If your argument is you are an expert but Hickey is not, criticising him on his language design skills seems like a logical mistake. He's one of the foremost language designers of the current era. "Maybe Not" is a speech by an expert talking in his field of expertise.
If your argument is that his confidence is unfounded, again, he's an expert talking in his area. He can reasonably take a confident attitude in that, even if he has unfounded confidence in other fields he isn't an expert in. Lots of experts do that, it is a well founded stereotype of smart people.
He doesn't need to be an expert in implementing types to judge whether they are a good language feature.