I read his comics in middle school, and in hindsight even a lot of his older comics seems crueler and uglier. Like Alice's anger isn't a legitimate response to the bullshit work environment she has but just haha angry woman funny.

Also, the Dilbert Future had some bizarre stuff at the end, like Deepak Chopra manifestation quantum woo, so it makes sense in hindsight he went down the alt-right manosphere pipeline.

It's the exact same syndrome as Yarvin. The guy in the middle- to low-end of the corporate hierarchy -- who, crucially, still believes in a rigid hierarchy! has just failed to advance in this one because reasons! -- but got a lucky enough break to go full-time as an edgy, cynical outsider "truth-teller."

Both of these guys had at some point realized, and to some degree accepted, that they were never going to manage a leadership position in a large organization. And probably also accepted that they were misanthropic enough that they didn't really want that anyway. I've been reading through JoJo's Bizarre Adventure, and these types of dude might best be described by the guiding philosophy of the cowboy villain Hol Horse: "Why be #1 when you can be #2?"

I had hoped that he had just gone off the deep end during COVID like so many others

If COVID made you a bad person -- it didn't, you were always bad and just needed a gentle push.

Like unless something really traumatic happened -- a family member died, you were a frontline worker and broke from stress -- then no, I'm sorry, a financially secure white guy going apeshit from COVID is not a turn, it's just a mask-off moment