The Last Chicago Boss

by Kerrie Droban

  “This is Monster from Sin City.” The voice threw me; the caller sounded white. Since when did a shine club sanction a brother from another race?

  “This is a respect thing,” Monster continued. “We respect the Outlaws. But we want reciprocation.”

  “Reciprocation?”

  “When you or your supporters ride into Indiana, just give us some notice.”

  That sounded reasonable enough.

  “Glad we have an understanding.”

  * * *

  Two days later, Monster called again. “I’ve been thinking about our conversation, and I just wanted to tell you that I appreciate the respect. I’m glad we can talk like this—means a lot.”

  “Everything okay, Boss?” Cockroach said as he poked his head into my office and dipped his hand into my jar of red Licorice Whips.

  “Fucking weird call,” I said. “Little issue with The Professor and Sin City Deciples.”

  “What’s the problem now?” He nibbled the candy vine like an insect.

  “Some guy named Monster said he’s the head of Sin City, but he spoke like a white guy.”

  “Monster, the ex–Hells Angel?”

  “Are you Monster, the ex-HA?” I asked when I called. I couldn’t help it; I was curious.

  “No, I’m the Monster from Sin City.”

  “Were you once a Hells Angel?”

  “I was once an Invader too.”

  Monster, the ex-HA, ex-Invader head of Sin City, invited me to lunch. He chose a quaint bistro in Chicago. When he walked through the door, he blocked the patches of sun on the little square tables.

  I tried to make light of his club choices. “Are you having some kind of identity crisis?” His black vest with red lettering barely covered his chest. Embroidered on his right shoulder: “These Colors Don’t Shit.”

  “I like this place—no booths.” At six feet eight inches tall, he would never have wedged onto a bench.

  His face was a planet. And I realized in that moment, as we shared spaghetti and glazed buttered rolls, that there were few places for freaks like him (like me) to really belong and not just fit. Here, he had a role, a purpose. He felt needed. Size, color, smarts: None of that mattered. Club politics was about respect and diplomacy.

  “So … Sin City?”

  “I thought I could help them out.” Monster tore apart his bun and ate only the crusted edges.

  “And they were … okay with that?”

  He shrugged. “Look at me.”

  He had a point.

  “How long are you going to do this gig?”

  “I’m actually thinking about moving west. Maybe I’ll become a Vago.”1

  * * *

  Pinkie smacked her gum in my ear. “I need a vacation. Florida, Disney World. Do you know anyone there who could show me a good time?”

  Besides Mickey Mouse? I made a few calls. “My partner is coming into town—take care of her for me, will you?”

  Cockroach, Boss of the South Side, called me a week later. “Brothers from Florida want to meet.” I met them in a parking lot, because all “cryptic” conversations deserved to be held outside, out of earshot of listening Feds. Cockroach pressed his oddly shaped torso flat against a car door.

  “Why we got to meet out here?” Cockroach asked.

  You probably had trouble getting out of the eighth grade, the Feds have a ninety-seven percent conviction rate … and their money is encrypted.

  “In case the Feds are listening.”

  He had huge black spots for eyes, long greasy hair, and a few stiff hairs that jutted from his mouth like antennae. Dozer, Boss of the Florida Outlaw chapter, folded his arms across his chest; he was pasty white, with a swastika branded on his arm. A zipper tattoo snaked across his neck. He resembled a pit bull: short, cropped ears and sleek, stocky build. His clan looked chiseled from the same stone, each with the same intense smile found only on the exceptionally dangerous.

  “We want to establish a white supremacist presence in Chicago.” Dozer leaned forward, baring his big teeth. In my mind’s eye, images of The Professor, Preacher Mon, and other shines I had befriended burned on imaginary flaming crosses.

  As chairman of the COC, I most definitely was not going to bless discrimination and risk disbanding clubs whose loyalty I’d worked hard to gain. Never mind that in 2000 the club modified its patch to remove the swastika because of its overwhelming appeal to white supremacists. Besides, I wasn’t into terrorizing people, at least not with hate crimes. I was trying to unite them.

  I looked to Cockroach, who suddenly found something fascinating on the floor in front of him.

