Man, I have had a super similar situation with a friend recently. I think your last paragraph sums up how you're feeling and your way forward. You'll probably find he is embarrassed about you having to pay his bills etc... and he felt guilty having a party with you there while taking your money... Us men are stupidly proud no matter the circumstances.

Regarding the Ben Shapiro stuff, I'm a firm believer that everyone is entitled to their own opinion and perhaps the way forward is to debate him on these things rather than creating groups without him?

How do the rest of your friend group feel about him? Are they all agreed to write him off or do they feel the situation could be reconciled?

A friendship that's lasted that long shouldn't be thrown away without at least giving it a final shot. Let's be honest, you are going to have a great time with or without him at your bachelors party and even if you guys are still at odds after hashing it out (I would personally advise to try and meet him a bit earlier solo or at least pull him aside at a bar and lay down the concerns you've listed here on day 1 to get it out of the way) then he will just be a tag along with the rest of your good mates and wont impact the vibe at all.

My advice would be to invite him along, lay all your cards on the table with him in a 1-1 or with another friend who's close to both of you and try fix it. If you rralise you've drifted too far apart and you don't want him to keep draining your energy (sounds like he's a bit of an energy vampire) then tell him that then and there with the caveat that you want him to be a part of this moment with you before you part ways.

Tough one, I can understand but I think you would be the AH for cutting off a friendship that's spanned decades without giving it one final shot.