Odysseus certainly suffered over the years. So much so that Dante even sent him to a rather deep level of Hell (the Bolge of the Evil Counsellors). I think this tells us that many of the stories about him are quite old. The whole concept of the clever/tricky man appears regularly in stories and tales from the eastern Mediterranean and Semitic regions. This may show the close cultural connections that the Minoans/Mycenaeans had with this region.

Somewhere along the way this all became rather embarrassing to the Greeks. They couldn’t do away with the stories altogether, but they downplayed them as much as they could. I know there were a few others who had “many turns”, but none are coming to me just at the moment. Autolykos, of course, who vanished almost entirely from the stories (I wonder how many others there were that were forgotten). Prometheus, in some ways, also suffered; I often feel that there is a sense of “he got what he deserved” in some of the stories about him. Hermes is a slightly different case with his theft of Apollo’s cattle and so on since gods get to play by different rules, but here too we hear more of the other stories and less of those that made him god of thieves.