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Macmillan Childrens Publishing Group

The Last Chicago Boss

My Life with the Chicago Outlaws Motorcycle Club

Peter "Big Pete" James with Kerrie Droban

St. Martin's Press




Outlaw is in my DNA.


My Outlaw training began with Risk: The Game of Global Domination, invented by French film director Albert Lamorisse and released as La Conquête du Monde (“The Conquest of the World”).

We gathered nightly at the kitchen table beneath a bright suspended bulb—my mother, sister, brother, father—fiercely attentive, poised to attack. The strategy board game depicted a political map of the Earth, divided into forty-two territories, grouped into six continents. The goal was to occupy every space on the board, and necessarily, decimate the competition. Players controlled armies and used them to capture territories from other players, their fate determined by dice rolls.

“What do you want to be when you grow up?” My father grinned as I marched across his enemy lines.


I was only twelve.

I lived in a town of thirty-two thousand people on the outskirts of Wisconsin. My father probably thought I was just being cute. After all, most kids had delusions of grandeur. But I wasn’t most kids. And I was hardly cute.

I was lucky my mom reminded me often. I got to keep my Christmas gifts every year.

The next night, my dad challenged me to a rematch, a game of chess. But in the quiet of our living room, amidst muffled farm sounds, I carefully used pawns to capture his knights and castles, and was dangerously close to snuffing out his king.


My father’s face puffed red.

“How did you do that?”

And he and my mother fought … about chess moves. Glasses broke; pieces flew across the room, motionless pawns, like bleached plastic soldiers, scattered across the linoleum tiles.

“Peter, my Peter,” my mom pleaded with me.

The fundamental flaw with chess was that a player had to sacrifice pieces (soldiers) to gain a tactical advantage.

I preferred the Chinese game Go; it involved takeover without sacrifice. Players took turns placing black and white stones in vacant spaces on a grid.

“And if a black piece lands horizontal to a white piece…?” My father needed clarification.

“The opposite color takes away the other stone’s liberty. And when there are no liberties left, that stone can’t stay on the board.”

“So that’s how you win?”

“Well … at the end of the game, there can be living and dead stones.” I could see that I was losing him. “There are areas on the grid called forbidden points.…”

“How do you win?” He orbited around me.

“When both players agree the game’s over, or when one player resigns.”


“Players can agree that stones that would have been inevitably captured are dead. And stones that cannot be captured are alive.”

“Hey, punk, want to play a real game?” My uncle took me to the horse races.

He’d graduated third in his class from Marquette University, a private Catholic institution in Milwaukee, and became a CPA. But then he discovered the horses and his life “tumbled.” When relatives spoke of Uncle Tony they lowered their voices, muttered phrases like “skid row” and “racetrack” and “broken promise.” Then the aunts (mostly my mom) tried to “save him.” They found him employment with Maidenform selling brassieres.

But when my uncle pulled up one morning in his marvelous Lincoln, I knew (even in the sixth grade) he no longer dabbled in ladies’ underwear. He wore a long trench and expensive-looking shoes and his fingers sparkled with rings. He had made new “friends”—real gangsters who showed him how to make “real” money fixing horse races. My uncle showed me Chicago, a dazzling city that always smelled wet.

“Like money?” He took me to lunch at a fancy restaurant where the tables had stemmed glasses and cloth napkins, and the staff wore bow ties.

“There’s a thirty-minute wait.”

Uncle Tony slipped the host a few bills.

“Right this way.”

“Watch and learn.” My uncle motioned for me to follow.

I did. It didn’t matter what he said. I saw what he did, and that mattered.

“Power plays happen at the subconscious level.” He tore apart a bread roll. I sampled my unpronounceable dish and used all three forks. “When people feel powerful they stop trying to control themselves. You understand?”

Got it. No self-control.

We made many more trips to Chicago. And after a while the aunts stopped worrying he might be a “bad influence.” My uncle plied them with carloads of beef, sweet peppers, and gravy. I watched. I learned. I wanted to be just like him.

“Play a real game with him,” my mom pleaded with my uncle as she left for work one day.

“All my games are real.” He winked at me, careful to pocket his dice and switch to Yahtzee when she returned.

