Studying the 2000 U.S. General Election, students read the word, "hanging chad." A dictionary definition reveals "fragments from holes made in paper cards," but leaves students dangling with uncertainty, which shortchanges the importance of this word in history. Is knowing the definition of "hanging chad" enough? When do we move learning a "simple" definition into something that has so many nuances over time and/or overwhelms the text that we're trying to illuminate? Consider another example. When reading about democrats and republicans in a history lesson, a student noted, "there isn't really a definition of a democrat." As the teacher reflected on the entire conversation, he inferred that the student's comments indicated a single definition was not enough (and the student knew it), but the student was not aware or ready for the broader concept of "democrat," nor did the text offer the historical layers of word meanings. What are the just-right interventions when word learning is not unidimensional (right there in the text), but contextually derived? When does learning a word help communicate with others and comprehend a text, and when does it actually distract from communication or derail content understanding? Like "democrat" or "republican," words in the history classroom become entangled in the national political dialogue as individuals wrestle with the meaning of terms within the context of socio-political reality. This article offers an approach to vocabulary learning that situates words not as isolated concepts, but rather as ideas tethered to people, time, and place.