Chuck Goudie talks Chicago Outfit

In this episode of Gangland Wire, retired Kansas City Intelligence detective Gary Jenkins sits down with veteran Chicago journalist Chuck Goudie, whose decades of reporting have made him one of Chicago’s most respected voices on organized crime. A fan of the show asked for more Chicago stories—and this conversation delivers. We dive into the legacy of the Spilotro family, sparked by the recent passing of John Spilotro, brother of the infamous Las Vegas mob figure Tony Spilotro. Chuck shares his reflections on how the Outfit has evolved, from its heyday of dominance in gambling, loansharking, and union racketeering to its much smaller—yet still persistent—presence today. Together, we revisit the Outfit’s historic ties to the Teamsters, the Strawman trials, and the legendary names like Anthony Accardo who shaped Chicago’s mob identity. Chuck solves a mystery and provides the name of the man who killed Sam Giancana. Chuck also offers personal insights into how mob families navigated the push and pull of blood ties, with some members rising into notoriety while others tried to lead straight lives under the shadow of organized crime. Our conversation shifts to Chuck’s recent investigative work on the disappearance of Jimmy Hoffa, exploring the long-standing theories and mob connections that keep the story alive decades later. This episode blends history, reflection, and storytelling—offering both an inside look at Chicago’s Outfit and a reminder of why these stories still captivate us today. 1:02 The Legacy of John Drummond 4:11 Current Status of the Outfit 7:28 The Last of the Spilotro Family 10:02 Family Dynamics of the Spilotros 13:18 Frank Calabrese's Las Vegas Fame 13:25 Giancana's Murder Investigation and who did it 18:18 Surveillance in the Giancana Case 22:03 The Straw Man Trials 25:40 Ken Eto's Gangland Story 27:52 Investigating Jimmy Hoffa's Disappearance 31:03 Closing Thoughts with Chuck Goudie Subscribe to Gangland Wire wherever you get your podcasts, and join us each week as we uncover the stories buried beneath the headlines—and the bodies. Listen now on Apple Podcasts, Spotify, YouTube, or your favorite podcast app. 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" To go to the store or make a donation or rent Ballot Theft: Burglary, Murder, Coverup, click here To rent Brothers against Brothers, the documentary, click here. To rent Gangland Wire, the documentary, click here Transcript [0:00] Well, hey, welcome all you wiretappers out there. Good to be back here in the [0:02] studio of Gangland Wire. This is Gary Jenkins, retired Kansas City Police Intelligence Unit detective here in Kansas City. And, you know, guys, I have, I was talking with a fan not too long ago from Chicago, I think on the, maybe the Facebook group, and he said, you need to do more Chicago stories. And I had to admit, I hadn't done that many Chicago stories. I got caught up in New York a lot, It seemed like, and anyhow, we're back to Chicago and another guy's mentioned to another guy and we were talking and, and somebody said, I don't remember who, maybe that original fan said you need to get Chuck Goudie on there. He's been doing a lot of reporting on the outfit over the years. And I didn't really know who Chuck was. So I started searching. He did a recent story about the death of the last spilotro brother, John spilotro. So I thought, man, this is, this is it. This is what I got to do. So welcome, Chuck Goudie from Chicago. Well, it's quite an introduction. Some might call it a eulogy, but thankfully that's not what he does. [1:02] Really? Now, I think I told you earlier, you know, last time I interviewed a Chicago newsman, it was John Bulldog Drummond. Bulldog Drummond, I tell you what, he was the dean of Chicago newsmen, television newsmen, when it came to reporting on the mob. There's no doubt about it.