Chicago's Headmaster: A Sequel to Chicago's Headmistress

By Loretta Giacoletto

During the height of The Great Depression in 1931 and due to unforeseen circumstances, Matt Pagano finds himself in charge of what was once Chicago's most innovative brothel. At 23 and with no leadership experience, Matt must depend on Ugo Sapone, the former owner's confidante and right-hand man, to help him bring Night School back to those glory days guaranteed to provide his employees a decent income as well as others, good or bad, the opportunity to profit from Night School's rejuvenation.

 

In addition to Matt's vulnerable Night School staff, his challenging new world includes the lowliest of Chicago's Underworld, the upper echelon of Chicago's finest, wealthy outsiders determined to expand their business opportunities, and those who care for the sick and dying as well as orphans with no homes and children hoping to reunite with their families. Matt promises himself not to mix business with pleasure—but some promises were meant to be broken. Or at the very least, reevaluated.

 

"Careful who you ask God to bless, Matteo," Ugo tells Matt several months after he takes over Night School. "Today's ally could be tomorrow's enemy."

• Language: English
• Publisher: Loretta Giacoletto
• Release date: Oct 16, 2020
• ISBN: 9781393785163

Loretta Giacoletto

Loretta Giacoletto was named a finalist in the 2015 and 2014 "Soon to be Famous Illinois Author Project" for her sagas, Family Deceptions and Chicago's Headmistress. She divides her time between Southern Illinois and Missouri's Lake of the Ozarks where she writes fiction, essays, and her blog Loretta on Life while her husband cruises the waters for bass and crappie. Their five children have left the once chaotic nest but occasionally return for her to-die-for ravioli and roasted peppers topped with garlic-laden bagna càuda. An avid traveler, she has visited countries in Europe and Asia but Italy remains her favorite, especially the area from where her family originates: the Piedmont region near the Italian Alps. Her novels are filled with bawdy characters caught up in problems they must suffer the consequences for having created. ITALY TO DIE FOR, from her Savino Sisters Mystery Series, shows how too much togetherness can spell disaster for two thirty-something sisters vacationing in Italy. In LETHAL PLAY a grieving widow is suspected of killing her son's coach, a man with more enemies than friends. FAMILY DECEPTIONS follows two generations of earthy characters who learn to thrive and survive through a series of misdeeds, the worst against those they love the most. FREE DANNER features a cynical young man whose troubled past and deadly encounters hinder his search for the father he has yet to meet. THE FAMILY ANGEL is an Italian/American saga about the an immigrant family of bootleggers, coalminers, winemakers and priests, and a mysterious black angel who enjoys sticking his nose in the family business. The previously mentioned CHICAGO'S HEADMISTRESS, a prequel and partial parallel to THE FAMILY ANGEL, follows a 1905 Italian street urchin's notorious rise to wealth and power as the headmistress of Night School, Prohibition Chicago's most popular and innovative men's club in the 1920s. Loretta is also the author of A COLLECTION OF GIVERS AND TAKERS, twisted stories about the good, the bad, the self-centered and disillusioned In addition to the horror anthologies, Damned in Dixie and Hell in the Heartland, Loretta's short stories have appeared in a number of publications including The MacGuffin, Futures Mystery Anthology Magazine, The Scruffy Dog Review, Allegory and Literary Mama, which nominated her story "Tom" for Dzanc's Best of The Web.

Book preview

1

Chicago, June 1931

The Alley

Here, this way, Pooch said. It’s quicker. He grabbed Matt by the elbow, forcing a sudden stop midway through a crowded block of Saturday evening pedestrians strolling through The Loop. Stick with these slowpokes and you can kiss the Lake-State opening act a sorry goodbye.

Il sapientone Matt’s Pa would’ve called Pooch, a know-it-all who didn’t know much of anything; but the only friend Matt could count on and even that, at times, was debatable.

