WEBVTT 00:00:00.000 --> 00:00:01.860 ain't there nobody that can shoot this guy so 00:00:01.860 --> 00:00:05.379 he don't bounce back that is uh such a wild thing 00:00:05.379 --> 00:00:07.320 to say right that is a direct quote from the 00:00:07.320 --> 00:00:10.820 infamous 1930s mobster dutch schultz and he's 00:00:10.820 --> 00:00:13.560 expressing what had to be just the most profound 00:00:13.560 --> 00:00:16.820 frustration of his entire criminal career because 00:00:16.820 --> 00:00:19.339 he was talking about a rival who simply refused 00:00:19.339 --> 00:00:23.000 to die exactly welcome to today's deep dive i 00:00:23.000 --> 00:00:25.640 am your host and with me is our resident historian 00:00:25.640 --> 00:00:28.320 to help break this all down glad to be here this 00:00:28.320 --> 00:00:31.170 is um A really unbelievable story. It really 00:00:31.170 --> 00:00:34.130 is. Our mission today is to unpack a truly defining 00:00:34.130 --> 00:00:37.289 chapter of prohibition history and 1920s organized 00:00:37.289 --> 00:00:40.189 crime. We are using a comprehensive historical 00:00:40.189 --> 00:00:43.450 profile sourced from Wikipedia to explore the 00:00:43.450 --> 00:00:45.649 completely bullet -riddled biography of Jack 00:00:45.649 --> 00:00:47.850 Legs Diamond. And that quote from Dutch Schultz, 00:00:47.909 --> 00:00:49.770 I mean, it captures a sheer disbelief that was 00:00:49.770 --> 00:00:52.049 shared not just by rival gangs, but by the police, 00:00:52.170 --> 00:00:54.250 the press, and honestly, the general public. 00:00:54.509 --> 00:00:57.429 Yeah, we are talking about a figure who survived 00:00:57.429 --> 00:01:01.000 so much lead. He seemed entirely immune to the 00:01:01.000 --> 00:01:03.979 consequences of his own lifestyle. And I want 00:01:03.979 --> 00:01:06.799 you, the listener, to just imagine for a second 00:01:06.799 --> 00:01:08.680 living in a time where Manhattan bootleggers 00:01:08.680 --> 00:01:11.620 were global celebrities. Oh, absolutely. Splashed 00:01:11.620 --> 00:01:13.659 across the front pages of international newspapers. 00:01:13.659 --> 00:01:15.840 Right. Yet they couldn't even sit in a hotel 00:01:15.840 --> 00:01:18.859 room without dodging actual gunfire. What's fascinating 00:01:18.859 --> 00:01:21.760 here is how Jack Diamond's life wasn't just a 00:01:21.760 --> 00:01:25.019 string of random violent acts. It functions as 00:01:25.019 --> 00:01:28.040 a perfect mirror for the era itself. How so? 00:01:28.620 --> 00:01:31.540 Well, when you examine his timeline, You are 00:01:31.540 --> 00:01:34.560 looking directly at the lawlessness, the systemic 00:01:34.560 --> 00:01:37.780 corruption, and the really ruthless hyper -capitalist 00:01:37.780 --> 00:01:39.879 spirit of the underworld between the world wars. 00:01:40.079 --> 00:01:41.760 Okay, let's unpack this from the very beginning. 00:01:41.859 --> 00:01:43.599 Because a person doesn't just wake up one day 00:01:43.599 --> 00:01:45.859 as the most unkillable man in New York. No, you 00:01:45.859 --> 00:01:47.760 have to be forged in a very specific environment 00:01:47.760 --> 00:01:50.519 for that. Exactly. So Jack Diamond was born in 00:01:50.519 --> 00:01:54.319 1897 in Philadelphia to Irish immigrants Sarah 00:01:54.319 --> 00:01:56.640 and John Diamond. And the socioeconomic reality 00:01:56.640 --> 00:01:59.959 for that family was, well, it was grim. Extremely 00:01:59.959 --> 00:02:02.239 grim. His mother suffered from severe arthritis 00:02:02.239 --> 00:02:05.180 and eventually passed away from a bacterial infection 00:02:05.180 --> 00:02:08.699 and a fever when Jack was just a teenager. And 00:02:08.699 --> 00:02:11.099 without any modern social safety nets to rely 00:02:11.099 --> 00:02:13.860 on, his father moved the boys to Brooklyn to 00:02:13.860 --> 00:02:15.860 find work. And you have to look at what Brooklyn 00:02:15.860 --> 00:02:18.860 was at the turn of the century. It was an incredibly 00:02:18.860 --> 00:02:21.800 harsh environment for a grieving, impoverished 00:02:21.800 --> 00:02:24.539 immigrant family. It's just brutal. Young men 00:02:24.539 --> 00:02:27.099 in those neighborhoods faced a really stark choice. 