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Dan O’Sullivan and The Outfit

Dan O’Sullivan and The Outfit

Update: 2025-09-29
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In this episode of Gangland Wire, retired Kansas City Intelligence Unit detective Gary Jenkins sits down with Dan O’Sullivan from the new podcast The Outfit to discuss the incredible story of Ken Eto, known in Outfit circles as “Tokyo Joe.” Ken Eto was unique: the only Japanese American member of the Chicago Outfit, and the only man to survive being shot three times in the head. Eto was the Outfit’s gambling kingpin on Chicago’s North Side, controlling operations along Rush Street, policy wheels in Black neighborhoods, Chinese games in Chinatown, and the Puerto Rican “bolita” numbers racket. His empire generated millions of dollars each year, placing him among the highest-ranking members of the Outfit. But success had its price. In 1980, the FBI caught Eto in a sting, and his Outfit bosses grew nervous—especially since he had ties to a cocaine deal with the Genovese family. Invited to dinner by a mobster who had never broken bread with him before, Eto knew it was a setup. Two gunmen shot him three times in the head. Miraculously, he lived, and his survival changed the history of the Outfit.

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[00:00:00 ] Hey, y’all, you wire tapers out there. Good to be back here in the studio of Gangland Wire.

This is Gary Jenkins, retired Kansas City. Missouri Police Intelligence unit detective with his own podcast. Now, believe it or not, I’ve been doing this for quite a while. Guys, if a lot of you guys have been following me for five, six years, you know, guys, you know, I was one of the first guys that did this podcast this kind of a podcast.

And so I have with us today, one of the, maybe the most recent iteration of a Mafia podcast. I have Dan O’Sullivan welcome, Dan. Thank you, Gary. And I like you staking your territory, you know, like that I’m I’m a Johnny. Come lately. It’s true. Yeah, yeah, yeah, yeah. And I’m a og. You’re the og. Exactly. I’m og.

Yeah, right. I mean, I’m an associate. You’re the godfather here, you know? And there you go. We gotta get the pecking order down. This is how. As was said to me by a historian, you know, the mob makes discipline in the military look like nothing, you know, so, yeah. However it [00:01:00 ] works, you know? Yeah. Well, yeah. That discipline is, and there’s no appeal either, right?

Yeah. So anyhow Dan and I, I think you’re gonna have a partner in that. You’re gonna have a podcast called The Outfit. Is that the name of it? That’s right. The outfit got, which is, go ahead. You got it exactly right, Gary. Yeah. We me and my co-host, Alana Hope Levinson our new podcast, the outfits launching August 14th and just every week we’re doing a different mob story that kind of explains something about, you know, America and, and you know, so whether it’s how the milk wars in Chicago led to us having expiration dates on milk cartons, that’s a crazy story to, you know.

Who we’re gonna talk about a little bit the history of Japanese Americans in the US or. Americans in Russia during the nineties and seeing that transition of democracy and the mob there. So we just we’re having a lot of fun doing that. But it’s great to be on your [00:02:00 ] show. I, I’ve loved your show for years, so really an honor to be here.

Well, thank you so much. You know, I when I do a program here in the city, I usually started off with a comparison of, I want you people to remember all Italians are not criminals. Yeah. And, and what happened during. The turn of the century is really, has happened here recently. Mm-hmm. What happened was, all these people from a really poor country, Southern Italy and Sicily, came to the United States.

They just wanted a piece of the pie. Right. They just wanted to, to have a, a way to get by. They wanted to earn, you know, earn a living and, and get a meal, and they weren’t able to do that. They come here. At that time, the Irish and the English and the Germans, we had all the good jobs, right? We had all the police jobs, the fire jobs, they were squeezed out. They really could hardly get that kind of a job. And so they had push carts and, and you know, spaghetti joints as they used to call ’em restaurants, you could always do that.

But they brought this thing from the old country called the Mafia, [00:03:00 ] and you’ve got all these young men who are bright and, and. Aggressive and, and you know, and then prohibition comes along and they take it. Yeah, they take it and they run with it. And, and you know, the same way today you got all these Hispanics come up and you got this narcotics thing, and, and they’re, you know, they don’t, you know, we’re keeping ’em squeezed out for the most part.

They don’t speak the language and look a little different, so you’re kind of squeezed out. So it is not comparing, not exactly apples and oranges, but there’s a lot of similarities there on newly arrived immigrant populations. And they’re not all criminals. It’s such a good point that this repetition just, you know, I mean, look, I’m a journalist.

I’ve covered the mob. I’ve written about it and, and tried to get really educated on it. Just you see this cycle over and over again. You know, like you said, my last name’s O Sullivan, the Irish. By the time the Italians and Jews started coming more. Numbers to the us. Well look at Chicago. The Irish first off had been gangsters too, but they had just clammed up the ladder a little bit where they [00:04:00 ] controlled the political machinery.

They controlled police, fire departments, these civil service jobs. So what was left, you know, by the time these guys came along, it was more just the same way, the more criminal thing. And you know, if you look at the stats today, I believe, I believe immigrants commit crime at a lower rate than native born Americans.

Yeah, true. So, you know, because most of them are coming here to work, you know? Yeah, I know. So yeah, it’s, it repeats itself. It’s absolutely true. Yeah. It wasn’t, I think it was Mark Twain said, history doesn’t always repeat itself, but it rhymes. That’s a, that guy the pride of Missouri, right? I mean, or is it Missouri Pride of Missouri?

Gotta quote him. Yeah. Yeah. Anyhow, Dan, so let’s talk about you know, some of the things you’ve done in your career. You’ve done a variety of things in the news and, and media. So tell us a little bit about what you’ve done in your past. Yeah, so I, I, we were talking earlier, I started out as a sports writer actually, which is, I, I was always interested in the mob for reasons I’ll, I’ll maybe get into, but doing sports [00:05:00 ] writing, I realized you kind of brush up against organized crime just in the course of doing that, you know?

Yeah. So I wrote a piece, God, over 10 years ago now about. Labor exploitation and pro wrestling and you know, that that was run a bit and still to a degree is, is run a bit along underworld lines, you know with these sorts of shady syndicates all over the country. And, and over time that changed with the WWF and WE but still very dangerous for the guys involved.

Obviously Hulk Hogan just passed away and, you know, kind of. And embodied it shifting from like a carnival thing to big business. But so I remember an outgrowth of that was the former boss of the WWE e Vince McMahon, it’s not well remembered, was prosecuted by the federal government. For trafficking steroids.

And they, it really was prosecuted like a mob case where they got a doctor to flip who was [00:06:00 ] supplying the, you know, whatever he wanted and shipping it across the country. So. I got into this bizarre story of a stabbing of an NBA player and the, the police subsequently breaking another. This was in New York, subsequently breaking another NBA player’s leg with a baton.

So I just started to drift towards crime. And then a few years ago, I wrote a story for Chicago Magazine. That was the history of the life of Kento, who I, I thought was just a, yeah. Fascinating figure, and I couldn’t believe no one had done a deep dive on him. So I, I did that and and here I am today, now doing, now doing a lesser version of your podcast.

Well, I’m sure it’ll be good. You’re gonna have high production values. I can see that already better than I had, especially when I first started. They’re a little bit better now, but they’re still not really. Good high production values. Well let, before we get into Ken Etto, le

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Dan O’Sullivan and The Outfit

Dan O’Sullivan and The Outfit

Gary Jenkins: Mafia Detective