Undercooked
The Remnant with Jonah Goldberg
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The Importance of Free Speech
I'll try and take all of your points in some coherent manner. Why I think it depends on the situation. On a Stanford question, Stanford is a private university. The first amendment does not apply. If you make a promise, whether you are a business or a university or an individual, you should keep it. As a matter of political tactics, it might in some cases be useful to fight the outlier cases. But I don't think that is the primary argument for defending what you describe as outlier extreme instances of speech. There is no reasonable or comprehensible rubric by which speech can be deemed by the government as virtuous or evil.
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