I'm in the "smarter than you think" camp, as far as the Worm goes.
However, I do want to add one further caution:
The Worm is lazy. This is not an advantage for us. Lazy people produce 90% of the world's progress, since they look for ways of doing things with minimal effort.
How'd the Worm get most of his "legacy" enacted? The laziest way possible - pen and phone and not bothering to work with Congress.
Well, he still has a pen. He still has a phone. He still has access to other people's money and a horde of adoring media and fans.
I expect him to be troublesome.