* * *

At the horse races, I already knew from playing Monopoly and rolling dice that the odd number 7 was the most common roll and the color red the most landed-on property. I considered 7, Chance. If I rolled a 3, 7, or 9, I was most likely to land on a red property and avoid going to jail. So I bet on odds, put $300 on “Hurry Home Harry,” a dark-horse contender, a real underdog, with a terrible chance at winning.

“Speed or skill has nothing to do with winning,” my uncle mentored me. “A horse is judged by its comparison to the speed of other horses … and by its wins and losses.”

We sat close enough to smell the dust from the track. Hooves thundered by, and my heart raced as I followed the progress of “Hurry Home Harry” on the backstretch. Come on, come on, win!

The bleachers rocked; spectators roared. My uncle waved his hands wildly in the air, never taking his eyes off his horse. The majestic beasts raced faster and faster, a blur of blinkers and shadow rolls. They resembled bandits racing from their locked gates—cloths across their noses blocked the track, prevented them from jumping shadows. They bolted sometimes two abreast, always in tight formation. Jockeys curled tight on their backs, whips in hand. Slashes of determination lined their faces.

“Hurry Home Harry,” looking washed out, his mane sticky with sweat, galloped across the finish line.

“How’d you do, punk?”

“Great, really great. I made—”

My uncle put a finger to my lips. “A real man never talks about the money he’s won or the women he’s fucked.”

Lesson learned. Nonetheless, I was so proud of my $3,000 winnings. Later, I learned my uncle had bet $44,000 on “Hurry Home Harry,” a life’s savings on a dark horse.

“Why…?” I couldn’t help myself.

“You need to keep your eyes open.” My uncle tapped a finger to my forehead. “The skid row guys are there every day at that track, every day they’re watching the horses race across that finish line. They know the score. They bet two dollars on ‘Hurry Home Harry.’”

I still didn’t get it.

“Because they have the most to lose, they’re more likely to win.”

Keep your eyes open. I did, but I wanted to do more than that: I wanted to see inside them, absorb their invisible intelligence.

I ran for student government … and lost.

“What happened?” my mom barked, hands on her hips. She looked disappointed.

“Nothing. I just wasn’t good enough.”

She marched over to me, cupped my chin in her hand, and uttered the words that would profoundly inform my life’s path: “If you don’t think you’re number one, don’t expect anyone else to think you’re number one.”

After that I left nothing to chance. I rigged every election—altar boy, student council, president of the Lettermen’s Club. My uncle’s words swirled in my head: “Perception is everything. It’s what others see that matters.”

I never did get to thank him. He “went away” suddenly—to a federal prison cell. It was somehow fitting. He had passed on his life’s lessons. His utility had ended. People, after all, were just moveable game pieces. Some were destined to be pawns, a means to an end, while others would go on to be king.

I replaced Uncle Tony with the next best teacher, Mario Puzo’s book The Godfather. Michael Corleone, the youngest son of the Mafia don, Vito Corleone, went to college. My uncle went to college. It was like a credential. I wanted that stamp of intelligence, not because I thought I would need it necessarily to become boss, but because I considered it a personal challenge and a social experiment with plenty of test subjects. (Never mind that I likely got into college because I played football.) I didn’t realize I might actually have to study or that grades mattered to get a diploma. So when I was in danger of failing I came up with a plan.…

“List your major influences.” The application for an internship with Wisconsin’s speaker of the house had a host of ridiculous questions.

The Godfather was mandatory reading, like the Bible. I’d memorized key passages and phrases, having read the book seven times before the age of twenty. I graduated to Sun Tzu’s The Art of War, Harry Truman’s biography Plain Speaking, and finally to Robert Sabbag’s Snowblind, which I credit to perfecting my considerable skills in the cocaine trade.

But somehow, I didn’t think those references would impress. It was a big deal in my family that I attended (but found it unnecessary to graduate from) the University of Wisconsin—Whitewater with a bachelor’s degree in political science.

“Why do you want this position?” The real answer? I needed the college credits to pull up my miserable GPA. But of course that’s not what I wrote.