  I covered my mouth when I spoke, paranoid about being videotaped. I didn’t want the Feds to lip-read.

  “Since our businesses don’t conflict, I wish you the best of luck.” Somehow it sounded better when Don Vito Corleone said it in The Godfather.

  * * *

  My phone rang at three in the morning. Caller ID flashed Pinkie’s number.

  “Shit. Shit!” Her voice shook.

  “You sound drunk.” I propped up on my elbow. Debbie slept soundly next to me.

  “The Feds want to talk to me.…”

  “Did you piss off Donald Duck?”

  “Not funny.” She sounded like she was about to cry.

  Debbie stirred. “Everything okay?”

  “Fine, everything’s fine.” I dismissed Pinkie’s call as paranoia—easy to confuse the Feds for the cops.

  “This is serious,” Pinkie spat. “I may have said some things.…”

  Now I was fully awake. I tossed off the sheets, dropped my legs over the side of the bed.

  “What things?”

  “I told them about you.”

  “Told who?”

  “The Feds.”

  “What about me?”

  “That you were my partner, that you were in tight with the cops up there.”

  What the fuck was she talking about?

  “I was in a lot of pain.” She started to cry. “I asked if he had any Vicodin.”

  “Asked who?”

  “Josh.”

  “Who the fuck is Josh?”

  She was sobbing now.

  I was on my feet, pacing. There could be only one reason Pinkie called in the wee hours of morning so distraught … only one reason the Feds would be interested in someone like Pinkie … if Josh turned out to be a confidential informant, if she cut a deal.…

  My mind raced as I recalled a second meeting in a parking lot, a white glazed man with penetrating blue eyes, passing me trinkets—hats, glasses, mugs, all marked with a swastika.

  “Is this a game show? What the fuck am I supposed to do with these?” I’d said. I was a smart-ass.

  “Everything okay?” Debbie mumbled. Yeah, sure, everything’s fine. Everything’s fine.

  “I’m so sorry.” I could barely understand Pinkie now. “I had no choice.…”

  My vision blurred. My head throbbed with the night’s activities. What the fuck was she talking about? My hair smelled of smoke. My boots still had wet splotches from spilled alcohol.

  “Josh was part of the Kavallerie Brigade operation. He helped the Feds infiltrate the white supremacists. The Feds think since you’re my partner … that you might be involved.…”

  Involved in what?

  “I’m so sorry.…” Her voice faded. This was unbelievable. I stared at Debbie. Her eyes flicked open.

  I knew her; knew her every mood, experienced her every emotion, knew when to approach, when to back off, when to comfort. I knew her well enough to finish her sentences, even her thoughts. I knew everything about her. But what I never realized until now was that Debbie could read me too, that she knew, despite my best efforts to hide it, when I was seriously disturbed, when it was more than just a normal thing, when it was something big, maybe life-altering.

  * * *

  We went for a ride, just the two of us, the way we sometimes did Sunday mornings, each on our bikes, past the bakery on t
he corner, windburned, the skyline enveloping the city in white gauze. Today was Debbie’s birthday. Somehow that seemed impossible, not that she was ever born, but that she ever survived another, different life before me, before the Outlaws, before definition and purpose.

  Pete and Debbie (EZ Rider rodeo Morris, Illinois)

  We stopped at our Dairy Queen, ordered swivel cones from the counter lady with the red lips and teased hair, and slid into our plastic Technicolor booth. We licked our ice creams, not saying much, smiling with our eyes.

  I wanted this sort of suspended animation to last. I wanted to be just Pete for a few minutes longer. Busy vanilla people surrounded us; they picked at their French fries and squeezed ketchup on their burgers. They chattered noisily with their kids. Some looked like they’d just arrived from church, garishly overdressed, smelling like incense and burnt hair.

  My cone was the size of my hand; I could have swallowed the whole thing in one gulp, but I consciously slowed the pace. No matter how anxious, fatigued, or even agitated I became at life, Debbie was my balm. But the interlude never lasted.

  * * *

  Later that night fists pounded on my front door.

  “What’s happening?” Debbie froze, her hands foamy with dishwashing soap.

