Bartender with Benefits

by Mickey Miller

  I owned the top floor of the first brand new, ultra-modern high-rise apartment that had been erected during the South Loop’s redevelopment. I could have had another much cheaper spot, but this one was important. The luxury surrounding me fit with the history of the site. While the view and scenery might have changed, the power hadn’t. My most infamous great, great, a few times removed cousin, Al Capone, once ruled Chicago with a tommy gun and grit from this very location, back when it had been the Lexington Hotel. Now, it was my turn. Power and dominion over the people were in my blood, an inheritance passed through my bloodline until the mantle rested upon my shoulders.

  At one point, I might have thought I could change my destiny. That idea had been short lived. What else was I supposed to be when death and ruthlessness lived in my very DNA? A middle school teacher? A leopard couldn’t change his spots, and a mobster couldn’t alter his future. I lived for the family, and I’d die for them. Doubtlessly sooner rather than later. Once I’d been promoted to Boss, every day my eyes opened was a gift. Every single man who had been at the helm of the Chicago Outfit died, rarely of natural causes.

  Maybe that was why I gravitated toward Kelly. She knew me before the power and the wealth.

  If only her family was from my ancestors’ boot-shaped European country instead of the Emerald Isle.

  Sal’s footsteps echoed on the marble floor as he rounded a corner. I recognized his heavy tread from the years he spent guarding Dad. It had only been a year since Dad passed, and a year since Sal’s fealty passed to me, though I knew he was loyal to the core. Of all the men now under my command, he was one of the only soldiers I didn’t doubt.

  “I’m surprised you’re out of the den,” I said when I caught sight of Sal’s reflection in the glass. He was past forty, but still rock solid. His shoulders broad, arms bulging with muscles. He stood behind me with his feet braced. He was ex-military, and even after ten years out of the service, he still maintained the demeanor.

  One of the four bedrooms the condo sported had been turned into a high-tech security outpost. Sal lived with me, while Luca rotated with other guards. Right now, Denny was manning the video feed staking out every entry and exit point in the building, while a scanner monitored police chatter. Sal might be my confidant, but he wasn’t big on socializing.

  “There’s something big going on with the Paddy’s,” he quipped.

  The tension I’d felt for the past week returned. The last time had been right before Dad died. He’d been another casualty of the seven-year curse. No matter how good of a boss the Outfit appointed, none of them made it to that lucky seven-year mark. If I wanted to see my thirtieth birthday, things would have to change. Whatever was in the wind would be bad. For the family, for the Irish, for Kelly, and for me.

  My fists balled in my pockets. I kept my voice neutral, not allowing Sal to see how the news bothered me. “Am I going to need a drink to hear this?”

  “It wouldn’t hurt, Boss.”

  I pivoted on my feet, walking to the wet bar which separated the living room from the den. “That sounds as if the city is going to hell in a handbasket.”

  Pulling the stopper on a bottle of scotch, I swigged a slosh of Macallan into a snifter. The same distillery that Kelly had served me, but a different vintage. Why did everything circle back to her?

  Dropping into the depths of a black leather occasional chair which faced the windows, I swirled the liquor and then took a sip. I motioned to Sal with my glass. “Alright, give me the debrief, soldier.”

  Sal’s shoulders stiffened. “One of the Underbosses said there’s a turf war brewing between the lower level dealers. The same ol’ shit of who is in whose territory pimping their dope.”

  I stifled a sigh. While the drug business was lucrative and kept the family flush with cash, it was also a thorn in my side. From laundering the drug money to bringing the coke into the country, it was a risk I wasn’t sure was worth it. The rich went through the powder as if it was something harmless, like pot. It wasn’t, and more than a few people died every day making sure Chicago’s elite had the best nose candy this side of New York.

  “That’s normal, isn’t it? What about the specifics?” Sal had been right. I didn’t like what he had to say. At all.

  My reflection warped the window as I gazed over the streets. My streets. I took another swig of alcohol, savoring the burn searing from my throat down to my stomach. I noticed my own eyes reflecting in the window the same color of the whiskey, burning as I turned to Sal again.

