The Last Chicago Boss

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The Last Chicago Boss Page 6

by Kerrie Droban


  “Don’t move from that spot,” I said.

  “Why aren’t you helping?” Frank stacked two crates at her feet.

  “My ol’ man told me to wait right here.”

  He looked amused. “Is that right? Who’s your ol’ man?”

  “Big Pete.”

  “Jesse!”

  We huddled inside the cab of Frank’s semi. Rain started to fall. Big plops smacked the windshield. Debbie didn’t move, not even when rain leaked through slats in the roof and soaked through the newspapers she sat on.

  “She’s got to help.” Frank said. “It’s how this works. It’s what broads do.”

  “Of course.” I knew that, but I hated to watch as Debbie lifted a crate, struggled a bit with the weight, smiled weakly at me and stepped into the rain. This life claimed casualties.

  After several more deliveries, Frank proposed I hit up my COC to buy cases of Biker Coolant, promising me a percentage of the profit. We didn’t know each other well, but when the head of the Outlaws asks to partner in business … “No” is not an answer. The power Frank yielded was so striking that even a federal judge would later marvel at the “influences of evil one person could have over another.”

  But when Frank didn’t pay up after the first large delivery of Biker Coolant, I debated whether to mention my missing percentage. No chance he simply “forgot” our agreement. If I let the debt go, I would establish a disastrous precedent. Frank might always “forget,” and eventually I would be free labor.

  “Jesse?”

  We sat in the cab after another delivery. A ball formed in the pit of my stomach, my hands clammy on the steering wheel.

  “You have a balance due.” It felt so good to get it out. Like releasing a fart.

  Frank raised an eyebrow. He blew out a sigh. I held my breath, not sure what to expect: denial, a punch to the jaw, return to probate status?

  He nodded, looked away. “How much?”

  I scribbled the figure on a piece of paper and slid it over the dashboard.

  “I was wondering if you would have the balls to confront me.” He glanced at the number.

  I didn’t say anything. I actually didn’t know what to say. I didn’t think of my demand as risky or bold or even stupid. After all, I’d earned the percentage. I was only asking for what was fair.

  “You’re a little different than most, aren’t you?” Frank laughed.

  I was. I really was. In fact, a guy like me only comes along every 150 years.

  “I suppose you want the money?”

  “It’s a substantial figure,” I said.

  Frank nodded. No apology, no explanation. Instead, he offered to pay up at the National in a week.

  I would have to drive my car. There was no way I was going to haul that much money in bills on my bike. We met in an abandoned hothouse with no electricity. Chipped paint peeled off the walls, nails were scattered on the floor, and broken windows gaped open to an alley. Frank handed me a wad of cash. “Want me to count it?”

  “Don’t insult me.”

  He grinned. “We’re good?”

  I tucked the money into my front waistband. “Yeah, we’re good.”

  “You staying?”

  “That wouldn’t be smart.”

  We stood in the dark in awkward silence for a few minutes, and then Frank said, “That Joliet chapter—it’s a real shit hole.”

  I shrugged, “Yeah, well…”

  “I’m heading to Thailand soon, but when I get back you should leave.”

  “Leave?”

  “Get the fuck out of there. Go to Chicago North Side. It only has six members, and Greek, their Boss, needs a complete overhaul.”

  Frank was either promoting me or hoping to create distance between us, not wanting the whole money issue to become a source of embarrassment or curtail future business dealings.

  * * *

  “Church starts at eight in the morning,” Frank said. “Good luck.”

  But I didn’t accept the promotion immediately. Instead I observed (for six months) as treasurer, watching the flow of money in and out of the chapter. I arrived at seven in the morning sharp for Church, to a dark and empty clubhouse. I had a set of keys, and ran my hand along the paint-chipped wall looking for a light switch. Frigid water soaked my boots. A white fuzz bathed the room. Pipes leaked; water stained the ceiling in a yellow-brown circle. A raw-sewage smell lingered in the air. A Confederate flag was draped over the bathroom door. A toilet had overflowed, and I half wondered if I wasn’t standing in urine. At eight-fifteen, eight-twenty, eight-thirty, members strolled in, ready for Church.

