In this study I set out to read Gen 25:23, YHWH’s oracle to Rebekah, as a trickster oracle. I argue that one should not read it under the a priori assumption that it coheres with other narratives of inverted primogeniture elsewhere in Genesis. Rather, in light of Robert Alter’s understanding of the biblical type-scene, what is seminal in understanding the oracle is how it differs from the convention of annunciation of birth elsewhere in Genesis. Against this backdrop, the oracle is seen to be ambiguous in matters of diction/meaning, syntax, and context, which thus further impels the narrative’s human characters—Rebekah and Jacob—to bring about their own interpretation of the divine will, which they succeed in doing by means of several deceptions. Against this backdrop, I contend that the final line in 25:23 is best translated with the more enigmatic “the greater will serve the lesser” rather than the more blatant “the elder will serve the lesser,” which ultimately has implications for the entirety of the Jacob cycle, including the character of God and the texts of deception. With this point in mind, I interpret two scenes of deception—Jacob’s extorting the birthright from Esau (Gen 25:27-39) and the deception of Isaac (Gen 27:1-45)—in light of the oracle. Given the oracle’s function, in all its vagueness, as an introduction to the entire Jacob cycle, God is both involved and complicit in the deceptions in various ways. Corroborating this point is the Bethel theophany, in which Jacob receives the ancestral promise solely at YHWH’s behest. And it is the perpetuation of this very promise, at times by deceptive measures, that is the principle concern of YHWH in Genesis. In the end, the oracle does not appear ever to have been concerned with Jacob becoming the greater. Instead, he is the greater from the womb, a status substantiated through his cunning and shrewd characterization as opposed to the dimwitted and overly-dramatic Esau. Why God has chosen such an individual, then, becomes clear: God the Trickster selects Jacob because it is he, not Esau, who is a trickster from the very start.