Urban slave life in ancient Rome was unlike the absolute bondage and physical labor historically associated with the term slavery. Cicero's administrative slave Tiro was a literary collaborator, a debt collector, a superintendent of sorts, a secretary, a financial overseer, a political strategist, a recipient and content-generator of Cicero's famed practice of letter-writing, and a connected component of Cicero's social scheming. Cicero's correspondence with Tiro praises him for his value and loyalty, but it also shows previously unrevealed rhetorical aspects of the ancient orator and his relationship with his slave, colleague, and friend.