The second chapter delves into slave flight to spaces of informal freedom in the urban South, the most immediate and easily reached destinations for runaways trapped in the second slavery. It considers why enslaved people chose to go to the trouble of fleeing bondage yet remain within the slaveholding states; the networks that helped them do so; the strategies they employed to hide their identities, sustain themselves, and remain at large indefinitely; and the risk they ran of recapture. The actions of these runaways went far beyond mere truancy, as is often suggested in the literature. Many fugitives to urban areas clearly attempted to live their lives there indefinitely. The chapter devotes considerable attention to the importance of family in informing freedom seekers' decisions to remain within the South, even if it meant foregoing more formal freedom in other parts of the continent. It also examines the importance of visibility in runaways' strategies of escape, exploring how they "passed for free" by looking and acting free, procuring false freedom papers and other documentation, and integrating themselves into urban free black communities so as to avoid detection.

Already by the 1820s, the national capital of Washington, D.C. had emerged as a significant depot in the increasingly professionalized domestic slave trade. The introduction sketches the history of slave dealing in the capital, William H. Williams’ emergence on to the slave-trading scene there, and the broad contours of how the slave trade functioned, often depositing its victims for sale in New Orleans, Louisiana. It argues that the story of William H. Williams and his one shipment of convict slaves purchased in 1840 provides a snapshot of the antebellum era socially, economically, politically, and legally.