  “I’ll handle this,” I said, but before I could respond, a federal task force stormed in, guns drawn, dressed in full battle gear: Kevlar vests, helmets, plastic shields. One aimed his gun at my bulldog.

  “Hey!” If they had shot my dog I was positive I would have shot them.

  My dog scrambled for cover under the couch. “Look, whatever you have on me I’ll go peacefully.” I was in gym shorts and a T-shirt.

  “We’re not here for you,” The federal task force swarmed Debbie. “We have a warrant for your wife.”

  Pete and Brutus

  “Pete!” The pot she scrubbed clattered to the floor.

  “My wife?”

  Debbie visibly paled as a Fed cuffed her soapy hands behind her back.

  “What are the charges?”

  “Drug possession.”

  “Drugs?”

  Debbie opened her mouth to protest. “Don’t you say a fucking word!” I told her.

  My heart dropped to the floor as Debbie disappeared into the black van.

  * * *

  “The Feds wanted her held without bail for possession of two Vicodin,” the lawyer explained over the phone a few hours later. “But I convinced the judge to set a cash amount at fifty thousand dollars. Your wife’s hearing is scheduled in a couple of days in Florida. You’ll have to retain a lawyer down there.”

  My head fogged. This was Debbie—college-educated, with two degrees and a real career. She was a Normal Person; she had focus and goals and ambition, an overachiever whose biggest worry in life was acing a final exam she had studied for weeks in advance.

  Jail didn’t happen to people like Debbie.

  “They’ll have to prove your wife was in Florida,” the lawyer continued.

  “Mr. James? There’s nothing we can do about it tonight. It’s almost midnight. Try to get some sleep.”

  I stood over my empty bed, my legs heavy, as if waterlogged. How did this happen? My mind reeled with horror scenarios as Debbie surely connected the dots and figured out how Pinkie fit. “You know he’s fucking her,” a faceless Fed whispered in the dark. There would be no coming back from that. I stared at the ceiling. Images of Caesar, Troy, Henry the VIII played tricks on the walls, all of them derailed by a broad. Everything I had built, fought hard to maintain and sustain, gone, just like that, in a finger snap, by a Vicodin-popping broad.

  I paid a Florida lawyer $10,000 to handle the mistaken-identity case and commissioned Bastardo to fly with Debbie as my proxy.

  “Get her the fuck out of this.” The thought of Debbie pacing a cold cell with concrete urine stains flipped my stomach. I dialed Pinkie’s number and left her a message: “I will solve this problem and then I will deal with you.”

  It was not an idle threat. But Pinkie disappeared before I could take action.

  The press characterized the arrests of six members (including my wife) as an “inept government investigation” that “cast too wide a net” hoping to “catch anyone doing anything.”

  “I hate to sound trite, but it’s kind of the Al Capone theory of prosecution,” the assistant state’s attorney remarked. Only instead of tax evasion, the government levied “heavy-duty drug charges to shut down active members.”

  “He handed the judge Debbie’s driver’s license,” Bastardo said, filling me in on the details of Debbie’s court hearing. “The detective couldn’t identity her. All he had to do was look at her license and he would have known he’d made a huge mistake.”

  “They didn’t even have the same eye color,” Bastardo relayed. “The confidential informant’s broad had blue eyes, jet black hair with purple highlights, and was covered in tattoos.” Pinkie.

  Debbie had green eyes, brown hair, and no tattoos.

  The judge dismissed the charges.

  27

  GAME OVER

  The die is cast.

  —JULIUS CAESAR

  One day it happened, like poison in the system. Extreme fatigue; my body shut down. Lights flickered inside—small bursts of power, then crippling darkness. I pissed blood, cramped, and doubled over with back pain.

  “What’s wrong with you?” Debbie stood at the bathroom door, barefoot, her painted big toe tapping.

  “Hangover.”

  The toe stopped moving.

  * * *

  Secretly I wished the mass on my kidney was a battle wound. I could accept that; I could understand that.

  “I have cancer,” I told Santa, and spent the morning fielding club crises, preparing run schedules, reviewing agendas, acutely aware of time passing.

