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Inside The Chicago Outlaws Motorcycle Club
Crime|Sep 29, 2017

Inside The Chicago Outlaws Motorcycle Club

Big Pete Served As The Head Of The Outlaws In Chicago For Twenty Years. We Talk To Him About His Life As The Boss Of A Motorcycle Gang.
Seth Ferranti

It was rush hour in 1994, and the traffic was deep on the West Side of Chicago, when three members of the Outlaw’s motorcycle club left a car packed with explosives right in front of the Hells Angels clubhouse. The bombs exploded with ill intentions – sending reverberations down the block, shattering the windows, and door to the Angels stronghold. The opening salvo in a biker war that engulfed Chicago and led to a string of retaliatory bombings, robberies and murders.

The Midwest had long been Outlaw territory, but the Angels were hell-bent on establishing a presence in the area by absorbing smaller, local clubs to bolster their ranks. Infuriating the Outlaws and their soon-to-be leader, Peter “Big Pete” James, who’s first job as boss was to deal with the Angel invasion. A situation that had led his predecessors to prison.

The outlaw biker world had slowly evolved into big business for many members. Egos as well as financial interests created many conflicts for territory and control. Like any successful business, expansion was essential and this was evident in the mid-90s, when the Hells’ henchman, located deep in the heart of Outlaw territory, became Hells Angels. “What followed were several murders, bombings and beatings,” George Christie, the author of Exile on Front Street: My Life as a Hells Angel, and Beyond, tells Penthouse. The Outlaws where so enraged, Christie remembers, that they decided to take the war to the West Coast.

“Chapters rolled into the Northside clubhouse dressed for war: black and white vests, checkered bandannas, skull face masks, beards tucked into belts, ponytails secured. We were armed with clubs, chains, knives and Maglites,” Big Pete writes in his new book, The Last Chicago Boss: My Life With The Chicago Outlaws Motorcycle Club. A riveting and gripping account that details what life in the Outlaws was like and chronicles his rise through the ranks of the infamous club to become a modern day Godfather in biker culture.

“I knew I was going to be a boss in Chicago,” Big Pete tells Penthouse. “I’d always been an outlaw in life and lived that lifestyle. Everything that I did, all pointed to one specific point in my life. It started when I was young. I had certain ambitions and my heroes weren’t normal heroes. My heroes were basically infamous characters.”

Home sweet home. Out the front of the Outlaw clubhouse in Chicago / Courtesy of Big Pete

Home sweet home. Out the front of the Outlaw clubhouse in Chicago / Courtesy of Big Pete

Being from Chicago you would think that Big Pete idolised Al Capone, the Syndicate’s gangster legend, but Big Pete names Tony Accardo as his hero. “He’s one of the greatest mobsters that ever lived,” he tells Penthouse. “Never spent a day in jail. He was my hero. He said make money and keep your head down. He technically made Al Capone look like a drugstore wise guy.” And Big Pete didn’t take the normal route to bikerdom either.

“I knew that graduating from high school, going to college, joining a fraternity – all those things would come back to help me later in life,” he says, “everything was pretty calculated for me.” While in college, Big Pete was driving down the highway one day, when two bikes quickly came up behind him. They almost converged on him, creeping up too close in his rear view mirror, before changing lanes and whipping around him. Their vests read ‘Outlaws.’

“I kept that in the back of my head,” Big Pete says. “I always wanted to be an Outlaw. In 1995 when I first came on the scene, the Outlaws were doing everything they could to take on the Hells Angels. A lot of them went to prison. A lot of them are doing life, and the Angels are still here. I understood why they did that, but I looked at it and said I can’t do the same thing. It wasn’t working.”

The Outlaws and other motorcycle clubs had been identified as organised crime groups and were being targeted by law enforcement for their one percenter ideology. A lot of club members knew that outlaw biker clubs were not criminal organisations, they were just organisations filled with criminals. Men who lived free of social constraints, like Vikings of the modern world. And being able to navigate the criminal underworld, as well as unite the different Outlaw factions and local biker groups into one functioning unit, was Big Pete’s goal.

“As I started to go up the ranks people had to come see me,” Big Pete tells Penthouse. “In the back of my mind I was like, this is a great opportunity to unite all the clubs and get them to not fight and not argue over bullshit. It would make it easier for me to hold the city. My goal was actually to make one big giant independent club. I finally convinced everybody to buy into it and more clubs were coming.”

But the dream of a united Outlaw Nation in Chicago wasn’t to be, as Big Pete fell sick with cancer. His underlings used his sickness as an excuse to grab power. A dispute arose, and after 20 years as Chicago’s boss, Big Pete bowed out. Leaving his former club to their own fate. A biker legend who walked away from the club he helped build. Big Pete never thought he would write a book about his life with the Outlaws – it’s frowned upon by the MC – but with how the people in the club had changed, Big Pete felt justified in telling his story. The true life tale of an Outlaw boss. 

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You can get a copy of Big Pete's book online through angusrobertson.com.au