The Last Chicago Boss

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  For my wife, Debbie

  AUTHOR’S NOTE

  This is a true story, though some names and details have been changed.

  PREFACE

  Death ends a life, not a relationship.

  —TUESDAYS WITH MORRIE

  “I’m dying,” Pete began our first conversation. He asked me to write his life story. “I am the last Chicago Boss of the Outlaws,” one of the most ruthless motorcycle gangs in the world. We could not have been more different; yet, as we embarked on this yearlong odyssey, involving hundreds of hours of interviews, recordings, intimate disclosures, confidential insights into gang life, and scary revelations about the ever-thinning blue line between cop and criminal and criminal cop, we formed a fierce friendship full of poetry, confession, and heart.

  But Pete “never wanted my heart, he wanted my soul.”

  He sent me classical compositions; his favorite, Chopin’s “Spring Waltz,” reminded him of rebirth and hope. Selections from Marshall Tucker and Bob Dylan conjured up abandon, open road, and the kind of lonely freedom reserved for pure outlaws.

  “Smile, Kerrie Kerrie. I’ve lived a charmed life.”

  He insisted I “saved him” from spinning into dark oblivion and then declared, “This isn’t my story, Kerrie Kerrie, it’s yours.”

  And perhaps in a way it is the culmination of my life’s work: the intense study of criminal pathology, dark subcultures, and the toxic cocktail that makes us all monstrously human. I am thankful, Pete—particularly in your world, where “women are more dangerous than shotguns”1—to have learned the most intimate parts of your soul.

  Pete riding down I-290 into Chicago (Sears Tower)

  Life is a state of mind.

  —PRESIDENT “BOBBY,” BEING THERE

  DARK RIDE

  When a man is denied the right to live the life he believes in, he has no choice but to become an outlaw.

  —NELSON MANDELA

  My Harley hugged the curves on the Dan Ryan Expressway. Tires dipped into small grooves full of glass chips, stripped rubber, and crushed bits of rock. Gold lights flickered off Lake Michigan. I led a pack of twenty Chicago Outlaws. We shot through nightfall in tight formation like vampire bats.

  Our patch, red-eyed “Charlie,” the skull-and-cross pistons that defined the Outlaws Motorcycle Club (OMG), glared at hitchhikers, trucks, and cars with zipped-up windows. One spooked motorist slowed to ogle our spectacle and collided into a meat truck; its side door caved in, crumpled up like tinfoil. Chunks of ice flew out, cracking windshields. Frozen packaged animal heads littered the roadway. Sirens wailed in the distance.

  I cracked the throttle wide open, pulling away from a potential pileup as car after car slammed brakes, honked horns, and swerved dangerously close to the guardrails.

  A lone biker zigzagged the white line; he was a moving target, easy to pick off with a shot to the neck, or a pop to his tire. His life depended on his colors and the turf he claimed … and whether he was a Hells Angel.

  The stranger sped up and tucked between two vans. His tire backfired, sounded like gunshot. A streetlamp burst. The rear van lurched and swerved and slammed his brakes, forcing the biker to veer sharply toward the exit ramp. His body sailed forward, skidding to a dusty halt like a stuntman rehearsing for an action film.

  Perhaps we should have rendered aid, but we were Outlaws in running formation, moving like a black mass, in sleeveless leather vests, skullcaps, and skeleton half-face masks. And Bob Dylan’s “Man of Peace” crooned in my ear: “Good intentions can be evil.” Those we notice least, those who blend into the crowd, might one day stand beside us, might one day shake our hand—“Sometimes Satan comes as a man of peace.…”

  And sometimes he comes as Hell’s Angel.

  PART

  I

  1

  BORN THIS WAY

  Outlaw is in my DNA.

  —BIG PETE

  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.

  “Boss.”

  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.

  “Checkmate.”

  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.”

  “What?”

  “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 Milwauk
ee, 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.”

  “Why?”

  “It’s closer to the Mexican border.”

  While the th
ought 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.