The Great Contradiction: The Tragic Side of the American Founding

Joseph J. Ellis
51 pages1-hour read
Nonfiction
Book
Adult
Published in 2025

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Character List

Meet the key characters, with insights into their roles, motivations, and relationships—spoiler-free.

Major Characters

The author and historical guide of the text. He reappraises the origins of the United States by focusing on the founders' inability to end slavery and avoid Indigenous removal. He rejects simplistic portrayals of historical figures as demigods or villains, instead emphasizing the historical context, demographic pressures, and political calculations that shape their decisions.

Key Relationships

Historian of George Washington

Historian of Thomas Jefferson

The first US President and commander of the Continental Army. He prioritizes national unity above all else, believing that confronting slavery directly will shatter the fragile new republic. Later in life, he struggles with his legacy as an enslaver, facing legal, financial, and personal obstacles to freeing the workforce at Mount Vernon.

Key Relationships

Husband of Martha Washington

Enslaver of Ona Judge

Commander of Henry Knox

Political Colleague of Thomas Jefferson

Commander of Alexander Hamilton

Correspondent of Robert Pleasants

The author of the Declaration of Independence and an enslaver at his Monticello plantation. He maintains deeply contradictory positions, condemning slavery as a moral tragedy while insisting that Black and white Americans cannot coexist. He demands the physical removal of freed Black people as a precondition for emancipation, a financially impossible scheme that permanently defers action.

Key Relationships

Political Colleague of George Washington

Enslaver of Sally Hemings

Friend of Marquis de Lafayette

Junior Colleague of Richard Bland

Political Opponent of Alexander Hamilton

A leading political strategist and constitutional thinker who helps orchestrate the Constitutional Convention. He acts as a pragmatist, consistently supporting compromises that protect the institution of slavery in order to secure Southern support for a strong national government. He uses complex rhetoric to manage debates and prevent the slavery question from threatening the union.

Key Relationships

Political Opponent of Benjamin Franklin

Political Ally of Thomas Jefferson

Political Colleague of George Washington

An elder statesman of the founding generation whose views on race evolve significantly over his lifetime. In his final years, he serves as acting president of the Pennsylvania Abolitionist Society. He uses his considerable public standing to force the issue of slavery onto the national agenda before his death.

Key Relationships

Political Opponent of James Madison

Colleague of George Washington

Supporting Characters

George Washington's Secretary of War. He rejects the theory that Indigenous peoples are conquered subjects, instead arguing that tribes are sovereign nations whose land rights must be protected by federal treaties. His efforts to establish a just Indigenous policy collapse under the pressure of rapid white westward migration.

Key Relationships

Subordinate to George Washington

Negotiator with Alexander McGillivray

A highly educated, biracial leader of the Creek Nation who skillfully uses complex alliances to protect Indigenous sovereignty. He travels to New York to negotiate directly with the Washington administration, attempting to secure federally protected borders for his people amidst aggressive settler expansion.

Key Relationships

Negotiator with Henry Knox

Treaty Partner of George Washington

A French-born immigrant and prominent activist in Philadelphia. He publishes influential pamphlets detailing the horrors of the Middle Passage and arguing for the full humanity of Africans. His work creates an organized opposition that challenges slavery just as revolutionary ideals of liberty gain prominence.

Key Relationships

Correspondent of Patrick Henry

The wife of George Washington. She brings dower slaves to Mount Vernon, individuals she legally controls but whom her husband has no legal right to free. She eventually emancipates her husband's enslaved workforce early, shortly before her own death.

Key Relationships

Enslaver of Ona Judge

Martha Washington's personal maid who self-emancipates from bondage. When located by her enslavers, she offers to return only in exchange for a promise of future freedom, a compromise the president rejects.

Key Relationships

Person Enslaved by Martha Washington

Person Enslaved by George Washington

A Virginia patriot famous for demanding liberty from British rule. He openly admits to abolitionists that he cannot morally justify slavery, yet he refuses to free the people he enslaves, choosing to live the contradiction rather than abandon the institution.

Key Relationships

Correspondent of Anthony Benezet

A nationalist, military officer, and prominent political figure who helps orchestrate the Constitutional Convention. During the Revolutionary War, he leads a crucial nighttime assault at Yorktown and supports arming enslaved men for the Continental Army.

Key Relationships

Subordinate to George Washington

Comrade of John Laurens

Political Opponent of Thomas Jefferson

A young Continental Army officer who recognizes the military potential of an emancipated Black force. His proposal to offer freedom in exchange for military service is decisively rejected by the South Carolina legislature.

Key Relationships

Comrade of Alexander Hamilton

Subordinate to George Washington

A French hero of the American Revolution who remains committed to the abolition of slavery. He visits Virginia late in life and maintains that formerly enslaved people can become equal members of a biracial society.

Key Relationships

Employer of Auguste Levasseur

An enslaved woman at Monticello who bears children with Thomas Jefferson. Her presence within the household stands in stark contrast to Jefferson's published arguments against racial mixing.

Key Relationships

Person Enslaved by Thomas Jefferson

The exiled royal governor of Virginia. He attempts to exploit the region's vulnerability by raising an Ethiopian Regiment of formerly enslaved men, an act that terrifies the enslaver class and pushes the South toward independence.

Key Relationships

Military Opponent of George Washington

A Quaker abolitionist from Virginia's Eastern Shore who emancipates all 80 of the people he legally controls. He writes to the president to warn him of how his legacy will suffer if he continues to support slavery.

Key Relationships

Correspondent of George Washington

A senior Virginia politician who presents legislation making it easier for enslavers to free their workforce. The resulting public backlash is so severe that it permanently damages his political career.

Key Relationships

Senior Colleague of Thomas Jefferson

A South Carolina delegate to the Constitutional Convention. He forcefully defends slavery and asserts that the new Constitution strictly prohibits the federal government from emancipating enslaved people within the states.

Key Relationships

Political Opponent of James Wilson

A Pennsylvania delegate who defends the Constitution during ratification by interpreting its clauses optimistically. He believes the new government possesses the tools to eventually eliminate slavery.

Key Relationships

Political Opponent of Charles Cotesworth Pinckney

A professor at the College of William and Mary who circulates a highly influential pamphlet following the Virginia legislature's debate on emancipation. He uses the logistical impossibility of removing the Black population to argue that all talk of ending slavery must cease.

Key Relationships

Ideological Successor to Thomas Jefferson

A Massachusetts lawyer whose early revolutionary rhetoric questions how the colonies can demand freedom from British policies while justifying the enslavement of Black people.

Key Relationships

Ideological Predecessor to Thomas Jefferson

The secretary to the Marquis de Lafayette. He meticulously records the economic and social stagnation of Virginia, directly linking the region's decline to its reliance on slavery.

Key Relationships

Employee of Marquis de Lafayette