The Yiddish Policemen's Union

Gather initial thoughts and broad opinions about the book.

1. Were you satisfied with the way the mystery wrapped up? Why or why not?

2. The novel borrows many tropes from hardboiled detective fiction. How did it compare to classics like Raymond Chandler’s The Long Goodbye or Dashiell Hammett’s The Maltese Falcon? What were the obvious similarities and differences?

3. What was your reaction to Meyer Landsman as a protagonist? Did you sympathize with his journey, or were there aspects of his character that prevented you from rooting for him?

Encourage readers to connect the book’s themes and characters with their personal experiences.

1. The novel wrestles with fate versus free will. In your own life, do you feel mostly in control of your choices, or do circumstances make you feel boxed in?

2. The book raises questions about whether violence can ever be justified in the name of belief. How do you feel about this idea? How does it connect with the way you’ve seen religion or ideology used in the world around you?

3. Landsman struggles to act on limited knowledge. When you face decisions, do you try to gather as many facts as you can? Or do you think it is better to go with your gut and deal with the consequences later?

4. Mendel Shpilman is forced to live under the burden of his family’s expectations for him. How do you deal with the expectations that other people have for you? In general, do you think it is important to meet those expectations or do you try to defy them?

Examine the book’s relevance to societal issues, historical events, or cultural themes.

1. How does the novel’s depiction of refugees facing impending displacement connect with the way refugees are treated in the real world today?

2. The book raises difficult questions about sovereignty and violence in the Middle East. Did it shift or complicate your understanding of current conflicts in the region? How does the novel frame the cost of trying to secure a homeland?

Dive into the book’s structure, characters, themes, and symbolism.

1. The novel uses an alternate history to develop its setting. Analyze what strategies Chabon uses to build this world and history and how he incorporates details about it within the plot.

2. Berko wrestles with his mixed heritage as a Jew and as a Tlingit. How does Chabon use his character to explore questions of identity, belonging, and cultural survival in Sitka?

3. Mendel Shpilman is portrayed as a reluctant messiah. How does this portrayal complicate traditional messianic archetypes?

4. In this novel, how does Chabon both rely on and critique noir conventions?

Encourage imaginative and creative connections to the book.

1. Imagine a new mystery for Landsman to solve after the events of this novel. What kind of case would challenge him most, given his character flaws and his personal history?

2. Chabon reimagines world history by altering one pivotal turning point. If you were to apply this “alternate history” methodology to radically alter the history of your country or local community, which historical moment would you choose to change? How might daily life look different today?