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I mean from where I'm standing the opposite has happened - he has been pretty resoundingly cancelled (mostly for the lukewarm HBD support) and is pretty permanently persona non grata in actual leftist spaces. I don't know what sort of people make up his social circles these days - other techie libertarians, probably - but it's very unlikely to be anyone actual leftists, let alone wokes, would recognize as allies they'd give the time of day to.
I don’t mean he spends time in left-wing activist spaces as an ally, I mean that I imagine his friends mostly take cultural left-wing fundamentals as a given. Trans stuff, race stuff*, homelessness, etc. I would be very surprised if he had friends who were actually right of center, let alone someone like Moldbug or Diseach. So he isn’t exposed to those perspectives any more except when he wants to be, and he’s made it pretty clear he doesn’t want to be.
*Yes, he hid his stance on HBD for a long time but even now he’s more open I doubt it actually makes any difference to his day-to-day behaviour.
Has it ever been different? The change in Scott's attitude is pretty clearly because liberals(ok, progressives[ok wokes]) were the main people who could hit him and then Trump started going after progressives, which he is and always was.
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Again, I'm just not sure how his friends could take the mainstream left-wing view of e.g. race and remain his friends. The mainstream left-wing view of race demands that you cut off anyone who gives the time of day to race science. And defines anyone who does as right-leaning by definition. Anyone who goes to parties with Scott is either not paying attention, or a very heterodox leftist indeed. I think accepting the premise in the original Red Tribe Vs Blue Tribe post that the Grey Tribe is a third, neutral entity is the only real way to describe what Scott's friends are like. He might very well be living in a tighter bubble than before, but it's not a left-wing bubble, because no actual left-wing bubble would tolerate his presence within itself.
(It's not just race, either, though that's the most prominent Schelling point. A mainstream leftist does not tolerate a friend who is outspokenly well-disposed toward capitalism - or indeed, one who casually, openly criticizes "wokeness", by that name. As an actual heterodox. This isn't to say all leftists are actively anti-capitalist and pro-cancel-culture, but nevertheless they treat it as a point of etiquette that the reverse opinions should not be embraced in public, for fear of looking like Those People. Scott, as a good Grey Triber, happily takes potshots at wokeness's illiberalism while taking it as a given that Capitalism is Good.)
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