Matt shook off Pooch’s grip with a quick jerk and stepped back. Down that dark, deserted alley? No way, man. Forget the rats, the stink alone could get a stranglehold on our balls, choke ’em ’til they turn black and blue.

Don’t be such a mama’s boy.

Matt scoffed. Me a mama’s boy, look who’s talking. That hooch from your ma’s bathtub must be rattling your brain more than usual.

Not mine, Pooch said with a shake of his head, its mop of unruly hair matching the color of Lake Michigan’s sandy beach. My ma didn’t raise no idiot for a son.

Neither did mine. God rest her soul.

Yeah, sorry ’bout that. I meant no disrespect.

None taken. Now cut the crap and let’s get a move on.

Your way or mine? While waiting for Matt’s answer, Pooch shot a wad a spit against the nearest brick wall.

This time yours, Matt said, but only ’cause I really want to see that opener.

Even though Pooch had come up with the shortcut, as always it was Matt who took the lead. They headed down an alley cluttered with overturned containers and cats searching through spilled garbage for anything worth eating. One of many squealing rats scurried past Matt’s foot, only to get crushed under the weight of Pooch’s low-cut boots, the only decent pair Matt had ever seen his buddy wear. Better his than mine, Matt thought, with a quick glance at the sheen protecting his pa’s wingtips.

He’d covered about a third of the alley with Pooch when to their right, a metal door banged open. Out staggered one helluva messed-up guy, his caramel-colored face battered and streaked with blood dripping from a cut over one eye.

Just as the door swung shut with a loud clunk, Matt stopped, more out of curiosity than kindness, He would’ve moved on but the stranger lunged forward and planted his lanky body in Matt’s reluctant arms. Up close he appeared around the same age as Matt and Pooch—early twenties, give or take. He reeked of fresh shit and with good reason, as Matt soon discovered on looking down to see shit leaking from under the stinker’s trouser leg and onto the wingtips his pa had treated as if they’d come from the pricey Marshall Field’s.

Leave him be, Pooch said, backing up to the brick wall. Else we’re gonna be late, dammit.

I would if I could but I can’t, Matt said. Damn, the stranger had dropped to the pavement and wrapped his arms around Matt’s knees, trapping him in a desperate hold. Wiggling to free himself, Matt lost his balance and landed in the stranger’s urine-soaked shit. After a twist in one direction, followed by a twist in the other, Matt managed to free himself, only to find the stranger now attached to one of Matt’s ankles.

Sweet Jesus, don’t leave me, the stranger begged. If that door swings open again and ... and ... I’m still here, it’ll be curtains for me. And if dying ain’t bad enough, he paused to let out a sob, when these alley rats get through picking my bones, there won’t be enough left for my poor ma to claim the body.

Pooch came out of the shadows, leaned down, and extended his hand. Come on, Matt. We ain’t making his problem our problem.

Don’t listen to him, Matt. The stranger pushed Matt’s hand away from Pooch’s and rambled on, his voice growing more desperate with each word. Not if you’re a God-fearing Christian, same as me only a different color.

Black or white makes no difference to me, Matt said. Or to my friend.

Yeah, Pooch chimed in. It’s all about knowing. And we don’t know you from Adam.

That’s ’cause I’m Ezell. Ezell Johnson. He stretched out his free hand to the one Pooch had already extended. Pleased to make your acquaintance.

Pooch expelled an exasperated sigh. He pulled Ezell Johnson to his feet, and offered a second hand for Matt to do the same. They were still getting their bearings when the metal door swung open again and out stepped a barrel-chested man wearing a white shirt, its sleeves rolled up to reveal massive forearms covered with enough dark hair to make a rug for his bald head. The six-footer moved quickly in Ezell’s direction.

Ezell took two steps back, stuck out a pair of skinny arms, and showed his upright palms. I said I was sorry, Oscar. What more do you want.

