In the speech, the ‘swag’ refers to america standing strong, unafraid of russia, and. 21 'free me swag out' = 'unpack my canvas bed roll with a mattress inside' a 'swag' (countable noun) is a traditional australian canvas bed roll with a mattress inside, carried rolled up by. The swag appears to be a clipped form of swagger, which the article accuses president obama of doing.
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Swag= very confident attitude or manner. Or what are they referring to exactly in this definition? Does confident here mean that you trust yourself to achieve something?