This chapter traces how historical analogies have enabled the use of the terms slavery and abolition in both the anti-trafficking and the anti-incarceration communities. By placing the often-contradictory approaches these two communities bring to the history of slavery, we trace how a belief in historical progress and an emotional investment in the power of innocence – both concepts embedded in our understanding of childhood – have helped to forge vexed and contradictory definitions of both slavery and freedom. Ultimately we argue that the complex work of historical analogy requires us to imagine history, and the solutions we create in response to history, outside of a developmental model that views the degradation of enslavement a stage we can outgrow or discard.