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  • Marijuana Mercenary – Ken Behr
    Jan 19 2026
    In this powerful and wide-ranging episode of Gangland Wire, host Gary Jenkins sits down with Ken Behr, author of One Step Over the Line: Confessions of a Marijuana Mercenary. Behr tells his astonishing life story—from teenage marijuana dealer in South Florida, to high-level drug runner and smuggler, to DEA cooperating source working major international cases. Along the way, he offers rare, first-hand insight into how large-scale drug operations actually worked during the height of the War on Drugs—and why that war, in his view, has largely failed. From Smuggler to Source Behr describes growing up during the explosion of the drug trade in South Florida during the 1970s and 1980s, where smuggling marijuana and cocaine became almost commonplace. He explains how he moved from street-level dealing into large-scale logistics—off-loading planes, running covert runways in the Everglades, moving thousands of pounds of marijuana, and participating in international smuggling operations involving Canada, Jamaica, Colombia, and the Bahamas. After multiple arrests—including a serious RICO case that threatened him with decades in prison—Behr made the life-altering decision to cooperate with the DEA. What followed was a tense and dangerous double life as an undercover operative, helping law enforcement dismantle major trafficking networks while living under constant pressure and fear of exposure. Inside the Mechanics of the Drug Trade This episode goes deep into the nuts and bolts of organized drug trafficking, including: How clandestine runways were built and dismantled in minutes How aircraft were guided into unlit landing zones How smuggling crews were paid and organized Why most drug operations ultimately collapse from inside The role of asset seizures in federal drug enforcement Hit me up on Venmo for a cup of coffee or a shot and a beer @ganglandwire Click here to “buy me a cup of coffee” Subscribe to the website for weekly notifications about updates and other Mob information. To go to the store or make a donation or rent Ballot Theft: Burglary, Murder, Coverup, click here To rent ‘Brothers against Brothers’ or ‘Gangland Wire,’ the documentaries click here. To purchase one of my books, click here. Transcript [00:00:00] well, hey, all your wire taps. It’s good to be back here in studio of Gangland Wire. I have a special guest today. He has a book called, uh, title is One Step Over the Line and, and he went several steps over the line, I think in his life. Ken Bearer, welcome Ken. Thanks for having me. Thanks for having me. Now, Ken, Ken is a, was a marijuana smuggler at one time and, and ended up working with the DEA, so he went from one side over to my side and, and I always like to talk to you guys that that helped us in law enforcement and I, there’s a lot of guys that don’t like that out there, but I like you guys you were a huge help to us in law enforcement and ended up doing the right thing after you made a lot of money. So tell us about the money. We were just starting to talk about the money. Tell us about the money, all those millions and millions of dollars that you drug smuggler makes. What happens? Well, I, you know, like I said, um, Jimmy Buffett’s song a pirate looks at 40, basically, he says, I made enough money to to buy Miami and pissed it away all so fast, never meant to last. And, and that’s what happens. I do know a few people that have [00:01:00] put away money. One of my friends that we did a lot of money together, a lot of drug dealing and a lot of moving some product, and he’s put the money away. Got in bed with some other guy that was, you know, legal, bought a bunch of warehouses, and now he lives a great life, living off the money he put away. Yeah. If the rents and stuff, he, he got into real estate. Other guys have got into real estate and they got out and they ended up doing okay. ’cause now they’re drawing all those rents. That’s a good way to money. Exactly what he did. Uh, my favorite, I was telling you a favorite story of mine was the guy that was a small time dealer used to hang out at the beach. And, uh, we en he ended up saving $80,000, which was a lot of money back then. Yeah. And then put it all, went to school to be a culinary chef and then got a job at the Marriott as a culinary chef and a chef. So he, you know, he really took the money, made a little bit of money, didn’t make a lot Yeah. But made enough to go to school and do something with his life. That’s so, um, that’s a great one. That’s a good one [00:02:00] there. That’s real. Yeah. But he wasn’t a big time guy. Yeah. You know what, what happens is you might make a big lick. You know, I, I never made million dollar moves. I have lots of friends that did. I always said I didn’t want to be a smuggler. ’cause I was making a steady living, being a drug runner. If you brought in 40, 50,000 pounds of weed, you would come to me and then I would move it across ...