  Sal wasn’t intimidated by my glare. He’d been weaned on fear and forgiveness by my father. His lips twitched slightly with a ghost of a smile. “I don’t think their balls are big enough to hit the main sausage plant. They’ll probably try one of the lesser businesses. Do you want to send one of the crew to do a piece of work?

  I gazed out at Chicago’s waterfront. Boats bobbed over the placid waves on the horizon. It was a perfect sailing day: flawless blue skies, a moderate temperature, and a good breeze. I could almost feel the wind on my face and taste the freedom on my tongue that the lake offered. How long had it been since I’d taken the boat out? Sometime before Dad died.

  Growing up I hadn’t expected to be the crown prince of the Chicago Outfit. Dad had been a low-level Capo in the American Cosa Nostra. Then a bunch of the higher-ups got nicked in a sting or had been killed, and he’d become an underboss. A few years before I’d graduated from high school, there had been a massive turnover, and Dad had been elevated. Moving into the huge suite at the Waldorf Astoria before Dad and Mom had found a house, I’d known our fortunes had changed, and my future had been re-written. I’d been learning the ropes, and was thrown in head first into the wet work as “the Executioner.” Still, I never expected to become “the CEO of Chicago” before I turned thirty. Shit, I was half expecting Forbes to do a write-up on me at some point, since half of my businesses were indeed legitimate.

  It was ironic to me that a year ago, I was knee-deep in blood and gore, flexing Dad’s muscle to the Russians who had been trying to weasel onto his turf. How many message jobs had I done? I was a pro at extracting tongues and eyes with minimal blood splatter, and then sending them giftwrapped in beribboned boxes to their cohorts.

  And now, I was one of Chicago’s most eligible bachelors. Only in the Windy City would that level of turnaround be possible. The transition between killer and boss had gone smoothly. Except for now. Our life-long enemy—the Irish Mob—was testing my mettle. Fuck, I was bone weary of the back and forth, the sparring, the battles, the constant fighting, and sniping. I didn’t want a war, but if they forced my hand?

  They would learn just how I earned my name as “the Executioner.”

  Fuck. A thought crossed my mind and I fought to push it out. It was so hypothetical. But what if, and this was a big ‘what if.’ What if Kelly found out about my dark past? Shit, why was I even thinking about this? She probably wouldn’t even want to see me.

  “Boss?” Sal echoed. I’d grown prone to bouts of reflection, lately. The fact that a simple phrase like ‘piece of work’ meant ‘kill a man in cold blood’ had been getting to me. Still, it was part of the job, and I couldn’t show weakness.

  The tension snaked down my arms and curled beneath my ribs and I brought myself back to reality. “Get a team prepared, but don’t send it out. Wait and see what they do first. There will be enough bloodshed. I don’t want an all-out war, but if they bloody my nose, I will break theirs.”

  Sal nodded and stalked quickly back to his den. Before the day was over, my orders would be passed down the chain. Every single member of the family would be prepared.

  I lifted my glass to my lips and took another sip of my whiskey.

  Letting my mind drift back to the very person I shouldn’t be thinking about, all I kept thinking was would Kelly forgive me if she knew just how many Irish deaths were heaped at my feet?

  Còig

  The tavern had been closed for an hour, and I was pouring over re
ceipts and balance sheets when a commotion blew in. The only people who had a key to the front door, and the security code to disarm the system, were Pops and my brothers.

  “Kelly,” Tommy bellowed. His voice cracked, and a bone-chilling fear sank its claws in. Something was wrong. Very, very wrong.

  I was up and moving before I registered the motion. I hurried out of my office in the back of the bar and came around the side. I skidded to a stop, gaping at the scene before me. There were at least four men carrying another guy between them. They knocked a few chairs out of the way and arranged the injured one on top of a table. It was hard for me to decipher who was who. They were dressed all in black, with black knit caps hiding the bright color of their hair.

  It wasn’t the chaos which paralyzed me. But the blood.

  So much blood. Pools of it were all over the floor in a trail from the front door to the table. A growing puddle was forming beneath the inert body, and dripping off the side with quiet plops.

  Oh, God, was Tommy hurt? I’d heard him, but where was he?

