The Last Chicago Boss

by Kerrie Droban

  Where you been lately?

  There’s a new kid in town.…

  Johnny come lately, the new kid in town.…

  And on a dangerously cold January day with a windchill warning of thirty degrees below, I threw my card in the hat and became an official probationary member of the Outlaws (aka a probate). I was forty-three, and suddenly a Regional Boss’s kid.

  But, my lightning-speed alliance with a Regional Boss created dissension in the ranks. Bosses (especially Regional Bosses) did not sponsor recruits. No one needed to know my “fast pass” into the club was cocaine. Further complicating matters was the fact that Greased Lightning was from the South Side chapter and his bodyguard, Backlash, was from Joliet. The Outlaws huddled at “Church” to discuss the conflict. In the end, the regional vice president (who was also from Joliet) informed me, “I’m sending you to Joliet.”

  * * *

  As a probate, I expected exhausting weeks of guard duty and errand-boy orders reminiscent of my fraternity days. Instead, my introduction to indentured servitude was the annual Daytona Bike Week at Daytona Beach in Florida. Every Outlaw was required to attend; the event attracted a mixture of hard-core gangsters, leather-clad professionals, topless “beer girls,” aging rebels, and kids on crotch rockets. Bikes and people paraded down Main Street in Daytona Beach. Classic rock blasted into the hot wind.

  My first post was guard duty for a row of unattended bikes on a hot, dusty lot. Sun blasted my face. My eyes watered from the brightness. Only two hours in and I already had a raging headache. My legs cramped from standing. Random fingers clicked at me, the sound reverberating hollowly inside my head, too loud, and I suppressed the overwhelming urge to snap the clicker’s neck with my bare hands.

  “Who’s your daddy?” the voice boomed.

  His words landed like punches. I wanted to pummel him, react with a hard jab to the throat. He spit, and the glob landed near my boot.

  “I’m probating for the Outlaw Nation.”

  The muscles in his face relaxed. He uncurled his fist. He reeked of alcohol. I knew I had narrowly missed a beating.

  “Beer.” He shook his hot dog at me. I wasn’t built for speed. Out of breath and sweaty from effort, I returned with a large, filled paper cup and resumed my post. My lips cracked from sun and dehydration, I heard the call again: “Probate!” Again, I trotted off to fetch the asshole beer. Inside the air-conditioned bar, Outlaw bigwigs drank.

  A probate tending bar handed me a foamy mug. He had two black eyes. A welt puffed on the side of his head. Fresh blood oozed from his lip. Blisters formed on his nose. Another probate, being led through the crowd like a tethered cow, recited the name of each brother in the room. But the crowd had swelled to more than fifty.

  “What’s my name?” an Outlaw in the back of the room shouted at the probate. He hesitated—punch! He said the wrong name. Punch! He tried again. Punch! He threw up. Punch!

  A chorus started in the back of the bar, “Probate! Probate! Probate!” The bartender slid the mug to me. I knew if he stayed beyond midnight he would likely be human pulp by morning.

  When I could no longer feel my legs and my mind had started to take trips to the ocean and I could literally taste salt water sloshing down the back of my throat, I heard, “Peter Pan, come with us.”

  I expected more torture scenarios, but instead my sponsor ordered me to “stoke the bonfire.”

  “He’s throwing sticks into flames?” Gold Region Boss Milwaukee Jack1 lost his mind. He sneered at me. “I ought to take you to Milwaukee, show you what it’s really like to probate.”

  “If my dad orders me to go, I’ll go.”

  “Who’s your dad?”

  I threw out my sponsor’s name.

  “Regional Bosses are not supposed to have kids.” Jack marched off to confront my sponsor. I knew he wouldn’t give me up. After all, I supplied him with unlimited cocaine.

  Big guys clustered together. My size, for the first time, became an asset. Even patched large brothers gave me deference. One even offered me a tip: “When you get off guard duty in twelve hours, take your shoes off.” On my breaks I began to air my feet. Heaven. Just that small tip rejuvenated me.

  “What’s your name?” the voice boomed in my head.

  “Probating Outlaw, Chicago, North Side, Pete.”

  “Peter Pan.” He sneered. “What’s my name?”

