The Losties were originally bought to the island via Desmond near-implosion of the hatch. In S2 he said to Locke: "I think I crashed your plane."
I think Mike returning was Ben acting (upon Jacob's will>) on behalf of the island, via Tom. The island stopped him killing himself and then, it seems to me, brought him back to the island (or near enough), to help in protecting it, possibly later killing him while he does this.
Back to Jack's attempts to return. To me, it seems the island is refusing to let him come back. Could this be because Jack is now a broken man, wanting to return, whereas on the island, as a respected leader, he spurned the island? Rather ironic, don't you think?
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