A long-forgotten Black abolitionist who liberated captive workers by the wagonload, brilliantly satirized slaveholders, and gave the underground railroad its name. Thomas Smallwood was a shoemaker by day and an organizer of mass escapes from slavery by night. Twelve years after purchasing his freedom from slavery, Smallwood took to the press and, over a 16-month stretch starting in 1842, pseudonymously published newspaper dispatches ridiculing and excoriating enslavers by name and offering sobering reflections on the depravity of slavery. With the pen that Smallwood called his “lash,” he leveraged mockery to flip the oppressive racial power structure of America. These dispatches, in which Smallwood was the first to use "underground railroad" in print, are the only accounts of escapes to be published in real time, imbuing Smallwood’s subversive wit with urgency and defiance. His 1851 memoir is prescient on the United States' tormented entanglement with race.