Smaug-7
Drauglin-2
Old Man Willow vs. Master of Laketown
In their own ways both were survivors. The Master
not only efficiently ran his town, and was correct in
doubts about the wisdom of riling the status quo
by provoking Smaug, but then made out rather well
with the worm's treasure until the tragic end of this
statesman. Had he survived mayhap his descendants
would have been valued bureaucrats in Eriador and
Rhovannion.
As for
Old Man Willow the question is how mobile
(and evil) were he and his followers. Could they have
skittered all the way to Fangorn, in say, 500 years?