My take on past players being mentioned here:
Rich - I didn’t watch the first series (if anyone has it on tape I’d gladly pay postage for a copy) but from what I’ve heard Rich had the advantage of playing the game against a number of opponents who didn’t realize there was a game. In all subsequent series, everyone played with the awareness that Rich had inspired. I think it’s an open question whether Rich would have done as well against the higher level of competiveness in the following years.
Ethan - He seems like a genuinely nice guy but in my opinion, he’s the least deserving winner the show’s ever had. He was simply a follower who got lucky. The real movers on his tribe were Tom, Lex, and at the end, Kim. The rivalry between these three led them to eliminate each other. But Ethan could have gone at any point and apparently never made any plans to protect himself.
Brandon - Perhaps the gayest man ever seen on network television. As I recall, he never even bothered to announce he was gay, because he correctly assumed everyone knew it. In fact, when the tabloids “outed” him they did it by announcing that he had once had a relationship with a woman.
And finally, two players who I think should have won: Mike from season two and Kathey from season four. Mike was the dominant player on a dominant tribe and he appeared to be going all the way with ease until his accident. He would have cracked the Tina-Colby-Keith alliance like an egg. Kathey, on the other hand, was the perpetual outsider who never quit. Without ever being at the heart of any alliance, she hung on week after week and worked her way into the final three. Then she lost it with a single second’s distraction at the pole. I have no doubt she would have otherwise easily beaten either Vecepia or Sweet Pea in the final vote.