The Last Chicago Boss

by Kerrie Droban

  “I don’t like hearing my voice on tape.”

  I ripped up several dollar bills and gave the various halves to each of the Bosses. “If I ever call to talk to you and there’s a problem, give your piece of the dollar to your representative. That person needs to give me your half; if the halves match, I’ll talk to them. Otherwise, I won’t.”

  * * *

  The next week, I stabbed chunks of sausage in the Omega, a greasy diner tucked into a back alley in Addison, and glanced at my watch: 2:30. Ray Rayner was late. I knew that somewhere in the clubhouse my cell phone was ringing.

  Pete in his Chair at Northside clubhouse where he made many decisions; in the background a picture of the history of the club.

  “I tried calling you,” Ray Rayner complained later.

  “Ever heard of GPS?” I reviewed the play with him again, and the next day sampled moussaka in the Artropolis. Again, he was a no-show.

  “What is it about this that’s so difficult?” I slammed my hand onto the large wooden table, bouncing a mug onto the floor; it shattered into chunks of glass. The five Bosses (minus Santa, who preferred to appear by phone) gathered around my desk, looking like children about to confess.

  “You’re speaking in code.” Big Butch spread out in one of my high-backed leather chairs.

  I’m not a sociopath, not really, but my whole body tingles when I want to hurt someone.

  Like any great quarterback, I switched tactics.

  “There have been Angel sightings, in some of the Polish bars,” I lied, though Angels had infiltrated the Polish community. “We’re going to hunt in packs. Plan to be out all night. The first person who whines is going to wear a probate vest.”

  I would have preferred a cash fine, but returning someone to slave status packed more punch. I stashed several probate vests on my bike, slipped on a pair of goggles, and geared up for the night watch.

  Chapters rolled into the North Side 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. Santa and his elves were conspicuously missing. When the rest of the chapters all assembled, we peeled out, a storm of Harleys thundering in the night sky.

  First we hit Orion, a Polish restaurant and bar in Garfield Ridge. We parked our bikes in rows curbside, hoping a square might knock one down so we could start a blood trail on the pavement; but really we didn’t need a reason. Inside, a DJ spun polka discs beneath decorative red bulbs. The crowded bar, already sticky with spilled beer, filled with smoke. The bartenders were Polish broads, a fact that made it nearly impossible for us to gather intelligence since typically we would have planted our own people inside as surveillance for the club. The waitresses dressed in high spiked boots, heavy lipstick, white blousy tops, scurried around with trays of shot glasses, lowering their gaze as they passed us. One tripped over an Outlaws’ boot. A soft mewl escaped her lips as a brother caught her elbow.

  “Careful, darling,” he said, laughing. “I’ll take one of those.”

  She had a chiseled face and purple highlights in her hair. “No English.”

  “Crown Royal.” I pointed to the bottles along the wall behind the bar.

  The tone of my voice attracted attention. Several men turned, drinks in hand, their faces shiny with sweat, their eyes overbright.

  “What are you staring at?”

  Before I could even react, my enforcer, Iron Mike, shot out like a cartoon boxing glove on a spring. He coldcocked one of the men on the side of his head and dropped him to the floor. Air left the guy’s lungs. He lay on his back, eyes startled open, short-cropped blond hair perfectly stiff. Screams erupted. The music skipped. Polish phrases slurred around me.

  A drunken free-for-all quickly followed as bodies slammed into walls, heads knocked against tile, and fists pounded flesh. Back doors swung open; patrons rushed into the alley, and the bar transformed from shades of bruised plum to black and white as Outlaws swung wildly with fists and Maglites and stomped random citizens with their steel-toed boots.

  I didn’t worry about cops. Chicago was the only place where criminals wore badges.

  * * *

  We hit a different Polish bar every week. The chapters rotated as we formed a kind of “fight club,” perfecting haymakers, back fists, hooks, and sucker punches. Sizing up opponents, jabbing at air, making up insults so we could retaliate. The rush was better than drugs.

  “Can we skip next week?”

  I ran cold water over my bloody knuckles. Ray Rayner peed.

  “Maybe it’s time to take a break, you know?” He zipped up his pants.

