Petitioning for freedom: Why did Henry Clay oppose this slave’s quest to be free?

Editor’s Note: As Lexington celebrates the 250th anniversary of its founding, the Herald-Leader and kentucky.com each day throughout 2025 will share interesting facts about our hometown. Compiled by Liz Carey, all are notable moments in the city’s history - some funny, some sad, others heartbreaking or celebratory, and some just downright strange.

Born a slave and sold to Kentucky’s prominent politician, Henry Clay, Charlotte Dupuy experienced life among free Blacks during her travels with the prominent Kentucky politicians.

Deciding she wanted that life, she’s one of the earlier cases of slaves asking their enslavers for their freedom.

In 1787, Charlotte was born into slavery in Cambridge, Mass. When her owner, James Condon, moved to Kentucky, he brought her with him.

There she met Aaron Dupuy, a slave owned by Henry Clay. Condon sold Charlotte to Clay so the two could be together, and Charlotte and Aaron married. They had two children while they lived and worked at Ashland, Clay’s home in Lexington.

In 1810, Clay moved to Washington, D.C., to serve as a U.S. senator for Kentucky. The Dupuys accompanied him, and they served in the house he rented throughout his Congressional career.

When he was appointed Secretary of State, the family stayed on with him in DC. Being on the East Coast near her childhood home meant Charlotte was able to visit her mother, as well as live a life of relative freedom in the capital.

In 1829, with his service ended, and Martin Van Buren taking his place, Clay readied to move back to Lexington. But Charlotte wanted to stay.

Charlotte’s mother was free, and Charlotte had been promised her freedom by her previous owner, Condon. So Charlotte filed a lawsuit against Clay for her and her children’s freedom.

Clay, assuming that his political enemies had put her up to it, dug in his heels and fought it. On Feb. 13, 1829, Charlotte’s attorney petitioned the courts to prevent Clay from removing her from Washington while the lawsuit was Being decided.

Her attorney argued that Dupuy and her children were “entitled to their freedom” and that a return to Kentucky would return them to a lifetime of slavery. The court agreed, but it came at a cost – Charlotte was allowed to stay, but her husband and children were forced to return to Lexington.

The case centered around Charlotte’s position as an enslaved person. While the courts ultimately determined her mother was freed after Charlotte was born, which meant Charlotte was born a slave, it still assumed her status as a free Negro since enslaved people had no legal standing in the courts.

Her lawsuit was nearly two decades before Dred Scott sued unsuccessfully for his own emancipation and was one of many lawsuits that forced the courts to wrestle with the issue of freedom for people of color.

Ultimately, Charlotte’s petition for her freedom was denied. After the ruling, Clay sent her to work for his daughter and son-in-law in New Orleans.

In 1840, Clay finally freed Charlotte and her daughter. Four years after that, he freed her son.

Just before his death in 1852 Clay freed Charlotte’s husband, Aaron. The couple reunited to live in Lexington, where Aaron worked for Clay’s son, John Clay, at Ashland.

Have a question or story idea related to Lexington’s 250-year history? Let us know at 250LexKy@gmail.com.