In this episode of Gangland Wire, I sit down with Salt Lake City author Flats to discuss his book, Ice Pick Willie: The Life and Times of Israel Alderman. We take a deep dive into the shadowy world of Israel “Icepick Willie” Alderman—a largely forgotten but deeply embedded figure in early 20th-century organized crime.

Willie’s criminal career traces back to Prohibition-era New York, where he began as a jewelry thief before evolving into something far more lethal. His nickname came from his preferred weapon: an ordinary household ice pick. In the 1920s, it was common, inconspicuous, and devastatingly effective. Flats explains how Willie’s method allowed him to carry out murders quietly and efficiently, often avoiding the attention that accompanied more public gangland shootings.

We follow Willie’s movements from New York to Minneapolis and eventually into the orbit of Chicago’s violent underworld. Along the way, he intersected with major figures of organized crime, including Meyer Lansky, Charles Luciano, and Bugs Moran. Flats outlines the shifting alliances and rivalries that defined the era, placing Willie within the broader context of gang wars that culminated in events like the St. Valentine’s Day Massacre.

The conversation also examines Willie’s transition from violent enforcer to gambling operative as organized crime evolved and shifted westward. As Las Vegas rose with legalized gambling, figures like Willie adapted—moving from street-level brutality to more structured rackets under established mob leadership.

Despite brushing against major historical events and powerful crime bosses, Icepick Willie faded into relative obscurity. Flats and I explore why certain gangsters become legends while others—equally dangerous and influential—slip into the margins of history. We also touch on Willie’s odd cultural afterlife, including regional pop-culture references that keep his name alive in unexpected ways.

This episode provides both a character study of a cold and calculated killer and a broader examination of how organized crime adapted from Prohibition chaos to structured syndicates. It’s a detailed look at a man who operated in the shadows—lethal, efficient, and nearly forgotten.

Flats’ book, Ice Pick Willie: The Life and Times of Israel Alderman, is available now on Amazon.

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Transcript

[0:00] Hey, welcome all you wiretappers. Good to be back here in the studio of Gangland

[0:03] Wire. This is Gary Jenkins. As most of you, I’m a retired Kansas City Police Intelligence Unit detective turned podcaster and documentary filmmaker. I got a couple of documentary films you can rent on Amazon if you choose. I’ll have links in the show notes. Or just go to Amazon and search my name and you’ll find my stuff. But anyhow, today I have a friend of mine from Salt Lake City called Flats. And he’s just Flats, all right? And he’s written a book about a man named Icepick Willie. Now, Icepick Willie has got a great, cool nickname. I’m surprised that he didn’t last through history a little better because people had an easy-to-remembering cool nickname. His real name is Israel Alderman. Now, Flats has been researching him. He got a hold of me because I did a show on David Berman, who ended up in Las Vegas. He was a Jewish gambler from Minneapolis. And ice pick ends up out there connected to him somehow. And I didn’t really stumble. I stumbled a little bit across that, but I couldn’t remember what it was. But anyhow, welcome flats.

[1:09] Glad to be here. Thanks for inviting me. All right. Go ahead. I’m sorry. I’m always open for any chance to talk about Ice Pick Willie, one of my favorite people. And if you guys out there know anything about Ice Pick Willie, get a hold of me and I’ll connect you up with Flats. And I’ll have his Gmail in the show notes. But either that or get a hold of me pretty easy. Any rumors or stories, lies, anything about him.

[1:38] But in the meantime, in a couple of weeks, actually, by the time this podcast is out, that book’s going to be up on Amazon. But you can always go back. You can always pull those down and add more information in and then put them back up if you want. So that’s a good way to go. Nicknames are interesting. I once talked about doing a show on nicknames and how people got them, and I just never got around to it. And many times you can see how people get their nicknames. Al Capone, Scarface Al. He’s got the big scar on his face, right? Here’s one. One of Icepick’s Willie’s contemporaries, a guy named Albert, was it Tannenbaum? Yeah, Tannenbaum. And he was called Tick Tock. And I looked that up because, like I said, he was a contemporary of Icepick Willie’s. And he got the name Tick Tock because somebody said you move all the time. You’re always like a watch. You’re Tick Tocking all the time. And, of course, there’s Anthony Accardo, who they called Joe Batters. And his guys gave him that. They used to call him Joe. And that was because he beat up somebody with a baseball bat so bad that Al Capone said, you’re a real Joe batters. But he also, many times the press will give people these nicknames. And they gave Anthony Accardo the nickname of the big tuna because he was big. And they had a picture of him with a huge big tuna he had caught. There’s Joe Bananas Bonnano. That speaks for itself, Joe Bananas. And I think the press gave him that. First question, Flats, you know how Icepick Willie got his nickname? The nickname came…

[3:06] From when he was in Minneapolis, he apparently picked it up. And this is something which he admitted to later on in his life. He claimed to have taken about 11, 12 victims out by using an ice pick in the ear.

[3:27] And ice picks were actually really common back in the 20s everywhere. People had them. Everyone had them in their homes. and they were a real popular tool among Murder Incorporated members. It’s a handy thing, small, quiet kind of a tool.

[3:49] Normally, a knife-pick killing was something that took maybe three or four people, not counting the victim. They’d crowd around him and grab his arms, whatever, and then somebody’d do him, they’d haul him off. Uh, Willie had managed to turn this into a one man operation. He’d take his victim.

[4:11] He’d be up at the bar with a drinking buddy, get this guy really liquored up, and he’d slip his ice pick out of his jacket. Boom, real quick in the air, ice pick’s gone, the guy’s down on the bar. Not much blood because it’s an ice pick. Forensics wasn’t real hot back in the 20s, so a lot of times they would diagnose this as a brain aneurysm. But the guy would slump over the bar, drunk, dead drunk, and then they’d just haul him off. The story is they’d take him in the back room, he’d go down the coal chute, which everybody had back then, out into a truck, they’d haul off the body. The people that went down the coal chute, they were all pretty much forgotten. But Willie, he seemed to have stuck around. Now, in Minneapolis, apparently he’s still a real popular figure. Memorable...