For starters, the money you owe. I told you when you sat your sorry ass at the table, nobody plays who can’t pay to stay in for more than a single game. The boss has a tough-as-nails reputation to uphold and my job is to make sure he does.

Yeah, but— Before Ezell could manage another word, Oscar popped him in the nose and followed up with a punch to the stomach. Ezell doubled over, gasping for breath.

How much? Matt said, ignoring Pooch’s kick to the ankle as he reached into the front pocket of his trousers.

Ten bucks, Oscar said. Not one penny less.

Matt counted out six ones before running out of money. He raised his brow to Pooch.

Damn, Pooch said, adding the other four dollars. There goes our night out.

Care to try your hand at our poker table? Oscar asked.

No pay, no play, Pooch said, pulling out his empty trouser pockets. Ain’t that what you just said?

For you I might make an exception. An advance in exchange for a shitload of cleaning chores later tonight. Oscar glanced in Matt’s direction, took a deep whiff, and curled his upper lip. Not you, leastways not ’til you baptize yourself in Lake Michigan. None of that sprinkle stuff. Total submersion like the Baptists. From Matt he looked at Ezell, who’d finally caught his breath. As for this one, never again. No way, no how.

Maybe another time, Matt said. He grabbed Pooch’s elbow, same as Pooch had grabbed his minutes before, and together they walked away, to the metallic sound of the door closing one more time.

Hey, wait for me, Ezell called out while limping to catch up.

See what you started, Pooch mumbled under his breath. From over his shoulder he raised his voice to add, Sorry, Ezell, or whoever you are. Me and Matt, we’re done for the night.

"Ain’t no such thing as done in my neighborhood, Ezell said, having caught up with Matt and Pooch. Where I come from, the city never sleeps and everybody who’s anybody knows Ezell Johnson."

And where might that be? Matt asked, slowing his pace to accommodate Ezell.

South Side would be my guess, Pooch said.

Bingo! Give that man a dollar, Ezell said with a grin of blood-smeared teeth. Ain’t no neighborhood in all of Chicago as good as what you can find on The Stroll. Bright lights, jazz, soul food, and—

Switchblades, from what I’ve heard, Matt said. Thanks but no thanks.

What did I just tell the two of you, Ezell said. Stroll’s where the action is and everybody there knows the likes of Ezell Johnson. My whole family for that matter. We’re as solid as the concrete pavement. Stick with me and ain’t nobody that’ll bother you.

And when you’re not around? Pooch asked.

Then you shouldn’t be either.

Here’s the problem, Matt said. In case you didn’t notice, my friend here—

You mean Pooch with No-last-name, Ezell said.

Pooch’s next step never materialized. Instead, he raised his fist and stopped midair position within inches of Ezell’s nose. You implying I’m a bastard?

Hell, no, Ezell said, stepping back from Pooch’s knuckles. He turned to Matt. Nor would I imply such a thing of Matt here.

Matt Pagano, Matt said, shaking Ezell’s sticky hand. My friend is Poo ... John Manucci.

"John Manucci ... as in Man-hu′-chee ... Pooch to my friends, he said, with a single shake of Ezell’s hand. For a guy such as yourself, who owes me his life and then some, I might make an exception."

"Eye-talians? Is that what you are? Hmm. Ezell looked from Pooch to Matt. Not that I’m holding that against either of you. We all gotta come from somewhere, right? My folks came from Missippi but not me. No siree, Bob. Ezell Johnson is Chicago born and raised."

So are we, almost, Matt said. Born and raised nearby. Not that there’s anything wrong with starting out elsewhere.

Amen to that. Some of my best friends are Eye-talians. One for sure, but he left town last week. He’ll be back one of these days, what with two kids stuck in an orphanage and no mama—ain’t that the shits.

Sure, but not mine, Matt said. "Now, as I was saying: in case you didn’t notice, Pooch and I emptied our pockets to save your ass, which means the two of us are now flat broke. He looked down, and snorted in disgust. To say nothing of this shit of yours decorating my trousers and my shoes."

