I see DHH as being stuck in one of those finger traps, he’s engaged with a bunch of people who have to have the last word and as such they’ve taken over his life and he is going to go from forced errors to unforced errors. Not least concepts such as ‘free speech’, debate and such are problematic in the age of disinformation, polarization, spam, industrial-scale scams, Russian trolls, etc.
His best bet is to pretend those people aren’t there and focus on positivity and what will happen is his opponents won’t know what to do and surrogates will turn up to give those people the smack down. The harder he fights personally though the deeper hole he digs for himself and he doesn’t get it.