It seems that in the sideways timeline, Jacob is correct, but the Monster wins the game. I believe that Jacob is correct in that one because Cooper and Sawyer have both chosen a more virtuous path, while Kate (claims that she) is innocent, Claire still seems to be good, while Sayid and Jin are up to some shady business (even though Sayid is really trying). In these situations, the island is gone and presumably the Monster left since Jacob is (assumed to be) dead but our Losties are still making very complex moral decisions, not simply being corrupted.
But, at the same time that Jacob is right, our Losties' corruption, arrogance, greed, lack of faith, and short-sightedness ended up destroying the island. Since I believe the island is the game board, that means the game was won by Smokey in that round, but is still being played in the main timeline.
Anyway, onto a question that I was wondering: If Flocke leaving the island means that "everyone goes to hell" then that means Jacob is wrong. But, if Jacob believes he is right, then why wouldn't he let Flocke go? There's no reason for him not to if there's good in everyone and everyone is truly capable of making that choice. In other words, Jacob can prove Flocke wrong by letting him go and proving that not everyone is corruptible as opposed to ruining lives on the island and making the game a protracted version of the story of Job.