I thought the story about Ulysses/Odysseus in Canto XXVI was very interesting. Dante recorded that Ulysses had wanted to "learn about man's vices, and his worth" (XXVI. 99). But Ulysses told the men with him that they were meant "to pursue virtue and knowledge" (Dante XXVI. 120). It seems like Ulysses was deceiving them about his purpose - how could these things be connected? He may have conned them into going on his quest. Ulysses had to conclude this story by saying, "the sea closed over us" (Dante XXVI. 142). I don't think he can trick his way out of this place.
P.S. I commented on Rebekah Dye's post.
I think that Ulysses' greatest weakness and strength was his ability to con people into doing what he wanted. It abled him to be a successful leader to the extent of doing what needed to be done, but being decietful is also his greatest flaw.
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