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Widmore is interesting to me because he was the leader of "the good guys", but he's extremely mean to Desmond for no real reason.
Maybe he's just really protective of his daughter, but it's intense. I always figured that his success in the real world was probably just the result of being such a powerful and influential person by nature, going from a leader on the island to a leader in the real world.
No clue though. I think his character became a major force late enough in the show that flashbacks weren't really being done anymore. He would have had an interesting flashback episode, if they saw fit to do so.
I also think Widmore is probably one of those characters that had their role evolved due to popularity. Desmond got very popular, and in turn Widmore probably saw an increased role/connection to The Island.
I wouldn't be suprised at all if his original involvement wasn't supposed to go any further than being a douchebag to Desmond about Penny. Who knows though.
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