Good thinking about Widmore being a former chosen one. It tracks. And it probably sheds some light on “the rules.” Maybe that has something to do with their service to the island - the rules that chosen ones are supposed to follow?

But I don’t think you’re right about Ben having been raised apart from his parents. Unless I’m misremembering, Ben was raised by his father, who worked for the Dharma Initiative.

If chosen ones really are raised apart from their parents, Alex is looking like another candidate.

Wikipedia says that Matthew Abbadon (who told John to go on a walkabout and said “when we meet again, you’ll owe me one” ) works for Widmore; I don’t remember where that was established. But it’s interesting that he and Richard Alpert (who tested the young John and found him wanting) work for opposing teams. Were they always opposed? Did the Others change their minds about John, or did Widmore see promise where the Others didn’t? Which team (if they were opposite teams at the time) tried to recruit the teenage John to science camp? And how (if at all) has Richard’s assessment of John changed? Remember it was Richard who egged John on to challenge Ben for the leadership of the Others.

I’ll be interested to see if it’s ever established how one loses one’s chosenness. Is it simply arbitrary, or did Ben (and potentially Widmore before him) forfeit the position by betraying the true faith?