I've noticed many criticisms here on hackernews of using artistic license in writing as coming off as pretentious or egotistical; it almost seems to be a bout of anti-intellectualism. I would personally love to be able to write at Jerry's level, he definitely has talent.

Exactly. My high school rhetoric teacher would do similar things, writing (or lecturing) in a way that is clearly impractical but for the live of the language. I can't see it as anything other than thrilling with the language. He's paid to write, dammit, so he'll darn well write!