Shit, you say? Ezell checked out the shoes in question. Holy Bejesus. Guess this makes us some kind of brothers—not blood, the other kind which is way better. Trousers, no problem. I got you covered. What size shoe you wear?

Ten D, Matt said.

Sweet Jesus, same as me. I got just the pair for you. Brand new, never been worn and still in their original box. Been saving them for a special occasion and ain’t nothing more special than you saving my life.

What about me? Pooch asked. Got any 9 Ds?

Can’t say for sure but I’ll take a look-see.

So, where do we get these shoes? Matt asked.

Where else but on The Stroll. Didn’t I tell you? Everything worth having can be found on The Stroll.

2

The Stroll

Shoes be damned along with the squishy feeling of every step forward. At the corner of Madison and State, Matt sensed a queasiness developing in the pit of the stomach. Gut-wrenching thoughts about venturing into the unknown prompted him to ask how far a walk it was to The Stroll.

Walk? Who said anything about walking, Ezell said. He stepped to the curb, preparing to stick out his thumb.

Taxi, taxi, just like that, Pooch said. How many times we gotta tell you. Thanks to the likes of you, me and Matt are flat broke. He circled the thumb and forefinger of his right hand. Zero. As in no money. As in a big, fat goose egg.

Ezell ran his tongue over his teeth, cleaning off the remaining bloodstains. After leaning against the nearest post, he lifted his right foot, removed his shoe, and then its inner sole. Stripped-down, his shoe now revealed a small stack of greenbacks and fivers that he took out.

Steam was all but shooting out of Pooch’s ears when he wrapped one hand around Ezell’s tie and pulled him so close their noses almost touched. Why you dirty, rotten, no-good piece of shit.

Hold on, Matt said, separating Pooch from the troublemaker before more blood got shed. Just pay what you owe us, Ezell, and we’ll walk away.

Walk away from new shoes and a decent set of clothes, Ezell said. Where else you gonna get something for next to nothing.

Next to nothing ain’t the same as nothing. Pooch snatched four of the bills clutched in Ezell’s hand. Two fivers should cover what you owe me and Matt, plus a couple extra greenbacks for the shitty inconvenience.

You okay with that, Brother Matt?

Pooch handed Matt half of what he took from Ezell, and said, Don’t be a fool, Matt. This guy’s nothing but a two-faced liar, worse than that, a grifter.

We don’t know it for sure, Matt said, even though he half-agreed with Pooch’s assessment.

Bullshit! Pooch countered. Just so you know, if you go with this guy, I’m going back to see Oscar about that job.

Hey, man. Do what you gotta do, Ezell said. Just don’t be telling Oscar about the money, okay?

Yeah, yeah, Pooch said. Even though you suckered me—

Tried to, but you were too smart for the likes of me.

Right. What’s more, I ain’t no snitch. How ‘bout it, Matt? You with me?

Matt shook his head with hesitation. Any Time Bar, I don’t know. A place like that could spell trouble.

Yeah, but think about the money, Pooch said. About catching up on the rent. Better yet, if we ask nice, Oscar might give us a share of the leftover grub.

Matt licked his lips. Having heard about the decent food Any Time served, he thought sticking with Pooch might not be such a bad idea after all, if only until something better came along, as in a real job. But when a yellow and green taxicab pulled up to the curb, he felt a determined tug on his sleeve.

Ezell wasn’t about to let go. "Come on, brother. We got us a ride to the South Side. I know this driver better’n our family preacher. Better’n anybody ’cept for my daddy. Trust me, you can’t go wrong with this righteous man. Ask anybody on The Stroll."

Having left Pooch grumbling a string of obscenities on the sidewalk, Matt followed Ezell into the back seat of the taxi. Before pulling away, the driver turned to Ezell, lifted his bushy brows and said, Does your mama know you’re hanging out in The Loop again?