00:02:27.400 --> 00:02:30.560 You either take a grueling, highly dangerous 00:02:30.560 --> 00:02:33.500 industrial labor job for pennies. Or you find 00:02:33.500 --> 00:02:35.979 an illicit way to survive. Right. The streets 00:02:35.979 --> 00:02:38.159 essentially became the primary educator for someone 00:02:38.159 --> 00:02:40.400 like Jack. And he certainly took that illicit 00:02:40.400 --> 00:02:42.759 route. He quickly fell in with a Manhattan street 00:02:42.759 --> 00:02:45.099 gang known as the Hudson Dusters. Which is a 00:02:45.099 --> 00:02:47.810 great name. It is. As sources note, this wasn't 00:02:47.810 --> 00:02:49.930 just some group of pickpockets. The dusters were 00:02:49.930 --> 00:02:52.370 notorious on the West Side. They were known for 00:02:52.370 --> 00:02:55.550 erratic, violent behavior, often fueled by heavy 00:02:55.550 --> 00:02:58.530 cocaine use. Yeah, they were intense. And they 00:02:58.530 --> 00:03:00.789 specialized in robbing cargo right off the shipping 00:03:00.789 --> 00:03:04.349 docks. So by 1914, Jack is already breaking into 00:03:04.349 --> 00:03:06.569 jewelry stores. He eventually gets drafted into 00:03:06.569 --> 00:03:09.349 the U .S. Army during World War I. But military 00:03:09.349 --> 00:03:11.789 discipline, as you can imagine, clashes completely 00:03:11.789 --> 00:03:14.090 with his street upbringing. It's oil and water. 00:03:14.289 --> 00:03:18.060 Completely. He deserts. Gets caught. and is sentenced 00:03:18.060 --> 00:03:21.060 to Leavenworth Military Prison for two years. 00:03:21.340 --> 00:03:23.360 Which is a crucial turning point. I mean, when 00:03:23.360 --> 00:03:26.120 you send a young, street -level criminal into 00:03:26.120 --> 00:03:28.759 a hardened military prison environment like Leavenworth 00:03:28.759 --> 00:03:31.439 in the late 1910s, it doesn't rehabilitate them. 00:03:31.539 --> 00:03:33.580 No, not at all. It acts as an advanced networking 00:03:33.580 --> 00:03:36.159 opportunity. It hardens whatever empathy they 00:03:36.159 --> 00:03:38.479 might have had left. So by the time he's released 00:03:38.479 --> 00:03:41.979 in 1921, he's perfectly primed for the explosion 00:03:41.979 --> 00:03:44.479 of organized crime that arrives with the 1920s. 00:03:44.520 --> 00:03:46.759 That perfectly sets up his entry into the... 00:03:46.759 --> 00:03:49.000 big leagues and around this time he earns the 00:03:49.000 --> 00:03:52.860 nickname legs ah yes the historical profile gives 00:03:52.860 --> 00:03:55.699 us two possible origins for this either he was 00:03:55.699 --> 00:03:58.240 an incredibly flamboyant energetic dancer at 00:03:58.240 --> 00:04:00.740 the local clubs or or he simply possessed the 00:04:00.740 --> 00:04:03.580 ability to run exceptionally fast when his enemies 00:04:03.580 --> 00:04:06.560 were chasing him right And given everything we 00:04:06.560 --> 00:04:09.080 are about to discuss, the running theory feels 00:04:09.080 --> 00:04:11.520 pretty practical. It certainly became a necessary 00:04:11.520 --> 00:04:14.300 survival skill. Definitely. So he starts working 00:04:14.300 --> 00:04:16.459 as hired muscle and eventually lands a role as 00:04:16.459 --> 00:04:19.160 the personal bodyguard for the legendary gambler 00:04:19.160 --> 00:04:22.759 Arnold Rothstein. And for those unfamiliar. Rothstein 00:04:22.759 --> 00:04:25.639 wasn't your average street thug. He was a titan 00:04:25.639 --> 00:04:28.120 of the underworld. He effectively transformed 00:04:28.120 --> 00:04:31.620 organized crime from a chaotic street brawl into 00:04:31.620 --> 00:04:34.300 a sophisticated corporate structure. But it's 00:04:34.300 --> 00:04:36.379 when prohibition makes alcohol illegal across 00:04:36.379 --> 00:04:39.079 the United States that Diamond steps out of Rothstein's 00:04:39.079 --> 00:04:41.819 shadow and really shows his own terrifying ingenuity. 00:04:41.959 --> 00:04:45.139 He finds his niche. He does. He travels to Europe 00:04:45.139 --> 00:04:48.300 to secure narcotics and beer. That actually fails, 00:04:48.420 --> 00:04:50.959 but he does secure a massive supply of liquor. 00:04:51.259 --> 00:04:54.040 What baffles me is how he solved the smuggling 00:04:54.040 --> 00:04:56.939 problem when the main ports were heavily policed. 00:04:57.019 --> 00:04:59.800 If we connect this to the bigger picture, Prohibition 00:04:59.800 --> 00:05:02.680 forced criminals to evolve from mere enforcers 00:05:02.680 --> 00:05:05.180 into highly innovative supply chain managers. 00:05:05.319 --> 00:05:07.319 Supply chain managers, yeah. Diamond realized 00:05:07.319 --> 00:05:09.660 that fighting a heavily armed Coast Guard at 00:05:09.660 --> 00:05:11.819 the New York docks was just bad for business. 