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Ok so i know i posted a similar blog awhile ago about what woke Boone up but i was thinking...was Widmore "awake"? Eloise was but i think that Widmore was still unaware. I mean Penny was the most important thing to him and he would want to spend as much time with her as possible, just like Eloise did with Daniel, so if he was awake i dont think he would send Desmond to two people he knew, Charlie and Eloise. Doing this had an extremely high chance of waking Desmond up and thus taking Penny away from him which is of course what happened