[DrewDevil]

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Captain Awesome,
I was stopped on the sidewalk the other day by a police officer who told me I was wearing an "offensive" t-shirt and he threatened me with a citation. Does the first amendment not protect my wearing an "offensive" shirt?

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The first amendment does protect you.

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To what extent? If I refuse to change the shirt, what's my play after getting a citation?

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Ask for a trial and tell the judge that your shirt is protected by the First Amendment. Find the Supreme Court case where the guy wore a "F*ck the Draft" T-shirt and show it to the judge.