I think it just means gently landing with grace. No matter how intense the wind blows and shakes the leaf to and fro when it lands it is almost with precision and without any damage.
This is from "Poltergeist 2" about the responsibility of a warrior. Whether this is what Wash was thinking at that moment, you'll have to decide for yourself (Lousy animation and sound)
I was watching a DVD of Robin of Sherwood, the line was said by Herne and later by the new Robin, ' I am a leaf driven by the wind '.
It made me wonder where the line by Wash came from.
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