The Last Chicago Boss

by Kerrie Droban

  “Be safe,” she said. “Call me when you’re headed home.”

  * * *

  Crowds formed at the entrance to the North Side clubhouse. Enforcers taped yellow adhesive to the floor, circling my chair as if I were a crime scene.

  I sat center stage, surrounded by Kreepy Tom, Sick Bastardo, Mr. Happy. Partygoers lined up like therapy patients, shook my extended hand, gushed about the opportunity to consult with “Big Pete,” thanked me for listening to their problems, and waited their turn to speak, trancelike, eyes rolled back, as if my very touch transformed them. Some stood for a minute and a half before me, others more than eight, depending on how important they were.

  Pete’s throne

  Some flashed their tits, thrust black Sharpies in my hand, and asked me for an autograph.

  “Nice to see you,” I’d say, but I didn’t see them; instead I studied the room the way a general notes exits, blended faces, and subtle shifts in expression.

  “Back the fuck up,” Bastardo would say, shoving the faces pressed too close to my space.

  More people grabbed my outstretched hand. “Thanks for the birthday wishes,” I repeated over and over, though it wasn’t my birthday. No one noticed. Wrong script, wrong play, wrong presentation. The room shrunk small as a television. “Heard you like red velvet candy.” A broad with thick black braids grinned and offered up the bag of melts wedged between her breasts. Another straddled my lap and whispered in the shell of my ear, “I wore loose jeans just for you.”

  “Okay, sweetheart, take two steps back.” My breath came in short, fast bursts, my claustrophobia crippling me.

  “Thanks for the Christmas gift.” More strangers shook my hand, though it wasn’t Christmas.

  I glanced at Bastardo, and he must have registered my pained expression.

  “Not too many more, Boss.”

  The line snaked into the back room. Women stared at me, their gaze so intense I began to feel like the last donut on the shelf. I listened to domestic issues, financial problems, health crises, as hours ticked by and my voice cracked.

  “I can’t sleep, man,” one brother said, sucking cigarette after cigarette, his eyes all scratched up with thin red lines. “I keep thinking they’re coming for me, you know? Every car that backfires—bang!” his voice exploded. “You know what I mean?”

  I did. I really did. I wanted to tell him to lay off the coke, but instead I advised him, “Get a dog.”

  A probate approached, his right eye swollen and waxy yellow. Though he stood in the middle of the room, inside the circle of yellow tape, he spoke freely, as if we were alone.

  “I got three kids.” His voice faltered. “One of them died last year.”

  He looked like he hadn’t seen sunlight in months. His skin had a grayish tint, suggesting slow decay.

  “You need to go home.” I knew what it was like to lose a child: My own daughter no longer spoke to me. “This life,” I began. “It takes casualties.”

  He stared at me, his mouth open.

  “You can’t be here,” I said. “Your child died. Your mind is elsewhere.”

  The probate looked confused.

  “Outlaws don’t have feelings.”

  He started to protest but I cut him off. “Being an Outlaw is a lifestyle, it’s a choice. Most of us are here because we don’t fit into the square world. We don’t want to fit in, see?”

  The probate nodded.

  “The club is our family. The brothers come first. God, country, your dog, even your old lady are secondary. You don’t get weekends off. There are no time-outs, you understand?”

  “But,” the probate protested.

  “You’re a liability. You have three kids still at home. You’ll be thinking about them instead of protecting your brothers.”

  A welt beneath his eye split and fresh blood oozed out.

  Behind him, near the bar, a drunken citizen bumped the shoulder of an Outlaw, spilled the contents of his paper cup onto the Outlaw’s steel-toed boot. Mr. Happy already had the guy in a headlock and, on my cue, punched him hard in both eyes before tossing him into the alley.

  “I get it,” the probate nodded. “I’ll think about it.”

  He had six months: 179 days, 23 hours, and 59 minutes.

  * * *

  As the night wore on and the crowd thinned, Bastardo disclosed he had just pierced his penis, a detail I found perplexing, since he had no other holes in his skin. But that wasn’t his issue.

