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I would say 20 to 30 years, but pretty much this. It takes time to see how their actions and policies actually shake out.
I would have placed Reagan in the Top 5 at the end of his term, but now after seeing the effects of him putting the so-called "drug war" on steroids, and embracing civil asset forfeiture and how simply wrong that is, he's dropped significantly in my eyes.
I expect Obama to settle in somewhere in the middle of the pack, after some time has passed.
A lot of Obama depends on what follows him and if they can keep improving on the economic progress of his term. If they can do that, he will get much credit for having laid the ground work and making slow but steady progress. On the other hand, if things fall apart, his assessment could go either way depending on how bad things get messed up.
I have always been intrigued with Truman and how he has risen up the ranks over time because when he left he pretty much got out of town without much regret on the part of anyone.