The Last Chicago Boss

by Kerrie Droban

  “At least you can brag that you were the last to ride with Backlash. If you want to be a real Outlaw, Peter, you have to keep the brothers safe. Not that I’m saying you should kill anyone.” He chuckled. “Unless, of course, it’s on purpose and you need to make a point. But do just enough to remind them that you’re willing. And if it looks like you’re going to go to prison, run.”

  Note taken. I had some rules of my own, specifically how not to get killed.

  Pete’s Rule #1: Study fingers. If a guy wears four rings more than likely he is unarmed—he won’t be able to squeeze his finger through the pistol guard.

  Pete’s Rule #2: If a van has no lock on the outside, chances are good there are men positioned with Uzis on the inside, just waiting to fling open the door and fire.

  Pete’s Rule #3: Always hug the fast lane against the wall; if you ride in the middle, someone can pull up on either lane and gun you down.

  Pete’s Rule #4: Study the club you want to be most like and apply what you learn.

  I studied the Hells Angels.

  After all, the best defense is a good offense. The Hells Angels had only a nominal presence in Chicago, thanks to the Outlaws’ “hush hush” elimination campaign. If given the opportunity, as one Outlaw unabashedly reported to the press, Outlaws were “to take a shot … try to kill [the Hells Angel] … go to other clubhouses [and plot ways] to burn ’em up, blow ’em up, shoot ’em up. That’s just what hunters do.”

  The Hells Angels had no official clubhouses, only sporadic gatherings in local bars and restaurants downtown.

  “There’ve been sightings” of Hells Angels, the Outlaws told me one day, adding that I should “collect intel, conduct reconnaissance, count heads, check rockers, report new, emerging support clubs.” All with the underlying message: Kill, kill, kill.

  A recent federal raid that had resulted in eleven Outlaw arrests and ninety-nine prosecutions for crimes (twelve of them cold-blooded murders) served as a sobering reminder of the brutality the Outlaws could inflict on the Hells Angels.

  Three executions in particular, of Hells Angels roped to cinder blocks and thrown into a rock pit, lingered in my mind. As did the brutalization of two of their ol’ ladies, one shot in the head with a speargun, the other disemboweled, her body dragged from the back of a boat until it broke apart.

  * * *

  Little Tony held a gathering at the Paradise Inn. “Want to go to a party?” I asked Debbie. “We’ll blend in better as a couple.”

  We dressed the part in silence. Meeting Little Tony required a certain panache: a plain black Harley T-shirt, no indicia of the Loyal Order. I needed to be ordinary, someone Little Tony believed he could intimidate. We climbed onto our bikes. Debbie fixed her bandanna, nodded. Ready. We communicated almost telepathically. And corny as it sounds, I cherished those ordinary fleeting moments when the masks slipped off, when we felt safe even as a bomb ticked softly under our skin. We shot off like two anxious teens on prom night.

  We missed our turn, zoomed passed the Inn, drifted into the gore, and made a U-turn at a busy intersection. We crossed over four lanes of traffic. Horns honked. A few drivers flipped us off. When we finally arrived at the upscale sports bar, Little Tony greeted us warmly, slapped a beer in my hand, and introduced me to the handful of brothers. I nursed the beer, taking inventory, picking up details I could use: Tony had a sweaty grip, small scuff marks on his boots, a scratchy voice. He cleared his throat before he spoke. The television blared above him, flashing snippets of news clips: random shootings, bar brawls, a headshot of a heavily tattooed convict sentenced to life in prison, reports of a gang “at large” responsible for “wildings,” like life imitating art.

  Several Invaders swiveled behind Little Tony on stools. They stared at Debbie, cannibalized her body, her beautiful, pale face. She studied stuck coins in the floor, careful to avoid eye contact. She played a part: an ornamental decoy. I resisted the urge to smash their heads into the counter. Focus, focus, focus.

  Life was a series of chess moves; Little Tony and his supporters were mere pawns, and Debbie, my queen. Queens could be sacrificed if it meant the king’s next move was checkmate. The more I sipped, the more Tony ordered shots, and it dawned on me: This meet and greet was not my audition, it was his. This was his show-and-tell. I made him look good.

