Flipping the Bird and the First Amendment
Can you distribute T-shirts giving a one-fingered salute to the City Council?
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Political speech is usually not considered obscene. In Cohen v. California, another Vietnam era case, a young man named Paul Cohen was arrested for wearing inside a courthouse a jacket on which he had written “F- the draft” (except that he spelled out the entire F-word). In overturning Cohen’s conviction, the Supreme Court stated that “It cannot plausibly be maintained” that the words on his jacket convey any erotic message that would meet the definition of “obscenity.”
Them’s Fightin’ Words
Under the doctrine of “fighting words” a person may be arrested for a “breach of the peace” if his or her words are spoken directly to a person and are likely to provoke violent retaliation. Whether the one-fingered salute can constitute “fighting words” has been the subject of various court cases. Unfortunately, the results haven’t been consistent. In 2000, a federal court in Arkansas held that flipping the bird to a police officer was protected speech and did not constitute “fighting words.”  However, on January 13, 2009, a federal court in Maine held that the First Amendment did not protect a man who was arrested for “disorderly conduct” for making the same gesture toward two game wardens. 
Neither of these cases, however, involved a mere picture of an extended middle finger. Whether Tim’s T-shirts are sufficiently inflammatory to drive men to violence would depend upon the situation on the mean streets of Exampletown.
School for Scandal
The State may be able to impose limitations on expression in certain other limited contexts. Under the Tinker v. Des Moines case I mentioned a minute ago, school officials could prohibit, say, the wearing of a provocative T-shirt if they have reasonable grounds to believe that the shirt would “substantially and materially disrupt the educational process.”
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 Miller v. California, 413 US 15 (1973).
 Nichols v. Chacon (W.D. Ark. 2000)
 Dube v. Boyer, Civil No. 8-165-B-K (D. ME. January 13, 2009)