No, she don’t. And she ain’t gonna know as long as you keep your mouth shut ’cause sure as hell I won’t be the one telling her.

She ain’t hearing it from me either. The driver faced forward, shifted into first gear, and edged into the traffic before asking his next question, Where to, Ezell?

Where else but home and a good wash-up. I promised my new brother here a good time on The Stroll and I aim to keep my word.

Your new brother got a name?

Matt Pagano, meet Elijah Washington. Me and Elijah go back a long way.

Elijah slammed one hand on the wheel and belted out a baritone laugh. Truer words were never spoken. I knowed his boy ’fore he came out of his mama. And that ain’t no joke. It was me who helped bring Ezell into the world. Birthing ain’t for sissies, that’s for sure.

Daddy would’ve helped, Ezell said, nudging Matt. But he was working at Dearborn Station. Not that I’m complaining, you understand. Other than my own daddy, ain’t nobody I’d rather have welcoming me into the world than Elijah Washington.

Your mama did her part too, Elijah said. She is one tough broad ... I mean lady.

I know what you mean, Ezell said. Ma would be okay with being called a broad, leastways by you.

Elijah snorted, then snorted again before asking, Pee-yew! What’s that I smell? Whatever it is puts the stockyards to shame. He rolled down his window and without being told, Matt and Ezell did the same to those in the backseat.

Matt breathed in the familiar breeze of Lake Michigan. He closed his eyes and tuned out the street talk between Ezell and Elijah, about people, places, and events that meant nothing to him, other than the recent death of Chicago’s most infamous madam. Her, he met one time, during his initiation into manhood. He was on the verge of dozing off when the taxi stopped at Thirty-fifth and State. Lifting one eye, he saw Ezell lean forward and after a few parting words, pay Elijah the one dollar fare plus a two-bit tip. Being righteous and almost family did have its advantages.

Ezell opened the door and hopped out, leaving Matt to follow in the gutter dust of his footprint. Another reminder of the mess Ezell had made of the wingtip shoes that were due for another resoling. Matt’s pa never let the heels run down too far.

First stop, clean clothes, Ezell said as they entered a three-story brick building sandwiched between two similar buildings.

Matt followed him up a steep flight of stairs to the first landing. Down the hall on the left, Ezell stopped in front of number 201. He knocked once and without waiting for an answer, opened the door, dragging Matt in with him.

Ma! Daddy! Ezell yelled. Getting no answer, he said to Matt, Good. They ain’t home, which means we don’t have to answer any of Ma’s well-meaning questions. Daddy, he leaves me alone, most of the time, anyways. Come on. Let’s get ourselves cleaned up.

In a bathroom smelling of the same vinegar and bleach Matt’s mom had used, he followed Ezell’s lead, stripping down to his underwear and washing from a basin of warm water. After they both removed every trace of shit and pee, Ezell handed Matt a ragged pillowcase and told him to put the soiled trousers and shoes in it. Can’t we just clean up the shoes, Matt said. They belonged to my pa and I’m not leaving without them.

What? You think I’d keep your daddy’s shoes? Worse yet, throw them away. What do you take me for? You’ll get ’em back, without the shit, and in better condition than when you first slipped your feet inside this evening. The trousers too, that is, if you insist. First, take a look at what I’ve got for you.

Ezell’s bedroom reeked of a mother who demanded orderliness. He opened his wardrobe, revealing a department store display of assorted shirts and trousers, all neatly pressed and ready to wear. The trousers Matt tried on were brand new, grey plaid, and pleated at the waist—nicer than any hanging in the wardrobe he shared with Pooch. A new pair of suspenders to hold up the trousers served as an added bonus he hadn’t expected. As for the shoes, Ezell pulled them down from the upper shelf. As promised, still in the box and never worn. Again, nicer than any shoes Matt’s calloused feet had ever tolerated, but still not his pa’s. Not that Pa would’ve expected him to wear the old ones ’til they fell apart.

