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Obviously, the landowner has a say, but I think someone made the essential point up the thread, that a couple of things govern:

Is the billboard covered by a contract? (Yes.)
Does the contract have a clause about content? (Yes.)
Does the contract respect the civil rights of parties to the contract, and of other persons such as tenants who might be governed by the contract? (In dispute.)

The Supreme Court made sure to draw our attention, several years ago, to a doctrine that says that contracts may not abridge articles of the Bill of Rights (as through a "black covenant", or by incorporating or referencing a "black code"). I have deed restrictions on my own property that have never been adjudicated, that restrict to whom I may sell it, but which are unenforceable under federal law.

The argument on the board, then, is whether the landowner acted improperly to abridge the First Amendment rights of persons renting space on the billboard because of "content" (as in, "vote for Bob, he's a Republican/Democrat/Libertarian"). I also have a deed restriction that purports to restrict political expression, by banning political signs in people's front yards -- I personally think that that provision is also unenforceable, but the chairman of the deed-restrictions enforcement committee, a property owners' committee supported by and reporting to the civic club (in a purely advisory way), happens to think diametrically the opposite.

So, what do you think? Did the heritage group get screwed by NASCAR and the landowner?