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It sounds to me like there's a lot of history of problems with this guy in the chapter.
If you're thinking about expelling him, I recommend that you try to consider all of the relevant circumstances. I do not think that anyone should be expelled solely for expressing a politically charged viewpoint. On the other hand, destruction of fraternity property does merit some sort of discipline, and it could be that the history this fellow has had with the chapter means that more discipline is warranted.
The fraternity should carefully consider how to weigh the freedom of expression question during its deliberations. As a legal matter, the First Amendment protects the individual from government punishment for his expression. It does not protect him from fraternity discipline. This does not mean that you don't still have to think about the question of free speech; it just means that there's no way he could somehow sue the fraternity if you expelled him based on his speech, except perhaps to demand a prorated refund of dues for time he ends up not spending as a member. (In fact, the First Amendment's freedom of association means that the government cannot force the fraternity to associate with expression of a viewpoint it loathes.)
Naturally, this is an emotionally charged issue. I would only advise you to think very carefully about it, weigh all the circumstances, including all the history with this individual.
Consider also the core principles of your fraternity. Most fraternities allow expulsion for the catch-all "conduct unbecoming a member of the fraternity." I have generally considered this to include "conduct violative of the cardinal principles of the fraternity," and I consider those to be much more important than whatever some random person on the street might find offensive. Applying the ideas tied up in such principles is often very hard to do in an emotionally charged situation. While you shouldn't state categorically, "well, this is against principle blah, so you're out," you might find that your core principles can guide you when you have a question that seems like it could go either way.
So, think slowly, think hard, and think carefully. Good luck to your chapter in handling this.
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