Night School, Chicago’s most innovative brothel. 1931 at the height of The Great Depression

Up close, he looked younger than from the short distance Paris Mallory had observed him two nights before. She figured Matt Pagano to be around her age but much shrewder. Running a well-established brothel would do that to any man or woman whether young or old. Eyes, an intense shade of green; dark, curly hair reminiscent of a gypsy, hollow cheeks, a mouth thin-lipped and determined. Observations she did not mean to be disparaging but rather intriguing.

During an exchange of the usual pleasantries, Paris noticed their threesome, which included Rance Osgood, had now expanded to a fourth. Standing—more like hunched over—next to Matt Pagano was quite possibly the most peculiar looking man she’d ever encountered. Matt introduced him as Ugo Sapone.

“I do hope we can be friends, Mr. Sapone,” she said, her firm handshake an unspoken apology for the superficial pettiness stirring within her.

“So nice to make your acquaintance, Mr. Sapone,” Rance said in his usual open-minded acceptance that encompassed people from all walks of life. “Your reputation precedes you.”

Really, Paris thought. Since when did Rance know anything about Ugo Sapone’s reputation? On the other hand, what did she really know about Rance Osgood, other than his musical talent, his gambling habit, and his propensity for men rather than women.

“Do call me Ugo, both of you.” The man spoke with half-closed lids covering his bulging eyes. He made a simple gesture to the bartender, prompting him to set four goblets in front of where they sat and to fill halfway with red wine. Hardly her first choice, but after one taste, she found herself wanting more. As did Rance. After draining his glass, he didn’t hesitate to accept a quick refill.

“I enjoyed your performance at Mrs. Brewster’s,” Matt said, acknowledging both her and Rance.

“Much appreciated,” Rance said, “which is why we’re here. Any chance of our getting an audition?”

Could life have gotten any sweeter or the reluctant Rance any bolder? Matt Pagano agreed to an immediate audition. As did Ugo Sapone, even though he did nothing more than issue an affirmative with those heavy eyelids. Paris found his overall demeanor as odd as his appearance but in a likeable way.

She wondered if Rance felt the same but didn’t get a chance to exchange observations before settling into their stage routine, him seated at a baby grand similar to Auntie’s, and her leaning against its cabinet, which could’ve used a good polishing. The so-called teachers had moved in closer, occupying cushioned chairs. As had the kitchen help, including one black man Paris recognized as a cook who used to lend an occasional hand during Auntie’s special events. Horatio … Horatio Jefferson … he must’ve found fulltime work at Night School. Good for him, Auntie would be pleased.

“How about those songs from the other night,” Matt said in a raised voice. Having resumed his seat at the bar, he swiveled to face the stage. “I’d like Ugo to hear that particular medley, unless you have something else in mind.”

After Paris and Rance repeated their set from the Brewster soiree, the Night School audience stood and applauded with far more enthusiasm than her auntie’s audience had shown. “One more,” Horatio called out, to which Matt gave his approval with a wave of the hand.

“Are you game?” Rance asked Paris.

“I am if you are.”

It was an opportunity too good to resist, ending the audition with one of their favorites, a song that gave hope to a country deep in the throes of the Great Depression entitled, “The Best Things in Life Are Free.”

The silence following that particular number was deafening. As for Matt Pagano, he remained seated, his face blank as a motion picture screen before the first reel started. As was Ugo Sapone’s, which hadn’t changed from the first note to the last.

“Good lord,” Flora yelled. “What the hell are the two of you thinking? All those words about free this and free that. The moon. The stars. Those damn sunbeams.”

That’s when Matt spoke up, in a voice that didn’t need raising, given the mood of the room. “Just remember where you are. Here at Night School, nothing comes free—well, almost nothing. If the students don’t pay, their teachers don’t get paid.” He stood and gestured broadly with outstretched arms. “And neither does anybody else who depends on Night School for a living. Nor outsiders looking for a chance to make a name for themselves.”

Paris didn’t have to look in a mirror to know her face had gone from pale pink to rosy red. Nor did she need to see the faces of her dumbfounded audience who had shown such enthusiasm for her and Rance’s earlier medley. While gathering up her few belongings, she mumbled an apology to Rance, then raised her voice to say, “Come on, we’d better go. I guess this means we’re not hired.”

“Evidently, you were only half listening,” Matt countered. “I’m willing to hire the two of you, for a period of one month, Tuesday through Saturday, five until midnight with time off between performances. If we see an increase in business, we’ll talk about more hours. If there’s no increase, we’ll part ways, with no hard feelings on either side.”

End of excerpt. Chicago’s Headmaster: A Sequel to Chicago’s Headmistress.

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