1. Discuss the ways in which Alexander Hamilton was a successful man. In what ways was he also a failure?

2. Alexander says only “honor” had an older claim to his heart than Eliza. Why was that? What else drove him, besides love and honor?

3. Elizabeth Schuyler did not believe the rumors of her husband’s infidelity. Why? Was she naïve? Were there other factors?

4. Whom did Alexander deceive more: his wife or himself?

5. If honor is key to Alexander’s motivations, what are the keys to Eliza’s character? How did they shape her actions?

6. How and why did Eliza come to accept her husband’s failings? Was she a feminist or a traditionalist?

7. Why did Alexander Hamilton cheat on his wife? Is there any evidence that Eliza’s behavior played some part in the distance that came between them?

8. Alexander Hamilton resigned as Secretary of the Treasury at the height of his powers? Why? Was that consistent or inconsistent with his character?

9. Is Alexander Hamilton tragic or triumphant in the novel? What about Eliza?

10. The Hamilton family was devastated by political partisanship. Are there parallels in our own time? What are the differences, and why?

11. What role does Ajax Manly play in the story? What does the reader learn about Alexander and Eliza through him?

12. Was Ajax Manly foolish for loving a slave? Is it believable that the first slave he loved was unwilling to run to freedom?

13. Alexander Hamilton, John Jay, John Laurens, the Marquis de Lafayette and Aaron Burr all endorsed abolition to some degree. George Washington freed his slaves upon his death. Why did others not challenge the institution, including Thomas Jefferson, James Madison and Eliza’s own family? Is it possible they did not think slavery was wrong?

14. What roles do Native Americans play in the book? Are they essential or peripheral to the story?

15. Parts of this story are well known, others less familiar. What surprised you? What techniques did the author use to create suspense about events like the final duel?

16. The book alternates between two points of view: Alexander’s and Eliza’s. What did Eliza perceive about Alexander that he might not have understood about himself --- and vice versa?

17. How does fatherhood shape Hamilton’s life? What were the effects of not having a father? Was he a good one or a bad one?

18. Alexander Hamilton was a critic of dueling, yet accepted Burr’s challenge. Why? Did he betray (or defend) his family by doing so?

19. The book is from the Hamiltons’ perspective. Who are the anti-heroes? Are they fairly portrayed?

20. Does the book change or confirm your view of America’s founders?