As an object of study, Pindar and riddles may seem a natural union of text and subject matter, since Pindar’s poetry is often judged by modern critics to be obscure. However, the notion of Pindar’s obscurity, a late critical development, says more about our own poetic tastes than the about cultural systems which produced epinician poetry. Contra Aristotle, speaking enigmatically in the ancient world did not constitute a lack or excess of signification but rather a specific and often successful mode of communication that was performed and enjoyed by many different kinds of Greek speakers. Therefore, by describing the Pindaric text in relation to the tradition of speaking enigmatically, my aim is not to “solve” the text. Rather, this study aims to further the valuable work of describing two kinds of associative networks in epinician poetry: logical structure and social meaning. As regards the first, I argue that enigmatic speech in Pindar is marked speech, which means that the text actively engages in signaling to the performance audience that it is enigmatic by devices such as narrative framing, signpost words, tropes such as the “cognitive road,” and the construction of an enigmatic speaker. On the second, I follow recent approaches to Pindar’s poetry which take seriously the social embeddedness of choral lyric. Thus I argue that the performance of enigmatic speech stages a series of dialogues: literary (Ch. 1), elite (Ch. 2), and communal (Ch. 3). Overall, the study advances a view of enigmatic speech, not as obscurity or window dressing, but as an expressive mode of speech that put diverse texts, individuals, and communities in conversation with one another.