  Finally, I could pick him out of the foursome. He hovered over the wounded man with his hands soaked in blood. Was he injured, too? My heart stuttered to a stop while my brain processed the fear. Only when he shifted, rocking back on his feet, did I realize where all the blood was coming from. I could make out who a couple of the men were and the parts they played in helping the seriously injured man in front of me. My cousin.

  Kyle laid on his back amid that growing pool of red around him. Whatever the three of them had been talking about earlier had gone down, and now the wounded were spread out in my pub.

  Welcome to the family business, Kel. Your cousin is dying on the floor. How’s that for a welcome home?

  “Snap out of it!” A man’s face floated in front of me. It took me a while to realize Seamus was part of the shaken crew gathered around Kyle. He shook my shoulders, jarring my teeth together. “We need to stop the bleeding. Get some towels and anything to pack the wounds.”

  When I didn’t move—how could I with my feet felt glued to the floor—he gave me a push.

  I stumbled into action and raced around behind the bar, gathering cloth and paper towels, and a bottle of vodka to disinfect the wound. Wait. Seamus had said wounds.

  What had they done? Had they really attacked the Italians? Didn’t they know the hell that would rain down upon us? And for what? Was the powder worth Kyle’s injuries?

  My sneakers slid as I hit a puddle of the blood when I rounded the bar area. Seamus caught my arm while Tommy grabbed the towels. One of the others, Pierce, maybe, by the shape of the nose, was working on Kyle. They’d torn his shirt away, exposing his lanky, tattooed chest. At least three bullet holes had punched through his torso.

  Bile backed up in my throat.

  “Shh, it’s okay,” Seamus whispered against my hair. I must have been making some wounded animal noises because his arms were around me, and he was rocking me as if I were a child.

  “I didn’t know where else to go, Kel,” Tommy babbled. He was losing it, and one of the others had taken his place.

  “How about to a hospital, Tommy!” I cried, on the brink of losing it.

  “You know we can’t. They ask questions when it comes to bullet wounds,” Seamus said quietly. “We couldn’t risk it.”

  Kyle’s body twitched on the table. He gasped a wet-sounding breath. Pierce looked toward Tommy who was raking his hands through his hair. “I think one of the bullets punctured a lung. We need a doctor, now.”

  “Who is closest?”

  “Doc Kavanagh is.”

  “Call him, get him over here.”

  “Tommy, he needs a hospital,” I whispered again, my eyes watery as I tried staying calm. Kyle was making horrible noises, a rattling sound in his throat. Every breath sounded labored.

  “We can’t, Kelly. Fuck. If any of us are seen dropping him off, we’re toast. They’ll toss us into lock up and there’s no fucking way Fitzpatrick will get bail for us. The coppers are just waiting for a chance like this.”

  I shook my head. “He’s dying, Tommy!”

  Tommy turned to the fourth man whom I didn’t recognize. There were so many cousins and extended family, I wasn’t surprised one had popped up who I wasn’t familiar with. “Get the doc here, now. Go, call him.”

  He nodded and pulled his cell free. He walked toward the other end of the bar and dialed a number. Before long his quiet voice could be heard.

  How could a doctor help Kyle without a hospital? There was a quasi-medical unit that was hidden under the guise of a veterinary office, I knew, but it wasn’t a state-of-the-art office.

  I dropped my face into my hands.

  Death was visiting the tavern tonight. I could feel it in my marrow. I was watching my cousin die, and there was nothing I could do to stop it.

  The doc arrived about a half hour later, rings under his eyes, but it was already too late. Kyle “Itchy Fingers” was dead.

  I wiped the tears from my face with the back of my hand and wondered if this would be a regular occurrence for me this summer. How many funerals would I be paying my respects at? How many family members would be flanked by gaudy flower arrangements and solemn hymns as they were laid to rest? How many renditions of Saving Grace would I be cursed to listen to? That song always brought the tears, and there had been far too many funerals peppering my childhood.

  My gut told me it would be far too many.

