Review: The Last Chicago Boss: My Life with the Chicago Outlaws Motorcycle Club by Peter “Big Pete” James with Kerrie Droban

The Last Chicago Boss: My Life with the Chicago Outlaws Motorcycle Club by Peter “Big Pete” James is a startling and unprecedented expose into the inner workings of the Outlaw Nation from the unique perspective of its renowned leader, all brought to life through never-before-revealed interviews, police files, wiretaps, recordings, and trial transcripts.

The Last Chicago Boss surprised me. To be honest, I’m not sure what I expected from the memoir of the ex-boss of one of those most notorious motorcycle clubs in the country, but this insider’s view of a tribe of people often feared and shunned by the general public reveals that, while some of the stereotypes of motorcycle gangs have a foundation in truth, there’s a lot more there than meets the eye.

Peter “Big Pete” James is a legend in the international motorcycle community. At the age of 45, he joined the Outlaws with the intention of being Boss of Chicago—but he didn’t stop there. Big Pete details in his memoir how he not only built up the Outlaws as the most badass and elite motorcycle clubs in Chicago but how he also created the Confederation of Clubs (CoC) to unite all kinds of clubs under his command.

The Outlaws were once considered white supremacists, but Big Pete put an end to all of that. The CoC was formed to unite clubs of a variety of backgrounds and ethnic groups. And if you think removing the swastika from the Outlaw patch was an altruistic move, think again. Big Pete is certainly not a white supremacist himself, but it seems that it’s because he just simply doesn't care enough to be one. He only cared about one thing—being the boss of the largest confederation of motorcycle clubs in the Chicago area. It’d be pretty hard to unite such a diverse group of clubs under one flag if that flag is associated with racists.

I guess the part of this story that surprised me the most is how militarized the Outlaws and the CoC were under Big Pete’s rule. It seems counterintuitive that a group of men determined to be on the wrong side of the law would have their own unbreakable laws. Those who stepped outside of this very strict code of conduct were punished in violent ways, often publicly to serve as reminders to their brethren. And they all revel in these spontaneous bursts of violence that they not only inflict on their fellow club members but also see to inflict on their rivals:

The back room was suddenly eerily quiet. I shifted on the stool, my right leg almost numb from the static. The gun warmed in my hand. I had never shot anyone, never killed anyone. The closest I had ever come to witnessing a murder was the man on the dock with Backlash’s knife pressed against his throat.

Still, I’d never felt so alive. And whether it was the idea of dying or the thought of never having really lived before that terrified me more, I wasn’t sure. But I had such clarity—the room, the lights, the bar flickered like the past fading in and out of focus. A fly buzzing on a shot glass sounded like a jet. My boots blended into the black floor. The jukebox played “Welcome to the Jungle,” and Axl Rose’s voice boomed to the ceiling, then whizzed from wall to wall. His was the sound of Power.

What isn't so surprising, however, is the treatment of women. There’s scene after scene of sex and drugs and prostitution, and while Big Pete never participates, it’s still a huge part of the culture. Sure, women could be members in their own right, but it was pretty rare and not generally accepted by all members. Women were often sex objects, and the married few were objects “owned” by their men. The only way men could keep their wives safe was to declare them as property.

Two months after I became Boss, my Regional Boss presented Debbie with her “Property of” vest. Most ol’ ladies received theirs in six months or more, but Debbie earned hers early and, though the production was unceremonious, it elevated her status; she was now part of a family, not just a civilian playing dress-up.

In the end, Big Pete was proud of all he built. And, surprisingly, he came out of it relatively unscathed despite multiple run-ins with Outlaw arch enemies (the Hell’s Angels being the most notorious enemies of them all), drug raids, and outbreaks of violence within the ranks. Always a smooth operator, Big Pete doesn't seem the type to give up ALL of his secrets, but even still, The Last Chicago Boss had enough to leave me with the feeling that I’ve had a glimpse at what the boys from Lord of the Flies might have been like all grown up.


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Ardi Alspach was born in Florida, raised in South Carolina, and now resides in New York City with her cat and an apartment full of books. By day, she's a publicist, and by night, she's a freelance writer. You can follow her on Twitter at @ardyceelaine or check out her website at


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