Which litigants have been the main named parties in at least two opinon-producing First Amendment (speech/press/association/assembly/petition, not Free Exercise Clause or Establishment Clause) United States Supreme Court merits cases, as the free speech claimants?
One example is the New York Times, which was involved in (at least) New York Times Co. v. United States (1971) (the Pentagon Papers case) and New York Times Co. v. Sullivan (1964). But I can think of four more as I’m writing this, and I imagine there must be others. A single lawsuit that goes to the Court twice in its life counts only as one case. Dissents from the denial of certiorari, or opinions respecting the denial of certiorari, don’t count. To count, a majority of the Justices must have discussed the First Amendment issue (though perhaps among other issues). Special praise goes to those who can attest that they gave their answers from memory, without running online searches or checking reference works, [UPDATE:] but please check your submissions before posting them, unless you have no doubt that you’re correct.