  “I need you to come to Chicago.”

  In my mind’s eye I saw Santa delayed, stopping first at Dairy Queen for an Oreo Blizzard because he liked them, because blazing heat and humidity made him forget he was supposed to be ruthless, Regional Boss of “a highly organized criminal enterprise with a defined, multilevel chain of command whose entire environment revolved around violence.”

  “Just until I get better.”

  Santa cleared his throat. “Okay, but you’re still going to run the COC, right?” That was a given; Santa had already betrayed the club’s trust by failing to curb Ray Rayner’s extortion of its members.

  Doctors removed my kidney. Das Jew visited me in the ICU; he was the only Outlaw apart from Bastardo who came to see me. I now thought I knew how Grease must have felt when he was in the hospital recovering from his shooting.

  “I made Das Jew wait in the hallway,” Debbie said. “He was wailing.”

  Even in my delirious postoperative state, I knew why “the skinny, bald guy with the sleeved arms” paced the hallway. And it wasn’t because he liked me. Das Jew needed me to like him. But when he repeatedly dissolved into sobs in my presence, Debbie told him politely to leave.

  And later, as I convalesced at home, Das Jew sent “care packages”: Carson’s rib specials, two full slabs in a box, complete with containers of coleslaw, potatoes, and brownies. Never mind that I had oxygen tubes shoved up my nose.

  Maybe he’d finally realized he needed me, because he tried other gifts too—a 42-inch television and a statue of knives.

  I hated that I had to “recover” from major surgery and was ordered to “take it easy.” It wasn’t me; Big Pete didn’t take anything “easy.”

  At the next regional meeting, the National Boss, Hillbilly, complained to Santa about the White Region: “According to the rules, an officer cannot maintain his position while on medical.”

  “You have to appoint successors,” Santa said.

  “I’ll be back in a few months.” I assembled Judas and Cockroach, because I could count on their bumbling leadership. Anyone else and I might not have had a position when I returned.

  “We’ll meet onc
e a week; I’ll give you an agenda.”

  But Cockroach missed the first meeting, and the next and the next. And in time, after multiple doctor visits, follow-up appointments, and mandatory procedures, I realized I wasn’t coming back, that I couldn’t lead from a distance. Cockroach and Judas were like frayed puppets cut loose from their master’s block.

  “I’m done,” I said. “It’s over.”

  Piercing truth hit me—I wasn’t getting out of this world alive, or even intact. Propped up on pillows, I was outraged that life continued, that shoppers went on pushing carts inside Wal-Mart, people still went to work, motorists honked horns, cops directed traffic, wrote tickets. The sun still shined. Nothing stopped. Nothing changed. Nobody really gave a damn about my cancer, my shattered world.

  “It’ll never be the same,” Nunn said. He was large like me, but with “texture”: a pocked face from acne scars, barbed-wire tattoos above his elbows that made his arms look oddly puffy. He had been in the club for just over sixteen years.

  “We need an election. What do you think about me running for Boss?” Thin red lines cracked across his eyes.

  “Run it by Bastardo,” I said.

  “Hey, Boss,” Bastardo gushed. “I won! The vote was 8–4.”

  He broke the news to Santa.

  “What’s really going on?” Santa left his post in Peoria to confront me at my bedside. “Judas says you manipulated the vote.”

  He looked shorter than I remembered. His white beard tucked into his belt, his boots caked with mud.

  “I have no idea what you mean.” I pointed to my rumpled sheets, drawn curtains, and bottles of prescription pain medications on the nightstand.

  He held an emergency meeting.

  “What the fuck is up with Santa?” Bastardo filled me in. “He’s taking a poll, asking every member whether you forced them to vote for me.”

  “Doesn’t he realize I could have appointed you instead of Judas?”

  A week later, Santa reversed Bastardo’s election.

  “Judas is back in.”

  “Why?”

  “I’m putting him back in.”

  “But he was voted out.”

  “The election was rigged.”

  In the muted darkness, I dozed off. Two inmates, chained together, appeared in a dream, at my window. One stared at me, cocked his head, pretended to listen; the other shut his eyes, but prompted me to answer with a soft clang of chains.