  “Do you think it’s normal for a broad to want her ribs bruised during foreplay?” I had to think about that; I knew of many who enjoyed rough sex, even asphyxiation. Hell, I had once lifted a broad by her throat and squeezed so hard the capillaries in her eyes burst. And when she hit the floor hard, nearly passed out, she’d sputtered, “Is that all you got?”

  “I think the girl might have issues,” I said to Bastardo. Maybe we all did? Behind him a few midgets strapped Velcro harnesses to their chests and encouraged drunken Outlaws to hurl them against concrete to see if they might stick.

  I lost track of time. Kreepy Tom brought me water in a paper cup. My legs numbed from sitting too long.

  Chuck, in between summaries of Green Acres reruns, announced his preference for BDSM1 and asked if I wanted to meet Lady Sarah (his BDSM dominatrix). Maybe.

  Chuck, who resembled a coke machine with a head, also wanted a tattoo, “a teardrop on my face.”

  “You can’t have one.”

  “Why not?”

  “Because you haven’t killed anyone.” And you haven’t been to prison, and you’re not mourning the loss of a loved one, and …

  “I want one.”

  “What the fuck, Chuck,” I said.

  “I like the way they look.”

  “It means something.” Never mind that any face tattoos would make him immediately memorable to the police.

  Chuck looked like he was about to explode. I knew he ingested steroids like candy but tonight he looked wired, hyped, and his nose leaked. He once boasted about taking ninth place in a weight-lifting competition, and I couldn’t help but wonder what color the ninth-place ribbon looked like.

  Lady Sarah nudged him. She was a stocky bodybuilder type and spoke with a lisp. She smiled at me, handed me a Sharpie, and asked if I would autograph her left tit. Chuck lived with his old lady in her basement. Twenty years his senior, she towered over him at a freakish six-seven.

  “Lady Sarah sits on my face sometimes.” He grinned. “I like it.”

  “Only with my jeans on,” Lady Sarah said as she slapped him playfully on the shoulder.

  My hand shook as I scribbled “You’re welcome, Big Pete” on her tit.

  “Hope I see you around.” She winked at me.

  “Do you ever think of me like that?” The next broad in line cocked her head to the side and fluttered her lashes. The lids blinked “Fuck me.”

  “Sure.” I smiled. “I’m thinking I’d like to smash a brick into your face and turn it into a hamburger.” She looked a little startled, laughed uneasily.

  “There’s no way you and I are getting together, see? I don’t care if you can suck a golf ball through a straw.” She sashayed away as if retreating from some invisible line that marked the end of one life and the beginning of another—one I never crossed. Sex was not my aphrodisiac.

  “Don’t let the small legs fool you. What you see is not what you get.” A midget twirled in front of me.

  “Darling, you have nothing I desire.” I wasn’t being cruel, just blunt. She sucked in her cheeks, reminding me of the broad I once slammed through a window after I found her fashioning a crack pipe out of a showerhead.

  “I’m sure you’ve never had a lap dance the way I could give you one.” She trailed her fingers along my vest. Something alive in me snapped. My reaction pure reflex, I slammed her head into my knee. Her nose cracked. She looked up at me as a dark bruise formed underneath her eye.

  “I don’t like to be touched.”

  Bastardo nudg
ed me. “Look who just walked in: the night’s release.” We called them “The Tens”—one was tall and lean, the other fat and round like the number zero. They winked at the row of brothers propped against the wall, grabbed some drinks, and strayed into a back room. The men lined up, one by one, for blow jobs, like they were waiting to use the same urinal. They turned the activity into sport and a competition of who could go the longest without exploding. Claps and cheers and gulps followed, along with a mock countdown: “Ten, nine, eight,” the men chanted with no pants on until the semen glistened on the Tens’ bellies and thighs. Some returned for seconds and thirds, and when the Tens emerged, smelly, sweaty, barely human anymore, Cockroach gave each a long, sloppy tongue kiss.

  “I’m heading home.” I said.

  * * *

  At the top of the Sears Tower, Chicago lit up the night like my personal Christmas tree. She spread wide, waiting for me to enter her like a lover bursting with secrets. Here, I could be completely alone, utterly myself. The air was so thin, I had to learn to breathe again.

  Soon it would be Debbie’s birthday. I decided to buy her a star.