  Some called to let me know they were running late. “What makes you so special that we should all wait for you?”

  “Can you believe this shit?” I complained to Debbie. “It’s like the ‘Home for Wayward Boys.’”

  She looked worried.

  “A chapter is a business,” I said the following week at Church. The six members had all shown up, but some of them had fallen asleep.

  “A house has to be self-sufficient. Club dues can’t go to pay for this shit.” I pointed to the cracked concrete walls and exposed electrical cords. I proposed a plan: “If each chapter pays a hundred dollars a month, the chapter is going to lose money. We need to charge twenty-five dollars weekly. With fifty-two weeks in the year, that’s an extra hundred dollars a year.”

  Some noticed the subtle change: I eliminated all balances, started the chapter at zero, and required all officers to pay dues.

  “You’re good at this,” Greek said as he rode with me to Church one morning. “We actually have more money than we’ve ever had.”

  “Maybe you should run for Boss,” a brother said as he pulled me aside one night.

  “Elections” are always over before they even happen. I agreed to “run” for the position of Boss, but only after I first informed Greek.

  “Would it be okay if I nominated you?” Greek stared at his hands. “You know I never wanted to be Boss in the first place. Do you have a plan to fix this mess?”

  “We’re going to go back to having fun,” I said. “And no one better be late.”

  Or there would be consequences: $100 fines, black eyes, a probate vest.

  But loyal recruits proved to be difficult to find: Being a one-percenter wasn’t a title, it was a lifestyle, a weird rescue from the mundane. Most recruits were either gangbangers (the good ones were either dead or in prison by the time they were thirty-five) or “ham-and-eggers”—unskilled and uneducated, with no social or economic credentials beyond a colorful criminal record.

  I subjected probates to tests:

  “We need eight-ounce plastic cups for the party.” Black Head led the charge. He scurried off to fulfill the order and returned with a plastic bag filled with sixteen-ounce cups.

  “That’s not what I ordered.” I shook my head. “These are going to cost the chapter money.”

  Black Head didn’t understand.

  “If you pour beer into sixteen-ounce cups you’re going to lose some profit.” I slowed down my words and tried again with another brother, Brutal. “We need A&W Root Beer for the party.”

  He returned with Mug Root Beer. Now I was really pissed off.

  “What’s the big deal?” Brutal asked.

  “The big deal”—my whole body tensed—“is that I asked for A&W. If you can’t follow simple directions…”

  I held meetings about following directions and arranged meetings about meetings and organized committees to supervise the meetings.

  “I’m telling you, it’s like Who’s On First,” I confided to Debbie later.

  * * *

  Two months after I became Boss, my Regional Boss presented Debbie with her “Property of” vest. Most ol’ ladies received theirs in six months or more, but Debbie earned hers early and, though the production was unceremonious, it elevated her status; she was now part of a family, not just a civilian playing dress-up.

  “Anyone can wear a wedding ring;
not anyone can get a Property vest,” she said as she modeled for the ol’ ladies.

  “I couldn’t do it. I’d be too paranoid.” One passaround shook her head. “Always on the lookout for violence, Feds, crime. You’re a moving target.”

  “You’re an important person’s wife now.” Gina laughed.

  With that came responsibility and a few do’s and don’ts:

  The property vest is not a costume;

  The Feds know all;

  Assume you are under surveillance;

  Watch the rearview mirror;

  Study people as if they will harm you;

  And, if you suspect you’re being followed, drive in a circle—make three right turns,

  and if by the third right the car is still there, get the license plate and lose the tail.

  I taught her other things, too, simple commonsense things, like never leave the porch light on at night.

  “That just signals I’m not home,” I told her. “Turn it on during the day and it will confuse people.”

  “And steer clear of vans that have their windows rolled down. Chances are there are guns pointing out.”

  She carried a knife.