  Well fuck, I forgot his name. I stood in a crowd of two hundred drunken Outlaws and spent the next hour trying to find out. I felt a little like the baby bird from P. D. Eastman’s book Are You My Mother?

  “I’m JD,” one of them said as he smacked me on the side of my head and grinned. I resisted the urge to smash him through the wall. Another patted his chest. “I’m Motherfucker.” I weaved in and out of sweaty bodies, searching for names that made sense that might relieve me from my inane search. But this was a test; they tossed me from brother to brother, mixed up their names, gave me false monikers until the room spun.

  “Enough! Get me a screwdriver,” a brother said, shoving me toward the bar.

  The bartender shook his head. “We’re out of orange juice.”

  I reported back the news.

  “So?” The brother shrugged. Off I went to the grocery store to buy orange juice. At least it was a chance to escape the heat.

  * * *

  The year I probated was the last year probates wore identifying markers on the back of their vests. Most, who looked at me from the front, dismissed me as a likely club supporter (and not a lowly probate) and left me alone. Still, I had my fair share of slave chores—fetching beer, lighting smokes, and supplying endless condoms and Rolaids to brothers in need. I carried a probate kit with at least three different kinds of toothpaste, toothpicks, tampons (in case someone bled out), rolling paper.

  “Peter Pan, got a toothpick?”

  I handed him my stash.

  “Got a round toothpick?”

  After that, I mastered disappearing. Big Butch helped.

  He always stuffed two Polish sausages in the side pockets of his vest.

  “Sometimes I get hungry when I ride,” he said with a shrug as wind blew little drops of ketchup down his chin and vest. The sausage wrapper stuck to his windshield.

  “We’re large,” Butch shouted through mouthfuls of onion and meat. “We’re good for manual labor.”

  Big guys had it easier.

  Still, no one called me “Big Pete”; instead I was nicknamed “Pete,” which sounded a bit like a cartoon character. (Personally, I liked the name “John Wayne,” but the serial killer John Wayne Gacy sullied the name for me.)

  “I really don’t like ‘Pete.’” I complained to Frank, whose real name was James Lee Wheeler.2

  “Peter James…” He thought about it a minute and then smiled. “I’m really Frank James. We used to have a brother in the club named Jesse James, but he’s dead. You can be my new ‘Jesse.’ We can be ‘Frank and Jesse, the James brothers’—you know like the Younger gang?”

  I could see that.

  The whole name thing reminded me of my fraternity days, when brothers prophetically called me King James.

  “Frank likes the big ones.” Butch grinned.

  “Big ones?”

  “Big guys. Like us.”

  “Big” was a title and a definition: “Big Butch”; “Big Mike”; “Big Pete.”

  * * *

  In my first month it seemed like every week a brother died. We rode miles to attend the funerals, sometimes two in one day; the cost alone—nearly $100 a person per funeral—was crushing (those chapters who didn’t show up were fined). To save money, I bunked in a shit hole with four guys stuffed to a room. We barely showered, slept, or even ate.

  We probates were like windup toys, climbing onto our bikes, zipping down expressways, sobering up for the services, barely remembering whose body was inside the casket, before mounting our bikes again and heading to another funeral. And another and another until finally the scenery blurred,
the cause of death—bike wrecks, diabetes, stabbings, shootings, overdoses—like a multiple choice, was just part of the cost of doing business.

  Debbie helped the probates—“but not too much,” she assured me. “I never wanted to enable them.” She hoped when they were promoted to patched Outlaws, they would remember “Debbie, Big Pete’s ol’ lady.”

  She elaborated, “It was important that I earned their respect.”

  She wanted them to remember she gave them garbage bags to transport trash to the Dumpsters. She cleaned toilets and mopped floors when probates suffered guard duty.

  “I did that. And I did a good job.”

  She wore a T-shirt with a printed message, “Ladies Love Outlaws.” Some salivated. But before anyone could paw her or ask her for beer refills, Debbie would replenish their cups or top off their water jugs. She carried extra forks in her pockets, “just in case an Outlaw asked for one, or dropped his, or used several to stab a hamburger off the stovetop.”

  “It’s survival,” Debbie said, before sharing with me the mantra seasoned ol’ ladies preached: “Make your ol’ man look good and no one will mess with you. Be ‘Pete’s ol’ lady, Property of Big Pete.’”