00:05:12.569 --> 00:05:15.550 Instead, he developed a completely decentralized 00:05:15.550 --> 00:05:18.730 logistics network. It's so clever. He arranged 00:05:18.730 --> 00:05:21.589 for the incoming ships to simply dump partially 00:05:21.589 --> 00:05:24.790 full barrels of liquor overboard into the ocean. 00:05:25.050 --> 00:05:27.550 Just right into the water. Miles off the coast. 00:05:27.790 --> 00:05:30.110 And the tidal currents would naturally carry 00:05:30.110 --> 00:05:32.269 these floating barrels right onto the beaches 00:05:32.269 --> 00:05:34.850 of Long Island. Which is brilliant. And he didn't 00:05:34.850 --> 00:05:37.550 even need a massive crew of mobsters to retrieve 00:05:37.550 --> 00:05:40.850 them. He just waited on the shore and paid local 00:05:40.850 --> 00:05:43.550 kids a nickel for... every barrel they dragged 00:05:43.550 --> 00:05:45.689 out of the surf and brought to his waiting trucks. 00:05:46.009 --> 00:05:49.269 A nickel a barrel. Just consider the elegance 00:05:49.269 --> 00:05:52.329 of that operation. He bypassed federal jurisdiction, 00:05:52.709 --> 00:05:55.930 weaponized the ocean currents, and outsourced 00:05:55.930 --> 00:05:58.050 the physical labor to neighborhood children looking 00:05:58.050 --> 00:06:01.389 for candy money. It's crazy. It illustrates exactly 00:06:01.389 --> 00:06:03.889 why federal agents could never fully shut down 00:06:03.889 --> 00:06:06.350 the illicit alcohol trade. The syndicates were 00:06:06.350 --> 00:06:08.550 simply out thinking the law. But the corporate 00:06:08.550 --> 00:06:11.389 logistics soon gave way to visceral violence. 00:06:12.300 --> 00:06:14.800 Following the murder of his boss, Little Augie 00:06:14.800 --> 00:06:17.660 Organ, Diamond seizes control of the downtown 00:06:17.660 --> 00:06:20.379 Manhattan alcohol distribution. He steps right 00:06:20.379 --> 00:06:22.639 into the power vacuum. He establishes his headquarters 00:06:22.639 --> 00:06:25.560 at a Broadway speakeasy called the Hotsy Totsy 00:06:25.560 --> 00:06:30.019 Club. And in July 1929, the business model takes 00:06:30.019 --> 00:06:33.459 a very dark turn. Diamond and an associate get 00:06:33.459 --> 00:06:35.860 into a massive brawl with some drunken patrons. 00:06:36.680 --> 00:06:39.579 Guns are drawn, three men are shot, and two of 00:06:39.579 --> 00:06:42.410 them die right there on the floor. This is where 00:06:42.410 --> 00:06:44.769 we see the shift from clever smuggling to the 00:06:44.769 --> 00:06:47.790 raw subversion of the justice system. The aftermath 00:06:47.790 --> 00:06:50.470 of the Hotsy Totsy shooting really reveals the 00:06:50.470 --> 00:06:52.589 sheer scale of intimidation these syndicates 00:06:52.589 --> 00:06:54.730 wielded. Because you have a double homicide in 00:06:54.730 --> 00:06:56.949 a crowded Broadway club, dozens of people saw 00:06:56.949 --> 00:06:58.649 it happen. But when the police arrive to build 00:06:58.649 --> 00:07:00.990 their case, the witnesses start vanishing. This 00:07:00.990 --> 00:07:02.750 is disappearing. The bartender goes missing. 00:07:02.930 --> 00:07:05.470 Three waiters disappear. Even the coat check 00:07:05.470 --> 00:07:08.019 girl vanishes without a trace. The authorities 00:07:08.019 --> 00:07:09.939 eventually find one of the missing witnesses 00:07:09.939 --> 00:07:13.259 shot dead across state lines in New Jersey. Diamonds 00:07:13.259 --> 00:07:15.519 is never charged with the murders, although the 00:07:15.519 --> 00:07:18.259 city does force the Hotsy Totsy Club to close 00:07:18.259 --> 00:07:21.560 its doors. Making an entire staff of civilian 00:07:21.560 --> 00:07:25.060 witnesses disappear requires an immense coordinated 00:07:25.060 --> 00:07:27.579 network of terror. I mean, they weren't just 00:07:27.579 --> 00:07:30.579 hiding from the police. They were actively dismantling 00:07:30.579 --> 00:07:33.240 the state's ability to prosecute crime. Yeah, 00:07:33.279 --> 00:07:35.379 it's a whole different level. And as Diamond's 00:07:35.379 --> 00:07:38.199 territory expanded, he began clashing with other 00:07:38.199 --> 00:07:41.360 rising power players, notably Dutch Schultz, 00:07:41.439 --> 00:07:43.660 who was aggressively expanding his own operations 00:07:43.660 --> 00:07:46.060 out of Harlem. And Diamond's tactics for dealing 00:07:46.060 --> 00:07:48.379 with that competition were brutal. He wanted 00:07:48.379 --> 00:07:52.060 total monopolies. In 1930, he and his crew kidnap 00:07:52.060 --> 00:07:54.459 