In a recent gaming session playing Freedom: The Underground Railroad with our students, we were struck by the the choice of imagery used on the box and instruction art, and the illustrations on the playing pieces, cards, and game board used to convey the story of slavery and the Underground Railroad. What began as a sketch for a larger project, soon became very involved, taking many turns. Ultimately, we decided to sit on the ideas to give us more time to construct a more thorough and cohesive argument. We also plan to flesh out some of these ideas with our inaugural podcast, which is planned in the next few weeks. What follows is a portion of the original introduction and some of the key questions that we are mostly concerned with. We welcome comments and criticism.