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The entirety of Freddie DeBoer's life outlook is that he loved hippies/bohemians in new york in the 90s and then turned out to be quite smart and a world view crystalized around that abstract attraction/memeplex. It was pretty clear in his infamous planet of cops piece and it explains exactly why he lives in a groundhog world of noticing the left has lost it's mind but waking up the next day completely forgetting that realization.

As for the 90s vs today, the tech sucked and was expensive, the domination of the moral majority sucked even though it's piercing light gave contrast to interesting subcultures just as much as modern progressivism sucks despite it's life giving contrast to communities like our own. The grass is greened by the lack of our, or at least my, current enemy but there is a cause for the sword in every era.

It was pretty clear in his infamous planet of cops piece and it explains exactly why he lives in a groundhog world of noticing the left has lost it's mind but waking up the next day completely forgetting that realization.

I think he know the left is nuts, but he also has a nice gig going on he would not want to give that up either. I think he is able to compartmentalize it well. Being a leftist who criticizes the far-left is a good niche to be. You get tons of spillover from both sides and minimal to no risk of being cancelled, deplatformed.