The job involved researching legislation to improve and update small claims courts in Wisconsin. And the judge who led the charge happened to reside in Los Angeles. Judge Katsufracus (the original Judge Joseph Wapner) apparently informed the federal marshal who met me at the airport that “an important visiting dignitary from Wisconsin would be arriving.”

“You?” The marshal lowered his sunglasses and arched a brow. “Somehow I thought you’d be a little older.”

In his chambers, Judge Katsufracus squinted at me. His black robe spilled around him, making him look like a curtain with a head. “What do you want to do while you’re here?”

“I like movies,” I shrugged.

The judge smothered a smile. “I have a contact at Paramount.”

In between working on legislation to improve the process of “burden of proof,” I visited the set of Moses and watched the Red Sea part, I straddled the motorcycle “The Fonz” rode, and shook Wonder Woman’s hand.

I pulled up my GPA and had enough credits to graduate.

“Now what?” I asked my father.

He didn’t know. But one day he surprised me in our garage. I was in the middle of sawing a cue stick in half. He glanced behind me at the packed bag of clothing and asked,

“Are you on the run?”

“Not yet,” I said. “But I’m moving to Dallas.”


“It’s closer to the Mexican border.”

While the thought of making a go at drug trafficking, even heading a cartel, sounded attractive, I wanted nothing to interfere with my plans to be the Boss of Chicago. So when the Feds paid me a visit in college and warned me about being an uncharged coconspirator in a drug trafficking case, I didn’t need further details.

Prison was not part of my grand plan. I didn’t want to be a criminal by trade. “Outlaw” and “criminal” were not necessarily synonymous. Drug trafficking was a liability; I could never completely control the dealers or stop them from becoming users.

So I hid in a posh lake house I couldn’t afford and each morning exchanged $20 bills for quarters, so I could access a pay phone on a moment’s notice. I never called anyone from the same phone twice, nor more than once in the same day. This is how I avoided the Feds’ suspicion and protected my drug dealers’ identities.

Safety always; it was a mantra drilled into me from birth, when my mother pinned a blue bead to my pillow and insisted the “evil eye” would “protect me against bad spirits.” I’m pretty sure she didn’t mean the Feds. Still, for years I carried a blue bead in my pocket … just in case. But the morning I accidentally broke a bathroom mirror, I considered other options (after all, I wasn’t about to stop leading a dangerous life), even a blue eye tattoo on the back of my neck just below my hairline. But my mother’s frantic voice replayed in my ear: “Peter, my Peter, please no ink.”

I had often fantasized about my tombstone and the simple words I wanted carved below my name: “Here Rests a Motherfucker.” But I respected my mom. No tattoos.

My future flashed before me one rainy midnight as two motorcyclists crested a hill, their bikes moving in unison like extensions of their bodies. Grace, power, and speed zigzagged through stalled cars and maneuvered potholes. Grinning skulls flapped on their back jackets.

But I wasn’t finished running.

I disappeared for eight years, moving from city to city, sleeping in hotels, on park benches, homeless, honing my skills as a hustler. Until one day my mom called.

“Your cousin has a job for you.” She sounded breathless, excited.

“I don’t want a job.”

“Please.” She was near tears. “You can’t live like this forever.”

I hated that she worried. Truth be told, I didn’t think I could ever get a job. I flunked a psych test once for a big corporate firm.

“We would never hire you,” the recruiter said. “Your scores are off the charts.”

“Too smart?” I hoped.

“Too scary.”

“Scary good?”

“Is there such a thing?”

The problem, he elaborated, was that I could not be controlled. I relented. I accepted a position in a quality control lab in a chemical plant. The company made wax additives for the printing industry, for magazines like Playboy and GQ, so the ink wouldn’t smear.

After several months working alongside chemists, I became the plant’s manager and earned a decent salary. But I atrophied; I was not destined to be Ordinary.

“You don’t fit in this place,” a coworker remarked one morning.

“Sure I do.”

He shook his head. “Nope. You’re resting. I know people like you. You’re waiting for the right time to escape.”

He had a point.

I called a lawyer buddy of mine. “I need an adventure.”

“Is that code for new motorcycle?” He laughed.

The Evolution engine had returned to the Harley-Davidson. No more “Shovelhead” trouble heads. I bought a new bike, and for the first time in years I exhaled.