  “I can’t work tonight, Pops. It’s okay, though, I got Megan to cover my shift because I know the boys will be mad without at least one pair of pretty eyes behind the bar on a Friday night,” I said. It was hard for me to be in the tavern, but I couldn’t run away from it. It was my future. My life. Still, I was haunted by Kyle’s death on my doorstep. I swear I could still smell the copper pennies from all that death and gore in the air.

  Pops leaned on the doorframe, gazing in on me. The last few days had been a whirlwind of funeral obligations, ending with the burial this afternoon. Many people had brought flowers by the bar to leave in Kyle’s honor. I liked the brightness and the aroma they gave to my space.

  “What are you doing on a Friday night anyway that you can’t be with your family? Especially at a time like this.” He was sympathetic but jaded. Pops had buried a lot of people in his lifetime. Kyle was just another in a long line of casualties.

  “Girls’ night,” I croaked. “A few of my old high school friends are getting together.”

  Pops pressed his lips together and nodded as he ambled around my office. He stopped at one particular arrangement of flowers. Sweat gathered between my boobs.

  “Blue irises. Who brought these in? I didn’t see anyone bring these by.”

  I bit my inner cheek. “Oh, I’m not sure.”

  “Well, what’s the note say?” He manipulated the flowers as he examined them.

  “No note,” I lied.

  “Huh. No note? Some people, I tell ya. They’re only half-way considerate. They go to the trouble of leaving flowers and don’t even attach a note or a prayer.” He shook his head.

  I closed my laptop and stood. “Anyways, Pops, I’m going to head home and get ready.”

  He smiled slightly. “Alright, honey. You know I can’t say no to a girls’ night. I suppose it’ll be good for you to relax a little bit.”

  My arms erupted into goosebumps as I left. If Pops knew just who I was meeting with tonight, there was no way he’d be this amicable. My running off to see Vince was dangerous, but I wanted to feel alive since the Grim Reaper had paid a visit.

  Pops might just kill me. Except that he obviously would never do that to his only daughter. I don’t know what he’d do to Vince, though.

  I took a Lyft to downtown Chicago, and once there I switched to public transportation, overshooting the Fullerton stop at first and then taking an almost empty train car to check for followers.

  This wasn’t exactly a relaxing night as Pops had said, but damn was I excited to see him. I
’d spent a solid hour trying on outfits—something that a tomboy like me hadn’t done in well, almost ever.

  I listened to my stiletto heels hit the concrete as I walked the four blocks to the Biograph Theater. I’d donned a romper with splashes of yellow, red, and blue floral on white. The bottoms were short, showing off my legs to perfection. My oversized 1960’s-style sunglasses probably looked ridiculous, but they gave me the feeling that I was slightly hidden from the world. At the very least, they could provide a buffer between me and reality. If someone from my family recognized me here with Vince tonight, God help me. God help both of us.

  I arrived outside of the theater a few minutes after six o’clock. A woman and a man walked by in full Gatsby-style clothes and bumped into me.

  “Oh, I’m sorry my darling,” she cooed.

  Delight shot through me, taking away a fraction of the doom-and-gloom I carted around. “It’s okay. Dressed up for the show tonight?”

  The man smiled. “Roaring twenties dress-up party tonight. Now, if you please.” He leaned forward and tipped his hat with a smile, his accent exaggeratedly proper.

  I spun around and bumped into another man, except this one was built like a solid brick wall. I looked up and recognized one of Vince’s bodyguards from the night he came into the bar.

  “Hello, darling.” He spoke matter-of-factly. Any tenderness the man had was masked under a charade of formality and strength.

  “Hello…”

  “I’m Sal. I’ve got your ticket. Follow me.” After speaking the bare minimum required for the interaction, he extended an arm to me. I followed him inside, where a nod from him was all it took to get into the venue. I still couldn’t get over the fact that Vince had multiple bodyguards on duty to protect him at all times. As big of a deal as he was now, I swear I still remembered those times, before he’d hit puberty, when I’d been the one defending him against the Irish bullies who were making fun of him and trying to beat him up. That had been how we’d met. It wasn’t easy for him being Italian in a mostly Irish school, what with a pack of my cousins who had been trying to introduce his face to the pavement repeatedly. I’d stepped in, and it’d been friendship from the first ass kicking.