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Content Warning: This section of the guide includes discussion of rape, racism, and gender discrimination.
Polly is one of the novel’s protagonists and narrators and is a Russian Jewish immigrant who has built a successful Manhattan brothel through shrewd management, discretion, and a hard-won understanding of the men who patronize her house. Arriving in the US as a 12-year-old and surviving a rape before drifting into the sex-work industry, she has taught herself to read powerful men, and she has parlayed that skill into a house whose clientele includes judges, columnists, and captains of industry. Polly prizes autonomy above almost everything else, and her narrative arc traces the slow erosion of that autonomy as the Combination tightens its grip on the city.
Polly is intelligent, self-aware, and mordantly funny, but she’s also lonely, and her friendships with her artistic clients reveal her hunger for intellectual companionship and social legitimacy that the “respectable” world won’t grant a madam. She is, in her own estimation, a businesswoman first, and the novel takes that self-description seriously even as it shows the psychological costs of the business, including the girls she can’t always protect, the payoffs that keep multiplying, and the friendships that curdle into transactions.
Her refusal to be broken by Dutch Schultz, by Lucky Luciano’s enforcers, or by the humiliations of arrest and public exposure makes her the novel’s most sustained portrait of dignity under duress, and her quest to regain her independence despite the steep personal cost grounds the historical legal drama in human emotion.
Eunice is the other co-protagonist and point-of-view character. One of her key traits is her strong sense of justice. This value was instilled in her from a young age due to her family history as the granddaughter of an enslaved man who made multiple attempts to liberate himself and the daughter of two civil-rights activists. She carries on her family’s legacy of courage through her trailblazing career as New York’s first Black woman district attorney. However, her work demonstrates The Personal Cost of Ambition, as her central role in Thomas Dewey’s prosecution of Luciano draws threats from the city’s criminal underworld and places significant strain on her marriage to Lisle Carter.
Eunice’s unlikely partnership with Polly is at the heart of the theme of Subverting Patriarchal Power With Female Alliances. Benedict and Murray use her perspective to deepen the novel’s examination of gender by exploring its intersections with race and class. Moments like Dewey’s initial resistance to allowing her to attend the trial that her work secured highlight the systemic barriers faced by Black women. Additionally, Eunice recognizes her own biases and becomes more understanding of other women’s struggles over the course of the novel, such as when Polly challenges her overly rosy understanding of sex work. The authors portray Eunice’s fight for justice as an act of great personal courage as well as a testament to the resilience of Black women.
Luciano is the novel’s principal antagonist and its coldest strategist. Where Schultz rules by terror, Luciano rules by organization: He envisions the Combination as a corporate enterprise that will absorb the city’s independent operators, including Polly among them, into a single hierarchy answerable to him. He’s charming when charm serves him and lethal when it doesn’t, and his patience distinguishes him from the older generation of gangsters he supplants.
The novel is careful to give him a coherent worldview rather than a caricature’s menace. He believes that the disorganized brutality of men like Schultz is bad for business, and that sex work, properly administered, is simply another industry deserving of modern management. His pursuit of Polly’s house drives much of the novel’s rising action and gives the book its central conflict. The criminal investigation into his operations and the subsequent trial provide the novel’s structure, and his brutal interactions with Polly and his organization’s threats against Eunice enhance the novel’s suspense. Luciano’s eventual conviction gives the story a triumphant conclusion that challenges Systemic Exploitation in the Sex-Work Industry and testifies to the remarkable possibilities created by Subverting Patriarchal Power With Female Alliances.
Lisle is Eunice’s husband. A successful dentist and a prominent member of Harlem society, Lisle is a key figure in the theme of The Personal Cost of Ambition. Throughout the novel, he pressures Eunice to quit her job on Dewey’s team lest they become targets of Mob violence: “I hope this grand crusade of yours doesn’t get you…and everyone in your family shot down in the middle of one of these safer Harlem streets” (28). The authors add nuance to Lisle’s characterization by showing how, despite their marital strife, he cares deeply for Eunice. In his speech at the NAACP dinner in his honor, an event that Eunice misses because she’s immersed in the case, he voices “how proud [he is] to be [her] husband” (344).
The moment near the end of the story when Lisle attends the trial marks a key victory for Eunice, signaling that they can repair that marriage and, by extension, that it’s possible for a woman to not have to give up her personal life for the sake of her professional one. Ultimately, Benedict and Murry use Lisle to demonstrate the pressure on women to fulfill traditional roles while also illustrating how it’s possible for men to support the success of the important women in their lives.
Schultz is a flat, static character who acts as a catalyst for the novel’s central plot. He’s depicted as volatile, violent, and paranoid. He’s a gangster who rules through brute force, and the novel uses him as a foil for the cunning and strategic Luciano. His actions at the beginning of the story, particularly forcing his way into Polly’s professional life and demanding that she host him and his crew in defiance of her established rules, disrupt her carefully maintained autonomy and foreshadow the greater threat of Mob control that follows his removal.
Schultz’s fixation on assassinating Dewey draws the attention and concern of other Mob figures, who correctly perceive that killing a special prosecutor would bring down consequences that none of them could survive. The power vacuum that follows his removal from the scene allows the more calculating Luciano to implement his plan for the Combination, thereby setting the main conflict in motion and demonstrating the novel’s argument that the older, showier gangsterism is being replaced by something more insidious.
Dewey, the crusading special prosecutor, functions as the novel’s instrument of legal reckoning and as an ambiguous figure of civic virtue. His campaign against organized crime supplies the external pressure that shapes nearly every choice the other characters make: Schultz plots to kill him, Luciano maneuvers to survive him, and Polly is eventually hauled before his investigators.
Dewey is portrayed as ambitious and self-consciously righteous, a man whose reforming zeal is inseparable from his political calculation, and the novel is unsparing about the way his prosecution of Luciano is part of his broader plan to campaign for higher office. His willingness to prosecute women like Polly to reach the men above them exposes the costs of his methods and complicates any easy reading of him as hero: The madams and sex workers he pressures into testimony are treated as means to an end, their reputations and livelihoods spent freely in the service of the mob boss’s conviction. Although Dewey fights the exploitation of sex workers by organized criminals, he upholds systemic corruption through his resistance to giving Eunice the credit she deserves, adding further nuance to Benedict and Murray’s exploration of Subverting Patriarchal Power With Female Alliances.
The women who live and work in Polly’s house function collectively as the novel’s most damning testimony against both the Combination and the Dewey investigation that claims to save them. Benedict and Murray give them enough interior life to resist the flattening categories imposed on them by gangsters, prosecutors, and reformers alike: Some are ambitious, some are traumatized, some are simply working, and none are reducible to the role of “victim” or “fallen woman.” Polly’s relationship to them is maternal, managerial, and guilty by turns, and the novel measures her moral standing largely by how she treats those who rely on her for protection. When Dewey’s investigators pressure them to testify, and when the Combination’s enforcers threaten them into silence, the girls become drafted into the novel’s larger arguments about women’s agency.



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