In City of Orphans by Avi, a young boy, named Maks tries to solve a mystery to prove his older sister Emma is innocent of stealing a valuable gold watch. Maks is a newsie, meaning he works on the street selling newspapers to make money in the late 1800s. The newsies have one fear, the Pug Uglies gang. The Pug Uglies target the newsies, beat them up and take the money they have earned. When Maks finds himself in an alley face-to-face with the Pug Uglies, Willa, a girl in tattered clothing who lives in the alley, protects Maks with her stick. The stick is a security blanket of sorts and Willa always keeps it with her for protection. As Maks and Willa become friends they realize that Willas missing father and the case of the stolen gold watch have things in common. Maks and Willa must work together to unravel the mystery and save Emma from jail.