  I dried my fingers on a paper towel, feeling my blood pressure rise. “We’re one-percenters. We don’t take breaks.”

  But I did disappear at times, hid in a private villa in a Chicago suburb, completely blocked from the outside world. The resort had no windows, no cracks of light, and no identifying markers on the street. Inside, there were private waterfalls, steam baths, vibrating Chinese bamboo chairlifts. No phone service; no computers, no technology.

  “Just forget everything,” Backlash said when he first gave me the villa as a wedding gift. “Go there when you can’t stand it anymore. Stretch it out.” He grinned. “If you do everything at once you’ll just be exhausted. Go there and just be Peter.”

  Just be Pete.

  * * *

  But within minutes of leaving the villa, I morphed again into character, into Big Pete. At Capri’s, Chef Corleone’s upscale Italian restaurant, I looked the part, dressed in a sleeveless black tank, heavy gold rings, black jeans, and combat boots. I sipped Crown Royal and scanned the crowd of suits and sparkly ladies.

  “Pretty fancy place,” The Hound remarked. He was one of the few who rode with me that night from Elgin. It was, and that was the point—to be as disrespectful as possible, to send a message to these wiseguys that we had no fear.

  “I like your tattoos,” a broad winked at me, fluttered over, and pulled up a chair. She wore a leather miniskirt and crinkly knee-high boots. “Do you like mine?” She flashed the compass tattoo on her inner thigh. She wore no panties.

  “Nice.” The Hound licked his lips.

  She laughed, tossed back her head, and walked away.

  “Let her go,” I said. “She’ll return.”

  “I’m going to walk around.”

  The Hound pushed back from the table; an imposing figure, he waddled to the bar and hovered dangerously close to the broad with the boots. I swallowed my shot. This wasn’t going to end well.

  A patron knocked The Hound’s drink to the floor. Whiskey spilled onto his shirt. Punches followed: a hard crack to the patron’s lower jaw, a thud to The Hound’s ribs. He groaned, doubled over, stumbled a little, and caught the edge of a bar stool.

  Concerned for The Hound, I hurled my chair at the patron, spindly metal legs slicing like little knives through flesh. The crowd came alive. Bodies lumped together in a dark mass. Disembodied arms swung and punched like windup toys. After a while my fists burned. Then I heard a crack as my gold-studded fingers smacked against bone. The man’s head whipped back and struck the edge of a concrete column, and he crumpled to the floor.

  I actually worried I might have killed him, but the fighting continued. Patrons stepped over his neck, circled his body outline. No one checked his pulse. No one moved him out of the way. Blood spotted his scalp. I had my own crisis: One of my gold rings had slipped off.

  “Stop!” I boomed. “Don’t anyone fucking move.”

  Patrons froze on the floor in wrestlers’ nelson holds. Sweat slicked their faces. All around me, labored breathing, broken glass, a woman’s screams. Irish-Italian slang hung in the air. Some in the crowd fled toward the exit.

  “Motherfucker, no one leaves.”

  Sirens exploded in the night. I fixated on people’s shoes.

  The Hound looked at me. A bruise spread on his cheek like an eggplant.

  “
I lost my fucking ring.”

  “Cops are coming,” he said.

  A waitress crawled on her hands and knees, tears streaming down her face.

  “I found it.”

  I ducked with The Hound into a storage room behind the bar just as the cops stormed in. I pressed an ear to the door.

  “My mom will be pissed.” The Hound lived with his mother.

  “Shhh.” I put a finger to my lips. “Be quiet.”

  “I can’t afford to go to jail tonight.” The Hound popped a can of beer and guzzled it down.

  The whole idea behind the bar fights was to create a presence in the city, maintain an outlaw image. I realized in time, as attendance dropped off and fewer and fewer chapters participated in the wildings, that the Outlaws didn’t really want to protect the city from Angels. Very few even had the skills to be criminals.

  Damn, I still had a baggie of coke in my front pocket.

  “This is a pretty nice neighborhood,” The Hound said. “We’re going to look like fucking freaks.”

  I decided to consume the drugs.

  * * *

  The cops handcuffed us together behind our backs and led us to an SUV.