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  • IRS Undercover on Frank Schweihs
    Jan 14 2026
    In this bonus episode of Gangland Wire, retired Kansas City Intelligence Detective Gary Jenkins takes listeners back to 1970s Chicago for a series of lesser-known yet revealing stories about the Chicago Outfit, centered on violent enforcer Frank Schweihs, also known as “Frank the German.” The episode begins with a personal side quest—tracking down the mystery of Tony Accardo and his rare red 1950s Mercedes sports car, possibly a 300 SL. These exotic cars were produced in limited numbers, and with Accardo’s history attached, the vehicle could be worth a fortune today. The question is: where did it go? From there, the story moves deep into Outfit territory. Schweihs was a feared figure who worked under Joseph Lombardo and alongside other notorious mobsters. I recount an undercover operation involving a wired Old Town business owner who helped federal agents capture Schweihs, extorting money, one of the cases that eventually put him behind bars. The episode also explores a remarkable undercover IRS investigation in which an agent posing as a criminal associate gained Schweihs’ trust. Listeners hear about crooked real estate deals, political corruption, bribe demands, and just how casually violence was discussed inside the Outfit’s inner circle—including talk of bombing a politician’s car when business deals stalled. These stories offer a raw, street-level look at how the Chicago Outfit operated during its peak years—how intimidation, corruption, and violence were everyday tools of business—and why figures like Frank Schweihs remain symbols of the Outfit’s brutality. Hit me up on Venmo for a cup of coffee or a shot and a beer @ganglandwire Click here to “buy me a cup of coffee” Subscribe to the website for weekly notifications about updates and other Mob information. To go to the store or make a donation or rent Ballot Theft: Burglary, Murder, Coverup, click here To rent ‘Brothers against Brothers’ or ‘Gangland Wire,’ the documentaries click here. To purchase one of my books, click here. 00:00 – Introduction and Chicago Bonus Episode 00:24 – Tony Accardo’s Red Mercedes Mystery 02:55 – The Chicago Outfit in the 1970s 03:31 – Frank Schweihs and the Extortion Case 04:42 – Undercover IRS Agent Inside the Outfit 06:33 – Corruption, Real Estate, and Political Payoffs 08:37 – Violence Threats and Taking the Case Down 09:35 – Windy City Mafia and Final Thoughts Transcript [0:00] Well, hey, all you wiretappers out there, Gary Jenkins, retired Kansas City Police Intelligence Unit detective here back in the studio with a little bonus episode, Gangland Wire. And I’ve been doing a bunch of Chicago stuff, as you know. Well, here’s one more before I stray away from Chicago. I had been away from Chicago for a long time and I missed it. I missed you guys up there. And, you know, here’s another thing before I really get started in this story. Okay. [0:24] I’m on a mission right now. I remembered an old story about Tony Accardo had a 1950s Mercedes SL, and I think it was a Gull Wing, but I’m not sure. It was a 300 SL. [0:40] He for sure had a 1950s Mercedes red sports car. And I always wondered, you know, I wonder what happened to that car. You know, I ought to be able to run that down. I interviewed a guy recently about an investigation into finding an extremely rare exotic car that was worth like $25 million or something. It was a teardrop, German-made, something about a Talbert Lago or some game like that. Anyhow, so it got me thinking. And they were talking about running down the cars and the history on cars, the Provence on cars. And they said, when you have a really good story attached to a car, it makes it worth a whole lot more money than normal. And I called up a friend of mine that wheels and deals in classic cars through Mecham’s. And I think there’s another auto auction. He said, oh, yeah. He said, man, you can find that car. If it hadn’t already had that priced into it, the fact that Tony Accardo sold it or owned it, then it would be worth a whole lot more money. So I thought, well, let’s just see if we can’t find that car. I started looking into it. These 1950s Mercedes 300 SLs, there wasn’t very many I’ve made. There was only a couple thousand I’ve made in over several years’ time. And the best I could tell, they’re all accounted for in some manner. I don’t know. I haven’t figured that out yet. I started asking around and trying to find people that could help me with sources on that. So if you know anybody that’s a real expert on these old Mercedes sports cars. [2:10] Send them to me. Have them email me at ganglandwire at gmail.com or something like that. And if you are, you know, give me a call, 816-931-3535. I just think it would be fun to find it. I’d do a little show on it if I found it. And find out what happened to it. Now, it might make somebody really happy. We can find it, and he didn’t know ...
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  • Did the Mafia Queen Open Springfield to the Genovese Family?
