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Was Henry Gales Ballooning trip orchestrated / guided by Eloise Hawkins to coincide with the appearance of the Island as happened in ‘316’? I get the impression that Henry was unwittingly recruited to land / crash on the Island for whatever purpose (possibly by Charles Widmore) as also happened with Desmonds boating antics.
There are also similarities to Desmond’s story, as Henry’s note is to Jenny (not that different to Penny).