As far as I'm aware, it's the former.
He has since made plenty of jokes at the expense of anarchist/libertarian leftists. The Antifa guy is frequently the butt of jokes in his Centricide videos. And in his non-series videos, he makes fun of breadtubers being hypocritical when they get rich
[1], creators in general who badger their (left-leaning) audiences to vote
[2] (or at least I interpreted that as a joke against lefties - convince me it isn't) and then of course, Antifa being the first to go after the communist revolution
[3]. It's worth noting those three videos came out within 10 days of each other in December 2019, although that is probably just a coincidence. And in another video, an entire joke is that he praises
Mein Kampf , which I doubt any internet leftist could bring themselves to do (when not
explicitly playing a character), no matter how committed they were to the bit
[4].
A friend of mine (who more-or-less occupies JayReg's former position, so take his opinion with a pinch of salt) thinks Greg became disillusioned and no longer truly believes in anything. December 2019 would be my best guess for when it happened, although it would have been starting to happen for a long time before that. And since so many of his jokes are self-deprecating, it's easy to see how he would have leaned into that more and more, the more centrist he became.
That anarcho-leftist slant in the Political Compass Rap was probably, in my opinion, a mask-slip in what was
supposed to a non-preachy video. If it was intentionally preachy, you'd know about it in more ways than that. So either he got a lot more skilled at avoiding the lethal mask-slip (unlikely), or his views realy did change. It sounds almost too good to be true, but then again, Political Compass memes have been known to de-radicalise people.
