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Here is my method for sorting out the deservingness of the winners:

Deserving:

Richard-This is pretty hard to dispute
Tina-She was very smart in terms of who to align with and how to get numbers. She made sure that she was surrounded by weaker strategic players at all times.
Brian-Hard to dispute this one, the guy was pretty much a sociopath out there and an incredible strategic player.
Sandra-It would be hard to say this if she had won any other season, but her strategy was great for PI. With so many other threats around, she would never be targeted and almost always approached with changes in plans.
Chris-The guy BSed his way through the girls alliance and kept BSing through the jury, and he was smart in who to take to the finals.
Tom-Hard to argue this one, since Palau was such a one-sided season, and he was a huge factor in that.
Todd-He played a brilliant strategic and social game, taking out threats when necessary and being on everyone's good side (except PG, really). He was taken on a ton of rewards, even though he never won any, and he had a strong enough social game to keep Denise on his side (Denise would have flipped if Courtney had been the target instead). The players in China were not that bad, just Todd made them all look like complete morons with his gameplay.

Kind of Deserving:

Ethan-The guy won a strategically weak season with mediocre gameplay. The Silas boot and the Brandon boot were the only things he did, and they really were not that hard.
Vecepia-Kathy should have won Marquesas, but she wasn't a terrible player in the season. She played a decent game for the most part, and she never game up, but she was by no means a strategic genius. She simply was good at setting herself up with people who would get booted before her to buy herself time, which did work.
Danni-She wasn't a bad player, but she did have a lot fall into her favor. Rafe should have won, imo.

Not Deserving:

Jenna-This has been beaten to death. I don't feel I have to say anything here other than the fact that her social game was pretty bad, just Matthew's was worse.
Amber-There are a few reasons why she didn't deserve it. She didn't play much, Boston Rob did all the work for her, and they ended up getting married, so he did basically get first and second place. Also, the second time around, nearly everyone else played worse (especially Lex and Kathy, who had so much to prove and who fell so far). Also, she didn't even deserve to be there in the first place. She was cast as a "wild card," whom production thought could do well given a second chance. But she failed her first chance. Giving a bad player a second chance sort of undermines the concept of having an allstar season, especially with so many other deserving players (John C, Sean R, Neleh, Helen, etc).
Aras-Aras has been beaten up on too, so I won't say much. Kind of a lackluster player, didn't do too much.
Yul-Basically carried to victory by the idol and the other players. He would have been destroyed in pretty much every other season.
Earl-Another player who was carried to victory by other players, though this time it was more because they had terrible social games.
Parvati-She also didn't deserve to be back a second time imo. CI had too much representation, and she should have been cut for someone from Guatemala or Palau. She was not that great the first time around, and the second time around she still wasn't great. She did a good job pulling in Cirie, and then Cirie did everything, and, along with some timely injuries and quits, it was enough for her to win.

Overall, I would say that the least deserving was Amber. She did pretty much nothing the first time around, shouldn't have been given a second chance, and then proceeded to do nothing again, and she did so in a less spectacular way than Parvati did it.