:59,786 It has to be up there, right? 430 00:27:00,662 --> 00:27:03,747 But despite Whitey's extraordinary efforts, 431 00:27:03,831 --> 00:27:06,000 the dream didn't last forever. 432 00:27:06,084 --> 00:27:08,377 We begin this morning with a bombshell arrest overnight... 433 00:27:08,461 --> 00:27:10,754 After spending 16 years on the run, 434 00:27:10,838 --> 00:27:12,673 the FBI has caught Boston mob boss... 435 00:27:12,757 --> 00:27:14,174 ...James "Whitey" Bulger 436 00:27:14,258 --> 00:27:16,343 is captured in a Santa Monica apartment house, 437 00:27:16,427 --> 00:27:19,680 ending a worldwide manhunt that spanned 16 years. 438 00:27:19,764 --> 00:27:21,599 Ultimately, Bulger was captured 439 00:27:21,683 --> 00:27:24,977 in large part because of a cat, of all things. 440 00:27:28,231 --> 00:27:31,692 There was a woman who was watching TV in Iceland, 441 00:27:31,776 --> 00:27:34,778 and she spent her winters in Santa Monica. 442 00:27:34,862 --> 00:27:38,449 And she had bonded with another woman over a cat. 443 00:27:38,533 --> 00:27:41,577 They were both cat lovers. This was Catherine Greig. 444 00:27:42,495 --> 00:27:44,246 The two of them were friends. 445 00:27:44,330 --> 00:27:48,542 And when she saw Bulger and Greig on TV years later, 446 00:27:48,626 --> 00:27:51,295 she immediately reported this to the FBI. 447 00:27:52,505 --> 00:27:55,591 Within 24 hours, authorities lured Bulger outside 448 00:27:55,675 --> 00:27:56,508 and arrested him. 449 00:27:56,592 --> 00:27:58,636 And confiscated nearly 30 guns 450 00:27:58,720 --> 00:28:01,639 and hundreds of thousands of dollars stashed in the apartment. 451 00:28:03,224 --> 00:28:05,977 We have captured one of the FBI's ten most wanted fugitives. 452 00:28:06,728 --> 00:28:09,605 A man notorious in Boston and around the world. 453 00:28:11,899 --> 00:28:15,069 Whitey's meticulous planning kept him alive and out of jail 454 00:28:15,153 --> 00:28:17,572 until the ripe old age of 81, 455 00:28:18,364 --> 00:28:21,451 making him one of mob bossery's true iron men. 456 00:28:25,872 --> 00:28:29,208 He chose a profession, the underworld life of crime, 457 00:28:29,792 --> 00:28:32,170 where the shelf life isn't particularly long. 458 00:28:33,379 --> 00:28:36,466 But he managed to survive for decades. 459 00:28:41,846 --> 00:28:44,515 But as impressive a feat as that was, 460 00:28:45,308 --> 00:28:48,560 achieving the ultimate promise of becoming a mob boss 461 00:28:48,644 --> 00:28:51,063 requires grander ambitions. 462 00:28:51,689 --> 00:28:54,733 For the playbook's final chapter, 463 00:28:54,817 --> 00:28:58,487 I'll show you how to harness your criminal skills into wealth, 464 00:28:58,571 --> 00:29:03,159 power, and influence beyond your wildest dreams. 465 00:29:05,953 --> 00:29:06,871 Your guide... 466 00:29:07,371 --> 00:29:12,710 who else but the king of cocaine himself, Pablo Escobar.