Holder v. Humanitarian Law Project ruled that knowingly providing material support to designated terrorist organizations is not protected by the first amendment. https://supreme.justia.com/cases/federal/us/561/1

But I'm curious about your take on this. How would you argue the first amendment protects this?

The USA has never had free speech. There's not one time in its history when the government wasn't trying to force people it disagreed with to shut up.