[basedrum]

Why do you find it implausible that he got money to develop this challenge? I work in the non profit space and we get these kind of gifts all the time, with minimal strings attached or sometimes the deliverables don't see the light of day. 20k is actually small in my experience and they often come from random people who support our mission. Sure we do investigate and sometimes refuse based on findings, but we don't know or find everything. Taking money doesn't mean you know and support everything the person who have the money ever did, thought, said...

[foldr]

Primarily because there is no evidence that the challenge exists, and it's hard to imagine what it could even be. Chomsky's own research interests didn't really lend themselves to setting some kind of math olympiad style 'challenge'. If he was excited about setting up prizes or challenges in linguistics, you have to wonder why he never once did it. He certainly could have if he'd wanted to.

[basedrum]

Just because you can't find it doesn't mean it didn't happen. Also just because you give it hard to imagine, does not mean that it didn't happen, or that people with better imaginations as you could accomplish that.