a truck driver named Grover Parks up in Cairo, 00:07:54.579 --> 00:07:56.790 New York. Just a truck driver. Yeah, they just 00:07:56.790 --> 00:07:58.649 want to know the origin point of Parks' load 00:07:58.649 --> 00:08:01.970 of hard cider. When Parks claims ignorance, Diamond's 00:08:01.970 --> 00:08:04.110 men subject him to a brutal beating and torture 00:08:04.110 --> 00:08:07.230 before finally letting him go. He actually repeats 00:08:07.230 --> 00:08:09.490 this tactic later that year, kidnapping a man 00:08:09.490 --> 00:08:12.870 named James Duncan. He's just using brute force 00:08:12.870 --> 00:08:15.569 at this point. Diamond manages to beat the state 00:08:15.569 --> 00:08:18.209 kidnapping charges, but the federal government 00:08:18.209 --> 00:08:20.709 finally pins him down with a four -year sentence. 00:08:21.149 --> 00:08:23.920 The walls were rapidly closing in. You have to 00:08:23.920 --> 00:08:25.899 picture the multi -front war he was fighting 00:08:25.899 --> 00:08:29.060 by the summer of 1930. The local police want 00:08:29.060 --> 00:08:31.319 him for murder, the federal agents are pursuing 00:08:31.319 --> 00:08:33.899 him for interstate crimes, and rival factions 00:08:33.899 --> 00:08:36.519 like Dutch Schultz's crew are actively trying 00:08:36.519 --> 00:08:39.539 to assassinate him to absorb his territory. Here's 00:08:39.539 --> 00:08:41.850 where it gets really interesting. It's August 00:08:41.850 --> 00:08:45.070 1930. The heat in Manhattan is suffocating in 00:08:45.070 --> 00:08:48.230 every possible sense. So Legs Diamond decides 00:08:48.230 --> 00:08:51.649 he simply needs a vacation. A vacation. He secures 00:08:51.649 --> 00:08:54.269 a ticket under the alias John Nolan and boards 00:08:54.269 --> 00:08:57.110 the transatlantic ocean liner Belgian Land, setting 00:08:57.110 --> 00:08:59.590 sail for Europe. Fleeing to Europe was a standard 00:08:59.590 --> 00:09:01.990 play for high profile figures looking to let 00:09:01.990 --> 00:09:04.649 the domestic dust settle. But the NYPD quickly 00:09:04.649 --> 00:09:07.110 realizes their prime target is missing. They 00:09:07.110 --> 00:09:09.129 search the manifests of ships like the Olympic 00:09:09.129 --> 00:09:11.549 and the Baltic, but come up empty. Finally, they 00:09:11.549 --> 00:09:13.830 send a wireless telegraph out into the Atlantic 00:09:13.830 --> 00:09:16.230 to the Belgian land. And they find him. The captain 00:09:16.230 --> 00:09:18.409 confirms they have a passenger matching Diamond's 00:09:18.409 --> 00:09:21.110 description. And what is the most hunted man 00:09:21.110 --> 00:09:23.830 in New York doing? He is spending the entire 00:09:23.830 --> 00:09:26.629 voyage lounging in the ship's smoking room, playing 00:09:26.629 --> 00:09:30.429 high -stakes poker. Meanwhile, the NYPD initiates 00:09:30.429 --> 00:09:33.240 a full -blown diplomatic incident. They begin 00:09:33.240 --> 00:09:36.100 frantically telegraphing Scotland Yard, the French 00:09:36.100 --> 00:09:39.059 authorities, the Belgian police, issuing a formal 00:09:39.059 --> 00:09:42.519 warning that Jack Diamond is inbound, basically 00:09:42.519 --> 00:09:45.580 labeling him a highly undesirable character. 00:09:46.120 --> 00:09:48.860 That sets off a spectacular international rejection 00:09:48.860 --> 00:09:51.600 tour. The Belgian land docks in Plymouth, England. 00:09:52.139 --> 00:09:54.019 Detectives from Scotland Yard are waiting at 00:09:54.019 --> 00:09:56.120 the gangway. They're not letting him off. No, 00:09:56.200 --> 00:09:58.700 they refuse to let him disembark. Diamond tries 00:09:58.700 --> 00:10:00.720 to play the innocent tourist for the swarm of 00:10:00.720 --> 00:10:02.779 reporters, claiming he is simply traveling to 00:10:02.779 --> 00:10:04.799 the French town of Vichy to take the cure for 00:10:04.799 --> 00:10:07.070 his health. Taking the cure referred to visiting 00:10:07.070 --> 00:10:09.629 natural thermal springs, which was a deeply amusing 00:10:09.629 --> 00:10:12.389 alibi for a man who made his fortune selling 00:10:12.389 --> 00:10:15.450 bathtub gin and dodging bullets. The European 00:10:15.450 --> 00:10:17.830 authorities certainly didn't buy it. They absolutely 00:10:17.830 --> 00:10:20.470 did not. So he stays aboard until the ship reaches 00:10:20.470 --> 00:10:23.549 Antwerp, Belgium. The moment his foot touches 00:10:23.549 --> 00:10:26.769 the dock, Belgian police surround him. Oh, man. 00:10:26.870 --> 00:10:29.429 They take him straight to headquarters, process 00:10:29.429 --> 00:10:32.049 him and physically place him on a train headed 00:10:32.049 --> 00:10:35.759 for Germany. The train. pulls into Aachen, Germany. 