I think each person is smart in their own way.
Doug is smart in the traditional sense, knows a lot about technical stuff, etc. Unfortunately that doesn't seem to get you very far in the zombie apocalypse.
Then there's the "survival smart" types. Each person seems to have adapted to the situation in their own ways. Chuck is smart in a "wise sage" sort of way. He knows what must be done to survive in this world.
Molly is smart in that she works with the walkers weaknesses, using their sluggish movement, low intelligence and overall poor mobility against them. I think she has the highest chance of survival with her methods, if she remains alone.
Lee just plain adapts to everything, always figures out how to keep going, how to keep winning and how to keep living(well...mostly). The main thing i see with Lee is that his actions and judgment are clouded when Clementine is in danger(hence why he's not careful with the walker in episode 4), and he loses everything for it. That's what i think, at least.
With regards to traditional "smartness", it would be Doug. Survival theories would be Chuck, survival tactics is Molly, and...survival action is Lee(I'm not good at this).
Out of these, i figure people like Molly would survive the longest, followed by Lee and a close second Chuck. Doug would probably die without a group to assist him.
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