    Jan 12 2026
    In this episode of Gangland Wire, Mafia Genealogist Justin Cascio joins Intelligence Unit detective Gary Jenkins to explore one of the most remarkable—and overlooked—figures of the Prohibition era: Pasqualina Albano Siniscalchi, the so-called Bootleg Queen of Springfield, Massachusetts. At the dawn of Prohibition in 1921, Pasqualina was a young widow living in Springfield’s South End when she inherited her late husband’s powerful bootlegging operation—one of the largest in western Massachusetts. Rather than step aside, she took control. Pasqualina ruled a crew of toughs and bootleggers, oversaw liquor distribution, and launched a relentless campaign of vengeance against rivals who challenged her authority. Newspapers dubbed her The Bootleg Queen, but her fight went far beyond rival gangs. She clashed with lawmakers, battled competing bootleggers, and even faced resistance from within her own family—all while operating in service of a secret society that would never fully accept her because she was a woman. Her story exposes the contradictions of organized crime: loyalty demanded without equality, power wielded without recognition. Cascio draws from years of meticulous research and family histories to bring Pasqualina’s story to life, revealing her pivotal role in early Mafia expansion in New England and the hidden influence women could wield behind the scenes. His book, Pasqualina: The True Story of the Bootleg Queen of Springfield, challenges long-held assumptions about gender, power, and the Mafia during Prohibition. If you’re interested in Prohibition-era crime, New England Mafia history, or the untold stories of women who shaped organized crime from the shadows, this episode is one you won’t want to miss. Learn more about Justin and his work on Mafia Geneology by clicking this sentence. Get Justin’s book, Pasqualina: The Bootleg Queen of Springfield, Massachusetts Listen now on Gangland Wire — available on all major podcast platforms and YouTube. 0:02 Introduction to Mafia Genealogy 1:16 Pasqualina Albano’s Story 2:30 Family Reunion Revelations 4:56 The Impact of Prohibition 7:45 Prejudice and Organized Crime 10:50 Connecting the Genovese Family 12:34 Views from Sicily 13:50 Cultural Differences in Dress 16:37 Encounters with Modern Gangsters 18:36 Gina’s Documentary and Art 23:53 The Romance of the Gangster 27:24 The Nature of Risk 28:46 The Evolution of Organized Crime 33:16 Closing Thoughts and Future Plans Hit me up on Venmo for a cup of coffee or a shot and a beer @ganglandwire Click here to “buy me a cup of coffee” Subscribe to the website for weekly notifications about updates and other Mob information. To go to the store or make a donation or rent Ballot Theft: Burglary, Murder, Coverup, click here To rent ‘Brothers against Brothers’ or ‘Gangland Wire,’ the documentaries click here. To purchase one of my books, click here. Transcript [0:00] Hey, all you wiretappers. Good to be back here in the studio of Gangland Wire. I’ve got on tap here a repeat guest. He’s been on before. I had a little technical glitch this morning with the internet, and I had to scurry around and do something different. I totally forgot about what I was going to talk about with Justin, but I knew Justin’s been on there before. I knew he does mafia genealogy, and I knew he knows his stuff, and so he doesn’t really need a lot of help from me. So this is Justin Cascio from the website and some books, some mafia genealogies. Welcome, Justin. Thanks so much, Gary. Great to be here. Really. And you’re from the Springfield, Massachusetts area. And so that’s been some of your emphasis has been on that area. But you’ve done a lot of other mob genealogy, correct? Yes. On my website, on mafiagenealogy.com, I write about a whole lot of different places that the mafia has been in the United States. In fact, coming up, I’m going to be writing about Kansas City. But for the last 25 years or so, I’ve lived in New England. I live about 20 miles away from Springfield, Massachusetts, which if you’ve heard of Anthony Aralata or Bruno or the Shabelli brothers, then you know the Springfield crew of the Genovese crime family. [1:12] And I’ve been following them pretty closely since I’ve lived here. A few years ago, I got into the story of Pasqualina Albano, who was a bootlegger in Springfield during Prohibition. [1:25] That’s what my new book is about. Yeah. Oh, that’s a new book, right? I’m sorry. I didn’t pick up real quick there. And she’s done a documentary recently that hasn’t been seen by very many people. And they really, she was a woman. They do use the A at the end. Those of us that know about romance languages would know as probably a woman, but she’s a woman. And she was running a certain segment of bootlegging back during the 30s and late 20s, exactly when it was, which is really unusual. She must have been a powerful individual. I think that she was ...