00:10:36.019 --> 00:10:38.179 The German police are waiting on the platform. 00:10:38.500 --> 00:10:40.860 It just keeps going. They arrest him, hold him 00:10:40.860 --> 00:10:43.440 in a cell for several days, drive him to the 00:10:43.440 --> 00:10:46.759 port of Hamburg, and toss him onto a slow -moving 00:10:46.759 --> 00:10:49.019 cargo ship called the Hanover heading right back 00:10:49.019 --> 00:10:51.799 to Philadelphia. This sequence reveals so much 00:10:51.799 --> 00:10:53.899 about the global perception of America at the 00:10:53.899 --> 00:10:56.820 time. The Manhattan bootleg wars were front -page 00:10:56.820 --> 00:10:59.679 news worldwide. European governments looked at 00:10:59.679 --> 00:11:01.860 the staggering violence of the Prohibition era 00:11:01.860 --> 00:11:04.460 and viewed American gangsters as an infectious 00:11:04.460 --> 00:11:07.460 disease. Basically a quarantine situation. Exactly. 00:11:07.639 --> 00:11:10.019 They treated Diamond's arrival as a literal threat 00:11:10.019 --> 00:11:12.480 to national security. So he rides that cargo 00:11:12.480 --> 00:11:14.940 ship all the way back across the Atlantic. He 00:11:14.940 --> 00:11:16.879 steps off the boat in Philadelphia and the local 00:11:16.879 --> 00:11:19.679 police immediately slap cuffs on him. They haul 00:11:19.679 --> 00:11:21.799 him before a judge that exact same afternoon. 00:11:22.080 --> 00:11:23.940 And what does the judge do? The judge looks at 00:11:23.940 --> 00:11:26.480 the exhausted gangster and says, I will release 00:11:26.480 --> 00:11:30.039 you, but you have exactly one hour to leave the 00:11:30.039 --> 00:11:32.580 city limits of Philadelphia. He traveled thousands 00:11:32.580 --> 00:11:35.100 of miles across the ocean, only to be handed 00:11:35.100 --> 00:11:37.679 right back to the exact ecosystem he was desperately 00:11:37.679 --> 00:11:40.379 trying to escape. And it is a miracle he survived 00:11:40.379 --> 00:11:42.840 the return trip because surviving was the defining 00:11:42.840 --> 00:11:45.759 characteristic of Legs Diamond. This is how he 00:11:45.759 --> 00:11:48.379 earned the moniker the Clay Pigeon of the Underworld. 00:11:48.419 --> 00:11:51.399 Right. Let's break down the timeline of the unkillable 00:11:51.399 --> 00:11:53.700 man because the sheer volume of lead he absorbed 00:11:53.700 --> 00:11:56.980 is staggering. What stands out to you about how 00:11:56.980 --> 00:11:59.519 this violence escalated? Well, for context, a 00:11:59.519 --> 00:12:02.200 clay pigeon is the fragile ceramic disc launched 00:12:02.200 --> 00:12:05.279 into the air during trap shooting. Its sole purpose 00:12:05.279 --> 00:12:07.919 for existing is to be shattered. The fact that 00:12:07.919 --> 00:12:10.259 the underworld gave him this nickname tells you 00:12:10.259 --> 00:12:13.120 how routinely he was targeted. It starts in 1924. 00:12:13.399 --> 00:12:15.759 Diamond is hit with shotgun pellets during a 00:12:15.759 --> 00:12:17.840 violent dispute over hijacked liquor trucks. 00:12:18.019 --> 00:12:20.360 He survives, brushes it off, and goes back to 00:12:20.360 --> 00:12:22.519 work. Just back to business. Then we jump to 00:12:22.519 --> 00:12:25.679 1927. He's walking down the street on the Lower 00:12:25.679 --> 00:12:27.940 East Side, acting as a bodyguard for his boss, 00:12:28.159 --> 00:12:30.600 Little Augie Organ. Diamond is actually just 00:12:30.600 --> 00:12:32.899 covering a shift for his brother, Eddie. A car 00:12:32.899 --> 00:12:36.730 pulls up. Gunmen jump out and open fire. Augie 00:12:36.730 --> 00:12:39.129 is killed instantly. Diamond takes two bullets 00:12:39.129 --> 00:12:41.210 straight to the chest, just below the heart. 00:12:41.370 --> 00:12:43.610 We really have to pause on the medical reality 00:12:43.610 --> 00:12:47.919 of 1927. Taking two bullets near the heart before 00:12:47.919 --> 00:12:50.600 the invention of modern trauma surgery, before 00:12:50.600 --> 00:12:53.740 widespread blood transfusions, and before antibiotics 00:12:53.740 --> 00:12:56.679 even existed. That's a death sentence. As usually 00:12:56.679 --> 00:12:59.259 a guaranteed death certificate. Yet he is rushed 00:12:59.259 --> 00:13:01.679 to Bellevue Hospital and manages a full recovery, 00:13:01.879 --> 00:13:04.080 and he perfectly adheres to the underworld code 00:13:04.080 --> 00:13:06.500 of silence. When the detectives surround his 00:13:06.500 --> 00:13:09.019 hospital bed demanding names, he refuses to offer 00:13:09.019 --> 00:13:11.779 a single syllable of cooperation. Incredible. 