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Citizens United
I've contemplated this off and on since the Supreme Court decision, and have come up with compelling arguments (I think) in both directions on this one. Except there's a catch. I think this decision exposes a very interesting aspect of government and laws in general. To put it into CS terms: Order of operations matters.
If we had the right disclosure laws in place for campaign finance / fundraising I think I wouldn't hesitate to be in favor of the Citizens United decision. Except they're not, and so now the powers that be have (to be modest about it) more power than they did before.
I guess I'm trying to figure out in what scenario it is likely that disclosure laws will come to the table at this point. I think the deep pockets would be remiss if they weren't on top of it and only funding candidates who are unlikely to push for reform in this area. That or holding incumbents at ransom.
Take away that extra power that Citizens United gives deep pockets and suddenly it appears (remotely) possible that our government makes progress with laws that force disclosure of financial contributions to political campaigns.