Gather initial thoughts and broad opinions about the book.

1. Rubicon is a work of narrative history that reads more like a fast-paced story than a traditional academic text. Did you find this style effective in bringing the period and its characters to life? Why or why not?

2. How does Holland’s account of the Roman Republic compare to his other works, such as Persian Fire (2005) or Dynasty (2015), if you’ve read them? If this was your first time reading Holland, does his approach make you interested in exploring more of his writing?

3. Of all the dramatic events described in the book, from Sulla’s march on Rome to Caesar’s assassination, which one stood out to you as the most pivotal or shocking?

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

1. The Roman concept of liberty was defined by the freedom to compete for glory and the absence of a king, not by a modern ideal of equality. How does this compare to your own understanding of freedom?

2. The guide notes that for the Romans, moral excellence and reputation were the same thing. How important is public standing to you, as compared to private values?

3. Was there a figure whose motivations you found particularly understandable or, conversely, completely alien? For example, did you sympathize with Cato’s rigid principles, Pompey’s desire for validation, or Caesar’s raw ambition?

4. Holland describes the Republic’s constitution as valuing tradition above all else. How do you personally balance honoring tradition against the need for reform?

5. What do you think of the intense pressure on aristocratic Romans to live up to the achievements of their ancestors? Are there any legacies you feel pressured to live up to?

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

1. The book chronicles how a republic can collapse from within, eroded by political polarization, systemic corruption, and the concentration of power. What lessons, if any, do you think the fall of the Roman Republic holds for modern democracies?

2. What parallels, if any, did you see between the political use of spectacle in Rome, like Pompey’s triumphal games or Clodius’s gang warfare, and the role of media and public performance in today’s politics?

3. Octavian successfully waged a propaganda war against Antony by portraying him as serving a foreign queen, Cleopatra. How does this use of xenophobia and moral panic as a political tool compare to similar instances throughout history or in the present day?

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

1. Holland opens the book with Caesar’s moment of indecision at the Rubicon before flashing back to trace the Republic’s history. What is the effect of starting the story at this critical turning point?

2. Holland avoids painting figures like Caesar or Pompey as simple heroes or villains. How does he create nuanced portraits of these larger-than-life individuals?

3. What is the significance of fortuna, or luck, in the narrative? How does Sulla’s branding of himself as “Felix,” “The Fortunate One,” represent a shift in the understanding of what constituted legitimate authority?

4. Cicero’s letters and speeches provide much of Holland’s primary source material. How does seeing events through Cicero’s often anxious and conflicted perspective shape your understanding of the Republic’s collapse?

5. How does Holland’s historical account of these events resonate with their famous depictions in literature, such as in Shakespeare’s plays Julius Caesar (1599) or Antony and Cleopatra (1607)?

Encourage imaginative and creative connections to the book.

1. The assassins of Caesar are described as having no plan for what to do after the deed was done. If you were to advise Brutus and Cassius, what steps would you have told them to take immediately following the assassination to secure their vision of a restored Republic?

2. If you were to adapt Rubicon into a modern television series, whom would you cast in the key roles of Caesar, Pompey, Cicero, Cato, and Cleopatra? What qualities would you look for in the actors to capture these complex personalities?

3. Imagine you are an ordinary Roman citizen, perhaps a merchant or a craftsman, living through the final years of the Republic. Faced with the choice between Caesar’s populist promises and Pompey’s defense of the traditional order, where would your loyalties lie?