  7

  WISEGUYS

  I was like a musician: I crossed all genres …

  —BIG PETE

  The Outlaws shared a symbiotic relationship with the Chicago Outfit (aka “Mafia”). Both organizations operated as shadow governments controlling legitimate businesses in completely unlawful ways and commanding an army of psychopathic killers. Both syndicates trained soldiers and bosses to single-mindedly focus—twenty-four hours a day, seven days a week—on “how to make money for the Family.” The oath was a lifetime contract; betrayal resulted in death (or prison, and then death). Any crime had to be cleared first through the Outfit.1 The Chicago Heights and Cicero crews used the Outlaws mostly to do their thug work, but there were also “earners”2 among them. Like me.

  “How about we put video gambling machines in all the clubhouses?” Chef Corleone said as he slid across from me one day, cigar in mouth. He dressed well3: silk gray slacks, shiny shoes, nice little shirt, moderate jewelry. I had a table off the bar at the Capri, Chef’s “fine dining” establishment in upscale Melrose Park.

  This exchange occurred in 1995, and the Outlaws already had a reputation as warmongers and murderous rogues known to detonate whole blocks of buildings, “virtually disintegrate” parked cars, gun down rival gangsters, and critically maim curious citizens.

  The battles for enemy turf involved street rumbles, fistfights, stabbings, shoot-outs, and bombings. At first, the wars were private affairs, club business handled in dark places away from public scrutiny. But the bombings of 1995, the “bang, bang, bang” that sounded at first like backfire from a Harley-Davidson, signaled the start of something gone “deeply awry in the underground world of motorcycle gangs.”

  We were officially at war with the Hells Angels and their club supporters.

  Chef tapped his thick finger on the table. “Think about it.” I had taken a giant pay cut to become an Outlaw, and wasn’t wild about sharing profits. If I was going to do this gambling thing, it was going to be a solo act, on my terms.

  * * *

  Back in the day, when the Feds arrested loan sharks, bookmakers, and small-time operators running illegal card and dice games, their sentences were suspended or they did jail time of a year or so at most. The Racketeer Influenced and Corrupt Organizations Act (RICO) and Title III electronic surveillance provisions implemented in the 1970s dramatically changed this.

  RICO was aimed at a systematic pattern of criminal activity. If any two criminal acts—murder, extortion, loan-sharking, and so on—could be linked to a particular family or organization, it allowed the government (in theory) to target members as a criminal enterprise, with far more severe penalties.

  Mr. Happy, a self-prescribed “fence” for the Chicago Outfit’s Cicero crew, invited me one day to “check out his shop,” after first saying, “Heard you’re putting machines in your clubhouses.”

  “I haven’t decided anything yet.”

  The Feds weren’t interested in run-of-the-mill gambling cases. They wanted the top guys, the movers and shakers.

  Still, several days later, I accepted Mr. Happy’s invitation to visit his cramped “pawnshop” (aka Goldberg Jewelers) in Cicero, an area a federal judge once dubbed the “epicenter of organized crime.” Mr. Happy sold “a little piece of everything”: cigarettes, electronics, and various goods from robberies of jewelry stores and homes committed by the criminal enterprise operating in and around Cicero.

  Behind bulletproof glass, Mr. Happy placed scales to measure precious jewels, acid trays to test gold, machines to remove serial numbers from shotguns and grenades. The Outfit owned the adjacent empty building and stocked it full with piles of cash. It was the same nondescript building I had stared at as a kid when my uncle rented a room across the street at the Shamrock Inn, a three-story motel famous for card games.

  After partying all night, I dragged myself into Mr. Happy’s “pawnshop” through the back gate, dressed in sweatpants and baggy shirt, my hair tangled. I stank of smoke. Wiseguys milled around me, studying me cautiously as Mr. Happy prattled on about the Outfit’s “interests” in loan-sharking, gambling, pornography, liquor service to restaurants and nightclubs, and produce and meat wholesale distribution.

  “Some business deals,” he cautioned, “required La Cosa Nostra’s (LCN’s)4 approval.”

  “You sweep the place, right?”

