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Gangland Wire

Chicago Heights Mob History: Al Capone, Frank LaPorte, The Chicago Outfit & The St. Valentine’s Day Massacre Connection

Gangland Wire

Gary Jenkins

Documentary, Society & Culture, True Crime, History

4.6647 Ratings

🗓️ 13 July 2026

⏱️ 25 minutes

🧾️ Download transcript

Summary

In this episode of Gangland Wire, retired Kansas City Intelligence Unit detective Gary Jenkins welcomes author Ray Franze to discuss his historical fiction novel The Heights, a story inspired by the real-life mob figures who controlled Chicago Heights and Northwest Indiana for much of the twentieth century. Drawing on FBI files, family stories, and historical research, Franze explores the rise of Frank LaPorte and the Chicago Heights crew, one of the most influential factions associated with the Chicago Outfit.
The conversation begins with the famous 1928 photograph showing Al Capone and several future participants in the St. Valentine's Day Massacre. Franze explains the long-standing belief that members of the Chicago Heights crew may have been involved in planning the infamous gangland murder and discusses the crew's close relationship with Capone and his associates.
Gary and Ray examine the unique position of Chicago Heights, located south of Chicago near the Indiana border, and how the area developed its own powerful criminal organization before eventually becoming part of the Chicago Outfit. They discuss the role of the Union Siciliana, the Beer Wars of Prohibition, and the alliance between Capone and local leaders such as Dominic Roberto, Jimmy Emery, and Frank LaPorte.
The discussion also covers the expansion of organized crime into Northwest Indiana, Calumet City, and Joliet. Ray explains how gambling, vice, and bootlegging operations flourished in these territories and how Chicago Heights became a major power center within the Outfit structure.
The conversation explores Frank LaPorte's leadership style and his remarkable ability to avoid publicity and law enforcement attention. Unlike many notorious gangsters, LaPorte remained largely unknown to the public while building a powerful organization through trusted family members, loyal associates, and strategic insulation from criminal activity.
Gary and Ray also discuss the Outfit's transition into seemingly legitimate businesses, including jukeboxes, vending machines, and cigarette distribution, as federal investigators increased pressure on traditional gambling operations. The evolution of mob-controlled businesses reflects the Outfit's efforts to adapt to changing law enforcement tactics.
Click here to get Ray's book, The Heights.
Another fascinating topic is the legendary Villa Venice nightclub, opened by Sam Giancana with appearances by Frank Sinatra and the Rat Pack. Ray shares family memories of the grand opening and explains how these firsthand accounts became one of the most authentic scenes in his novel.

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Transcript

Click on a timestamp to play from that location

0:00.0

welcome all you wiretappers. It's good to be back here in the studio of Gangland Wire. I am talking to a man in

0:06.0

Chicago. You can see his book behind him, The Heights. It's Ray France. Ray, welcome to the show.

0:13.2

Thank you, Gary. Now, Ray, this is a historical fiction, but it's based on real live mob or outfit people out of Chicago Heights.

0:23.3

Is that correct?

0:24.4

That's correct.

0:25.2

It is historical fiction.

0:27.4

It is quite historical.

0:28.8

And it takes place from about 1913 until about 1971.

0:34.3

Oh, another thing, guys, you'll be interested in this.

0:36.9

All you guys who are on the Chicago outfit Facebook pages, another thing, guys, you'll be interested in this. All you guys who are on the Chicago

0:39.1

outfit Facebook pages, you've seen the photo of Al Capone on the lawn. And so Frank LaPorte

0:46.9

is one of the people in that photo, right? Do you know anything more about that photo?

0:51.8

So from what I've been told from Luzi and John Binder, it was taken in the

0:57.0

late fall of 28, just months before the St. Valentine's Day Massacre. And if you look at

1:04.9

that photo and who's present, there's a lot of Valentine's Day Mask massacre guys involved in that. So it's been alluded

1:14.0

to that photo was actually a planning meeting leading up to the massacre. And it was always

1:21.3

rumored that the Chicago Heights guy played a part in that event. All those rumors unsubstantiated, they kind of had floated

1:29.5

around the Heights during the decades. But based on who was in that photo and the fact that it was

1:35.8

just taken a few months prior to the Valentine's Day massacre, I kind of feel like the guys in

1:41.1

the Heights were involved in that planning. So yeah, there was definitely ties from the Valentine's event to the guys in the Heights.

1:50.0

No doubt because Fred Killer Burke, when he was arrested,

1:54.0

they found one of the machine guns in his possession that they linked

...

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