Written by a petty bureaucrat and diplomat for Lorenzo de Medici, a member of one of the ruling families of Europe, Niccolo Machiavelli's "The Prince" is a slim volume concerned primarily with advising Medici on how to acquire, maintain, and sustain power over a state. Its difficult and often archaic vocabulary aside, at first glance it hardly seems an ideal text for the sophomores the author often teaches. Nearly 500 years old, it features a glib attitude about violence and a cynical opinion of humankind. And hardly anyone teaches the book in its entirety at the secondary level--probably because it's repetitive, dense, and sometimes frustrating. Ironically, the things that make it a questionable choice also make it an excellent challenge, or "stretch" text, one that would require considerable attention and effort by young people. That history textbooks still reference Machiavelli demonstrates that his ideas are still considered relevant. Drawing on "The Simpsons" and other contemporary references, the author describes how the 15th-century classic can still resonate with young adults.