  “We could use a guy like you.” Little Tony ordered another beer.

  And I could use a guy like him.

  4

  THE LOYAL ORDER

  I was a mythological figure.

  —BIG PETE

  The National Coalition of Motorcyclists (NCOM), founded in 1986, formed as a nationwide umbrella organization designed to join motorcycle groups, clubs, and associations for the purpose of mutual exchange of information, legislative strategy, and solidarity. With over two thousand members, the organization served as a united group run by bikers for bikers, with an eighteen-member board of directors representing nine geographic regions across the United States.

  At NCOM conventions, patch-holder meetings opened with prayer and the Pledge of Allegiance (my hypocrisy only went so far). Awards presentations followed: trophies given for “oldest bike,” “fastest bike,” “best bike,” and even “world’s fastest probate1.”

  Attorneys and lobbyists spoke and reviewed bikers’ rights and explained relevant parts of the constitution. The goal of NCOM was to fight against biker discrimination through awareness and education. And those in attendance represented a strange amalgamation of one-percenter2 and square; Outlaws, Bandidos, and Sons of Silence shared space with Free Masons, Leathernecks, Christian Unity Bikers, Bikers for Christ, and Soldiers for Jesus. Amidst raucous applause, we received “police harassment cards” to help us document patterns of abuse (P.S.: These never worked).

  “If you get arrested,” an attorney took the podium, “you’ll want to give the department this.” He flashed another card and read: “I [insert name] give [insert name] power of attorney to collect my shit and take possession of my bike, which is being held at [insert location].” (P.S.: total bullshit).

  We learned about the First Amendment, freedom of speech and assembly.

  “When you fly your patch, that is a form of speech,” the lawyer continued. “When you get together at a meeting like this you are exercising your right to assemble.” A few people clapped.

  “You are also exercising that right when you go to a poker run or a rally or a fairground.” More applause.

  “We have done nothing wrong,” a patched member said as he pounded his fist on the podium. “But everywhere we go, we are persecuted. People are afraid of us. They say we carry weapons. How many of you are packing today?”

  He raised his hand. No one in the audience joined in.

  “I am,” he shouted, and raised a copy of the Bible high over his head.

  The crowd was on its feet, whooping, clapping. Some hollered “Amen,” and another added, “We are armed with the constitution.”

  * * *

  That night, I replayed footage from my favorite televangelist, Jim Bakker. I studied his perpetually sweaty face and marveled at his tearful delivery at the podium, the amazing passion in his voice as he rallied an audience of thousands. He used no notes, no prompter, and took no breaks. He cast a spell. I practiced dramatic pauses in the dark of my bedroom as parts of his famous speeches raced through my head.

  * * *

  And so when an Outlaw, Rider, approached me about a “little problem” he needed “handled,” I was more than willing to oblige.

  “It involves the Rebel Knights.” The club’s members were mostly cops. Rider and I met in a local bar, grabbed a cramped booth in the back, and ordered drinks. “The fuckers are trying to form a confederation of clubs, a small army of allies. If they succeed they will control all of Chicago.” He swallowed his beer and said, “We have to do it first.”

  My body tingled at the very prospect of power and control. I appreciated how he included me in his “we.”

>   “The problem”—Rider wiped the back of his mouth with his hand—“is that we have to be discreet, stealthlike—we can’t make it look like the Outlaws are in charge. I mean we’re not fucking bullies, right?” He let out a belly laugh. Sweat slid down the side of his cheek. Hell no. He leaned in close, narrowed his gaze, I could tell he was going to ask me something important.

  “The Outlaws need a chairman—you.” He pointed his finger at my chest and ordered another beer. He could barely sit still. “We need you to appear neutral. You’re a Loyal Order. If you’re in charge, you can convey the message to the other clubs that they are either going to support the Outlaws or they’re not going to exist.”

  That sounded reasonable enough.

  Rider’s plan was brilliant—not the Outlaw part, but the me-as-chairman part. As the designated leader of the confederation of clubs, I would gain instant credibility with the Outlaws while also converting and recruiting a city of loyal supporters who would ultimately pledge their allegiance to me.

