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Content Warning: This section of the guide includes discussion of physical abuse, emotional abuse, racism, gender discrimination, substance use, and addiction.
On January 22, 1936, in New York, Eunice analyzes new wiretap transcripts obtained using information from her informant, Polly. Polly implicates Dave Betillo, a known killer for Luciano, which captures Dewey’s full attention. The wiretaps confirm that Betillo runs the day-to-day operations of the sex-work racket and identify other key figures, including enforcer Thomas Pennochio and bookers Ralph Liguori and Jack Ellerstein.
Murray shows Eunice a newspaper article that leaks specific details of their investigation, confirming a leak within their office. Eunice and Murray learn from Dewey that the article prompted Luciano to flee the city. Seizing the opportunity, Eunice proposes a plan: First, they must move to arrest all the bookers and bondsmen. Then, on the following night, they’ll raid 80 brothels simultaneously. With their protectors in jail, the arrested women will have no one to call for help, which Eunice believes will force them to cooperate. Dewey approves the plan immediately.
On January 31, Polly maintains an appearance of normalcy at her brothel, concealing her hatred for Luciano’s men as she plots her revenge. Two visiting gangsters, Jack McGurn and Bugsy Siegel, cause a brief disturbance. A regular patron, columnist Walter Winchell, asks about Virginia. Polly lies and says that Virginia is visiting family, though Winchell is skeptical. Polly is privately tormented by Virginia’s absence and continues a discreet search for her.
The Lion gives her a subtle signal to check for a message. Polly has another girl distract the gangsters while she escapes through a secret entrance behind a bookshelf. Remembering what happened to Virginia, Polly resolves to see the plan through, whatever the cost.
On the dangerously icy night of February 1, 1936, Eunice goes to Harlem to witness a raid on a notorious brothel, a key part of the operation she orchestrated while Lisle is out of town. The night before, her team arrested Dave Betillo, Thomas Pennochio, Jesse Jacobs, and Pete Harris, among others. The raid’s commanding officer, Deputy Chief Inspector David McAuliffe, is furious at her civilian presence, but she insists on staying. She watches as men flee and officers escort the women, many inadequately dressed for the freezing weather, into paddy wagons. Among them is the infamous and defiant madam Red Sadie.
Later, at a processing center on the floor beneath the prosecution offices inside the Woolworth Building, Justice McCook arraigns the women, setting an unprecedentedly high bail of $10,000. During questioning, the women, including one named Daisy Wilson, mention the Combination but are too terrified of the Mob to cooperate further. Eunice believes that three nights in jail will change their minds. The next morning, Murray informs her that a leak allowed nearly half of the brothels to be tipped off, including Polly’s. Eunice reflects that keeping Polly safe was part of their deal.
By March 5, 1936, Polly is in Honolulu, Hawaii, having been on the run for a month. Eunice upheld their deal by warning her before the raids, allowing Polly and her girls to escape. Polly has been funding the girls’ hiding places while she travels west. After a tense visit with her father in Chicago, Illinois, and a cold reception from some former clients in California, she sought refuge in Hawaii.
At the Royal Hawaiian Hotel, Polly reads about the arrested sex workers, now dubbed “white slaves” by the press. She feels a surge of guilt because she didn’t intend for them to endure long jail stays. She runs into the writer Robert Benchley, and they become intoxicated at the hotel bar. Polly lies, claiming that she narrowly escaped the raids because one of her employees saw another brothel getting raided. Drunk, Benchley loudly announces her identity to the entire bar as “the world’s most famous madam” (211), destroying her anonymity.
A month after the raids, on March 12, Dewey’s prosecutors are frustrated because none of the arrested women will testify about the Combination or its leader. Eunice, however, reports that some girls have mentioned enforcers and a leader they only call “the Boss.” Recognizing Eunice’s unique ability to gain the women’s trust, Dewey assigns her to handle all their interviews.
Alone with Dewey, Eunice is stunned when he voices doubt that Luciano is the boss since no witness has named him directly. Eunice argues that Luciano is simply well insulated. Back at her desk, she concludes that the terrified girls won’t break the case; her only path to Luciano is through the madams. She focuses on Red Sadie, the most defiant of the group, and resolves to find a way to make her talk.
Still in Honolulu, Polly is hounded by financial troubles and local criminals who want her to open a brothel. On March 12, she receives an urgent telegram from Eunice asking for information on Sally Kaplan, also known as Red Sadie, to compel her testimony.