00:13:11.899 --> 00:13:26.320 But the violence just keeps compounding. 5 bullets 00:13:26.320 --> 00:13:29.240 at close range. The kinetic energy alone should 00:13:29.240 --> 00:13:31.360 have dropped him permanently. But instead of 00:13:31.360 --> 00:13:34.139 dying, Diamond drags himself to his feet. Before 00:13:34.139 --> 00:13:36.559 he staggers out into the hotel hallway to scream 00:13:36.559 --> 00:13:39.600 for help, he manages to pour himself two neat 00:13:39.600 --> 00:13:41.919 shots of whiskey and drinks them down. You can't 00:13:41.919 --> 00:13:44.789 make this stuff up. He is rushed to Polyclinic 00:13:44.789 --> 00:13:48.490 Hospital and, defying all medical logic, he recovers 00:13:48.490 --> 00:13:52.990 again. Which brings us to April 1931. He's dining 00:13:52.990 --> 00:13:55.509 with friends at the Aratoga Inn, a roadhouse 00:13:55.509 --> 00:13:58.830 near Cairo, New York. Gunmen ambush him, shooting 00:13:58.830 --> 00:14:02.049 him three more times. He collapses by the front 00:14:02.049 --> 00:14:04.149 door, gets driven to an Albany hospital by a 00:14:04.149 --> 00:14:05.929 local resident, and delivers one of the most 00:14:05.929 --> 00:14:09.049 famous quotes in mob history. He looks up at 00:14:09.049 --> 00:14:11.409 the surgeon working on him and says, They have 00:14:11.409 --> 00:14:13.470 not yet made the bullet that will kill me. This 00:14:13.470 --> 00:14:15.389 raises an important question. When an individual 00:14:15.389 --> 00:14:17.870 survives that level of repeated catastrophic 00:14:17.870 --> 00:14:21.269 trauma, what does it do to their psyche? It has 00:14:21.269 --> 00:14:24.929 to change you. It creates a dual effect. Externally, 00:14:24.929 --> 00:14:27.909 his rivals like Dutch Schultz begin to view him 00:14:27.909 --> 00:14:30.389 as a mythological figure, questioning if he is 00:14:30.389 --> 00:14:33.509 genuinely invincible. But internally, surviving 00:14:33.509 --> 00:14:36.230 that many assassination attempts breeds a fatal 00:14:36.230 --> 00:14:38.529 level of recklessness. You start to believe your 00:14:38.529 --> 00:14:41.279 own myth, which makes you bolder. less cautious, 00:14:41.320 --> 00:14:43.940 and ultimately a much larger target. And he pushed 00:14:43.940 --> 00:14:46.700 that luck further than anyone in his era. But 00:14:46.700 --> 00:14:48.759 the mathematics of probability eventually catch 00:14:48.759 --> 00:14:51.360 up with everyone. This brings us to the final 00:14:51.360 --> 00:14:55.519 fatal chapter. It's December 1931. Diamond is 00:14:55.519 --> 00:14:57.860 up in Albany, New York, standing trial for the 00:14:57.860 --> 00:15:01.259 kidnapping of James Duncan. On December 17th, 00:15:01.259 --> 00:15:04.110 the jury reads the verdict. Not guilty. Think 00:15:04.110 --> 00:15:06.789 about the adrenaline of that moment. He has outmaneuvered 00:15:06.789 --> 00:15:08.809 the federal government, survived countless mob 00:15:08.809 --> 00:15:11.129 hits, and just walked away from a massive state 00:15:11.129 --> 00:15:13.669 trial. He must have felt entirely untouchable. 00:15:13.789 --> 00:15:15.549 He is celebrating like a man who has conquered 00:15:15.549 --> 00:15:17.409 the world. He goes out to dinner with his family, 00:15:17.450 --> 00:15:19.690 and then around 1 .00 a .m., he sends his wife 00:15:19.690 --> 00:15:21.870 home and takes his mistress, a showgirl named 00:15:21.870 --> 00:15:23.809 Kiki Roberts, to the Rainbow Room at the Kenmore 00:15:23.809 --> 00:15:26.230 Hotel. They drink heavily into the early hours 00:15:26.230 --> 00:15:28.330 of the morning. Setting the stage for disaster. 00:15:28.769 --> 00:15:32.289 Around 4 .30 a .m., heavily intoxicated, he stumbles 00:15:32.289 --> 00:15:34.870 back to a rooming house at 67 Dove Street and 00:15:34.870 --> 00:15:37.470 passes out on the bed. He is completely isolated. 