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  • Chicago Outfit Informants
    Jan 5 2026
    In this episode, we delve into the intricate world of the Chicago Outfit’s informants, featuring insights from my late friend, Cam Robinson, and Paul Whitcomb, a well-respected expert on the mob. This special compilation draws from past interviews and shorts that once highlighted various informants who operated during the notorious 1980s era of organized crime in Chicago. Through a series of concise segments, we explore the lives of key players who chose to turn against the Outfit, revealing the complex motivations and consequences of their decisions. We kick things off by revisiting the tale of Paul “Peanuts” Pansko, an influential figure leading the Polish faction of the Outfit. Pansko’s criminal activities, including a racetrack heist, not only placed him in dangerous territory but also set into motion a chain of events that would later link to the infamous Family Secrets trial. It’s during this journey that we outline how interconnected the informants’ narratives are, showcasing how Pansko’s actions inadvertently unraveled parts of the organization. The discussion shifts to more dramatic stories, including Mario Rainone. Rainone’s infamous decision to cooperate with the authorities opened the door to significant revelations about Lenny Patrick, one of the highest-ranking Outfit members to switch sides. Rainone’s tapes ultimately led to the dismantling of major sections of the Outfit’s operations, including political connections that had long shielded them from legal repercussions. We also explore the tale of Ken “Tokyo Joe” Eto, a Japanese mobster who thrived within the Outfit’s ranks. His attempts at self-preservation after surviving an assassination effort highlighted the stark realities faced by those who navigated the perilous landscape of organized crime. As he eventually became a witness for the prosecution, Eto’s insights illuminated the internal workings of one of Chicago’s most feared organizations. The episode further examines dramatic betrayals and deadly encounters that shaped the Outfit’s legacy. From the chilling events surrounding the murders of the Spilotro brothers, orchestrated by their own associates for reasons steeped in loyalty and betrayal, to the grim fate that met informants like Al Toco and the impact of domestic discord on organized crime, each tale is a window into the bleak realities faced by both mobsters and informants alike. As we round out the episode, we reflect on the cultural dynamics surrounding informants, particularly how personal relationships and family ties heavily influenced their decisions to cooperate. It becomes clear through the interviews that while fear of retribution often compels loyalty, the specter of betrayal looms large within the mob. This multifaceted examination blends personal stories with historical context, providing a deeper understanding of the Chicago Outfit’s complexity and its operatives. Join us in this retrospective journey through the shadows of organized crime as we pay homage to those who bravely shared their stories, revealing the inner workings of a criminal empire that continues to fascinate and terrify in equal measure. Hit me up on Venmo for a cup of coffee or a shot and a beer @ganglandwire Click here to “buy me a cup of coffee” Subscribe to the website for weekly notifications about updates and other Mob information. To go to the store or make a donation or rent Ballot Theft: Burglary, Murder, Coverup, click here To rent ‘Brothers against Brothers’ or ‘Gangland Wire,’ the documentaries click here. To purchase one of my books, click here. Transcript [0:00] Well, hey, guys, after listening to Bob Cooley, one of the more damaging sources and witness and informant to the Chicago Outfit outside of the Calabrese family, [0:13] Nick and his nephew, Frank Jr., I got the rest of the Chicago Outfit informants on tap here. No, not really. They’re not coming in. But I did do a story. I did a series of shorts a few years, or I don’t know, two or three years ago, maybe. [0:32] I interviewed my late friend, Cam Robinson, rest in peace, Cam. So you get to hear from him again. And Paul Whitcomb, who is a Chicago outfit expert, he’s been on this. They used to have some kind of a round table show up there. I don’t know if they still have it or not with the Seiferts. But anyhow, I got these guys to sit down with me and talk about all the different informants in Chicago during the, it was during the 80s. So this is just kind of a series of shorts that I put up before. They’re six or eight minutes long, I think, each one of them, that they talk about different informants. This kind of threw it together as another little bonus episode we’ve done. And I went to Chicago, if you notice, after Johnny Russo, which I apologize for in a way, I don’t know. I mean, the guy’s got some crazy-ass stories, doesn’t he? Who am I to say that he didn’t do it? But most people know that ...
