So, the conservatives on the court decided that free speech really should be free when it comes to politics, but that it isn't free when you are a student and you are saying something the school doesn't like.
The liberals are holding a view that would seem to illustrate why big cities like liberals and everywhere else is getting more conservative. What the liberals said in those two rulings is that students should be able to publicly advocate drug use or anything else they want, anywhere they want to, including on school grounds. But people or groups with money should not be able to speak about politics in public.
Teens can say anything anywhere, but a group of people can't get together and comment on politics.
The other side, however, is much easier to make clear because it is just easier to boil things down to their essence and then choose what is obviously right:
"Discussion of issues cannot be suppressed simply because the issues also may be pertinent in an election. Where the First Amendment is implicated, the tie goes to the speaker, not the censor."
I really wonder, though, if Roberts couldn't have achieved a unanimous vote on both.
Look, I know this is a stretch, and it shows my Libertarian bent, but what if Roberts said to Souter, "David, really, if you really think kids should be able to say anything anywhere, I don't like it and my wife will kill me because I have small kids, but I could handle all that and vote with you because a bunch of potheads aren't going to get anyone else to smoke dope with some nonsense signs anyway. Also the schools have plenty of ways of keeping those punks in line. I'll suck it up and vote with you on that if you will embrace the spirit of free speech that you advocate for in that case, and apply it to the political speech case and vote with the majority. This way you get half of what you want, rather than being zero for two."
I know vote trading is wrong, illegal, etc., but with a couple of unanimous or at least near-unanimous decisions the court could really let everyone know that this is still America, and we really do have free speech.