00:15:37.830 --> 00:15:40.970 No bodyguards. His senses dulled by alcohol and 00:15:40.970 --> 00:15:43.769 a deep sleep. He has finally let his guard down. 00:15:44.029 --> 00:15:46.389 About an hour later, two men slip quietly into 00:15:46.389 --> 00:15:48.889 the Dove Street room. One man physically pins 00:15:48.889 --> 00:15:51.570 the legendary Legs Diamond to the mattress, while 00:15:51.570 --> 00:15:53.490 the second man presses a gun to the back of his 00:15:53.490 --> 00:15:56.570 head and fires three times. The clay pigeon finally 00:15:56.570 --> 00:15:59.929 shattered. An incredibly abrupt, unceremonious 00:15:59.929 --> 00:16:01.909 execution for a man who had lived his entire 00:16:01.909 --> 00:16:04.929 adult life at maximum volume. For decades, historians 00:16:04.929 --> 00:16:06.929 and the public debated the obvious question. 00:16:07.269 --> 00:16:10.179 Who finally killed Legs Diamond? The suspect 00:16:10.179 --> 00:16:12.820 list was endless. Dutch Schultz wanted him dead. 00:16:12.980 --> 00:16:15.080 The Ollie brothers wanted him dead. The family 00:16:15.080 --> 00:16:17.299 of Red Cassidy, another gangster Diamond had 00:16:17.299 --> 00:16:20.360 clashed with, wanted revenge. However, the historical 00:16:20.360 --> 00:16:22.740 profile highlights a much more complex theory, 00:16:22.840 --> 00:16:25.259 famously detailed by author William Kennedy in 00:16:25.259 --> 00:16:27.399 his book O Albany. And this theory fundamentally 00:16:27.399 --> 00:16:30.120 alters the narrative of 1930s organized crime. 00:16:30.509 --> 00:16:33.110 Kennedy's account suggests the hit wasn't ordered 00:16:33.110 --> 00:16:35.850 by a rival bootlegger or a syndicate boss from 00:16:35.850 --> 00:16:38.750 New York City. The order allegedly came from 00:16:38.750 --> 00:16:41.230 Dan O 'Connell, the powerful boss who controlled 00:16:41.230 --> 00:16:43.830 the local Democratic political machine in Albany. 00:16:44.230 --> 00:16:46.629 Kennedy actually conducted a recorded interview 00:16:46.629 --> 00:16:50.090 with O 'Connell in 1974, where the aging political 00:16:50.090 --> 00:16:52.909 boss essentially outlined the entire dynamic. 00:16:52.929 --> 00:16:55.110 The quotes from that interview are staggering. 00:16:55.960 --> 00:16:58.299 O 'Connell stated that Diamond called him up, 00:16:58.340 --> 00:17:00.460 announcing he wanted to set up an insurance business 00:17:00.460 --> 00:17:03.220 in Albany. Which was just code for selling strong 00:17:03.220 --> 00:17:05.599 -arm protection rackets to local merchants. Right, 00:17:05.720 --> 00:17:08.019 and O 'Connell sent a message back saying, absolutely 00:17:08.019 --> 00:17:10.599 not, you are not operating here, and you'd better 00:17:10.599 --> 00:17:12.880 be out of town by tomorrow. O 'Connell explained 00:17:12.880 --> 00:17:16.240 the philosophy bluntly, stating, in order for 00:17:16.240 --> 00:17:18.319 the mafia to move in, they had to have protection, 00:17:18.440 --> 00:17:20.220 and they know they'll never get it in this town. 00:17:20.359 --> 00:17:23.039 We settled that years ago. The theory posits 00:17:23.039 --> 00:17:25.759 that Albany Police Sergeant William Fitzpatrick 00:17:25.759 --> 00:17:27.259 was the man who actually pulled the trigger. 00:17:27.859 --> 00:17:30.779 The lore suggests Fitzpatrick sat with Diamond 00:17:30.779 --> 00:17:33.519 earlier, warned him to keep moving, and when 00:17:33.519 --> 00:17:35.920 Diamond stayed to celebrate his acquittal, the 00:17:35.920 --> 00:17:38.420 police sergeant acted as the assassin for the 00:17:38.420 --> 00:17:40.859 political machine. Let's pause on the implications 00:17:40.859 --> 00:17:43.930 of that. The standard historical narrative frames 00:17:43.930 --> 00:17:46.349 the Prohibition era as a battle between righteous 00:17:46.349 --> 00:17:49.289 law enforcement and corrupt gangsters. Good guys 00:17:49.289 --> 00:17:52.930 versus bad guys. Exactly. But the Albany theory 00:17:52.930 --> 00:17:55.470 suggests that in some cities, the local political 00:17:55.470 --> 00:17:57.849 apparatus and the police department were the 00:17:57.849 --> 00:18:00.809 dominant organized crime syndicate. They held 00:18:00.809 --> 00:18:03.289 a state -sponsored monopoly on vice and gambling. 00:18:03.569 --> 00:18:06.170 When they assassinated Legs Diamond, they weren't 00:18:06.170 --> 00:18:08.769 upholding the law. They were violently eliminating 00:18:08.769 --> 00:18:11.250 a corporate competitor. And the aftermath certainly 00:18:11.250 --> 00:18:14.009 supports that dark theory. Sergeant Fitzpatrick 00:18:14.009 --> 00:18:16.329 was subsequently promoted to chief of the Albany 00:18:16.329 --> 00:18:19.569 police. And in a fittingly violent twist, Chief 00:18:19.569 --> 00:18:21.990 Fitzpatrick was shot and killed in his own office 00:18:21.990 --> 00:18:25.769 in 1945 by one of his own detectives. The cycle 00:18:25.769 --> 00:18:27.789 of violence just consumed everyone it touched. 