Pirates capture the imagination, span centuries of history, have great clothes, conform to surprising codes of conduct, and invite a wide variety of themes and subjects for teaching. Piracy can be a seductive topic for all ages. In spite of the imaginative appeal of the topic, piracy is insufficient as a starting point for a well-connected social studies, science, math, and English unit until teachers ask challenging questions, like what are the deepest meanings of this theme? How is the topic useful emotionally, spiritually, and academically? In this article, the author describes how she developed a piracy unit and shares her experience teaching the topic to alternate school students. Following a narrative is a complex intellectual task of fitting things together, identifying what is important, constructing emotional meaning, and synthesizing the parts into a reasonable whole. Some teachers do this well, but others struggle to identify important themes, or fail to connect emotionally with the subject. For this reason, the author argues that teachers would benefit from occasionally acting like philosopher pirates when they teach their children. As she contemplates the success of her pirate unit, the author looks for significant events and considers her project as it relates to imaginative teaching and learning. (Contains 1 footnote.)