Hurry up, Ezell said as they slipped into the clean clothes. We ain’t got all night. Well, actually, we do; but I don’t want you missing out on any fun.

Matt left the bedroom feeling like a new man. As for Ezell, he’d taken on a whole new persona. Funny what the right or wrong clothes could do for a man, no matter what his station in life at that moment. Same goes for women. Streetwalkers, for one, as compared to high-class hookers—all performing the same basic service but at a substantially different pay rate, depending on their location and representation. Not that Matt was being judgmental, just making an observation and nothing more, from one who’d given up his virginity at eighteen with no regrets.

He and Ezell didn’t get any farther than the living room when the outer door opened and in walked a man and woman. Ezell’s parents, of that he had no doubt, what with the woman’s caramel-colored skin and the man’s general build and mannerisms.

Ma, Daddy, this here’s my new friend, Matt Pagano. He’s Eye-talian, like Mister Charlie. And got himself in trouble, just like Mister Charlie did a few years back. I couldn’t just walk away and leave him, just like Daddy couldn’t leave Mister Charlie.

Both parents came forward to stand before Matt. The woman narrowed her eyes to him and spoke in a deliberate voice. How do. I’m Essie Mae Johnson. You speak English?

Matt opened his mouth to speak only to have Ezell cut him off.

Some, Ezell said. Better than most, which ain’t saying a lot, I know. Right now, he’s still in a state of shock.

Ezell’s father stuck out his hand. Elijah said to expect you. Name’s Roscoe Johnson.

Matt shook hands with Ezell’s pa, while debating if he should come clean, confess to being American born and educated, and not recovering from a traumatic incident but rather Ezell’s stupidity. But before he could offer one word of explanation, he felt Ezell pulling him toward the door. So, he smiled and nodded while backing into the hallway. With any luck, he’d never have to lay eyes on Essie Mae or Roscoe Johnson again.

***

Back on the street, one thing was for sure: Ezell had not exaggerated his opinion of The Stroll. Every strolling man and woman was dressed to the nines, although a little too gaudy for most white folks, of which there were none to be seen other than Matt, making him relieved to be wearing the new trousers and shoes Ezell had given him. After walking a block or so, he and Ezell hit a bar that served decent beer; better yet, a trio of black musicians playing Dixieland jazz. So sweet the sound Matt wanted to camp there all night. And would’ve if Ezell hadn’t insisted he was hungry and therefore Matt must be too, a reminder that he hadn’t eaten anything since the creamed chip beef on toast he’d eaten for lunch, courtesy of his landlady who’d taken a liking to him but could barely tolerate Pooch.

Matt walked beside Ezell for another block or so before arriving at The Black Pearl. Jazz ain’t quite as good as the other place but this one has the best soul food, Ezell said. I’m talking best down home cooking for black folks. From the heart, if you get my meaning.

From the heart, oh yeah, Matt thought. Nothing could’ve beat his ma’s from-the-heart, but he saw no point in starting an argument with Ezell over a no-win topic. Especially in Ezell’s world.

Two of your best premium beers, Ezell told the waiter with a wink.

After the waiter left, Matt raised his brow. Premium, really?

Near beer according to what it says on the barrel, which makes it legal here at the Black Pearl. Now if you’ll excuse me, I gotta see a man about a dog.

More like two men standing at one end of an impressive teak wood bar. They wore colorful double-breasted suits and white spats over black patent leather shoes, along with toothy smiles that soon faded into toothless frowns. After few minutes the conversation turned ugly, so heated Matt considered joining Ezell to even up the sides.

Don’t even think about it, said the mind-reading waiter while setting two mugs on the table. "And don’t be messing in business that ain’t yours to mind. Ezell can take care of himself and if he can’t, you best make tracks before those two take notice of you, as