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  • Bob Cooley and the Deadliest Man Alive
    Dec 30 2025
    In this special short episode of Gangland Wire, Gary Jenkins presents a wild and largely forgotten chapter from Bob Cooley’s life—the former Chicago Outfit fixer, gambler, and lawyer whose career straddled the worlds of organized crime, corruption, and courtroom drama. Fresh off a long-form interview with Cooley, Gary pulls out a standalone story that feels almost too strange to be true: Cooley’s first real legal case, involving the infamous Chicago martial arts cult figure Count Dante, self-proclaimed “Deadliest Man Alive.” The episode revisits 1970s Chicago, when Count Dante ran multiple dojos across the city and cultivated a fearsome public image. A rivalry with a competing martial arts school—the Green Dragon Dojo—boiled over into violence when Dante and his followers stormed the school armed with medieval-style weapons. The confrontation ended with one man dead, and Dante charged with murder. At the time, Bob Cooley wasn’t even officially a lawyer yet—he had just taken the bar exam and was still working as a Chicago police officer. Despite that, Count Dante tracked him down, hired him on the spot, and insisted Cooley would be his attorney. What followed was a surreal two-year relationship involving Chicago nightlife, the Playboy Club and Mansion, mob figures, bar fights, and mounting public attention. When the case finally went to trial, the courtroom devolved into chaos as rival martial artists from both sides reenacted the violence with shouting, threats, and theatrical testimony. The judge, fed up with the spectacle, dismissed the case outright—instantly launching Bob Cooley’s reputation as a lawyer who had “beaten” a murder charge. Get Bob Cooley’s book When Corruption Was King. Hit me up on Venmo for a cup of coffee or a shot and a beer @ganglandwire Click here to “buy me a cup of coffee” Subscribe to the website for weekly notifications about updates and other Mob information. To go to the store or make a donation or rent Ballot Theft: Burglary, Murder, Coverup, click here To rent ‘Brothers against Brothers’ or ‘Gangland Wire,’ the documentaries click here. To purchase one of my books, click here. [0:00] Hey guys, this is a little shorty, uh, part of the long interview I did with Bob Cooley, former Chicago outfit, mob fixer, lawyer, uh, general man about town gambler been in, uh, not in witness protection, but he has been off the radar for several years and in hiding. He recently came back and he got hold of me and he wanted to come on the podcast. And you know, I’ve done one story about him, part of his story. This is another part of his story that’s kind of separate from everything else. It’s about a guy by the name of Count Dante. Now, he was kind of well-known in Chicago at the time back in the 70s. You’ll see some images of him in the show. He liked Bob. He got hold of Bob, and he wanted him to defend him. And Bob wasn’t even out of law school yet, but he wanted him to defend him. He had got in an argument with something called the Green Dragon Dojo. He had a dojo, and he had a whole bunch of dojos around town. [1:04] And he was pretty successful, but he built himself as a deadliest man alive. And this other dojo, they said something bad about him or something. I don’t know exactly how it started. So he took a crew of his and went over to the Green Dragon Dojo and kicked in the front door and went in. they had a big battle and they had maces and spears and, and a huge big fight. And somebody ends up getting killed in this fight. So they charged the count with murder and end up going to trial. Uh, Bob’s got, he’ll talk a little bit about it and, and, and his relationship with the count. They became good friends and he did a lot of stuff with the count over two years. It’s, uh, he didn’t say a lot, but, uh, enough to let you know that he and the count were, were pals for a while. In the end, Bob defends him. He’s just out of law school. It was first case, really first client, I think maybe. And they go to trial and, and both the prosecution puts on all their. [2:03] Prosecution witnesses, which are people of this Green Dragon dojo. And then Bob puts on the count and some of his people. And by the time they get done screaming and yelling and almost replaying this whole fight in the courtroom, the judge is so fed up with the whole thing that he just dismisses the whole case. And of course, when the count, he goes around telling everybody how Bob Cooley helped him beat a murder case. And from then on, you know, that’s the start of his reputation as a lawyer so it’s a it’s a hell of a story i’ll tell you that right now it’s a it’s a heck of a story so i’m in the police station now i’m in in fact after that that’s when i got involved out there with all the mobsters and the rest of them in the 18th district when i wasn’t able to work i was i was working undercover out there with them because it was something ...
