The Flamingo Club

The Flamingo Club stands on Pennsylvania Avenue in Baltimore as the second-best nightclub on the city's historic Black entertainment strip, a place that Shell Gordon, its owner, desperately wants to be respectable even as he runs gambling, prostitution, and a growing drug trade on the side. It is a club caught between two worlds: it books the second-best acts available, always losing the best ones to the Phoenix, and it serves a clientele that is mostly Negro even as its bartender is a white man. The club's significance in the story is double-edged: it is the workplace where Cleo Sherwood spent her final months, and it is the place where the official investigation into her disappearance effectively stopped caring.

A Club of Contradictions

The Flamingo is defined by the tension between Shell Gordon's ambitions and his actual business. Gordon makes most of his money on gambling and running whores, and he is moving into drugs because there is too much cash to be made to ignore it. Yet he loves the Flamingo and wants it to be a really classy joint, as if he is at war with himself. He wants to be legit, but there is too much money on the other side, and he needs the crooked money to be legit. The club itself is run with strict rules that reflect this conflict: the girls who work there are managed to find the sweet spot between hosting and serving, and Gordon will not tolerate any of the whorehouse stuff at the club itself. If the girls want to date the guests, that is okay, but it has to be on their time, in their own clothes. The club is not running a whorehouse; it is a respectable place where gentlemen and ladies should feel at home, even though Gordon has plenty of other places to run girls, and truth be told, that is how a lot of Flamingo girls end up.

Cleo Sherwood's Workplace

Cleo Sherwood worked at the Flamingo as a cashier and helped behind the bar, a job that her family described with some defensiveness. Her mother, Merva Sherwood, explained to Maddie Schwartz that the family is not a drinking family, but there is nothing wrong with serving people who do drink, since it is legal after all. Cleo made pretty good money there, enough to pay her family for taking care of her two boys while she tried to get herself situated. The job also allowed her to buy herself nice things, like the ermine stole with the pink acetate lining that looked like silk, which Maddie later inspected as evidence. The club was where Cleo was last seen for sure, heading out on December 31, early January 1, for what she told everyone was going to be a big, big night. Tommy, who worked the bar at the Flamingo, remembered her last words: "They say whatever you're doing on January first is what you'll do all year. I don't need to eat any black-eyed peas to know that 1966 is going to be a great year."

Maddie Schwartz's Visit

When Maddie Schwartz visited the Flamingo in July 1966 as part of her investigation, she found it a bit of a disappointment, not because of its lack of grandeur—she had very low expectations for the second-best club on Pennsylvania Avenue—but because of its humdrum ordinariness, its very lack of danger. At six P.M., early for decadence on anyone's clock, the club struck her as not that different from the Woodholme Country Club on a theme night. She took a seat at the bar and ordered a vermouth, but the white bartender, a stocky man with dark hair and hooded eyes, leaned back with his arms folded, making no move to prepare her drink. He told her that the club prefers its lady customers to be accompanied by men, and even then, they are not seated at the bar, because the owner finds that disreputable. The bartender was the one who had described Cleo Sherwood's date to police, and Maddie had not expected a white man in a club owned by a Negro, which served mainly Negroes. She assumed a white man would be less hostile to her, but the encounter proved otherwise.

The Club in the Investigation

The Flamingo's role in the official investigation was dismissive from the start. When the city editor at the Star, Harper, discussed the discovery of a dead Negro woman in a fountain, he said he would not even lead the metro section with it, noting that Diller heard it was probably a woman who disappeared earlier this year, a cocktail waitress from the Flamingo, Shell Gordon's joint. The Afro-American had been all over it, but there did not seem to be any real news there. This casual dismissal infuriated Maddie, who saw her anger over the callousness of the men at the Star as a kind of tribute to her lover, Ferdie Platt. But Ferdie laughed at her and explained the brutal truth: "Because she's a Negro, Maddie. That's why it wasn't a big deal when she went missing." The club, then, becomes the symbol of how Cleo's life and death were devalued—a place where a Black woman could work and earn money, but where her disappearance would not even merit a lead in the metro section.

A Regular's Haven

The Flamingo also served as a refuge for Ezekiel "EZ" Taylor, Shell Gordon's favorite guest. A big man, shy and not much for talking, Taylor came for the music and hardly ever drank, ordering a port to keep others company, nursing it all evening, then picking up the tab. He was polite that way, always wanting everyone around him to feel good and be comfortable. That was what Gordon saw in him: his give-and-take with others, and his mind for numbers, almost as good as Gordon's own. Taylor's connection to the club would later prove significant, as he became a figure of interest in the changing neighborhoods of Baltimore, opening a new EZ Kleeners location in a neighborhood just beginning to tip from white to Black, a fact that Maddie noted with her sharp eye for the signs of racial transition.

Significance

The Flamingo Club encapsulates the racial and social dynamics that run through the entire story. It is a place where a Black woman could earn a living and buy herself a nice fur stole, but where her disappearance would be treated as no real news. It is a place where a white bartender could refuse service to a white woman customer on the grounds of respectability, enforcing a code of conduct that had nothing to do with the actual dangers of the street. And it is a place where a man like Shell Gordon could aspire to legitimacy while running a criminal empire, a contradiction that mirrors the larger contradictions of a segregated city in transition. The club is not just a setting; it is a measure of how the world values—and fails to value—the people who pass through its doors.