  “I can’t climb into that,” I said, my heart racing. “I’m too big.” Never mind that The Hound had just managed it.

  Five squad cars parked along the street. Red and blue wig-wags lit up The Hound’s face. His eyes were watery and bloodshot. The cops huddled, glanced my way and shook their heads.

  “If I uncuff you and you bolt, I swear I’ll Tase you.”

  I looked at him, absorbed his fresh clean-cut face, his pudgy blue pants and utility belt, his little cap with the gold piping, and said, “You’re fucking kidding, right?”

  “Do I look like I have a sense of humor?” The cop uncuffed me.

  * * *

  “Is anyone pressing charges?” I removed my rings one at a time and placed them in the property tray. I already knew no one would. No one would dare. The Outlaws were still considered “one of the most ruthless gangs in the world … involved in biking, brotherhood, and bombs.”

  “You’re lucky we don’t charge you with use of a weapon.” The cop rattled my rings. “These are like brass knuckles.”

  “Someone probably went to the hospital,” The Hound said as we sat on a bench in the booking area, then added, “I have to take a piss.”

  “Seriously?”

  He stood and, because we were attached, I stood too. “You coming?”

  “I’m not pissing with you.”

  A cop uncuffed The Hound, escorted him to the toilet, waited while he pissed, then re-cuffed him with me to the bench. A few minutes later, The Hound raised his hand. “I need to go again.” The charade of cuffing and uncuffing The Hound so he could piss continued for another hour, until finally I snapped, “Stop.”

  “Stop what?”

  “Stop pissing.”

  The Hound dropped his hand, slouched on the bench, swung his feet, and said, “They’re not going to press charges, are they?”

  “Nope.”

  “You think this will hit the paper?”

  “Probably.”

  “You think maybe we could skip next week?”

  12

  RUN

  Skipping weeks was never an option for an Outlaw, but I could at least switch gears. In between organizing “Angel Hunts” with my fellow Outlaws, I focused on my other responsibilities. As chairman of the COC, I organized “run sheets” (party planning) for thirty-six clubs in the confederation. My goal was to maximize support for each event, streamline costs, and ensure high attendance. With no conflicts, clubs had no excuses; the more participants who showed up at another club’s event, the more cash flow, the more visibility for that club, and, ultimately, the more allegiance to me.

  Though each club had its individual members governed by a club Boss, all followed civil rules of procedure implemented by the board (aka me). Like a federal government trumping state laws, I regulated and organized dysfunction. Bosses from thirty-six clubs in the Chicago area spread their calendars on the conference table. Shines, Polacks, Latinos, Irish, Outlaws all touched shoulders. They were Knight Keepers, Wanted Mayhem, Tru Dat, Orange Crush, Axemen, Fugarwe Tribe, Gor Gor, Legacy, and on and on.

  I went around the table. “Everybody have their fucking dates?”

  As each Boss recited time and month, the COC secretary, Yo Adrienne, jotted down notes. Later, she converted the dates to a computerized spreadsheet and distributed the calendar to all clubs. The process involved several days of data entry and cross-checking to avoid duplications.

  Yo Adrienne was my perfect foil. Petite and tough, she was a member of the Low Lyfz MC and rode her own Harley. I appointed her because the COC was about nondiscrimination, broads included. And, she was a single mom and needed a job and I liked her.

  “Why is a broad calling the shots?” Ray Rayner had promptly tattled to Santa, who’d called me.

  “She’s my conduit. Anything she says, texts, or otherwise communicates is coming from me exactly as if I were speaking,” I told Santa.

  “I don’t get it.”

  “Listen, fuckhead, if you think for one minute I would allow a broad to order brothers around…”

  “But she is.”

  “I’m telling her what to say.”

  “Oh … like a ventriloquist?”

  I hung up.

  * * *

  “Runs” were not just parties, they were moneymaking opportunities and meet and greets. Any scheduling questions or issues I deferred to the secretary; any serious fuckups, it was “Yo, Adrienne, fix it.”

  But it was hard to fix stupid. Ray Rayner sent his flunky, Scooter, to the meetings for scheduling purposes and, in case it somehow wasn’t obvious, assured us, “Anything Scooter does, says, or communicates is at Ray Rayner’s command.”

