The Crooked Connection

That’s the thing about this city, downtown Chicago was a magical place and someday I’d be heading straight to the top. It was 1925 for goodness sake, everywhere you looked we were building and enterprising the way to the future! Whirring electric trams and flashing neon lights glowing through the haze of cigarette smoke and cars honking as they rattled through the busy streets, it never felt like you were alone in Chicago.

No matter what Bert Stone said, I was gonna be somebody. I’d been pedalling his newspapers for a while now and I was good, I could sell. As long as no one nicked my corner, I could set up my board to catch the sharp-suited men whose oversized coats billowed as they headed to Union station and tempt them with the Evening News or Examiner. But from my spot I could also pull out the muckrakers to catch the lowly eye of steelworkers as they trundled past after working on either the Wrigley or Jewelers building, most likely. With their flat caps and cigarettes coupled with their scraggy vests, they had a style different to the office men straight from Vogue (as I imagined not being willing to sell those for 55¢ a copy) but had a rustic working man’s charm all the same.

Not a bad day, 79 papers sold, I’d made 30¢ this week, I was glad of it too. The bustle started to dissipate as I folded my board and slung my newspaper bag onto my shoulder to walk home to Dorothy in time for supper. She hated being called Grandma or Nonna so Dorothy it was, one of the many rules of living under her roof, but it was home. Even though her sherry stash had long since ran dry under this ‘tyrannical’ reign of prohibition she’d say I was lucky my great grandparents had risked their lives coming over here or I’d be stuck with Mussolini, although I was never sure if this was worse than the sherry shortage. Still, it was bearable, especially when she was busy trying to tune that new-fangled radio set of hers which, “Will put you outta a job if you’re not careful,” to try to catch a snippet of the evening jazz crooned by some smooth sheik.

Distracted by my daydreams, I realised I was meandering through gangster territory, these were a sketchy few streets down between 18^th and 22^nd. Usually, these dingy alleys would conceal the clink of tub gin bottles or moonshine barrels hauled here by bootleggers looking to profit from selling them underground. It fascinated me but I knew better than to sniff around, it was a sure way to be a rich man, but it was ruthless, rife with rivalry and a sure way to end up face down in the river. So I kept my head down when I heard the door of a speakeasy crack open releasing the blare of jazz and whistles no doubt meant for the flapper girls into the alleyway. The muscle who opened it was a bruno for one of the local gunners who was asking a couple of mols in their gladrags the password. They had to keep out any strangers or snoopers looking to drop a dime or nail them for bootlegging.

A few blocks down the sound of jazz had long floated away behind me when I heard two men in the next alley talking as one was being lead to a doorway, clutching something in his hand anxiously. I hid behind a pile of junk or they’d see me as I walked on by so waited for them to finish their business and leave before I moved along. They tentatively paused at the door and the nervous guy eyed the other cat suspiciously, the latter, a shabby kinda guy even in the blue stripes of probably his finest three-piece suit, brown trilby and polished loafers. Sensing danger, he turned on his heel and stumbled back up the alley towards where I was frozen in fear. At the same time the rusty door swung open revealing powerful frame draped in a silk shirt and with his hands cockily in his pockets, his pinstriped jacket fell open to show a tommy gun not-so hidden behind his suspenders. Recognising his infamous silhouette as the Bull Tamer of Southside I knew what was next, he was the number one bootlegger boss south of the river and was untouchable with protection from the respect of rival mobsters and bribes he slipped the local buttons.

The Bull Tamer whipped out his weapon, cackling as he peppered the fella who crashed into the trash that was acting as my only shield. He stowed his gun casually so he could hand over a wad of dough to his accomplice after enjoying blowing him away. He nodded to a couple of goons in the doorway to bring the Caddy round and get him the book before they cleaned up. I crept low against the wall not daring to breathe, trying to back away into the shadows. A hand pulled me back, I waited for a shot but looking over my shoulder, it was the man they’d fired at. Sprayed with blood and lead he was barely alive but dragged me toward him to utter a strained whisper as he thrust the leather- bound book he’d been guarding into my paper bag, “Take it, kid, use your noodle but don’t trust no one if you wanna live.” I ripped my shirt from his grasp as he collapsed and bolted, straight into hood of the Caddy the knuckleheads were screeching into the alley. I slid between its shiny fender and the grimy wall and darted down a narrow passage not slowing to hear the answer to if they should bother bumping me off too. I didn’t stop all the way to our sixth floor apartment near the north side where I shot up the stairwells and didn’t ease up till the door was slammed behind me.

