Born into the richest planter family in the Northern Neck of Virginia, Robert Carter III's life is anything but typical. A neighbor of George Washington and the Lees of Stratford Hall, Carter is destined to be a gentleman farmer, slaveholder, and leader in the church, militia, court, and government. Carter has no idea that one day he will rebel against everything he is taught.

While growing up, he spends time with his best friend and personal slave, Sam Harrison, who provides him with a first-hand look into his less than ideal life. After Carter comes of age, he escapes to London where he encounters the Enlightenment. At age twenty-three, he returns home to take over his eighteen plantations and live a productive life. But as a chain of events drives him to chart new territory for his time, Carter is ultimately led to make a decision that shocks and alienates his class and his family and forever changes the lives of over five hundred people.

Never Pleasing to the World is the story of how a child of privilege, influenced by slaves long before the Civil War, creates a community of freed slaves in the most powerful state in the South.