  “I feel like I’m back in school,” Debbie told everyone.

  “I went to school once.” Backlash’s ol’ lady, Gina, giggled.

  Debbie brightened, hopeful that maybe she had found some commonality with the broads after all.

  “What did you study?”

  “Prison.”

  Debbie had a genuinely pure soul, and I worried she might not fit in my world, but she felt she “finally belonged somewhere. Being here is what gets me through my life. My job is to serve. Everyone has the same responsibility. It isn’t confusing. I’m not weird, and if I can make it here, I can survive anywhere. I just have to remember the Outlaws are real people.”

  “We’re pigs.” Poison smacked Debbie’s ass. “You’re lovely. What’s your name?”

  “Big Pete Chicago North Side’s old lady.” She refilled his mug.

  “I like you. You’re lucky. I might not hurt you.”

  * * *

  One night the power shut off in the clubhouse, suddenly, inexplicably, and panic erupted. Lights, air, music, fans—all gone. Glass shattered, screams were muffled, chairs scraped back, toilets flushed. Bodies slammed into me. Some scrambled toward the exits, mowing down brothers in their stampede.

  In the pitch darkness, Debbie called out my name. “Pete? Pete?”

  The fear in her voice stopped me cold. This was my wife. This was suddenly real. I couldn’t protect her here. More important, concern for her safety could get me killed. This lack of control spun me into a kind of mad-slapped frenzy. But before I could reach her, the room flooded with light again, and with Backlash’s maniacal laughter.

  He clapped slowly, dramatically in the center of the room. Aftershock surrounded him. Broads shook, sniveled; fat tears wet their cheeks. Brothers scrambled to their feet, crunching on shards of broken glass. A crack split the wall mirror behind the bar. A brother grabbed a rag and dabbed his temple.

  Backlash cupped his hands to his mouth and said in an exaggerated announcer’s voice, “That was just a drill; I repeat, that was just a drill.” More laughter.

  Debbie sat on the edge of our couch, visibly shaken. Maybe for the first time, she grasped the Outlaws’ dangerous lifestyle. The club wasn’t just about partying, and her role in it wasn’t just about service. The specter of prison was real.

  “Backlash likes to fuck with the probates. The first thing the Feds do when they raid a place is shut off the power.” I wasn’t very good at being comforting, or protecting her. “I don’t think you should come with me to the clubhouse anymore.”

  She started to cry.

  “The only way I can keep you safe is to make sure you know nothing. The Feds will try to get to me through you,” I said. “Don’t even whisper my name.”

  “But I want to help. I serve a purpose.”

  “Get your tops off,” Backlash said as he pounded his fists on the counter the next day. A row of slobbering drunks chimed in, and soon a chorus of “Take it off, take it off” filled the space.

  Debbie froze in the melee of peeled T-shirts, ripped bras, and other stray clothing. My chest tightened. I resisted the urge to drag her out of there. She didn’t belong in this place, and I realized she was here because of me, because I chose to join the Outlaws. And that I couldn’t protect her.

  The broads writhed to the heavy pulse, kept beat to the wild claps. Some stripped to G-strings and recklessly buried Outlaws’ faces in their crotches.

  “You don’t have to participate,” Backlash’s ol’ lady told Debbie. “It’s your choice. You can decide how you want to be treated. If you want to be a drunk, a slob, a stupid cunt—”

  “I want to be Pete’s old lady.”

  “That’s a good start.” Gina laughed. “We women don’t matter anyway.”

  6

  DECONSTRUCTING CHARLIE

  You’re here to break down doors, not mix drinks.

  —BIG BUTCH

  Northside Clubhouse Crew. Left Back Row: Maurice, Das Jew, Big Butch, Rabbi, Stones. Front Row: Iron Mike, Bastardo, Big Pete, Chavez, Judas, Blockhead, Pots.

  On July 31, exactly six months and one week after I began probating, Frank tossed me an Outlaw top rocker and said, “Hope you know how to sew!”

  Cheers erupted from the crowd, followed by “Sew it on, sew it on, sew it on.” Shot glasses were raised; I was doused in Crown Royal. My eyes stung. Pride swelled inside me as I waved the top rocker like a flag. Outlaws bear-hugged me, backslapped me, and howled their congratulations. I had made it! I couldn’t fucking believe it. I was an Outlaw, part of a criminal organization. I grinned so wide my face hurt.

