The Great Contradiction: The Tragic Side of the American Founding

Gather initial thoughts and broad opinions about the book.

1. Ellis frames the book’s two central tragedies as either a “Greek tragedy” (inevitable) or a “Shakespearean tragedy” (avoidable). How did this central question shape your reading experience and your final judgment of the founding generation?

2. How does this book’s focus on the “downside” of the founding compare to other works you may have read by Ellis, like Founding Brothers (2000), or to the way this period is generally presented in popular history?

3. What part of the author’s argument did you find most surprising or challenging to your previous understanding of the American founding?

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

1. The Founders repeatedly chose to defer action on slavery for the sake of national unity. Think about a time when you’ve seen a difficult moral issue get postponed to maintain harmony within a group, whether at work, in a community, or in a family. What are the costs of such a deferral?

2. George Washington’s deep concern for his historical legacy influenced his thinking about emancipating his enslaved people. How important is the way you will be remembered when you make difficult decisions? Has thinking about your future reputation ever influenced a choice you made?

3. Ellis highlights the concept of “unpainted pictures,” referring to the important, often brutal, realities of history that are left out of popular narratives. Can you think of a story from history that you learned growing up that now seems incomplete or romanticized after reading this book?

4. James Madison is presented as a “prudent revolutionary” who repeatedly relied on compromise to preserve national unity. Think about a time when you accepted a compromise because it seemed necessary to achieve a larger goal. Looking back, how do you decide whether that compromise was justified?

5. Ellis draws on historian David Brion Davis’s phrase “perishability of revolutionary time” (19), a brief window when radical change feels possible before things settle into a new normal. Have you ever experienced a similar moment in a community or organization where there was a fleeting opportunity for major change?

6. Patrick Henry frankly admitted that he couldn’t justify slavery but chose to continue the practice anyway. Have you ever recognized a conflict between your principles and your actions? What made it difficult to bring the two into alignment?

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

1. How might Ellis’s critical examination of the nation’s “great contradiction” complicate the way Americans commemorate and understand the country’s founding?

2. Ellis identifies a recurring “backlash pattern” in American history, where significant steps toward racial equality are met with powerful resistance. How persuasive do you find this pattern as a way of understanding contemporary debates over racial equality? What examples, if any, come to mind?

3. The federal government was unable to enforce the Treaty of New York as settlers continued to cross Creek borders with support from Georgia. What does this failure suggest about the limits of federal authority when state governments and large numbers of citizens resist national policy?

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

1. Ellis analyzes the failure to end slavery and the failure to prevent Indigenous removal through his distinction between “Shakespearean” and “Greek” tragedy. How does placing these two failures within the same tragic framework shape the book’s historical argument?

2. What is the significance of the metaphor of slavery as the “Ghost at the Banquet” during the Constitutional Convention (79)? How does this image help you understand the Founders’ strategy of deliberate avoidance?

3. Ellis ends the book with chapters centered on Mount Vernon and Monticello. How does his treatment of these two plantations illuminate the different ways that Washington and Thomas Jefferson confronted the contradictions between their ideals and slavery?

4. What does Ellis’s phrase “enlightened obfuscation” reveal about Madison’s approach to slavery, particularly when considered alongside his central role in shaping the Constitution?

5. Compare Benjamin Franklin’s late commitment to abolition with Jefferson’s continued inaction on slavery. What personal, political, and intellectual factors does Ellis identify as contributing to their different responses?

6. How does the theme of Demographic Pressures and the Limits of Reform connect the nation’s failure to end slavery with the tragic outcome of its policy toward Indigenous peoples?

Encourage imaginative and creative connections to the book.

1. Imagine you’re curating a museum exhibit based on the book’s concept of “unpainted pictures.” What three scenes from the Revolutionary War era would you choose to depict to give visitors a more complete and challenging understanding of the period?

2. If you were to write a satirical essay in the style of Franklin’s “Historicus,” what modern public debate would you tackle? What contemporary arguments would you parody to expose their contradictions or assumptions?

3. Imagine you’ve been hired as a consultant for a film about the Treaty of New York. Would you advise the filmmakers to center the story on Henry Knox’s attempt to reform federal Indigenous policy, Alexander McGillivray’s efforts to protect Creek interests, or the tension between their goals? What would your choice emphasize about the treaty and its failure?