  It was my way in.

  “We would be in charge, only not in charge because you would be in charge,” Rider repeated.

  I would be in charge, all right … of the whole fucking city.

  My COC—Confederation of Clubs—would be like a mini United States, an extension of NCOM.

  * * *

  I orchestrated the first meeting at the Moose Lodge and, in the spirit of NCOM, invited a virtual “Who’s Who” of motorcycle clubs in the Chicagoland area, including the DC Eagles, Fugarwe Tribe, Brothers Rising, Rebel Knights, the Outlaws, the Hells Angels, and Mextecas, even black and Polish clubs like the Hell’s Lovers, Sokol Riders, and Legacy made the list. The rules (which I wrote) permitted each club to send its Boss and two patched members to the meeting. The goal: unification. The clubs were meant to meet once a month to fight discrimination against patch-holders.

  “They’re arriving.” The Outlaw named Jaws peered into the street, the parking lot already overrun with Outlaws. By this time the club had left NCOM (citing “security concerns”).

  “No one gets frisked,” I reminded him.

  “What if they’re packing?”

  “No one gets frisked.” I hoped to convey an atmosphere of mutual trust.

  But within minutes of the respective Bosses convening in the Moose Lodge, conflict erupted.

  “Rebel Knights have cops in their club,” a DC Eagle said, looking like a racehorse ready to charge the starting gate. He refused to sit at a table with the Rebel Knights’ Boss—a sergeant who headed the organized crime unit of the Chicago Police Department. The DC Eagle paced, snorted, looked like he was ready to bolt.

  Little Tony arrived with an entourage of two; his eyes bugged when he saw me dressed as a Loyal Order with an Outlaw support patch. He hesitated in front of me, shook his head. No one mingled. No one veered far from his own club. Everyone stood ready to put a bullet in his rival.

  “This is going well,” Jaws said under his breath. After a few more minutes of tense silence, the National Boss of the DC Eagles stepped forward to lead the meeting.

  “Get the fuck back,” the Outlaw Poison said, and slammed the Eagle’s head into a glass sliding door; a loud crack resounded. And the scene unfolded like a movie montage of my own re-creation: rival biker gangs squaring off, neck veins bulging, eyes popping with rage. I envisioned the cameras slowly circling the room, zooming in on everyone’s face, everyone’s back.

  Then Cal, the director (some neutral peacemaker) yelled, “Cut!” No one moved. Most clubs subscribed to an “all on one” philosophy; fight rules were memorialized in club charters, penned as bylaws: “When one fights, we all fight.” Fists flew reflexively. Assault “victims” didn’t exist; offenders (all of us gangsters) expected to fight. In fact, under my direction the scene would have gone something like this: thrashing bodies, fists and boots to skulls, and, in the end, a Buck knife jammed into the losing offender’s throat.

  Blood sprayed across the tiles. A speck stained the shirt of Vito, an old gangster who worked as a spy for the Creative Underground. The DC Eagles’ Boss, doubled over, moaned, held his nose; it began to swell and bruise.

  Calmly, Vito walked behind the bar, wet a towel, and dabbed at the spatter on his shirt.

  Sirens ripped into the night. Shit, my first meeting and we were all going to jail.

  “Better mop that up.” Vito tossed the towel to the DC Eagle.

  “Got a place to hide?” I asked. Jaws ushered me toward the back of the room.

  Minutes later, all of us had squeezed into a tiny crawl space behind the stage on the second floor, united briefly against a common enemy: the cops. Hells Angels mashed against Outlaws; Rebel Knights pressed shoulder to shoulder with Hells Angels. DC Eagles shared space with Shines. Guns and knives cut into our waistbands. I gulped dry air like a guppy in a shallow fish tank. Bodies were too close. This wasn’t at all how I envisioned my COC. The DC Eagle with the cracked nose turned a slight shade of purple, and my thoughts became consumed with the blood on the floor.

  Little Tony’s face pressed so close to mine we both narrowed our gaze to a bug wedged into the grout as we listened to footsteps below us, chairs scraping, sirens, and loud commands.

