Макс Коллинз - Road to Purgatory

The Colony Club, at 744 North Rush, had two devout neighbors: the Methodist Publishing House, next door, and (a block south) Quigley Preparatory Seminary, where young boys prepared for the priesthood. The Colony, however, catered to sinners seeking not salvation but a damned good time.

And the ultra-ritzy club’s pretty hostess, Estelle Carey — a willowy green-eyed golden blonde who looked ten years younger than her thirty-one years — saw to it that the patrons got whatever kind of good time they might desire.

At the moment that meant Estelle singing. Perched on a stool in a slit-up-one-side dark blue gown, bodice covered in sequins, in a corner of the bar next to a baby grand, her accompanist Roy tickling the keyboards lovingly, Estelle kept couples at tables nearby enthralled with her small, sweet, smoky voice. Her favorites were Dinah Shore and Ella Fitzgerald, and she sounded a little like both, which was intentional, aided by doing a lot of their hit tunes.

Estelle was a star attraction at the Colony; though various big bands that played in the spacious dining room were national names, locally the name Estelle Carey meant something — something naughty, perhaps, but something.

She’d started out life part of the crowd, with a last name — Smith — to prove it. Daddy Smith died when Estelle was a toddler, and much of her childhood had been spent in an orphanage; she’d left high school early on for waitressing. But her beer-budget background had somehow spawned champagne tastes, and her salary and tips from a Logan Square restaurant had been supplemented by sharing more than just a smile and a wink with male customers.

Estelle had always liked men — liked the power her good looks gave her over these powerful creatures, enjoyed the physical act of lovemaking in a way many girls at least claimed not to. From a junior high teacher she’d seduced at thirteen to every boss she’d ever had, Estelle had improved her life by generously sharing her considerable charms.

Still, she did not in the least consider herself a harlot — she had never made love for money in her life.

On the other hand, she’d never gone to bed with a man without the next morning receiving money to help out her sick mom, or make up a rent shortfall, real or imagined. Now and then, over the years, a steadier boyfriend might lavish gifts upon her, from fur coats to rent-free apartments. This was to be expected.

Waitressing at Rickett’s on North Clark Street had been Estelle’s breakthrough into a better life. Not that Rickett’s was posh; heck, it was just your typical white-tile restaurant. But it was open all night and attracted show people and the artsy crowd from Tower Town... and even Outfit guys like Nicky Dean.

With his mop of well-oiled black hair, Nicky was like some smooth George Raft — type movie gangster had walked down off the screen and into her life. Tall, dark, roughly handsome, Nicky looked like a million in a dinner jacket; he had style and charm and clout with the Outfit... also a wife, a little chorus cutie he’d married maybe ten years ago, but Mrs. Dean was sickly, and Nicky treated Estelle better than a husband treated a wife.

Still, some would say Nicky made Estelle earn every expensive stitch of clothing and even “pay” the rent on various fancy flats, by putting her to work. Even now, people said that — look at her in the Colony Club, singing for her supper.

But Estelle Carey had never been lazy. She liked to work, and just as Nicky was no one-woman man, she enjoyed other lovers, just not on an extended basis. Nicky didn’t even mind Estelle entertaining the occasional Outfit guy, because he seemed to take pride in having them taste a dish just once or twice of which he could partake any ol’ time.

What had gotten Estelle into the newspaper gossip columns — and turned her into a local celebrity — was her continuing status as Chicago’s most famous 26 girl. She rarely played the game herself these days — the bar at the Colony had half a dozen stations where gorgeous girls took care of those duties.

Twenty-six was a game played all over Chicagoland in watering holes from the lowliest gin mill to the poshest nightspot. At a table or podium, an attractive, well-built doll would shake dice in a leather cup and roll for drinks with a male customer. Though playing for quarters, the customer — who was often drunk — might manage to lose as much as ten dollars.

What had got Estelle into the papers, though, was taking a Texas oil millionaire for an astonishing ten thousand dollars at the penny-ante game. And the guy loved her for it. Always sought her out when he was in town.

Which was what made Estelle Carey the queen of dice, and provided the basis for what she taught her girls: a man needed to feel that a 26 girl was his friend, even a sort of sweetheart, and that the bar was a home away from home.

The 26 girls at the Colony, handpicked, handtrained by Estelle, knew how to spot compulsive gamblers or otherwise potential high rollers, and (earning a nice bonus for each sucker) steer them to the “private” club upstairs — a full casino where many fortunes were lost and only a handful were made... Nicky’s and Estelle’s, among them.

The club had an art-moderne decor out of an RKO musical — chromium and glass and shiny black surfaces. The casino upstairs was less chic — just a big open space with draped wells and subdued lighting, noisy and smoky, rife with the promise of easy money that almost never delivered, and the promise of easy women, who more frequently did.

That had been Estelle’s idea, and Nicky told her how Capone, Nitti, and others in the Outfit had praised her genius: no one ever figured out a better blow-off for a burnt customer than this. A high roller who’d been stung — often with an off-duty 26 girl on his arm, who’d egged him on at the tables — would be invited up to the third floor, where private suites awaited. After some behind-closed-doors time with a beautiful dame, many a loser walked away from the Colony Club wearing a winner’s smile.

Estelle was good to her girls. On slow nights, she allowed them to take a non — high roller up to a suite for fifty bucks; on a less slow night, the price bumped to a hundred (either way, the house got its cut). If the Colony’s first floor was largely legit, the second-floor casino and third-floor beauty parlor were definitely not; this meant hefty monthly payments to the cops and politicians, and the Outfit was obviously a fifty-fifty partner.

Estelle was perched on her stool, singing “Fools Rush In,” when she noticed that kid again, sitting at the bar, almost looking like a grown-up in a sharp gray suit, pretending not to be watching her as he nursed his Coca-Cola. She hadn’t seen him right away — this was Saturday night, so the place was hopping, the tables filled, a fog of cigarette smoke drifting across the bar.

Michael Satariano. The city’s celebrated Congressional Medal of Honor winner. And she was pretty sure the kid had a crush on her. Which didn’t depress her, not hardly — he was one good-looking boy; the scar near his left eye only gave him character, helping him not seem so goddamn, cradle-robbing young...

Something maternal rose within her, a surprising sensation, all things considered; but part of her wanted to scream at him, Get away from these people! What was a kid who had the world by the tail doing hanging out with Outfit goons? She herself had had no other choice, really; the likes of Nicky Dean had been her best ticket to a better life.

But this kid shook the president’s hand! This kid was famous, not just locally, but all across the nation. Wasn’t a business in the country that wouldn’t give him a job, a good job, a real job, and on a damn platter.