One of the original plot points from the network executives was that LOST was going to be like a real life Survivor show. In the game show TV series, contestants are flown off to faraway places to live and compete in bare minimum conditions in the hope of being able to win a million dollars as the last man or woman standing in the end.
The principles of Survivor was Outwit. Outplay. Outlast.
In LOST, we don't know what the characters were actually "playing" for. It could have been rescue, salvation, friendship, adventure, power or none of the above.
Who outwitted the most people? Ben certainly used enough mind games and terror techniques to ascend to the powerful leadership role of the Others. However, Ben was clearly outwitted by Flocke/MIB/Smoke Monster in getting Ben to stab Jacob. But in some circles, it was Jacob who outwitted everyone because he was looking for his "replacement" for centuries. He could not kill MIB or MIB could not kill him, so Jacob played a game with MIB - - - he could escape the island if it killed the island guardian, him. Jacob could only be replaced if he died, and in an elaborate ruse, he got MIB to find someone to do it and another person to slay MIB to take victory away from it.
Who outplayed the most people? It depends on the game. Hurley hustled on ping pong, and Kate bested Jack in island golf. But in the oldest game of all, romance, it was quite the mixed bag. Sawyer charmed himself into the most action, but Kate kept herself in the game as the elusive prize. But the symbolic game of LOST was ancient backgammon, Senet, played by Jacob and MIB and later taught by Locke to Walt. It should have been a more developed element of the story, but in one respect was clear. When Jacob continued to bring candidates to the island, they represented game pieces. The object of the game was to remove all your pieces from the game board (the island). There was a systematic elimination of candidates throughout the series by various means of death. But in the island's end, there was only one candidate left standing: Hurley.
Who outlasted the other characters? One has to assume "outlast" means "survives" the longest, and the ability to remove oneself from the island dangers has to go to the person who left the island alive. Kate and Frank both left the island together twice. They were rescued and if the goal of the castaways was to leave the island in one piece, then they were co-winners. Kate may get extra credit for voluntarily coming back to the island for another round while Frank was hijacked into crash landing a plane. But if the goal of LOST was to make it to the after life with one's "soul mate," then there were several winners: Kate, who got Jack; Desmond, who found Penny; Hurley, who met Libby; Jin and Sun who had each other, and Sawyer who had Juliet.