In Hippias Minor, Socrates gets into a most unusual debate with Hippias, a famous sophist and Homer scholar, over which kind of liar is best. Socrates makes the surprising claim: that an intentional wrongdoer is better than the unintentional wrongdoer.
Is this the same Socrates who says that man should never intentionally commit injustice? (The Crito)
As always, context is key. The debate is rooted in a literary question about whom Homer intended to portray as the better man, Achilles or Odysseus. This soon turns to questions on the nature of the courage and wisdom.
Is this a debate Socrates wants to win? Or does he intentionally throw the fight? Readers for centuries have been hard pressed to judge the match.
We can trust something bigger is at work behind the scenes as a conversation on lying surely has something to say about the nature of truth.