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  • Bob Cooley Outfit Fixer Part 2
    Dec 29 2025
    In this episode of Gangland Wire, Gary Jenkins sits down with Bob Cooley, the once–well-connected Chicago lawyer who lived at the center of the city’s most notorious corruption machine. After years out of the public eye, Cooley recently resurfaced to revisit his explosive memoir, When Corruption Was King—and this conversation offers a rare, firsthand look at how organized crime, politics, and the court system intersected in Chicago for decades. Cooley traces his journey from growing up in a police family to serving as a Chicago police officer and ultimately becoming a criminal defense attorney whose real job was quietly fixing cases for the Chicago Outfit. His deep understanding of the judicial system made him indispensable to mob-connected power brokers like Pat Marcy, a political fixer with direct access to judges, prosecutors, and court clerks. Inside the Chicago Corruption Machine Cooley explains how verdicts were bought, cases were steered, and justice was manipulated—what insiders called the “Chicago Method.” He describes his relationships with key figures in organized crime, including gambling bosses like Marco D’Amico and violent enforcers such as Harry Aleman and Tony Spilotro, painting a chilling picture of life inside a world where loyalty was enforced by fear. As his role deepened, so did the psychological toll. Cooley recounts living under constant threat, including a contract placed on his life after he refused to betray a fellow associate—an event that forced him to confront the cost of the life he was leading. Turning Point: Becoming a Federal Witness The episode covers Cooley’s pivotal decision in 1986 to cooperate with federal authorities, a move that helped dismantle powerful corruption networks through FBI Operation Gambat. Cooley breaks down how political connections—not just street-level violence—allowed the Outfit to operate with near-total impunity for so long. Along the way, Cooley reflects on the moral reckoning that led him to turn on the system that had enriched and protected him, framing his story as one not just of crime and betrayal, but of reckoning and redemption. What Listeners Will Hear How Bob Cooley became the Outfit’s go-to case fixer The role of Pat Marcy and political corruption in Chicago courts Firsthand stories involving Marco D’Amico, Harry Aleman, and Tony Spilotro The emotional and psychological strain of living among violent criminals The decision to cooperate and the impact of Operation Gambat Why Cooley believes Chicago’s corruption endured for generations Why This Episode Matters Bob Cooley is one of the few people who saw the Chicago Outfit from inside the courtroom and the back rooms of power. His story reveals how deeply organized crime embedded itself into the institutions meant to uphold the law—and what it cost those who tried to escape it. This episode sets the stage for a deeper follow-up conversation, where Gary and Cooley will continue unpacking the most dangerous and revealing moments of his life. Resources Book: When Corruption Was King by Bob Cooley Hit me up on Venmo for a cup of coffee or a shot and a beer @ganglandwire Click here to “buy me a cup of coffee” Subscribe to the website for weekly notifications about updates and other Mob information. To go to the store or make a donation or rent Ballot Theft: Burglary, Murder, Coverup, click here To rent ‘Brothers against Brothers’ or ‘Gangland Wire,’ the documentaries click here. To purchase one of my books, click here. 0:03 Prelude to Bob Cooley’s Story 1:57 Bob Cooley’s Background 5:24 The Chicago Outfit Connection 8:24 The Turning Point 15:20 The Rise of a Mob Lawyer 23:54 A Life of Crime and Consequences 26:03 The Incident at the Police Station 50:27 The Count and His Influence 1:19:51 The Murder of a Friend 1:35:26 Contracts and Betrayal 1:40:36 Conclusion and Future Stories Transcript [0:00] Well, hey guys, this is a little prelude to my next story. Bob Cooley was a Chicago lawyer and an outfit associate who had been in, who has been in hiding for many years. I contacted him about six or seven years ago when I first started a podcast, I was able to get a phone number on him and, and got him on the phone. He was, I think it was out in the desert in Las Vegas area at the time. And at the time he was trying to sell his book when corruption was king to a movie producer And he really didn’t want to overexpose himself, and they didn’t really want him to do anything. And eventually, COVID hit, and the movie production was canceled. And it was just all over. There were several movie productions were canceled during COVID, if I remember right. A couple people who I have interviewed and had a movie deal going. Well, Bob recently remembered me, and he contacted me. He just called me out of the clear blue, and he wanted to revive his book and his story. He’s been, you know, way out of the limelight for a long time. And so I ...