Polly is shocked that Eunice found her but realizes that she must continue to help to bring down Luciano’s Combination and secure a safe future for her girls. She recalls overhearing two of Luciano’s top men, Dave Miller and Jimmy Frederico, discussing their work with Sadie. This information could provide the direct link Eunice needs. Polly bribes the hotel messenger to discreetly send a telegram back to Eunice, telling her to use the names Miller and Frederico to pressure Sadie. Polly prepares to leave Hawaii.
On March 27, Eunice tricks Red Sadie into a meeting at the prison. She tells Sadie that the District Attorney’s Office, needing a high-profile conviction, has decided to move forward with her prosecution, a move that would mean 15 years behind bars. To make the threat credible, Eunice uses the names Polly provided, telling Sadie that they know she worked with Miller and Frederico.
Feeling abandoned by the Mob and facing a long prison term, Sadie agrees to cooperate in exchange for protection. She details the Combination’s operations, the widespread corruption, and the roles of key players. Terrified, she warns Eunice that naming the boss will put both of them in danger. Finally, she confirms that the leader of the racket is Luciano. Elated, Eunice leaves the prison, only to find her car in the garage splattered with red paint. Shaken, she reports her breakthrough to Dewey but deliberately conceals the paint incident, fearing that news of threats will silence potential witnesses and slow the investigation. Just then, Dewey receives a note informing him that Luciano has fled the city again. Recognizing that they’re out of time, Dewey decides to indict him.
Back in New York on March 27, a financially strained Polly sells her beloved fur stoles. She has moved to a cheaper apartment and is living on savings, unable to safely run her business. She meets Eunice at the secluded Ladies Pavilion in Central Park. Eunice confirms that Red Sadie named Luciano as the boss.
Eunice turns to the next gap in the case, focusing now on Mildred Balitzer, a madam with a substance addiction whose testimony could strengthen the prosecution’s chain of evidence. Polly reveals that Mildred is the common-law wife of Pete Harris, a booker also in custody, and that the two are deeply in love. From this, Eunice sees that she can use the relationship to pressure both of them to cooperate. Pressing Polly for more details, Eunice makes clear that she intends to pursue every available thread, and Polly resolves to help until Luciano is convicted.
On April 1, 1936, newspapers announce Luciano’s arrest in Arkansas. After the paint incident, Lisle left a for Eunice note saying that he needed time away. Her friend Regina joins her for an appointment at a Harlem beauty salon, celebrating Eunice’s success. Eunice confides in her friend about the threats and Lisle’s departure. When Regina suggests that she quit, Eunice explains that her work is about achieving personal freedom from the societal expectations that have always constrained her, comparing her struggle to her enslaved grandfather’s fight for liberation.
That evening, at the Apollo Theater, Lisle unexpectedly joins her. During the show, Duke Ellington publicly acknowledges her from the stage as “Mrs. Lisle Carter” for her work with the prosecutor’s office. As the theater applauds, Lisle proudly helps her to her feet, giving Eunice hope for their future.
On April 22, as Polly prepares to meet Eunice, she receives a phone call: Her mother, whom she hasn’t heard from in 25 years, has immigrated from the Soviet Union and is in Brooklyn with Polly’s brothers. Polly is both overjoyed and terrified that her mother will discover her true profession. At her meeting with Eunice in Central Park, Polly’s news about her mother elicits a moment of shared empathy from Eunice over being separated from their family members.
Just after leaving the park and heading toward her apartment, at the corner of 65th Street and Central Park West, Polly is forced into a car by mobsters. She’s driven in a three-car caravan to a secret office. She concludes that Luciano must know that she has been feeding information to Dewey’s investigation and that he’s sent his men to abduct and murder her.
Polly is brought before a council of the country’s top mobsters, including Joseph Bonanno and Tommy Gagliano. They explain that they need her help to discredit potential witnesses in Luciano’s trial, proving that they don’t know she’s the source of the investigation’s information. The mobsters are specifically interested in Mildred Balitzer. Polly carefully confirms Mildred’s heroin addiction, suggesting that they could use it to make her an unreliable witness. An attorney for Luciano then shows her a list of other potential witnesses. Polly identifies two women she has heard of who may work for another madam, Diamond Lil.