  Later, when the pace slowed, Frank gathered everyone in a huddle and said he had something special to read to me.

  “He’s quite the poet,” Butch whispered, leaning on me for balance.

  Frank raised his right hand, and I did the same. “Repeat after me,” he said, and recited his original Oath.1

  “I, Jesse, will show honor, loyalty, and brotherhood.” Repeat.

  “I will never dishonor the Outlaw Nation or all brothers present.”

  Repeat.

  “I will do my best to be a true Outlaw brother; I swear this to the Outlaw Nation and to all brothers present.”

  Repeat.

  I was tipsy, euphoric; the words tumbled out of my mouth. I raised my shot glass again and slammed back another Crown Royal.

  “This club will break your heart.” Frank’s tone sent a chill down my back.

  * * *

  The following week, Santa and the twenty-two members of his clean-and-sober club, the New Attitudes, who prospected with me, patched over in one breath, like a one-size-fits-all, though I had no idea why a group that strived to live “alcohol-and-drug-free” would possibly want to join the Outlaws. Unless, of course, they were masochists. That fit; it would sort of be like inviting Alcoholics Anonymous to a party fully stocked with booze.

  “At least they’ll have no excuses if they fuck up!” Butch laughed.

  True. Santa’s club accepted their patches with measured enthusiasm, like the last players chosen for flag football. In time, most gave in to temptation; only seven remained clean and sober.

  “They’re like elves.” Debbie slid across from Butch and me on a picnic bench and bit into a cheeseburger. Dusk cast our faces in shadow. “I don’t trust Santa.”

  “It doesn’t matter. I’m only going to use him.” I reduced people to mathematical equations so I could predict their next move. Santa was an algebra problem (indecisive + sneaky=untrustworthy=easily manipulated).

  Being an Outlaw was about respect.

  “You should have seen the boil they lanced off my balls last week.” Butch squeezed a glob of ketchup onto his bun. Debbie paled mid-chew, and slowly returned her half-eaten burger to her paper plate.


  “So much pus on the thing doctors had to bandage it up with a maxi pad.”

  Debbie left the table.

  “Where the fuck are they going?” Butch motioned to Santa and his New Attitudes/Outlaws/Elves.

  “We’re calling it a night, folks,” Santa plastered a smile to his face and waved. “It’s getting a little late for us.”

  Butch stopped chewing, looked at me, his mouth open and full of food, and said, “It’s only eight o’clock.”

  * * *

  I wanted to make it up to Debbie, involve her in something significant. I surprised her at work.

  “What are you doing here?” She smothered a smile and drew me into her suffocating cubicle. Several pushpins stabbed yellow sticky notes to the corkboard wall behind her computer; meeting reminders, to-do lists, appointments, a wedding photo with a Magic Markered black heart outlining our heads. She wore pressed white slacks, a stiff poplin blouse, and wedge heels. Her coworkers gawked: I collected her fully dressed as an Outlaw.

  “Thought you could use some fresh air.” I grinned.

  “I only get an hour for lunch.”

  “This might take a little longer. Frank needs our help … moving water.”

  * * *

  “Heard you once owned a soda pop company?” Frank pointed to the rows of skinny bottles with frosted tips stacked on the far wall of the bar. The labels read “Biker Coolant.”

  “Bottled water?”

  “Biker water.”

  He explained his monopoly: Monthly, he sold fifteen to twenty cases of his product, Biker Coolant, to clubhouses and support chapters in and around Chicago, and “made a killing.”

  As he spoke through his tangled salt-and-pepper beard, I conjured up other saleable products, like bottled oxygen, carbonated “vitamin liquid,” and funky clear plastic containers filled with tap water. (This was before Evian, Fiji, and Dasani appeared on the market.)

  “Are you in?”

  * * *

  Frank backed his semitrailer into the driveway of the Gary, Indiana clubhouse and unhitched the back flap. In an overgrown, grassy field, high wooden fence posts lined the property like an Old West cavalry.

  The crates, stacked in a back barn, resembled moonshine. Debbie climbed onto a pile of old newspapers.