  “We should do this again soon,” Jaws said.

  I planned on it.

  But the second meeting was held at a different Moose Lodge, so that I could keep everyone separated. Still, the Hells Angels refused to show and the DC Eagles returned without their Boss. Nine other clubs—Low Lyfz, Madmen, Fugarwe Tribe, Wicked Saints, The Brothers, Sokol Riders, Arm, New Attitude, Death Mauraders, Sojourners—also came. At the third meeting I held mock elections, became chairman of the board, and filled the seats of vice chairman, treasurer, and secretary with my closest friends.

  And, I nominated the first broad to an official position—Yo Adrienne who’d serve as corresponding secretary in charge of minutes.

  Jaws on his bike

  “You can’t do that,” some Outlaws protested.

  “The COC is about equality,” I preached. “Just because we wear patches doesn’t mean we have to act like assholes.”

  In time, meetings moved to the South Side clubhouse after the COC’s $5,000 donation to Mooseheart went unacknowledged.

  My real challenge came when I decided to probate for the Outlaws. I needed an edge—criminal “bona fides” to help me accomplish my goal: control of Chicago. And staying a Loyal Order wasn’t going to get me there.

  “You don’t think that’s going to be a conflict?” Jaws asked.

  “What’s the problem?”

  “Aren’t you supposed to be neutral?”

  “Yeah.”

  “Don’t the Outlaws discriminate against—”

  “Compartmentalization,” I cut him off. “Acting. I can play two roles.”

  5

  ON THE ISLAND OF MISFIT TOYS

  The man at the top of the mountain didn’t fall there.

  —BIG PETE

  Probating reminded me of college and my freshman year, when I pledged the TKE (Tau Kappa Epsilon) fraternity, referred to by some as “an all-male secret society.” I solicited so many members that TKE headquarters in Indianapolis invited me to apply to be their national recruiter. Though the fraternal structure held some fascination because it involved calculated manipulation—prospects, sponsors, hazing, loyalty tests, club dues, and brotherhood—I was really more enthralled with organized crime. (In fact, had I not decided to become a gangster, I would most definitely have been a television evangelist.… Maybe in the end they’re the same thing?)

  Greased Lightning sat near the bar, his legs dangling several inches from the floor. Backlash pulled Debbie close, winked at me, and said, “You’re a good ol’ lady. You make Peter shine.”

  I could tell Debbie was nervous; she came from corporate America, managed an IT department, rooms and rooms of button-down, pasty-faced men doing the jobs they were trained to do, never asking why, just working, working until the fuz
zy white glow above their cubicles dimmed long after the day disappeared. Maybe Debbie felt alive here, in this world that existed Outside: Out (of the) Law, hence Outlaws. Broads in this world had defined roles, scripts, costumes, and understudies. They wore “Property of” vests, filled orders for Bosses and brothers, and stayed mostly marginal, mostly ornamental.

  “There’s no pressure here to be … anything,” Debbie said. She found relief in invisibility. “Women need to feel safe,” she enlightened me later. “That’s it. That’s our big secret.”

  Still, I debated whether to leave the safety of the Loyal Order for the danger of the Outlaws.

  “You’ve always wanted to be a part of something that mattered.” Debbie insisted the transfer to a “real biker gang” would be a personal challenge for her as well.

  “I want this group of misogynists to treat me like a human being, to respect me and refer to me by name. These men who hate women will not hate me. I’ll be the best ol’ lady the Outlaws have ever seen.” She smiled. “My whole purpose will be to make you look good.”

  That sounded reasonable.

  I studied the room of scantily clad broads serving up shot glasses of Crown Royal to drunks at the bar. In a corner, a brother dropped his pants to his ankles and spread his legs wide. A blond head bobbed between them. A skinny broad with hollow eyes danced provocatively on a makeshift stage. Outlaws whooped and clapped, their laughter resounding like tin in my ears.

  I may have been the “new kid in town,” but I made sure I would not go unnoticed. I headed to the jukebox, flipped through Southern rock tunes, Lynyrd Skynyrd, Guns N’ Roses, AC/DC, the Eagles. I dropped in my coins, and the lyrics resonated.…