1969 Tinker v. Des Moines
1971 U.S. v. New York Times The Pentagon Papers
1975 O'Connor v. Donaldson
1978 Smith v. Collin
1992 R.A.V. v. Wisconsin
1995 Lebron v. Amtrak
Only at length could I explain why I think each of these cases were wrongly decided. In many cases, it has to do with the failure to distinguish between public and private spheres of conduct. In others, it has to do with the right of a community or state to promulgate laws for rational purposes (for example - to allow peaceful assembly on common sites and prevent violence likely to be incited by certain expressions otherwise protected by free speech rights). In the Pentagon Papers case, national security was recklessly breached and people's lives endangered in the name of free speech, which is not and never has been an absolute right, even in a society as blessedly free as ours. Many of the rights that we enjoy result from the ability of our government to protect us against enemies foreign and domestic, and that sometimes results in limitations on individual action and/or expression. The limits to such intrusion are codified in the Constitution as a whole, which exists exclusive of, and not dependent on the Bill of Rights.
It is quite true that ConsistentLibertarian chose very old cases for the most part. What he ignores is the thousands of "cases" in which poor schools or organizations are threatened with financial ruin into settling with the ACLU for lack of resources to even get to court. We are all aware of these cases. It is a long time since Skokie. They simply are NEVER on the side of anyone not representing an extreme-left viewpoint or countercultural position.
The ACLU would NEVER EVER have intervened in the California State recall effort had Pete Wilson been the target. Can anyone dispute this? They are a purely left-wing group with a jihadist agenda to undermine traditional American values, and to create new "rights" for Marxist-supported groups which were never enumerated in the Constitution.