When the lawyer asks how she managed to evade the raids, Polly delivers her practiced alibi about an employee tipping her off. The lawyer remarks that she was “very, very lucky” (268). Polly masks her fear with her signature bravado, inviting the gangsters to her house for a party once the trial is over and her business can resume.
On April 26, Eunice conducts a final interview with Mildred, who’s now motivated to cooperate to secure her and her husband’s freedom. Mildred provides important testimony, describing a direct conversation in which Luciano refused to let Pete Harris leave “his business,” explicitly referring to “his rackets” and describing Pete’s role as one of his “top bookers.” This directly links Luciano to the sex-work ring.
Thrilled, Eunice returns to the office to find that she has been excluded from a key meeting. Dewey informs her that she will not be on the trial team, citing concerns that her race would be a distraction for the jury and the press. He assigns another lawyer, Barent Ten Eyck, to prepare the female witnesses. Devastated and furious, Eunice goes to Grand Central Station for a meeting with Polly. While waiting inside the terminal, she decides to quit her job to save her family.
Eunice tells Polly this will be their last meeting because she has been removed from the trial team. Polly is furious, accusing Eunice of abandoning the girls out of selfish careerism. Eunice fires back that Polly is the one holding out, refusing to share her own firsthand knowledge of Luciano to protect herself. The accusation hits home, and an emotional Polly says that she’s fought to protect her girls, including Virginia.
Eunice’s demeanor changes. She reveals that she met Virginia after her arrest in January but that the Mob’s lawyer arrived to bail her out. Eunice confesses that she secretly helped Virginia escape from the station, sacrificing valuable testimony to save the woman’s life. Polly apologizes to Eunice and tells her, “You are not who I believed you to be” (283). Acknowledging that Eunice is the only one who truly cares for the girls, Polly vows to find a piece of evidence so significant that Dewey will have no choice but to put Eunice on the trial team.
On May 1, consumed by guilt, Polly recalls how, two days after her Grand Central meeting with Eunice, she got her girls drunk on champagne to gather intelligence. One of her girls, Rosalie, recounted a rumor about Nancy Presser, one of Luciano’s favorite girls. Nancy had allegedly overheard Luciano at Keen’s English Chop House personally giving orders to his lieutenants to use violence against uncooperative girls and madams. This was the direct evidence Eunice needed.
The memory is interrupted by a commotion. Polly’s parents are at her door, holding a newspaper with her picture under the headline, “Why Isn’t the Vice Queen in Jail?” (291). Her father disowns her, but Polly retorts that he’s the one who should be ashamed for sending a child alone to the US to be exploited. Heartbroken, Polly is embraced by the Lion and her girls, who offer her unconditional support.
On May 2, Eunice has a brief, celebratory dinner with Lisle, who has won a prestigious award. She then meets with Dewey. She tells him that she has evidence that will strengthen their case against Luciano but demands a seat on the trial team in return.
Dewey expresses his concern that her race will be a “distraction.” Eunice argues that her contributions have earned her a place at the prosecution table. She reveals that Nancy can testify to hearing Luciano personally order violent enforcement of the racket. Recognizing the power of this direct evidence, Dewey relents and agrees that she will be at the trial. Back at her desk, Eunice feels a giddy sense of victory. She picks up Polly’s latest note, tucks it into the case file, and closes the drawer.
In Part 2, the authors use Eunice’s orchestration of the massive police raid to examine The Personal Cost of Ambition. Watching as inadequately dressed women are herded into police wagons in the freezing cold, Eunice confronts the human price of her brilliant tactical maneuver. The raid is a large-scale intelligence-gathering tool, but it also treats the women as collateral, a point underscored by the press’s labeling of them as “white slaves,” a term that sensationalizes their plight while erasing their agency. Eunice’s professional authority grows in direct proportion to her domestic instability. She orchestrates the dangerous raids while her husband is away, and the Mob’s swift retaliation, which takes the form of “red paint […] splattered across the door and hood” of her car (228), pushes their marriage to its breaking point. Her authority is also constantly challenged from within her own ranks. She must argue with a police inspector just to witness the raid she designed, a stark reminder of her precarious position as a Black woman in a white, male-dominated field.
