It's now down to the final six--Tom, Ian, Gregg, Jenn, Katie, and Caryn--on Survivor. Faithful readers will notice that this group comprises Greater Koror, plus Caryn. The endgame is always the most interesting phase of the game, not just because it determines who will win, but also because now is the time in the game when strategies start to get more complex. Where before a contestant might base his vote on who is the weakest, or who is outside of her alliance, now people have to start thinking about who they could beat in an endurance challenge, who's going to be on the jury, or who they would have to face in the final two. And in a change from Survivor's past seasons, I could see almost any of the final six winning the whole game. Let's see how each player might accomplish this.
Tom:
The only way for Tom to stay in the game is to keep winning challenges. Everyone in the game knows full well how threatening he is, and so they'll likely take the first opportunity they get to vote him off. He's well-positioned to make it to the final two by brute force alone, and given the way he led his tribe to a perfect winning streak in team immunity, he's got a good shot at winning a jury vote, no matter who he's up against. It's rare on a Survivor for someone to take a leadership role for so long and not ruffle any feathers, and Tom has basically done just that so far. Sure, Coby and Caryn have bitched in the past, but neither of them seem to hate him--in fact, Caryn was well-positioned to vote him off last week, but she didn't. And I can't see anyone else they would be more inclined to vote for. So I think if Tom's in the final two, he wins. The only person who might be able to even put up a challenge would be Ian, so Tom would be well-advised to get rid of Ian as soon as he can. The best way for him to do that, I think, would be for him to win the final three immunity challenge and take whoever isn't Ian with him to the final two. I think Ian would be able to accept that without seeing it as a betrayal, given that his primary alliance is with Katie.
Ian
Being Tom's little buddy has served Ian well up to this point, but from here on out it will be more of a liability. Here's why: everyone recognizes the threat Tom poses, but as long as he keeps winning challenges, the only way to attack him is to attack his allies. And Ian is Tom's closest ally. In fact, if I were in Jenn, Katie, Gregg, or Caryn's position, I would try to get the rest of the four to agree to vote out Tom or Ian, depending on who loses the challenge. Ian's only hope, then, is to either win immunity or hope that someone hasn't thought through their best interests. Katie would be the most likely candidate to do this. She has a pre-existing alliance with Ian that may blind her to the reality that Ian can't help her win as much as vice versa. So if Ian and Tom can get Katie on their side, they only need to flip one more person. Their best bet would be Caryn. She no longer has any allies, and would probably cling tightly to anyone who would have her. This would be a bad move on her part, considering how easy it would be for Tom, Ian, and Katie to boot her afterward, but as I said, Ian has to depend on other people making bad moves to stay alive.
Gregg & Jenn
Gregg is in a good position to win the game. He's number three on the threat list, behind Tom and Ian, so he can fly under the radar to a great degree, simply because they'll draw all the fire. In any event, it's impossible to get rid of either of them without his help (unless they betray each other, which doesn't seem likely at this point) so he'll get a pass to the final five. Once in the final five, he'll need to beat whoever is left between Tom or Ian, because with the women in the majority, they'd be smart to go after the remaining men. If he succeeds in this, he'll be the last man standing, and will have an advantage in the next remaining challenges, provided they are largely physical. If he makes it to the final three with two women, he could probably win a jury vote no matter who he takes with him, but it would be smartest to take Jenn. First, everyone knows they're an item, and it will be seen as a betrayal if he doesn't choose her. Second, he doesn't want a woman scorned on the jury. While this strategy didn't quite work for Rob in All Stars, he was a much more polarizing figure than Gregg is, so the jury would probably rather award the person who did all the work to get there than the remora who coasted. Nevertheless, Jenn's best play would be to stick with Gregg and hope he steps on enough toes on his way to the top, that there will be a Rob & Amber Redux. Any other scenario would have to involve her not only winning immunity challenges, but having some assurance that she would be able to do so, both unlikely.
Caryn
Surprising as it may seem, Caryn actually has a decent shot to win here, if she's smart. (It doesn't look like she is though. Her best bet was a women's alliance, but she blew that last week when she had a choice between Steph and Tom.) Caryn's greatest strength is actually her weakness as a player. Any of the men would love to be opposite her for the final two; conversely she's probably the only one Katie or Jenn could beat. It seems, from the previews and the last episode, that she's trying to ingratiate herself in with the men, and poison them against Katie. This is probably her best play; if it succeeds, she'd take Katie's place in the Tom-Ian-Katie alliance, meaning that after they get rid of Katie, she'd be the swing vote between the Gregg-Jenn axis, and the Tom-Ian axis. Since she'd probably realize that she couldn't win the final three immunity and that if she went with G & J, they'd probably choose each other over her, it would be smarter to stick with Tom and Ian, and try her luck with the jury.
Katie
Katie's strategy for the win should be the same as Caryn's and she ought to be more secure in it, except she spent the last episodes trying to oust Tom and failing. At the same time, she was showing disloyalty to Tom, Caryn was showing loyalty. Add to that the fact that Caryn has no other options but to play ball with Tom and Ian, and it would make sense for Tom to try and swap her for Caryn. Her only hope is that Ian has some loyalty to her and tries to save her.
In the end, I think the scenario I outlined for Caryn is most likely. I'm thinking Katie, Gregg, and Jenn will be the next three to go, in that order, and the final two will be Caryn with either Tom or Ian.