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

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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. And so I really welcome you, Chuck. You’re kind of the new modern John Drummond. Thanks, Gary, for that. I’m happy to be mentioned in the same sentence or thought with John Drummond. I had the good fortune of working kind of side by side with him, different networks in the 1980s and into the 90s when he was still at it. And he certainly did. He set the stage for mob coverage in Chicago. The outfit, as it’s known here, and John is still up and at him. And the times that I’ve spoken to him recently, we talk about the fact that on TV news in Chicago, I’m kind of the last person standing to keep track of these things. And so it’s a heavy case of documents, as we say, to carry around these days. But there’s still interest in it in Chicago. with not only the history of it, but where things stand in 2025.

[2:20 ] Yeah, I’ve noticed that on the Facebook groups, and they’re real heavily participated in might be the right word, because a lot of comments, a lot of people know, a lot of family members of mob guys that seem like are participating. It’s true.

[2:37 ] So you got to be careful what you say if you live up there. Kind of like that here in Kansas City. I kind of have to be careful. We got all these family members around.

[2:45 ] That is true. Well, I’m always careful. And I do hear from people when I report on the deaths of old timers or even new guys who are trying to run the show these days. People do pay attention to it. That’s for sure. Yeah, they still got something going. What would you say, just to encapsulate what the outfit is today in Chicago?

[3:09 ] Well, there is a little bit of a range as to what the outfit status is these days, depending on who you talk to. The FBI still contends that the outfit is operating, that there are people who are still in positions of power, and that the street crews are still in place as they were even 50 years ago. Everybody seems to agree that it doesn’t have the numbers that it once did. And I think that that should be evident. Some people think there may be only 10 or 15 day-to-day active members of the Chicago mob these days. But I think most people agree that it’s in the dozens, but certainly no more than 100. And the rackets are the same, similar kinds of things. but not the amount of money trading hands these days. But they still run in the same circles.

[4:07 ] It’s still the same rackets that we saw decades ago in Chicago. Loan sharking, prostitution, a healthy, illegal gambling business that the outfit oversees, even as gambling largely is legal here and other places these days. Some union racketeering underway still. Um, so the same kinds of things, maybe just not as potent as it once was. Interesting.

[4:36 ] So speaking of the union racketeering now, let’s go back into history a little bit. You were in Kansas City during the straw man trials when that’s what really, to me, it was the peak of the outfit’s national influence at that point in time. Because they owned the Teamsters and the Teamsters Pension Fund and can make all those loans. So that was quite a time, wasn’t it? Those days of straw man in Kansas City was the heyday, certainly in terms of dollars changing hands and the interconnection between the Kansas City mob, Chicago outfit, Cleveland, to some degree, New York and some organized crime families in the Northeast. And then Las Vegas, obviously, was the linchpin of it all, at least when it came to straw man. Yeah. And that’s when really Tony spilotro, his name rose to the top. It wasn’t before I have a, I listened to a wiretap where Joe Augusto was in Las Vegas is reading a newspaper to Tuffy DeLuna about, uh, that there were, somebody was writing out there and said, uh, spilotro and Aiuppa moving West. And Nick Civella in the background says, oh, God.

[5:54 ] Well, as you know, there’s a body of thought that Tony spilotro basically engineered his own demise by the way he operated in public. And if he had just kept quiet and not been as public about it, he probably would still be around today. So we’re into the spilotro family. Yeah. The demise of the spilotro family. That’s John spilotro. I’d never heard of him. Tell the guy, and I don’t think most people have, tell us about him a little bit. I had never heard of John spilotro either. I probably saw him on a list of spilotro family members years ago, but he wasn’t a major player. He certainly kept the quietest of all the Spalatros, certainly far more than his brother Tony did.

[6:39 ] John spilotro lived in Vegas, Uh, apparently went out there with, uh, with the other brothers who landed in Vegas in the late seventies, early eighties. And, uh, and John spilotro kept quiet, although he was thou