  14

  THE OTHER ME

  My home fit me. Oversized sofas circled a television on the wall the size of a movie screen, dwarfing my large frame. My tub resembled a Jacuzzi. Here, like valves releasing steam, I decompressed. The layers of Big Pete, Outlaw Boss, peeled off, leaving just Pete.

  “Full moon is coming in two days.” Debbie actually marked the date on the calendar. She warned our neighbors and friends. That was their cue to disappear.

  “If he goes off, don’t make eye contact,” Debbie told them.

  I paced the halls, rage building inside me, thoughts blowing through the dark, wide spaces; ghostly faces pressed against glass behind my heavy bedroom curtains.

  I ripped electric cords from the walls. Help me, the voices whispered. I smashed bulbs suspended from the ceiling, knifed my couch until foam spewed from the cushions.

  “You okay in there?” Debbie would call.

  * * *

  A week later Lady Sarah sent me a photo: Whip in hand, she straddled a client bound at the wrists and ankles with leather straps, a death head-tattoo stretching across his chest.

  “We should meet,” I said when I called her later, not at all interested in her skills, but in her clientele. If she could lure Hells Angels and other prominent rivals into her dungeon, the earning and intelligence-gathering potential would be huge.

  Business was business, after all.

  Lady Sarah wore a tight corset that revealed her considerable chest, thigh-high spiky boots decorated down the sides with grommets, and a miniskirt.

  “Want a tour?”

  I stepped inside “The Dungeon,” a cavelike dwelling easily accessible from the airport and the Loop. The place, immaculate and inviting, divided into several play spaces, each with a theme and purpose, well-equipped and secluded. A sign above the door read, “I am your sin. I am your soul. I am.”

  Clients ordered off the menu, fantasies I could never imagine: coprophilia, ruby showers (menstrual urine), mummification, toilet slaves, and special restraints that included plastic wraps, body bags, even a latex vacuum bed. Other offerings, like “ball busting,” cage and rope bondage, straitjackets, and “sploshing,” were available upon request.

  Lady Sarah cut right to the chase. “I’m looking for a partner. A financier. I work five days a week and pull in two to four sessions a day. If you help me, you could earn a thousand dollars a week or more.”

  I was in.

  Being an Outlaw was expensive—weekly club dues, tombstone taxes every time a brother passed (and sometimes there were multiple deaths in one month), national dues, contributions to the legal defense fund, event fees (which only increased for brothers if they invited their old ladies).

  The role of Lady Sarah’s muscle required little effort. She serviced influential people—Bosses, CEOs, high-ranking mobsters, lawyers, government officials: “wonderfully brilliant men” who sometimes needed reminders that she was in charge. Being a dominatrix was risky business; Lady Sarah had information on people that made her a killing target.

  “It’s exhausting always being the leader,” Lady Sarah explained domme-submissive psychology to me. “These men come to me to escape from life’s stresses. The theatrical fantasies of sexual surrender offer a release, a vacation, from always being in charge.” Her beautiful brown eyes sparkled. “It’s a hell of a lot cheaper than going to the Bahamas, I promise you.”

  But not all of her clients suffered from an imbalance in power. Some were just kinky regular folk—blue-collar workers, cabdrivers, bikers who needed to feel desired for a few hours.

  “She’s stealing my clients,” Lady Sarah complained one day about her rival, Midnight High, a veteran domme whose dungeon was just a few blocks away.

  I made an agreement with the rival, borrowing my favorite line from The Godfather: “Either you put your name on a noncompete contract, or I’ll put your brains on it.”

  I never had to say much; mine were subtle threats. Midnight High moved on.

  * * *

  I recruited alone, scoured the fashion shows for prospects. My goal was to lure five or six girls at a time into the escort business and offer each some reprieve from the murky world of pole dancing. Rapport was an art; I knew the girls had handlers.

  Broads paraded around me in tight-cropped tops, fitted jeans, spiked heels, their doll-like eyes with fake-glued lashes blinking in the harsh lights. Some looked chiseled, like carved stone.

  Most strippers had been numbed to the bait—squatty bald men in white muscle shirts who tossed small bills and coins onto their stage. I looked for the moths, the fragile, soft creatures that clung to the walls, waited near the exits, and slowly, slowly flew toward the flame.