  Exactly as if Ray Rayner were speaking.

  As a rule I paid little attention to Ray Rayner or his Elgin chapter; both were a source of irritation. But since he occasionally contributed to moneymaking enterprises … he wasn’t completely useless.

  Scooter focused on a dark spot in the ceiling. It was the same stare I had seen on the televangelist Jim Bakker when he paused for dramatic effect disguised as boredom, or simply lost his place, or forgot a crucial part of his speech. Scooter, the wannabe Ray Rayner, Bozo the Clown look-alike, with his shock of bright orange hair, Fu Manchu mustache, and giant, almost grotesque, hands, had “forgot” his calendar.

  “We usually have two runs, one in May, the other in September.…” His voice trailed off; he left the room to make a phone call.

  “You’re holding up the meeting.” I snarled. The Outlaws looked ridiculous. I wanted to appear fair, but in fact I favored the Outlaws. Everyone else had come prepared. They’d brought their calendars. They’d planned their runs.

  Scooter returned minutes later. “I can’t get ahold of anyone.”

  “Do you want me to wait for his dates?” Yo Adrienne asked.

  “No, put his party as a footnote.”

  * * *

  Ray Rayner called the next day. “I have the dates—the runs will happen on the twentieth.” He sounded sure.

  “You embarrassed the Outlaws in front of all the other clubs,” I began my tirade, rambling on and on until finally he cut me off: “It won’t happen again.”

  “No, it won’t.”

  He called a week later. “I made a mistake. Our runs are actually on the eighteenth.”

  “Will that be another footnote?” Yo Adrienne revised the run sheet again, adding footnotes and asterisks.

  “I think you’re missing the point of the run sheets,” I said, pulling Bozo the Clown aside. “We want the support clubs to come to our parties and spend their money. They support the Outlaws. But if we don’t tell them when our runs happen, they can’t come. And we’ll lose revenue. Understand?”

  * * *

  Ray Rayner hosted Elgin’s party that weekend.


  He introduced his bodyguard. “He’s on me tonight.” Bozo’s muscle was the size of a fat building; he had no neck, arms like tree stumps, and looked like he had been recruited from a movie set to play “The Thug.”

  “What do you mean?” I said.

  “He’ll make sure nobody gets to me.”

  “Who’s going to get to you?” First of all, it was Elgin, thirty-five miles northwest of Chicago. Its tallest building was a Kmart. “You’re in an Outlaw clubhouse. Do you honestly think someone is going to assassinate you here?” Besides, you’re not important. Nobody shoots the fourth-in-charge.

  13

  LIFE OF THE PARTY

  Finally, it was my turn. A party was a production, a carefully staged play that began with perception and costume. And so, in the quiet of my bedroom, curtains drawn, I morphed into character, became my own darker version of me. I put on my costume, pulled on my black T-shirt and jeans, laced up my combat boots, and headed downstairs to sit in my high-backed leather office chair. I loosened my belt just enough to slip in my KA-BAR straight-edged knife.

  Next, I rubber-banded my thick ponytail every two inches so my hair would not tangle and adjusted my bandanna above my jeweled earrings, two one-carat diamond studs in the left ear, a white gold hoop with five diamonds in the right.

  “How does this look?”

  Debbie smiled. “Good.”

  I clasped my heavy gold “Charlie” medallion around my neck; black and white diamonds encircled the skull, with two ruby eyes. I slipped on my vest, tucked two pistols into hidden slits sewn inside the fabric, shoved cigarettes and a lighter in the right pocket and slid my phone into the left. Last, I put on my rings; several pounds of gold bands adorned my fingers. My index fingers I kept free in case I had to pull a trigger.

  I mounted my bike, gunned the engine, and rode full throttle up my street, flipped a U-turn and waved to Debbie. I repeated this maneuver at least three times, sometimes making a sharp left turn, then a right, weaving in and out of nearby neighborhoods, hoping to ward off snipers and potential stalkers.

  Meanwhile, Debbie stood in the doorway, arms crossed, brow wrinkled.