It looks like Christmas came a little early this year, in the form of a sweet Lost: Missing Pieces this week. Merry Christmas to all of us!
Taking place during the timeline of "The Man From Tallahassee", this episode features a few bits of Losty goodness packed into two mintues of video. The two main points?
1. Ben comments that he "won't prevent Jack from getting home", but that he can't vouch for the Island doing the same. Although Jack laughs him off, questioning how the Island could "sink the sub", it turns out to be horrible irony since that's exactly what happens.
If you think about it, John Locke (a member of Team Island - remember that theory from months ago) is basically acting as the body for the desires of the Island / Jacob / Whatever The Heck is Going On. Locke blowing up the sub is the equivalent of the Island blowing up the sub - so Ben was absolutely right.
However, I don't think it was so much that the Island wanted Jack to stay - as much as it didn't want Jack's departure to lead to others finding the Island... but we all know that didn't work out so well either. Perhaps the Island would have been better off letting Jack escape on the sub - it may have at least bought a little more time before Jack and his inevitable search party returned, as opposed to Jack swiping Naomi's walkie-talkie and calling the calvary.
2. Ben hints that even if Jack does leave, he may regret it - wanting to return to the Island someday, but not being able to. Again with the irony, this is precisly what we saw during the flashforward of "Through the Looking Glass". How did Ben know that this could potentially happen? Did he truly realize the paradise of the Island, or had others made this same mistake in the past?
Either way, it seems to lend some weight to the theory that Ben was the person in the coffin during the Season Three finale. Ben represented someone who understood the power of the Island, and warned Jack about leaving. Jack, living what looks to be a miserable post-Island existence would have totally regreted his decision to leave the Island, proving Ben right... and Ben's death just might spurn Jack to drastically and suddenly reach out to Kate about going back.
(Also, allegedly Ben cheats at the game of chess with his last move. I'm no Deep Blue, but I'll take Lostpedia's word for it. Just goes to show that Ben appears to be a man of his word, but is really someone that would cheat in order to win. Juliet was right, he is a liar!)