Widmore has been on Jacob's side all along by Alejandro Tamargo

I've been thinking about Widmore's recent arrival on the island and the fact that his team is setting up those anti-Smokey pylons the D.I. used which indicates that he came there with the intent of doing battle with ol' Smokes. I also had to think back to last season when Widmore told Locke that a war was coming, and if he wasn't on the island when it happened that the wrong side was going to win. We can only assume he was referring to the war between light and dark; Jacob and Smokey. I am also making the assumption that the "wrong side" is Smokey, because even though Locke's return is ultimately what allowed Smokey to kill Jacob, I don't think that was what Widmore had intended. Widmore seemed genuinely surprised and confused when Locke told him that he was told by Richard that he needed to die. I think Widmore wanted Locke to return to the island alive, because he knows he's a candidate. But I have to ask then,! how the heck would Widmore know any of this stuff? The upcoming war with Smokey, or the candidates (assuming my assumption is correct and he did indeed know that Locke was a candidate). Ben certainly didn't know anything about any of this stuff. Neither did Richard. So how is Widmore, way far away off the island, privy to this information? I think the answer is simple. Jacob told him. Jacob has been keeping him up to date, and every thing Widmore has done has been under Jacob's instruction.

Let me start by going back to a couple of the key characters whose arrival to the island was facilitated by Widmore. First off Locke. Do you remember what got him so gung ho about going on a Walkabout in the first place? A strange orderly by the name of Matthew Abaddon. And who did Abaddon work for? Charles Widmore. The Man in Black said that Jacob manipulated the lives of the candidates to push them toward the island, but at least in this particular case, it almost appears that Widmore was the one manipulating events to push Locke toward the island.

Then we have Desmond. His importance to the island, I think, has not been fully realized. Ms. Hawking told him last season that the island was not done with him yet. I think his importance to the island goes far beyond just pushing the button. I think Jacob wanted him there for a purpose yet unknown. And who do we have to thank for Desmond going to the island in the first place? Mr. Charles Widmore of course. I think the whole MacCutcheon's stuff was a bunch of theatrics. Widmore didn't want Desmond to marry his daughter not because of his station in life, but because he knew Desmond needed to go to the island. And it was Widmore's refusal to let Desmond marry his daughter that started Desmond on his path toward the island.

Now then, to buy into this theory, you also kinda have to buy into another theory I've had for at least a couple seasons now, and that is that Libby was an employee of Charles Widmore. Because if you can go along with that, then it only makes sense that Libby would be the one who gave Desmond the sailboat that carried him to the island.

We've also seen Libby in the mental hospital with Hurley. Perhaps she was there to keep an eye on him. Perhaps to make sure he got the numbers and was on his path to the island. I doubt Libby knew that much detail. I'm sure she just had some vague orders which she was following. And I'm not even sure how much detail Widmore himself knew. He was just following instructions from Jacob. And it doesn't seem Jacob is really big into specifics.

Now then, the thing that really doesn't seem to fit in to all this and could possibly used as evidence to detract from this theory is the freighter Widmore sent suppossedly to kill everyone on the island. Is that what he sent it for though? Remember that this is what BEN told everyone. But Ben knew nothing about any of Jacob's plans. He knew nothing about candidates; he knew nothing about the war with Smokey. He was just looking out for numero uno because he believed Widmore was coming to take the island back. Yes I know that Keamy was a psycho path who seemed hell bent on killing everyone. But recall that absolutely everyone else on the freighter who was not on Keamy's team were dead set against him. Don't forget also the scene in which Matthew Abaddon instructed Naomi to get out of there without anyone getting hurt. Keamy was a rogue. Widmore did not order him to go psycho like that.

I think Jacob told Widmore to send that freighter to extract Ben. Possibly because Jacob knew everything would turn out the way it has. Jacob seems to have had everything very carefully planned out. Although Miles said that Jacob to his dying breath still had hope that Ben wouldn't kill him, I think that Jacob even had considered his own death as part of the plan. Let us not forget the runway the Others were building, presumably under the orders of Jacob, which happened to be the perfect landing strip for Ajira Flight 316. I think everything Jacob has done he has done for a reason, though all those reasons may not yet be clear. And this includes everything he asked Widmore to do, including sending that freighter to the island.

So why would Jacob entrust Widmore to be his right hand man when he never trusted Ben nor Richard to do this? I think it goes back to what Jacob said about giving people chances to prove that they are good; without interference from him. Widmore certainly didn't do this while he was on the island. By all appearances, he was at least as murderous and treacherous as Ben was when he led the Others. However, after his banishment, something might have changed. Widmore might have "seen the light" as it were, and done something that made Jacob really proud of him. Maybe Jacob still had hope that he was wrong about Ben; that Ben was still a good person; because he had already seen that he was wrong about another former leader of the Others; that this other former leader of the Others, Charles Widmore, did in fact redeem himself and prove to Jacob that he was a decent human being. What Widmore did to earn Jacob's approval remains to be seen. But I think whatever it was, it caused Jac! ob to approach Widmore, probably for the first time ever in person, and say, "Hey. Do you want to work for me again?"