As we all know, Charles Widmore claimed in "The Life and Death of Jeremy Bentham" that he led the Others ("his people") for thirty years . We saw Charles Widmore on the Island as a member of the Others in 1954, and it did not appear that he was their leader at all at that point in time.
We also know that Widmore blames Ben for the fact that he left the Island. He says that Ben exiled him and tricked him into leaving. Apparently this is after thirty years of leading the Others. Assuming that he wasn't leading them in 1954, this puts his exile some time after 1984 (meaning he was leading the Others during the time of LaFleur). In the Season 5 premiere, "Because You Left," Miles states that Widmore has been looking for the Island for twenty years. This puts his exile around 1985...31 years after he was a punky 17 year old kid who met John Locke.
My guess is that Widmore somehow was found out to be extremely "special" by Richard and/or Jacob and therefore was allowed to become leader at that very young age. This would have been around 1955, possibly a year or two later. He then leads the Others for a good thirty years, through the time that Dharma comes to the Island. Somehow, a good 8 or so years before the Purge even happens, he is likely working with a younger Benjamin Linus to carry out the Purge when he is tricked to leave the Island. I think Richard may have had a hand in this, reaching out to Ben that they want a change much like he did with Locke in "The Man Behind the Curtain." And after this, Widmore will do anything to get back to the Island and ger revenge on Ben, which is partially why he amasses such a fortune and seems to be interested in the Dharma Initiative.
As for Penny, she had to have been born by the 80s, so there is a possibility she was born on the Island. She also could be like Alex is to Ben, not truly his biological daughter, but he cares for ner nonetheless. Perhaps she was a Dharma child that he kidnapped before leaving the Island, like Ben did to Danielle. Theory by Legend
We also know that Widmore blames Ben for the fact that he left the Island. He says that Ben exiled him and tricked him into leaving. Apparently this is after thirty years of leading the Others. Assuming that he wasn't leading them in 1954, this puts his exile some time after 1984 (meaning he was leading the Others during the time of LaFleur). In the Season 5 premiere, "Because You Left," Miles states that Widmore has been looking for the Island for twenty years. This puts his exile around 1985...31 years after he was a punky 17 year old kid who met John Locke.
My guess is that Widmore somehow was found out to be extremely "special" by Richard and/or Jacob and therefore was allowed to become leader at that very young age. This would have been around 1955, possibly a year or two later. He then leads the Others for a good thirty years, through the time that Dharma comes to the Island. Somehow, a good 8 or so years before the Purge even happens, he is likely working with a younger Benjamin Linus to carry out the Purge when he is tricked to leave the Island. I think Richard may have had a hand in this, reaching out to Ben that they want a change much like he did with Locke in "The Man Behind the Curtain." And after this, Widmore will do anything to get back to the Island and ger revenge on Ben, which is partially why he amasses such a fortune and seems to be interested in the Dharma Initiative.
As for Penny, she had to have been born by the 80s, so there is a possibility she was born on the Island. She also could be like Alex is to Ben, not truly his biological daughter, but he cares for ner nonetheless. Perhaps she was a Dharma child that he kidnapped before leaving the Island, like Ben did to Danielle. Theory by Legend
