As a child, Peter James loved playing Risk with his family. Only twelve years old, he appreciated the strategy involved in commanding armies and taking territory from his opponents. One night, during a game, James’s father asked what he wanted to be when he grew up.

“Boss,” James replied. A few decades later, he was a boss, all right—Chicago’s regional vice president of the Outlaw Motorcycle Club.

Just like Risk, the “Big Four” motorcycle clubs have competed for territory throughout the United States for the past 50 years. The Outlaws are the oldest, founded on the outskirts of Chicago in 1935, and still based in the Great Lakes region. The Hell’s Angels are the largest, with chapters in more than 50 countries. The Pagans claim most of the eastern seaboard, and the Bandidos hold sway in the South, primarily in Texas. All four are considered “outlaw motorcycle gangs” by the FBI, subject to prosecution under the federal RICO Act.

Peter James has since left the Outlaws, but in a new book, The Last Chicago Boss (St. Martin’s Press, co-written with Kerrie Droban), he reflects on his time in Chicago’s most infamous motorcycle club. If you’re hoping for an exposé on the inner workings of an organized crime syndicate, you’ll have to stick with fiction like Sons of Anarchy, but James’s story is nonetheless an interesting look at life in a tight-knit—sometimes violent—Chicago-area motorcycle club.

We recently spoke with him about biker culture, the impact of motorcycle gangs on TV, and his favorite local rides.

What do most people misunderstand about motorcycle clubs?

Not everybody that joins a motorcycle club is a criminal. They just have a certain philosophy of life, an “outlaw” outlook. I look at rules as suggestions: Most of them are pretty good, but if there’s one I don’t think pertains to me, then I don’t believe I have to follow it.

Are there criminals? Yes. There’s documentation all over the place. I’m not going to deny that. But as times have changed, views have changed. Same with the mob, the Chicago Outfit.

Given the criminal allegations against the Outlaws in the past, were you ever worried about the legal ramifications of writing this book?

This has happened to me in other interviews… I get asked a question, and it’s not as simple as the question makes it sound. I could go on for a half-hour about the reality of what I lived [with the Outlaws] versus what you’ve seen and heard. And therein lies part of the problem.

Even [last year] in the Sun-Times, that was a fair article, but what it spawned was incredible. Some guy wrote a blog saying I was intimidating federal witnesses. Well, if that was true, I would be in prison. You don’t intimidate federal witnesses and just get up and walk around. I did get a call from a few law enforcement agencies asking what I was trying to do. And I was like, “What do you mean? I’m just answering questions.”

How did real motorcycle clubs react to Sons of Anarchy?

One of the worst things that could ever happen to motorcycle clubs was Sons of Anarchy. Jax, the main guy, he’s not a biker. He’s a serial killer.

What that show spawned, for a guy like me, was a big headache. New groups started to form their own little clubs and throw some silly patch on their jackets, guys with no understanding of club history or protocol. It turned into a free-for-all.

I’d tell them, “Look, you guys have no clue. You might as well just put on Bulls jackets and ride around. You might be OK here in Chicago, but if you decide to ride into Indiana or Wisconsin, and you have this on, people there might not like you. You’ve got to live with the stereotype. If you walk into a bar with colors on, you better be willing to defend them. You’re saying, this is who I am.”

What’s your favorite bike? What should people know before they buy?

My personal favorite is the Harley Heritage Softail. I’m a big guy, so I needed a big, rugged bike, but I didn’t want to be on a “bagger,” with a big pizza box on the back and bulky saddlebags and windshields. I might as well be in a car. At least then I’d have air conditioning.

If you’re gonna go buy a bike, what I tell people is to sit on every model and swing your leg over. Whatever model puts the biggest smile on your face, that’s the one you should buy. The other important thing is that you feel safe. If you get on a bike and you can’t put both feet on the ground, you’ve got a problem.

Any favorite places to ride in and around Chicago?

You go where there’s the least amount of traffic and the smoothest roads. One of my favorite rides was to go east on 290 onto Lake Shore, then go north and turn around at Sheridan and ride all the way back down, then take I-55 south to 355, then take that down to Lockport.

I live in the western suburbs near La Grange, and one of my favorite rides was down Archer Road toward Lockport, but that’s changed a lot because of new developments. Sometimes I feel like a wild animal whose habitat’s been taken away.

If you go up US-41 on a Sunday toward the Wisconsin border, there are hundreds of bikes. And then IL-173 toward Richmond, that’s a nice ride, and there’s a ton of places along there to stop, bars and burger joints.

What do you think about while you’re riding?

If I’m leading a pack, with like 25 or 30 bikes behind me, I’m thinking about how to keep the pack moving, making sure everybody stays together and stays safe. But when I’m by myself, or with just one other brother, that’s when I let my mind wander.

Riding a motorcycle isn’t as dangerous as some people think, but if you make a mistake, it’s unforgiving. If you think of the road as a jungle, the trucks are the elephants. They do whatever they want to do. Cars are like the lions, they don’t pay attention to anyone else. And then we’re the gazelles. If we’re not fast enough, the elephants and the lions will do us in. That’s why I tell people, you better have good tires and good brakes. You’ll lose a leg if you don’t pay attention.