Polly’s flight from New York initiates a crisis that strips away her carefully constructed identity, externalized by the sale of her fur stoles. The furs represent her ascent from a sweatshop worker to a woman of influence, embodying a hard-won status and the illusion of invulnerability. When she’s forced to sell them, the stoles transform into a motif illustrating the cost of ambition and expose the precarity beneath her seemingly glamorous life. This loss of control intensifies in Hawaii when her friend Robert drunkenly announces her identity as “the world’s most famous madam” (208), shattering her anonymity and forcing her to confront her public notoriety. The unmasking is both external and internal. Polly’s alibi for escaping the raids is tested when she’s abducted and brought before a council of mobsters. There, she must deploy her “sassy Polly Adler” persona to survive (268), doling out just enough information on witnesses like Mildred to appear helpful without revealing her role as an informant. This high-stakes performance contrasts sharply with the raw vulnerability she shows after her father disowns her, where she’s forced to confront the origins of her persona.
The alternation between Eunice’s and Polly’s perspectives highlights the parallel pressures they face while navigating hostile, male-dominated systems. Polly’s escape from her brothel through a secret passageway mirrors Eunice’s reliance on covert meetings and back-channel communications to build her case within the rigid, exclusionary legal system. Both women are powerful insiders in their respective worlds, yet both are forced to operate from the margins to achieve their objectives. This parallel is sharpened when Polly is abducted and brought to the secret mob meeting in an anonymous office building. Meanwhile, Eunice is excluded from Dewey’s official meeting where the trial team is selected. The settings of a hidden gangster conference room and a closed-door legal strategy session become twin arenas of male power from which both women are either controlled or barred. These scenes demonstrate that despite their opposing social and legal standings, Eunice and Polly are engaged in a similar struggle against patriarchal structures that seek to limit their agency.
In these chapters, the secret meetings between Eunice and Polly evolve from a transactional exchange of information into a genuine, if fraught, alliance. When Polly accuses Eunice of abandoning the case for personal ambition and Eunice accuses Polly of withholding important testimony to protect herself, their mutual suspicions and differing stakes are laid bare. The argument fractures their fragile trust until Eunice reveals that she secretly helped Virginia escape police custody, sacrificing essential evidence to save a woman’s life. This confession of an illegal, compassionate act demonstrates to Polly that Eunice’s motives transcend professional gain. By breaking the law to protect one of the very women the system exploits, Eunice establishes a foundation of shared humanity with Polly. This moment crystallizes the theme of Subverting Patriarchal Power With Female Alliances, showing that their combined strength is forged from a mutual recognition of the compromises required to protect women within a corrupt system. Polly’s subsequent vow to find evidence to force Dewey’s hand solidifies their partnership, transforming it from one of informant-handler into a collaboration between equals.
Dewey’s decision to remove Eunice from the trial team because her race would be a “distraction” is a painful culmination of the institutional racism she has navigated throughout the investigation. Despite being the intellectual author of the case, her success is nearly nullified by the very system she serves. This professional betrayal forces Eunice to articulate her deepest motivations. In a key conversation with her friend Regina, she reclaims her narrative, linking her struggle to her enslaved grandfather’s fight for liberation. She’s fighting against shackles that “aren’t always made of iron” (248), reframing her professional ambition as a deep quest for personal and ancestral freedom. Her newfound clarity is publicly affirmed at the Apollo Theater when Duke Ellington acknowledges her work, placing her firmly within Harlem’s proud cultural leadership, a powerful counterpoint to her marginalization by the white legal establishment. When she finally confronts Dewey, she’s no longer just an employee but a power broker, leveraging the very intelligence that her female alliance produced to bargain her way back onto the team.
This section brings both protagonists’ family dynamics to a crisis, contrasting the fragility of biological ties with the resilience of chosen families. Lisle’s departure leaves Eunice’s marriage in peril, a direct consequence of the dangers that her ambition has invited into their lives. Their quiet reunion at the Apollo, however, signals a potential path toward reconciliation built on Lisle’s pride in her accomplishments. Polly’s story offers a bleaker resolution. The long-awaited reunion with her mother is immediately followed by a brutal rejection from her father after he discovers her profession. Her retort, “You are the one who gave Pearl no choice but to turn into Polly” (292), is an indictment of the parental abandonment and economic desperation that fuels the Systemic Exploitation in the Sex-Work Industry. In the raw aftermath of being disowned, Polly is embraced by the Lion and her girls. This juxtaposition argues that for women operating outside conventional society, chosen families forged through shared struggle offer a more authentic and reliable form of support than biological relationships.



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