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  • Bob Cooley Outfit Chief Fixer Part 1
    Dec 22 2025
    In this gripping episode of Gangland Wire, host Gary Jenkins sits down with Robert “Bob” Cooley, the Chicago lawyer whose extraordinary journey took him from deep inside the Outfit’s criminal operations to becoming one of the federal government’s most valuable witnesses against organized crime. Cooley pulls back the curtain on the hidden machinery of Chicago’s underworld, describing how corruption, bribery, and violence shaped the Chicago Outfit’s power in the 1970s and beyond. As a lawyer, gambler, and trusted insider, Cooley saw firsthand how mob influence tilted the scales of justice—often in open daylight. Inside the “Chicago Method” of Courtroom Corruption Cooley explains the notorious system of judicial bribery he once helped facilitate—what he calls the “Chicago Method.” He walks listeners through: How defense attorneys worked directly with Outfit associates to buy favorable rulings. The process of approaching and bribing judges. Why weak forensic standards of the era made witness discrediting the key mob strategy. His personal involvement in the infamous Harry Aleman murder case, where clear guilt was erased by corruption. Life in the Outfit: Gambling, Debt, and Mob Justice Cooley recounts his early days gambling with Chicago Outfit associates, including Marco D’Amico, Jackie Cerrone, and John DeFranzo. Notable stories include: The violent implications of unpaid gambling debts in mob circles. Tense interactions with bookmaker Hal Smith and the chaotic fallout of a bounced check involving mobster Eddie Corrado. How D’Amico often stepped in—sometimes with intimidation—to shield Cooley from harm. These stories reflect the daily volatility of life inside the Outfit, where money, fear, and loyalty intersect constantly. Bob Cooley has a great book titled When Corruption Was King where he goes into even greater detail and has many more stories from his life inside the Chicago Mob. Hit me up on Venmo for a cup of coffee or a shot and a beer @ganglandwire Click here to “buy me a cup of coffee” Subscribe to the website for weekly notifications about updates and other Mob information. To go to the store or make a donation or rent Ballot Theft: Burglary, Murder, Coverup, click here To rent ‘Brothers against Brothers’ or ‘Gangland Wire,’ the documentaries click here. To purchase one of my books, click here. 0:06 Introduction to Bob Cooley 1:32 Life as an Outfit Gambler 2:00 My Relationship with Marco D’Amico 10:40 The Story of Hal Smith 11:05 A Dangerous Encounter 20:21 Meeting Sally D 22:23 A Contract on My Life 22:37 The Harry Alleman Case 34:47 Inside the Courtroom 51:08 The Verdict 52:26 Warning the Judge 53:49 The Case Against the Policewoman 58:36 Navigating the Legal Maze 1:08:14 The Outcome and Its Consequences 1:11:39 The Decision to Flip 1:24:38 A Father’s Influence 1:33:57 The Corruption Revealed 1:50:12 Political Connections 2:02:07 The Setup for Robbery 2:20:29 Consequences of Loyalty transcript [0:00] Hey, guys, my guest today is a former Chicago outfit associate named Robert Bob Cooley. He has a book out there titled When Corruption Was King. I highly recommend you get it if you want to look inside the Chicago outfit of the 1970s. Now, Bob’s going to tell us about his life as an outfit gambler, lawyer, and I use payoff to judges to get many, many not guilty verdicts. Now, I always call this the Chicago method. This happened for, I know, for Harry Ailman, a case we’re going to talk about, Tony Spolatro got one of these not-guilties. Now, the outfit member associate who is blessed to get this fix put in for him may be charged with a crime, even up to murder. And he gets a lawyer, a connected lawyer, and they’ll demand a bench trial. That means that only a judge makes the decision. A lawyer, like my guest, who worked with a political fixer named Pat Marcy. [0:53] They’ll work together and they’ll get a friendly judge assigned to that case and then they’ll bribe the judge. And all that judge needs is some kind of alibi witnesses and any kind of information to discredit any prosecution witnesses. Now, this is back in the olden days before you had all this DNA and all that kind of thing. So physical evidence was not really a part of it. Mainly, it was from witnesses. And they just have to discredit any prosecution witness. Then the judge can say, well, state hadn’t really proven their case beyond a reasonable doubt and issue a not guilty verdict and walk away. Now, our guest, Bob Cooley, is going to take us inside this world. [1:29] And it’s a world of beatings, murders, bribes, and other kinds of plots. He was a member of the Elmwood Park crew. He was a big gambler. He was a big loan shark. And he worked for a guy named Marco D’Amico, who was their gambling boss and loan shark in that crew. Among other bosses in this powerful crew were Jackie Cerrone, who will go on and become the underboss and eventually the boss for a short [1...
