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Anyway any tips to dump a friend??

Sounds like the dude might be on the autistic spectrum with some ADHD thrown in. These people can be toxic in this state and it's hard to get them to move on without they themselves wanting to.

Have you ever hung out with him and "the guys" in a while? Maybe he misses the "good old days" and hasn't realized people have changed. Doing another might push him to that conclusion himself, and it would be a good way to get him pointed in a more constructive direction. If the dude is anti authoritarian and hates modern culture, getting him to get a civil engineering degree might be the catalyst to break him out of the cycle.

If you do this, I would have at least one of y'all be prepared not to "refute" his claims but nudge him to a new discovery; if he brings up sidewalks being authoritarian say something like "oh, interesting. Have you read any of Jane Jacobs' work? I think you'd like it."

However, it shouldn't be like an intervention. Try to let him have fun—have drinks, games, a bouncy castle, I dunno—and go at his pace. People like him just need a push in the right direction before they hurt people.

Wow more than one pandemic friend casualty in here. Had a friend who had been getting more and more libertarian and self-destructive since dropping out of college, and when the pandemic hit he started getting extremely joe rogan about everything with a mixture of that insufferable "magic is real you know but big academia doesn't want us to know" after abusing psychs. Eventually the friendship died when I realized I couldn't have a single conversation with him that wasn't like arguing with a 4chan poster.

He also eventually revealed that he was interested in my tragically straight self during an lsd comedown which meant that when I started to cut contact a few months later I felt especially guilty and horrible.

Yes. Literally don't miss him. Who cares, there's lots of people just make new friends.

Don't owe anyone friendship but just to play the other side, I've kept a few friends after most of our mutual friends dumped them, I know a few difficult people mostly who are that way because of mental illness; autism, chronic depression, alcoholism and drug addiction, etc. I also have some old friends who annoy the shit out of me often just because of their personalities. I just think it's nice that tough people or people having a tough time in society should also experience friendship, and it makes their antisociality better vs isolation making it worse. There's always a line but in general I think it's virtuous to be patient with our difficult friends because nobody is perfect and heaven knows we can be difficult too sometimes. The key is having good boundaries though, you can be friends with someone and not talk to them all the time or put up with their bullshit. Even take months breaks if you need to

I've friend-dumped my entire high school friend group once I left for college. I didn't think they liked me enough to keep ties, so I didn't bother trying to maintain friendships. I felt like these were friendships of convenience. Of course this was likely due to low self-esteem but maybe there was truth in what I thought. They were all friends since elementary, and I only knew them our freshman year. I've taken more care to maintain friendships with my college friends though. But lemme tell ya, deep down I do feel a little sad when I see them all having fun on social media.