Then fate intervened.

“You should come to the Moose Lodge,” a friend suggested. What the hell was that?

“The Loyal Order of Moose; it’s a fraternal service organization. They’re having a dinner.…”

The Lodge, a palatial two-story building with a spacious dining area, kitchen, and bar on the first level and offices tucked upstairs, made a perfect clubhouse.

But first things first: I had to become a member of the Loyal Order of Moose—the LOM.

And so, after several more dinners at the lodge, I participated in a forty-five-minute initiation ritual for the Order.

I wore a loud Hawaiian shirt and boat shoes; the Moose wore matching yellow suits and ties and eyed me warily. The governor of the lodge asked the sergeant-at-arms to administer the Moose obligation.

“Do you believe in a Supreme Being?” he began.


“Place your left hand over your heart and raise your right. Do you promise not to communicate or disclose or give any information—concerning anything—you may hereafter hear, see, or experience in this lodge or in any other lodge?”


I was then directed to face Mooseheart (Illinois), bow my head, and mumble a silent prayer in what members called “the 9 O’Clock Ceremony.”

“Suffer little children,” I mindlessly repeated under my breath, “to come unto me and forbid them not, for such is the Kingdom of Heaven. God bless Mooseheart.”

“The children of Mooseheart are supposed to kneel at their bedside in prayers as well,” the lodge chaplain explained before he launched into the ten “thou shalts.”

“Thou shalt believe in God and worship Him as thy conscience dictates,” he ordered. “Thou shalt be tolerant to let others worship each in his own way.” Other “thou shalts” pertained to patriotism, service to fellowmen, protection of the weak, avoidance of slander against a brother Moose, love of the LOM, faithfulness, and humility.

The governor grasped my hand while the members sang “Blest Be the Tie That Binds.” Meanwhile, my thoughts spun into forming my own club, and how I could best gain control of the Loyal Order of Moose to accomplish this goal. The governor administered the second part of the obligation: “Do you promise to support Mooseheart, Moosehaven [a retirement community in Florida], help fellow Moose, settle disputes within the Order, and not join any unauthorized Moose organizations?” Absolutely. The prelate offered another prayer at the altar, and I joined in singing “Friendship We Now Extend.

Being a Moose was all well and good, but if I was to control the lodge and, more important, the treasury, I had to hold an officer’s position. And that was only going to happen if I had sufficient votes. Typically only five members ever decided anything of importance (the same was true when I interned for the state legislature). The same five people showed up and formed “the Majority.” I couldn’t risk five people deciding my fate. So I recruited thirty-five of my loyal friends and indoctrinated them into the Loyal Order of Moose.

“How long do we have to do this?” one of them complained.

“Long enough to vote.”

The governor was perplexed. It was “unheard of” to attract so many Moose in such a short period of time. The lodge had an incentives system: If a member recruited three prospects in a month he received a pin; five, a watch; thirty-five, a Palm Beach sports jacket. I quickly became a marvel in the Moose world—“exemplary Moose material.”

Thirty-five votes later, I became the governor.

“I’m forming my own club,” I announced one night at dinner.

“You mean a club within a club?”

“Yeah, something like that. I’m going to call it the Loyal Order, like the Loyal Order of Moose.”

I had already designed the colors. The top rocker was going to be black and embroidered with “The Loyal Order,” the bottom rocker silver with “Illinois” (because The Outlaws already claimed “Chicago” and would never approve), and on the centerpiece, a gold crest. I added intrigue with swords and skulls, a random #8, and a death card.

“Who’re you going to recruit?”


“And Women of the Moose?” Debbie, my ol’ lady, chimed in.

Well, it could never be 50/50. In any organization or partnership it could only ever be 49/51. In fact, Debbie would only ever make 49 percent of all significant decisions; 51 percent of the time the hard calls, the unpopular votes, the truly gut-wrenching judgments would be mine.

Equality didn’t exist. It couldn’t.

Women of the Moose received a special handbook with resources to help them become independent and productive. But broads didn’t need a handbook. They, like everyone else, got what they earned.

Copyright © 2017 by Peter “Big Pete” James with Kerrie Droban