It wasn’t until I’d finished Dorothy’s homemade polenta, paying extra attention to the wireless not that it would announce a murder they were adept at disguising, said our daily prayers (Nonna being a strict catholic) and collapsed in my room that I remembered the little black book stowed away in my satchel. I opened it carefully, every page was scribbled on with hand-drawn maps and lists of nicknames like Mossy, Tough Tony and the Fox with random numbers jotted here and there scrawled down the edges as if the secrets were bursting out of the pages. I spent hours deciphering the little diary as though my life depended on it, which it may, if the Bull Tamer figured out I was the one who had the book he’d personally snubbed someone out for. It appeared tatty and meaningless, but it acted as some form of ledger for transactions bootlegging? Gang member hits? Maybe even arms dealing, I wasn’t sure. But with the cash they’d been getting on one page alone, I knew it wasn’t legal. Some of the numbers could be dates, or coordinates, some were meaningless to me but all pointed to the dark, criminal side of this magical city where one wrong turn or faulty deal could blow you away.

I carried on buying and selling papers as usual but more watchful of the guys and molls who passed me by. Bert sold me a bundle of 100 papers most days, calling me his famous entrepreneur- as always- scoffing that I’d never be a man of means one day. “In Chicago you gotta be in the papers not selling them if you wanna be a big shot. They want a story that catches their eye not a newsboy!” He snorted, if only he knew what I had hidden away under my bed. On my way home a few evenings later, a couple of seedy looking men who’d been loitering earlier followed me up past the Levee and were still on my case as I abruptly turned and headed down toward the south loop instead. I ditched my satchel and ran for it, closely shadowed by the thugs no doubt working for The Bull Tamer. I lost them by squeezing through a gap in the chained-up fence that was a busy construction site by day but abandoned this late.

As I breathlessly made it home, I stumbled into more danger. Nonna Dorothy was waiting. And she was angry. She had the book and was firing questions at me like the Chicago lightning down by 22^nd street, half in Italian, half in English, but angry in both. “What is this, you running for the mafia now? I didn’t raise you like this! They been prowling round here shaking down neighbours looking for this, you get out and don’t come back till you give it to the polizia, you hear me?” Thrust into my hands once again, I stuffed it into my pocket and scurried off to Maxwell street precinct which was closer and hopefully less deadly than going anywhere near 22^nd street again. Every few yards checking behind me and jumping at every shadow or barking dog, people like Bull Tamer had eyes everywhere.

Inside the station the beat cop shunted me to a corner by the door where until some haggard detective came to hear my story that the uniform obviously didn’t buy. He sidled over, looking tired and skeptical, “So kid, you got dirt on not one but every mobster in Chicago, this oughta be good. Either you’re some child grifter or someone added jiggle juice to the joe, what’s it to be?” I opened my mouth to plead the truth but noticed one of the men sniggering over his shoulder. Same shabby striped suit. Same brown trilby. It was the snitch from the alley who was a detective but also on the mafia’s payroll by night. Without another word I barged through the swing door and out into the night again.

I couldn’t go to the police, I didn’t know which were dirty. I couldn’t give it to any gangster, it had dirt on others and they’d kill me when they had it. I couldn’t go back to Dorothy without telling her everything and putting her in danger too. I had to be smart. But I didn’t know how to do that, I was a newsboy from downtown who didn’t know anything except how to sell papers. Bert was right, I’d never be a big shot. But maybe I had all I needed in this little black book. I studied it for hours like a madman, every detail, every date, every amount until it was engrained in my mind. It felt like a lifetime of pacing back and forth. But, I had a plan.

I pounded on Bert’s door and by sunrise he’d printed nigh on 40,000 copies of our coded messages in all the papers that would be hawked on every street corner in Chicago by sunset. We knew which mobs bought which papers so it was easy to offer in code the secrets of rival gangs for a hefty sum without it being stumbled upon. Using the paper as the source I stayed anonymous and gave a drop off location for the dough. We’d called Maxwell precinct once we’d cracked the cryptic list of dirty cops and knew the tired detective wasn’t taking backhanders. After raking in $15,000 in greens from the bosses which kept them at bay while we handed the book over to the fuzz, while uniforms raided every den and illegal operation in that book. But I went home with $15,000 dollars plus half the profits -five grand- that Bert gave me from selling him more papers in over 20 years and the feeling that for once I was the story. I was an entrepreneur, king of old Chicago, but if this town has shown me anything, fame and fortune switches round here quicker than rolling dice.