In contemplating depictions of the crucifixion, observers have generally overlooked an important provocative element: Jesus is put to death as a latro, an outlaw, between two other latrones. For this reason, references to latrones in the Bible, in Eremite and monastic texts, as well as in later Christian writings are more than a mere literary device. They offer a previously unexplored and underappreciated window into a theology of freedom.