00:18:28.029 --> 00:18:31.150 So what does this all mean? We look back at Jack 00:18:31.150 --> 00:18:33.490 Legs Diamond, a man whose exploits commanded 00:18:33.490 --> 00:18:35.869 international headlines and forced diplomatic 00:18:35.869 --> 00:18:40.099 standoffs. Yet... His end was remarkably hollow. 00:18:40.500 --> 00:18:43.319 Very hollow. When he was buried at Mount Olivet 00:18:43.319 --> 00:18:45.799 Cemetery in Queens a few days after the Albany 00:18:45.799 --> 00:18:48.299 shooting, the press noted the glaring absence 00:18:48.299 --> 00:18:51.900 of his peers. Out of the 200 spectators, not 00:18:51.900 --> 00:18:54.500 a single underworld figure attended the funeral. 00:18:54.680 --> 00:18:56.660 Because the loyalty of the syndicates is entirely 00:18:56.660 --> 00:18:59.359 transactional. The moment you are no longer a 00:18:59.359 --> 00:19:02.500 threat or an asset, you cease to exist tragically 00:19:02.500 --> 00:19:04.779 the fallout didn't stop with him a year and a 00:19:04.779 --> 00:19:08.559 half later in july 1933 his widow alice kenny 00:19:08.559 --> 00:19:10.880 diamond a woman who historically never supported 00:19:10.880 --> 00:19:13.440 his criminal enterprises was found shot to death 00:19:13.440 --> 00:19:15.740 in her brooklyn apartment the prevailing theory 00:19:15.740 --> 00:19:18.079 is that his enemies murdered her simply to ensure 00:19:18.079 --> 00:19:20.160 she never shared anything she might have overheard 00:19:20.160 --> 00:19:22.359 during their marriage it serves as a grim marker 00:19:22.359 --> 00:19:24.859 of the collateral damage these enterprises generated 00:19:24.859 --> 00:19:27.640 the violence always bled outside the boundaries 00:19:27.640 --> 00:19:30.519 of the gang itself But Diamond's mythology did 00:19:30.519 --> 00:19:32.960 embed itself deeply into pop culture. Oh, definitely. 00:19:33.119 --> 00:19:35.680 He inspired movies, an episode of the television 00:19:35.680 --> 00:19:38.579 series The Untouchables, and in the late 1980s, 00:19:38.579 --> 00:19:41.319 a Broadway musical titled Legs Diamond starring 00:19:41.319 --> 00:19:44.319 Peter Allen. Though the musical was a spectacular 00:19:44.319 --> 00:19:47.960 flop. closing after just 64 performances. Not 00:19:47.960 --> 00:19:50.500 everything can be a hit. True. In more recent 00:19:50.500 --> 00:19:53.000 decades, Raekwon from the legendary hip -hop 00:19:53.000 --> 00:19:56.039 group Wu -Tang Clan adopted the alias Lex Diamond 00:19:56.039 --> 00:19:58.940 for his solo projects, proving how enduring that 00:19:58.940 --> 00:20:02.500 outlaw persona remains. The outlaw persona is 00:20:02.500 --> 00:20:05.119 captivating, but I want to leave you with a final 00:20:05.119 --> 00:20:07.460 thought to mull over, building on the reality 00:20:07.460 --> 00:20:10.569 of his death in Albany. If the theory holds true, 00:20:10.730 --> 00:20:13.289 if the political machines and the police departments 00:20:13.289 --> 00:20:15.450 of the 1930s were operating their own violent 00:20:15.450 --> 00:20:18.089 monopolies on vice, it makes you wonder about 00:20:18.089 --> 00:20:19.910 the history we've been sold. That's a great point. 00:20:20.069 --> 00:20:22.410 How much of the glamorous, terrifying myth of 00:20:22.410 --> 00:20:24.609 the outlaw gangster was actually just public 00:20:24.609 --> 00:20:27.809 relations, where figures like Legs Diamond amplified 00:20:27.809 --> 00:20:29.910 in the press to serve as convenient boogeymen, 00:20:30.109 --> 00:20:32.210 distracting the public from the fact that the 00:20:32.210 --> 00:20:34.470 most successful, untouchable crime syndicates 00:20:34.470 --> 00:20:37.329 were the very institutions sworn to protect them. 00:20:37.589 --> 00:20:40.769 That is an incredibly provocative way to re -examine 00:20:40.769 --> 00:20:43.750 the history of the 1920s. Thank you so much for 00:20:43.750 --> 00:20:46.029 joining us on this deep dive. It's been a fascinating 00:20:46.029 --> 00:20:48.369 journey through the complex, bullet -riddled 00:20:48.369 --> 00:20:50.789 logistics of the Prohibition underworld. Keep 00:20:50.789 --> 00:20:52.730 questioning the narratives of the past, keep 00:20:52.730 --> 00:20:54.650 exploring the history around you, and we'll catch 00:20:54.650 --> 00:20:55.450 you on the next one.