In the pages that follow, the case files of more than three hundred enslaved individuals who sued for freedom in St. Louis (in 287 cases, several of which involved multiple enslaved plaintiffs) will serve as the basis for a broader discussion of the legal culture of slavery and the processes of negotiation that occurred in and around freedom suits. The St. Louis freedom suits are located in the Missouri State Archives’ St. Louis branch, as part of the St. Louis Circuit Court Historical Records Project, and are nearly all available online through the Historical Records Project website. A handful of newly discovered freedom suits from the General Court for the Territory of Louisiana (which included St. Louis and the territory that became Missouri) came to the author’s attention in the final stages of this project. More freedom suits undoubtedly exist in this collection of early territorial court records and will be an exciting avenue for future research into early St. Louis. Additional local St. Louis court cases—debt cases, disputes over slave sales, and other types of legal action—and legal records relating to the freedom suits and local legal culture, such as circuit court record books, execution books, and manumission records, help to flesh out the use of the legal system by enslaved individuals and their enslavers.