City of Orphans is a 2011 middle-grade novel by Newbery Medal-winning author Avi. Set on the Lower East Side of New York City in 1893, it centers on 13-year-old Maks Geless, who works as a newsie to provide for the needs of his immigrant family. When Maks’s sister is jailed for theft, he is tasked with gathering clues to help save her.

Plot Summary

Maks spends his days selling papers with his newsie friends and traveling through New York City dodging the filth and crime of the industrialized urban life. Until now, his most formidable foe has been red-headed bully Bruno and his Plug Ugly Gang. Attempting to outrun the gang, he trips over a young orphan girl named Willa living in an alley. Taking her home for a hot meal, Maks discovers he has more to worry about than just the Plug Ugly waiting for him on the street corner. His sister Emma has been accused of stealing a valuable watch at the Waldorf Hotel, where she works as a maid. Maks and his immigrant family live on slim margins as it is and have no spare income to pay for a lawyer, so it will be up to Maks to find a way to prove her innocence.

With his newfound friend Willa and her trusty club by his side, he sets out to find someone in the city to aid him in unraveling the details of the theft. They find Bartleby Donck, a former detective turned social justice warrior, in a squalid tenement flat very clearly suffering from end-stage tuberculosis. Donck struggles to even hear them but agrees to help sleuth out the truth. Meanwhile, the children must constantly dodge Plug Uglies waiting to pounce on them. Though Willa is happy to have a full belly and roof over her head, she is unsure about this new path her life has taken, and she will have to beat back the trauma of her past to help Maks save his sister and become a part of the Geless family forever.

While working tirelessly to find clues to help his sister, Maks must also manage his family. His father and mother lack the skills to navigate edgy American city life and are nostalgic for their home back in Denmark. Maks’s younger brothers idolize him, and he must work to keep a cool head around the house so as not to further frighten them. Emma is not the only Geless daughter in trouble. The younger Agnes is trying and failing to hide symptoms of consumption. Once again, the family’s financial woes prevent Agnes from receiving treatment, and her cough worsens daily.

Donck trains the children in basic detective work and scores Maks a job at the Waldorf through an old friend, Mr. Packwood, who manages the hotel. Going by Maks Brown, Maks works as a bell boy and scours the hotel for clues while trying not to be distracted by the luxury of its décor and patrons. Maks discovers key details that reveal his sister was set up by a stealthy criminal, but he will need Donck’s help to put together all the pieces. He is also carrying the news that Willa’s father is alive and staying at the Waldorf. Meanwhile, the clock is ticking for Emma as she languishes in The Tombs, a wretched and detestable prison.

Tensions rise as Willa is kidnapped by the Plug Uglies and Maks must gather his newsie friends to rescue her from the gang’s secret hideout in an abandoned building. When the building catches fire, Maks rescues Willa just in time, but not before Bruno escapes out a slim alleyway.

Bruno may be a bully on the surface, but behind his tough exterior, he is a troubled, angry teenage boy. Since unsuccessfully mugging the gangster Brunswick, he has been his bondservant with the unpleasant task of taking down the newsies. Bruno reaches his breaking point after narrowly escaping death in the fire and vows to break Brunswick’s hold on him once and for all.

The novel reaches its climax as Bruno, Maks, and Willa all arrive at the Waldorf looking for Brunswick, who is Willa’s father. Bruno barges in wildly swinging a shovel, and Brunswick fights in defense. As Bruno goes for Brunswick’s pistol, he fatally shoots Brunswick. Packwood arrives just in time to take down Bruno. All this unfolds as the children watch in horror. Willa sits with her father as he breathes his last breath, and Packwood finds the missing watch on the ground. Though traumatized by what they have witnessed, the children return home to a rejoicing family. Emma will be saved. Packwood stands in for a now bedridden Donck, presenting the evidence to the judge, who throws out Emma’s case and releases her immediately. The Geless family is reunited. The novel ends with a hopeful tone as all the children find steady work to support the family and still pursue their education.

Avi traces Maks’s coming-of-age journey, set against the backdrop of a New York emerging from the 19th century into a new, modern era. The author addresses systemic xenophobia, governmental corruption, and economic hardship while painting a picture of familial love and hopeful altruism.