Why Widmore Does What He Does by SubRosa

I think Daniel Faraday was marked for death, and both of his parents knew it. If Widmore hadn't sent Daniel to the Island, Daniel would've been hit by a car, shot in a convenience store holdup, etc. The universe would've course-corrected.

So who's Daniel's only hope? Desmond Hume, the most unique man in the universe. Only he has the ability to embody paradox (as we saw in the Daniel-knocking-at-the-hatch scene, plus the many times Desmond prevented Charlie's death). Only Desmond has the ability to rescue Daniel from a timeloop that invariably ends with his death.

Every time we condemn someone on this show (with the possible exception of Keamey and Anthony Cooper), the show takes a step back and rounds out the character. It's possible that everything Widmore has done has been an attempt to get Desmond into position so he can save Daniel's life.

Why did Widmore go off-island, cheat on Eloise and conceive Penelope? Because he knew Penelope had to be born if Daniel were to survive, because Penelope would draw Desmond to Widmore (and would save Desmond's life by serving as his constant). Why did Widmore purposely anger Desmond? To manipulate him onto the Island, so he could hook up with the 815ers and eventually meet Daniel. Why did Eloise insist on Daniel's mathematics studies? He had to have the knowledge to save Desmond when Desmond became unstuck in time. Why did Widmore send Daniel to the Island, knowing he would die there? Because Daniel would've died off-island anyway---the difference being that, on the Island, he can connect with Desmond and have a chance at altering his fate.

Why did Widmore send Keamey to kill everyone? He knew Keamey would fail---but the hostilities Keamey instigated actually led to a detente between the Losties and the Others, thus (once Keamey was dead) providing a measure of safety for Desmond and, once Daniel joined up, Daniel himself.

I have no idea if we'll get a Widmore-centric episode in Season 6, but if we do, I think it would be interesting if Widmore's life has actually been as centered around Desmond as Desmond's has been centered around Widmore. Did Widmore maybe have something to do with Desmond's father's death? (Maybe the elder Hume was putting Desmond in danger, and Widmore stepped in?) Did he play a role in Desmond's mysterious imprisonment in a military jail (to keep Desmond out of harm's way)? It seemed pretty clear after Jughead that Widmore doesn't really hate Desmond. I think it would be interesting if, after all this time, it's revealed that Widmore really loves his son-in-law.