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  • James Ragen Chicago Race Wire Story
    Dec 19 2025
    Retired Kansas City, Missouri, Police Intelligence Unit Detective Gary Jenkins tells the story of the unsolved murder of James Ragen. Gary Jenkins digs into an old-school Chicago Outfit story pulled from a vintage newspaper clip by legendary columnist Drew Pearson. The article centers on James M. Ragen,” a key figure in the Continental Press and Racing Wire—and what happened when the Outfit decided it wanted total control of the race wire business. This is a gritty snapshot of how Chicago’s underworld allegedly dominated legitimate businesses in the 1940s—bars, taverns, suppliers, and especially gambling infrastructure—then used violence and influence to keep it that way. Gary returned to Chicago Outfit history after spotting an old Drew Pearson column: “A Songbird Who Sang, Murdered.” Who James Ragen was: a major player in distributing horse racing results nationwide How race wire services powered mob-controlled bookmaking across U.S. cities The Outfit’s push to muscle in with a competing racing wire—and the warning: don’t compete with Chicago Mob-linked figure Mo Annenberg and the money behind race wire “tolls” and kickbacks. Outfit names mentioned in the takeover fight, including “Greasy Thumb” Jake Guzik and others from the era. Pearson claimed that Ragen gave information about mob domination in Chicago to the U.S. Attorney General Tom Clark, and that resulted in his murder. The broad daylight attack: a fruit truck pulls alongside, and a machine gun ambush erupts at a stoplight, and James Ragen goes down in a hail of .45 bullets. The “stranger-than-fiction” twist: Ragen later dies, and an autopsy allegedly finds a tube of mercury in his stomach. Why the case remained murky: the coroner allegedly refused to pin it cleanly as murder (per Pearson’s reporting) Gary frames it as a reminder of how deep the Outfit’s influence ran in city systems and politics. Memorable Moments Ragen/Reagan’s fatalistic line (as told by Pearson): “If they want you, they’re gonna get you.” The bizarre mercury detail and Gary asking listeners if they’ve ever heard anything like it Why This Story Matters This bonus episode connects the dots between information networks (race results), organized gambling, and the Outfit’s approach to business: control the pipeline, control the profit—and crush anyone who won’t move aside. Gary invites listeners to share any other “old but gold” Chicago Outfit stories or clippings worth covering in future bonus episodes—and reminds everyone to check out his books and films (search Gary Jenkins on Amazon or visit his website). Hit me up on Venmo for a cup of coffee or a shot and a beer @ganglandwire Click here to “buy me a cup of coffee” Subscribe to the website for weekly notifications about updates and other Mob information. To go to the store or make a donation or rent Ballot Theft: Burglary, Murder, Coverup, click here To rent ‘Brothers against Brothers’ or ‘Gangland Wire,’ the documentaries click here. To purchase one of my books, click here. Transcript James Ragen race wire story Speaker: [00:00:00] Well, hey, all you wire tappers. Good to be back here in the studio. Gangland wire. This is Gary Jenkins, retired Kansas City, Missouri Police Detective, formerly of the Intelligence Unit. I spent 14 years there investigating organized crime in Kansas City. Best 14 years of my life. Speaker: I think sometimes you know, I’ve got this True Crime podcast and we focus on the mob and I haven’t. Been to Chicago for a little bit, it seemed like. And I was, I was looking through some stuff from the Chicago outfit Facebook page, and there’s a newspaper clip on the, the, the group that has newspaper clips on it that had an article by a man named Drew Pearson. Speaker: Now, drew Pearson was a real famous columnist back in the forties and fifties, and the title of it is A Songbird Who, mur, who Sang, murdered. Now he starts off talking about the singing of Joe Vce. I guess he, he wrote this article about the time Joe Vce had all the newspapers, Andre, and talked about the New York mob. Speaker: But he had [00:01:00] a guy who talked about the Chicago outfit. He said that, he feels, he said that he felt responsible for the death of this informant outta Chicago. So he dropped in, he said he dropped into the morgue of Chicago’s American newspaper to refresh his memory just about this guy and, and what he said. This guy was a man named James M. Reagan, who was a of the continental press and racing wire. He was machine gunned down from a fruit truck. In August 14th, 1946, Speaker: Reagan, before he died, had told him many things in, in 1946 four years before the Koff Commission and just before he got killed. Reagan told Drew Pearson about the Chicago Mob rule and gave him permission to take it to the Attorney General of the United States, Tom Clark. Now, Tom Clark is the same guy who [00:02:00] commuted the sentences of. Speaker...
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