THE TOLL

A new clue opens this discussion of the big premise.

"We Sin Toll."

It is an anagram.  TPTB loved to put anagram Easter eggs throughout the series.

We can all agree that Flight 815 was the biggest piece of the puzzle. It was of critical importance because those 324 people on board were either destined, kidnapped, trapped or caught by the island.

There were great pushes and pulls to get the main characters on that flight. Sun was supposed to leave Jin at the airport to flee her marriage, but relented at the end. Hurley rushed through the terminal and barely got on board. Sayid was not supposed to be on the flight at all, but he made a last minute change to stay a day to bury a friend that he had betrayed. It was more than just coincidence that the passenger manifest turned into cherry picking candidates for Jacob's lighthouse.

Jacob said that he had spied his candidates from the island. He knew about them. He had gone to see them. He touched them. He found each of them to have a common trait: a miserable life like his own. That is why he brought them to the island. 

The question is whether Jacob manipulated each candidate or gave them the free will option to follow him. It would seem that Jacob had power over them and supernatural powers to get them to the island.

In Greek mythology,  Charon or Kharon is the ferryman of  Hades who carries the souls of the newly deceased across the rivers Styx and Acheron  that divided the world of the living from the world of the dead. A coin to pay for passage was sometimes placed in or on the mouth of a dead person. Some authors say that those who could not pay the fee, or those whose bodies were left unburied, had to wander the shores for one hundred years (which may explain the island "whispers," trapped spirits who cannot move on.)

It is possible that Jacob was Charon, the ferryman who directed souls toward their after life journey.

Which brings us back to the new anagram. 

There was always a question on where Jack was seated on the plane. There was confusion of whether it was Seat 23 A, 23 B or just before the crash, 23 C.  In the plane scenes, there was no one seated next to Jack. However, during the eulogy at the memorial service for the dead passengers (Claire using the passenger manifest),  Harold Wollstein was named as the person who was seated in 23 C.

We never saw Wollstein, in person or his body in the wreckage.  However, the anagram for "Wollstein" is "We Sin Toll."

Was he, or better yet, Seat 23 C, the trigger for the ferry ride to the after life? In a plane load of sinners, was Jack marked to be the "toll" for everyone who "survived" the crash to begin their journey through the levels of the underworld to arrive in their sideways after life? In order for anyone associated with Jack to have a chance for a happy ending in heaven, Jack had to sacrifice himself on their behalf. Is that why Jack was last to awaken? Is that why Jack had no other life after MIB's defeat (like we presume Sawyer, Claire, Kate, Miles and Frank did after they left the island)?

If you believe in the big premise that the passengers died in the plane crash, but "lived" on in the underworld called the island, then Jack's "destiny" to become the island guardian and to save his friends souls would all be tied back to Jack being on Flight 815, and in the seat of from which "the devil" (as Jacob was called by MIB) extracted his toll.