  I began in the rural areas, where dancers earned less than $2 a move. I studied them as if they were rare finds that required modest refurbishing. Dressed in full Outlaw regalia, I wanted to appear like dipped gold.

  A few fluttered around me. One was a pixie waif with dry blond hair, drugged-out eyes. I shooed her away: “When I want you to come over, I’ll ask.”

  Soon, another came, and another, until I’d collected six or seven rescues, the score reminding me of the time when, in the seventh grade, while my classmates glued pretty butterflies onto presentation boards, I cut up a cockroach into six different parts and stuck the bits and pieces onto cardboard: wings, legs, an eye, a head. I told the teacher, “The wind blew apart their insides.” The teacher smiled at me, patted me on the head, and praised my “resourcefulness,” my ability to make something out of nothing.

  * * *

  Some mornings, instead of recruiting, I rode my bike through deserted alleys, crushed littered cans with my tires and marveled at the unique plate-glass towers, rows and rows of red-brick buildings and ghostly steel spires that jutted into the skyline, claiming “The White City” as its own among the clouds. Marked by resilience and strength, the progressive structures rose from the ashes of the Great Chicago Fire, determined to “not be derivative, not follow the status quo.”1 Buildings on the outskirts, Beware!

  Riding alone was Zen-like; the city absorbed into my skin. I became fully aware of just being in the moment. And with my senses heightened, I could taste the sky, see the color of the wind, feel the vibration of the bike as if it were my very life beat. The Outlaws MC insignia looked like it was sewn onto the tank. My beloved Chicago skyline, including the Sears Tower, covered one chrome fender, and on the front shined the one-percenter diamond.

  Chinatown, with its neon signs, ornate pagodas, and gold-painted buildings, offered a kind of tenderloin. Dragon kites blew from bank windows. Red paper lanterns rattled in the wind. The whole town felt thin, like something make-believe, a child’s garish painting.

  Pete’s Bike

  I rode to a massage parlor. A flurry of dainty, porcelain-like broads stripped my boots, soaked my feet, placed wet cuc
umbers over my eyelids as I tumbled into a dark hole, a hole I alone inhabited. Here, the stress of acting human fell away. When I emerged an hour later, transformed, jellylike, I rode to the campus of College of DuPage, where I audited philosophy classes on negotiating and logic. One required text was Alice in Wonderland. I devoured the book, highlighted passages, memorized whole sections, admired the White Rabbit, and when the final exam came and contained only one question, “Why?” I wrote, “Why Not?”

  By the time I arrived at “work” in the late afternoon, my chapter was just starting to wake. No brothers guessed my other life; as far as they knew, I slept in, exhausted from the night before.

  * * *

  But I was never refreshed enough to deal with Das Jew, a fixture in the Outlaw biker community, an old-timer who quit the club once the bombings started in 1995 and later rejoined when he deemed it “safe” to be an Outlaw again. He reminded me of the cop who craved the title but feared the role and hid instead in his local elementary school as a D.A.R.E. officer, hoping no one noticed.

  Das Jew worked at McCormick Place, a massive convention center near the shore of Lake Michigan and just a few kilometers south of downtown Chicago. He was useful, employed a lot of bikers and mob guys in various jobs with the teamsters, riggers, and Decorators Union, doing ghost payrolls, forklift work, and other jobs.

  “He’s here again?” I said.

  Bastardo grinned. “Fucking mama’s boy.”

  “I need to talk to you.” Das Jew’s large-framed glasses slipped down the bridge of his nose. He followed me into my office, his boots clicking on the hickory floor. He blinked at me, his eyes wet and overbright. It was truly beyond me that his ol’ lady was a bank vice president. I had no clue why Das Jew was in my office, except maybe to kiss my ass.

  “What’s up?” It was like my whole body was braced for his impact.

  “It’s my mom.” His voice caught, and then it was all over. He dissolved into sobs, convulsive, inconsolable crying.

  I shut my office door. It was far too early in the afternoon for me to practice compassion, but Das Jew was never going to leave if I didn’t at least pretend to care.