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This essay seeks to open up the concept of pirate to interrogation by exploring its trace in the Greek root pirao. In so doing, we learn pirao, and thus pirate, also means “to get experience,” which I interpret as a positive affirmation of the self. In order to accomplish this task, I draw from the popular cultural curriculum of all four installments of Pirates of the Caribbean, in particular, the contradictions structured between Jack Sparrow and other pirates to Davy Jones and his crew of the Damned. Drawing from postmodern, postcolonial and posthuman frameworks, I explore this contradiction in relation to education’s role as it renders problematic the privateer/pirate binary and what we are learning in the process.