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Trump run as an outsider. is it legit for the man who holds the office to continue positioning himself as an outsider? >> it's not legitimate. i think it will be difficult for him to do that this time around because of the point you made because he is holding the oval office. i think he will try to do that. i don't want to put words in kailey's mouth but i think he will try to position himself as an outsider even though he's a creature of washington. he's part of the swamp. he's the driving force behind the swamp. it will be that much harder to try to detract himself from that situation and tr...