Lila and Jesper
"If he's really got an angel in his back pocket," Lila said, looking at Jesper, "that could be more easily said than done." She had not been raised religious, but angels were reputedly very powerful. Having a literal guardian angel would definitely improve Dean's odds.
"Besides," she added, drinking a little beer. "What would we wager? I don't think anyone has much money here, and it wouldn't be any good if we did."