Almighty Gaylords Update

Gaylord PicnicThe Almighty Gaylords are a Chicago street gang involved in guns and drugs. I wrote two posts on them: an overview and a look at some recent gunrunning arrests. A member of the Gaylords got in touch to bring me up to date about the gang’s fortunes.

He told me rumours of the gang’s demise are exaggerated. The Gaylords are alive and well and spreading across the US, with new chapters in places like Florida and Indiana.

It’s true that there’s no longer any central leadership, and individual areas in Chicago like Addison and Sayre Park run as separate gangs under the Gaylord banner. This fragmentation fooled outsiders into believing the Gaylords were on the skids. In reality it introduced enough flexibility to keep the gang alive after it was pushed out of its traditional Chicago inner city territory by demographic change. And it gave Gaylords who left the state the freedom to set up fresh chapters in their new homes.

The media paints the GLs as a gang of soft-bellied old racists mourning the loss of white Chicago. The truth is different.

Cross is Boss

The Gaylords have been carrying around a reputation for racism ever since they found themselves on the front lines of Chicago’s population changes of the 1960s. News stories talked about street battles with Hispanic gangs, KKK graffiti on the walls, and African-Americans chased down for walking through the wrong neighbourhood.

Most of it was true. As Chicago’s white population shrank, the Gaylords fought block by block to keep their territory. They were white; their opponents now mostly Hispanic or black.

But gang members insist membership was always more open than the media liked to admit. Even the earliest incarnation of the gang had a few Mexican members. These days about 25% of Gaylords are non-white. When Sergio Toutges was caught up in 2011’s gunrunning case, the authorities tried to paint him as a racist for some comments caught on tape (‘I can’t wait to unload on a nigger with it’) as he tried out a new gun. Those who know say Toutges is a Puerto Rican who’s spent most of his life behind bars. He’s fluent in hood slang not racism.

Membership has always been more about local connections and friendships than skin colour.

If you grew up in the neighbourhood your ethnicity didn’t matter as long as you were an American and had love for the GL cause‘.

Not everyone is a card carrying defender of social justice. When some meth dealers were picked up in Mississippi back in 2011 they turned out to have links to Gaylords – and be members of the Aryan Brotherhood, the white supremacist prison gang.


The changing face of Chicago pushed gang members out to the suburbs. Some left the state entirely.

Most of the exodus was down south. There is a significant Gaylord presence in Southern Indiana, Kentucky, Alabama, and South Florida. A few years back Indiana police picked up Brian Bowling, a hollow-cheeked tough guy with charisma to spare and a prison record, on meth and gun charges. A look at the records revealed Bowling was a long time Gaylord active in Chicago as long ago as 1981.

These days the Gaylords in Chicago and nearby areas number about 350, including those in prison. At least 1,000 are active around the rest of the country. Members tend towards being fortysomething veterans of the streets but there is a younger generation coming up.

The gang now does most of its business off the streets. It owns bars and clubs, has regular meet-ups. Every year in the week of 12 July there’s a Gaylords picnic in Chicago and a few other locations nationally. The date is alphanumeric: 7-12 is G-L.

Members like to sell the gang as a social club with muscle. The police claim the Gaylords are still involved in guns, drugs, and other crime.

Moving Pictures

It’s difficult to imagine life in a street gang for those on the outside. Movies like Goodfellas and tv shows like The Sopranos give an insight into the Mafia world. There are books about bank robbers like  John Dillinger and Pretty Boy Floyd. But the Almighty Gaylords have stayed off the cultural radar.

I asked a member of the gang if any movies give a feel for what it’s like to be a Chicago Gaylord. He recommended The Warriors and The Wanderers, a pair of movies from 1979 about New York street gangs. They deal with camaraderie, violence, and the importance of home turf. Take a look if you want an idea of why the Gaylords are still going strong more than sixty years after they started.

Here’s some clips from the 1981 Chicago documentary What’s Uptown? Skip to the 2:00 mark for a young Brian Bowling impressing the camera crew. The background of African-Americans mingling with a young skinhead in a White Power t-shirt is telling.

If you want to show some love for this blog then feel free to buy my books in paperback or ebook:

Lost Lions of Judah: Haile Selassie’s Mongrel Foreign Legion [or]


Katanga 1960-63: Mercenaries, Spies and the African Nation that Waged War on the World  [or]


Franco’s International Brigades: Adventurers, Fascists, and Christian Crusaders in the Spanish Civil War [or]


4 thoughts on “Almighty Gaylords Update

  1. Pingback: The Almighty Gaylords of Chicago | Christopher Othen

  2. Pingback: Gunrunning Gaylords | Christopher Othen

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