Gather initial thoughts and broad opinions about the book.

1. What was your overall experience reading a character-driven, narrative account of a complex financial collapse? Did Sorkin’s focus on the personalities and motivations of figures like Charles Mitchell and Thomas Lamont make the 1929 crash more understandable for you?

2. The guide mentions Sorkin’s bestselling book Too Big to Fail (2009), which covers the 2008 financial crisis. For those of you who have read it, how does his portrayal of the 1929 crash compare to the more recent crisis? What parallels or key differences did you notice in the behavior of the key players and the government’s response?

3. The book is filled with larger-than-life figures, from the speculator Jesse Livermore to the reformer Senator Carter Glass. Which character’s story arc did you find most compelling or surprising, and what did their journey reveal about the era?

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

1. John Raskob famously promoted his investment trust with the idea that “Everybody Ought to Be Rich.” What phrase would you use to encapsulate your view of the financial sector’s role and purpose? Why, and what does this mean to you?

2. The Pecora hearings revealed that many practices, like tax avoidance schemes and “preferred lists,” were legal yet viewed by the public as deeply unethical. Think of a time when you made a decision in an ethically or legally gray area. How do you feel about your choices and why?

3. Sorkin describes the self-fulfilling effects of a crisis in public confidence. Think of an economic or political event which has caused you anxiety. Why did you feel this way? Did it turn out better or worse than you feared at the time?

4. The 1920s saw a boom in consumer credit and installment plans that normalized household debt. What experiences have you had with credit, debt, and savings or investments, and how have these shaped your attitudes toward them?

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

1. A central theme is the tense conflict between Wall Street’s desire for self-regulation and Washington’s push for public oversight. Where do you see this same dynamic playing out today in debates about the regulation of finance, technology, or other powerful industries?

2. The book shows how an often-complicit financial press and orchestrated publicity campaigns helped fuel the speculative bubble. How does the role of the media in shaping public economic perception in 1929 compare to the influence of financial news networks, social media, and online forums today?

3. What is the role of a public “reckoning” after a major societal crisis? The Pecora hearings served this function after the crash, providing a forum for accountability. Do you think our society still has effective mechanisms for this kind of public accounting after national failures?

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

1. Sorkin begins the book in medias res, with Charles Mitchell’s personal crisis on the eve of Black Tuesday, before starting the main narrative  eight months earlier. How did this structure affect your reading experience and your perception of the characters’ actions as the inevitable crash approached?

2. How does Sorkin use contrasting language to portray the gap between the “old guard” of finance, embodied by Thomas Lamont’s discreet and patrician style, and the “new guard” of Charles Mitchell’s populist, mass-market approach?

3. Do you consider Sorkin’s message to be one primarily of optimism or pessimism? Explain why, using examples.

4. Analyze Sorkin’s use of varied primary sources. How does the form and style of source material underpin the narrative at significant points of action or tension?

5. The Empire State Building is presented as a symbol of the era’s ambition. What other symbols or motifs, helped you understand the psychological climate of the boom and the despair of the bust? How were these used by Sorkin?

Encourage imaginative and creative connections to the book.

1. Ferdinand Pecora’s investigation is presented as a masterclass in public theater, turning dry financial matters into a national drama. You’ve been tasked with designing a museum exhibit based on the Pecora hearings. What key documents, artifacts, and interactive elements would you feature to convey the tension and historical significance of this public reckoning?

2. Many key players wrote private letters that revealed thoughts that sharply contrasted with their public statements. Choose one character, like Thomas Lamont, Herbert Hoover, or Charles Mitchell’s wife, Elizabeth, and write a short letter from their perspective during a key moment of crisis. What would they confess or complain about that they couldn’t say publicly? Who would they write to?

3. You are a journalist hired for a modern-day publicity campaign. Instead of damaging a reputation like Charley Michelson, your goal is to restore public trust in the financial system after a major scandal. What would your three-point communication strategy be, and what narratives would you try to shape to rebuild confidence?