  I became increasingly uneasy with his banter. The government had bugs, zoom lenses, video cameras, surveillance equipment. And right now, given how disheveled and wasted I was, I probably looked like a psychopathic killer.

  “It’s fucking alarmed.” Mr. Happy waved me over to a window and pulled out a pair of binoculars. “Check this out.” He zeroed in on a white van parked across the street.

  “The Feds sit out there because they can’t get in here,” he said.

  * * *

  “Who are you talking to about machines?” Chef asked me the next week.

  Now I was really pissed. “Look, I haven’t agreed to do this.”

  * * *

  Two days later, I visited Mr. Happy’s shop again, saying I was in the market for rings. (I purchased a grenade ashtray instead.) A line formed behind the bulletproof glass. A man wrapped in rags tried to sell tools he’d probably stolen from a repair truck.

  Mr. Happy nodded. “Yeah, okay.” But before he showed me his inventory, he insisted “some guy” wanted to meet me.

  “What guy?”

  Mr. Happy glanced at his watch.

  The room grew suddenly quiet, too quiet. My exit shrunk to a small slit in the concrete. My head clouded, the way it did when my claustrophobia took hold.

  “He’ll be here in five minutes.”

  “The Large Guy” appeared in the doorway, backlit by street globes, looking every bit a mobster; pinstripes, chunky cuff links, felt flat cap, and leather gloves. He was wide like me, with fire-tipped hair, a clean-shaven chin, and droopy brown eyes. I expected to “walk and talk”—take mindless trips around the block, up and down alleys, left turns, sharp rights, past the Feds’ white van with its windows zipped down, recording every hushed tone.

  But instead, we spoke freely in the back room, surrounded by stacks of crates.

  “Things happen a certain way around here,” the Large Guy began. “Chef … He’s just a cook, you know?”

  Yeah okay.

  * * *

  My paranoia increased. Clusters of precious jewels lay exposed in a basket in the front entrance of my home so thieves would have something quick to snatch. At parties I ordered random strip searches, because wands and transmitters could only detect wires that were actually switched on. I worried about phones and never answered unknown numbers (the calls were either from telemarketers or Feds). I never answered doorbells, either (probably delivery guys—the kind that wore explosiv
es).

  “Are you sure it’s safe to talk in here?” I asked Mr. Happy again and again.

  * * *

  I consulted Audrey, a tarot reader a few blocks from my home.

  “I’m worried people are talking about me,” I told her.

  Audrey flipped over the hourglass and closed her blue-eye-shadowed lids. Loose curls draped her shoulders. Her body disappeared inside a flowery tent dress as she shuffled cards and formed three even piles on the table.

  “Left, middle, or right,” she took my hands in hers and whispered a prayer.

  “Middle,” I said.

  She spread the cards in a Celtic cross and flipped over the Devil and Fool.

  “That can’t be good,” I said.

  “Take an empty mayonnaise jar.” She stared at me intently. “Write the person’s name in white crayon on black crepe paper and put it into the jar and fill it with water.”

  Later that night I did exactly as Audrey instructed. I placed the jar on the windowsill and watched the paper turn to paste.

  * * *

  “What’s with the empty mayonnaise jar?” Debbie asked.

  “Jessica wants me to meet her new boyfriend.”

  “And you put a spell on him?”

  I probably should have. My daughter so rarely asked me to play Father.…

  I wanted to bring her something, a token of my gratitude, but what gift would a daughter want from a father who was mostly absent?

  “Thanks.” Jessica looked a little puzzled as I slid a small television across the restaurant table. I resisted the urge to tell her she could choose anything she wanted from an entire warehouse of electrical goods. She had her mother’s olive complexion. Sparkly hoop earrings dangled to her shoulders; she wore a plain white blouse and sensible wedge shoes.

  The boyfriend looked ready to bolt as he sat on the edge of a cracked foam cushion and ordered coffee. Tall and thin, with a whip ponytail down the small of his back, he extended a sweaty hand.

  “Good to meet you.” The veins in his arms formed little blue rivers beneath his skin.

  “What do you do for a living?”

  Jessica stared at the menu.

 

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