The Chicago Outfit...Wiseguys of the Windy City

The Chicago Outfit...Wiseguys of the Windy City

Since the Roaring 20s, the Chicago Mob has been at the forefront of organized crime in this country...let’s take a look at some of the “Outfit's” more colorful gangsters.

https://thenewyorkmafia.com/chicago-outfit-wiseguys-of-the-windy-city/

Good stuff as usual Fischetti brothers were cousins of Sinatra.

Hollander, great song. Lol.... and Sinatra was VERY close with both the Fischetti brothers and Giancana. Best friends for a years. He even fronted for Mooney in ownership of the Cal Neva Lodge in Reno.

In NYC Old Blue Eyes' guy was a little known Genovese soldier named Louis (Louie Dome) Pacella out of East Harlem.

Going way back to Hoboken, NJ where he was raised, it is said that Sinatra's REAL guy was Gyp DeCarlo and Willy Moretti who I highlighted earlier today for the forum with a Bio I had done on Gyp. Supposedly Gyp was the guy who originally pushed Sinatra's career as a young singer with the Tommy Dorsey Band. Gyp and Moretti were alleged to be the guys who told Dorsey to release Sinatra from his contract with Dorsey's band.

That release (under duress of course lol) gave Frank his opening to soar.... And the is history as they say!

An extra bit of trivia for you, Sam Mooney and the boys from Chicago loved this song. Every time Frank was singing in Chicago or Vegas for that matter, if they walked in, or he knew they were in the audience he'd had the band stop midstream from whatever song they were playing and swing right into "Chicago is my kind of town" lol

This is Part #1, if well received we are considering doing a Part #2 for the Chicago crew down the road.



PS: by the way fellas, although we initially do try to proof read all our stories before posting, after posting this story I noticed that although the info was correct, several "lines and sentences" jumped into bios that were intended for a different thumbnail. One of the most obvious is my reference to Daddano. I think it is where I speak of his brother Frank (Skippy) Cerone. This sentence was obviously intended for Jackey the Lackey Cerone's thumbnail. There are 2 or 3 little "oops" like that. Lol

We will make a few minor corrections later today. Sorry for any mixups.

By request, in the near future I'm going to try and focus on writing a short story about Hollywood, the mobs involvement in the entertainment business, and more specifically about Frank Sinatra and Dean Martin. Their early involvement with the mob, and the stigma that followed them nearly their entire careers because of it.

Mooney and Ole Blue Eyes were very close for years (among many other wiseguys Frank befriended).... so I think this should be an interesting storyline.

Love your articles NYMafia!
Might I suggest you read board member Toodopeds articles regarding Chicago? That guy's got some Great informative threads about the Outfit guys and how things were done.

Great Job all in all, wish there were a little more written about the guys in your article

Also Might you one Day include the power struggle of the century turn? The Zizzo disappearance and the Chiaramonti hit for instance and the Outfit overall of that era

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I will def check out Toodopeds posts. Thanks for the heads up Luxurydog.

I am also planning to do a Part #2 of the Chicago thumbnail bios. And I will try and go more in-depth next time for each name I pick (as best I can ok). I am not as familiar with Chicago as some of the other cities, aside from the top guys we are all familiar with. But I will be researching and learning ok. I also like to pick little known guys I find interesting as opposed to just the big names.

I will keep my eyes open for any gangland murder intrigues and the Zizzo situation as well ok..... NO promises. Lol... but I'll try.


I would like to do extensive bios for either Placidio DiVarco aka "Joey Caesar", or Joseph Gagliano aka "Joe Gags". Or both if I can dig out enough intel and background on them to make it worthwhile. I wrote a thumbnail of Di Varco, but I'm not sure I can gather enough to go further.

Sounds Great! Looking forward to Reading more of your articles!
Hope someone on this forum is able to help you! I am far from any expert so.. 😂

Thanks LuxDig

Hehe..another favorite of the boys.

My kinda town!