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Giuliani and the First Amendment

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I was wondering what people think about Giuliani's past in being struck down by courts for violating the First Amendment. For instance, while mayor, an advertisement was put up on a New York City subway that criticized Giuliani. He quickly had the advertisement removed and was sued for violating the First Amendment--and lost. Now we may all agree that Giuliani did not violate the freedom of speech since he did not violate anybody's right to find a private means of displaying or broadcasting anything. However, by case law, he did seem to have violated the First Amendment.

Now if one were to argue that it's okay to violate the First Amendment so long as you don't actually violate freedom of speech, then a couple of questions arise. First, which other laws might it be fine for an official to break? Second, considering that Giuliani believes in constructivism in law, should he not follow the letter of the law himself?

One might take a different approach all together and say that Giuliani simply didn't know that he was violating the law. Moreover, he was more than ready to submit his actions to the judgement of the courts. After all, it is highly non-obvious that his action violated the First Amendment--that would take some decent case law knowledge. So why did he not ask somebody knowledgable about case law? If he thought that he did not need to ask because he didn't think there was a question of legality, does that justify it?

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One point is that Giuliani wasn't actually the defendant. Section 50 of the NY Civil Rights Law could protect him in this case and the contract had an approval clause concerning the character of advertising, so the restriction was quite reasonable. Now I don't know whether I agree with the court's reasoning in the case because the legal issues are extremely complicated, but under the "public forum" presumption -- which MTA denied -- the 1st amendment argument becomes credible. But you cannot know that in advance, until the courts have ruled. That's just the nature of our legal system.

First, which other laws might it be fine for an official to break?
It's never "fine" and if you do break a law, your action will be undone by the courts. As it was in that case. But you can't know that it's a violation until you get the court ruling.
Second, considering that Giuliani believes in constructivism in law, should he not follow the letter of the law himself?
But he did. The courts disagreed. This happens every day.
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But he did. The courts disagreed. This happens every day.

This is a useful point to emphasize more generally; it's relevant, for example, to some of the controversies over the Bush administration's handling of suspected terrorists, or the NSA intercept program. Laws, by their nature, are written in terms of concepts, and are consequently abstract. This means that their application to specific situations is not automatic and may not even be obvious. (This is doubly true today, when the laws are often also non-objective, contradictory and vaguely written.) The simple fact that two parties disagree about how a law should apply in a specific case does not mean that the party who loses the resulting lawsuit was deliberately flouting the law.

To my mind, the two relevant questions to ask in such a situation are (1) whether the losing party had a colorable position, i.e. was their interpretation of the law backed by at least some evidence and logic; and (2) how does the losing party react to their loss?

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