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On a random side note, I remember in the first season I really didn't care about a "good strategic winner." I was really into the fact that one person would get booted each week and somehow the ultimate Survivor would rise to the top. I think I would actually be perfectly happy if it was still that way. That said, I do like strategy even if game discussion has become 90% of what we're shown out there.

I think Chris was a lucky winner, and a classless winner, but I think he was somewhat proactive in his victory. The stupid, arbitrary decision to "boot the young guys" except for Chad was cooked up between him and Sarge. It was a dumb thought process, but it worked. He was manipulated by Julie and Twila to boot John K. and subsequently lost most of his alliance and any hope of winning after taking out Rory. His decisions only started to really cook when he was working his endgame...but as someone pointed out Twila had a lot to do with that. Hell, I think I just convinced myself that he was pretty terrible.

My vote for the "worst winner," if there is such a thing is still Jenna. From what I recollect, she didn't have a whole lot of power in her old tribe. During the shuffle up she didn't strike me as one making any ideas and the merge game was essentially a Rob/Deena show 'till Deena wanted to boot Alex. The only real decision we saw her make was getting angry at Deena, and even then it was Rob doing most of the plotting. I truly don't remember a single thing Jenna did to secure victory other than winning the final two immunity challenges and taking Matt instead of Rob. She was in dominate alliance most of the time as well, she was just never a power player or, really, someone that struck me as that interesting.

Vecepia, to me, has always been kinda underrated. I don't think she was stunning as a winner, but she picked the right style of play for that game. She was UTR, but I never got the impression she was being strung along by a more aggressive player. In Marquesas, alliances were firing back and forth at each other and laying low was the perfect way to dodge all of it.

Glebe220 wrote:

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I, too, would put her as one of the "worst" winners in Survivor, but to be honest I think of all the winners she'd be one of the best at excelling in any situation, not just the one she was in during her season, up there with Tom, Brian, Rich, and maybe Yul.

Tom is someone I'd question as far as being able to excel in any situation. I think Yul and Rich were both flexible enough to earn that distinction, but I feel Tom had potential for an early merge boot had his tribe not been in complete control of the pre-merge situation. Coby was very willing to defect as was Gregg to a certain degree. It's a little hard to determine, especially because imagining how he'd react in a different situation is a big hypothetical, but Tom W. always seemed to me like a player who's style fit his season well. He mindfucked Ian well enough and I think he played Caryn like a fiddle. While I had a distaste for the Tom W. character as presented, he's a fine winner. I do think considering his strength and leadership he would have been targeted in games where it wasn't dominated so completely by one team.