Will and Squares Begin Searching for Sheila

Will Klein and Squares begin searching for Sheila Rogers by looking backward: their investigation follows the traces of her earlier life, from the streets where she first arrived as a runaway to Louis Castman, the pimp who once controlled her. The search turns a private absence into a chain of testimony and leads, while revealing how vulnerable young people can disappear into a street life that Covenant House tries to reach but cannot always undo.

The Search Begins with the Past

When Will says he has to find Sheila, Squares agrees to help and points out that Will will not manage the search alone. Their first decision is to investigate her history rather than pursue an immediate destination. Squares frames that approach as looking back before moving forward, a method that becomes the search’s organizing principle: Sheila’s whereabouts are unknown, so the men begin with the people and circumstances that shaped her earlier life.

The investigation takes place against the work of Covenant House outreach. Its van moves into areas where runaway young people may be found, seeking out those who do not come to the shelter’s doors. The narrative describes street outreach as an effort to connect with the community’s most difficult corners and reach young people often dismissed as throwaways. It also stresses the limits of that work: more young people are lost than saved, and the longer a child remains on the street, the harder it is to help them leave. That institutional perspective gives the search a wider human context. Finding Sheila matters to Will personally, but her story belongs to a pattern of youth exposed to exploitation and difficult to retrieve once they have been drawn into it.

Tracing Sheila’s Street History

Squares explains that Sheila could have been among the women working the streets. She had come from the Midwest as a runaway, arriving by bus and entering street life. Will finds the possibility painful because Sheila is not an unknown young person to him but someone he loves and remembers with profound tenderness. The contrast between that intimate memory and her documented history makes the search more than a procedural inquiry: each fact about her past revises what Will must confront about the person he thought he knew.

Squares has consulted Sheila’s file. It records her first arrest at sixteen, followed by three more arrests within eighteen months, for prostitution while she was working for Castman. A later arrest involved drugs and a knife, though the attempted charges were dismissed. These records establish that Sheila had been entangled with the criminal justice system while still a teenager; they do not explain her whole life, but they identify Castman as the first concrete lead the search can pursue.

The search also exposes the racial tension within Will and Sheila’s relationship. Will recognizes that Squares’s reference to Sheila being Black is not a racist dismissal, but an acknowledgment of strain that Will had observed between them. He understands that the tension existed alongside, and was less powerful than, their love. The detail complicates the account of their closeness without reducing it: the search is driven by Will’s attachment, but the story does not present love as a force that makes every difference disappear.

From a Rumor to Castman

At a later stop, Squares asks Raquel whether she remembers Castman. Her immediate reaction is alarm: her expression goes slack, and she looks around. When Will asks where they might find him, Raquel offers only a rumor, directing them to a place near Wright Street and Avenue D. She then walks away, and Will watches her disappear into the night. The lead is uncertain, but it advances the inquiry from Sheila’s records to the network of people who may know Castman.

When Will and Squares locate him, they first hear from Tanya, who describes Castman’s past violence toward her and leaves the room. Her account gives the men reason to confront him, and Squares asks whether he is Castman. The encounter makes clear that their questioning concerns an alleged abuser, not merely a name in an old file. Later, when Will asks about Sheila directly, Castman recognizes her name and agrees to speak. His recollections become a central, though self-interested, source of information about her early years.

What Castman’s Account Reveals

Castman says he met Sheila roughly ten or fifteen years earlier, when she arrived by bus from Iowa or Idaho. He describes waiting at a terminal for new arrivals and presenting himself as a respectable, patient businessman. His account reveals the calculated way he sought out young runaways and drew them into his control. He also recounts subjecting Sheila to coercion and exploitation. The details establish the severity of what she endured, while the restrained account here keeps the focus on what the disclosure changes: her early street history was not simply a series of choices or arrests but a period in which an adult predator exercised power over a vulnerable teenager.

Castman says Sheila worked for him for two or three years. He claims she began attracting regular customers, then connected with more powerful drug dealers and started carrying and delivering drugs. He also says she was getting clean. When he considered pressuring her, according to his account, men with influence warned him to stay away; one of them was Lenny Misler, a mob attorney who represented Sheila after she was arrested carrying drugs. Castman says he never saw her again. He had heard that she was going to college but could not name the college and was unsure whether the report was true.

That uncertain ending defines both the value and the limit of the search’s early progress. Will and Squares uncover a history, identify a former exploiter, and learn that Sheila may have escaped Castman’s control with help from people more powerful than he was. Yet Castman cannot tell them where she went, and the college story remains rumor. The search therefore yields no confirmed location; instead, it replaces an unexplained absence with a more troubling and more specific account of the risks Sheila faced, the violence she survived, and the possible break in her life that left her whereabouts unknown.