From my experience the "First Amendment" issue is a last resort. The ACLU has more important things to deal with, believe it or not. Only a US Court can make him stop producing the shirts. The decision will be based on previous case law and there are plenty of examples. If it does go to a lawsuit he better keep great records of everything involved in producing the shirts. During "discovery" they will want a copy of everything. Think paralegals making copies and stapling things together all day long at $85.00 per hour. Even if his attorney is pro bono the firm will never write off all the misc. paper bs. What should happen is it will be decided with a Judges "Summmary Judgement" Hearing, if it goes that far. The printer will win and still be able print the shirts and all his counter suits will be thrown out at the same time. I believe this shirt has a small shelf life, so you need to strike the iron when it is hot. People are already printing similar shirt as we speak and they will not be sued. So after he wins no one will be buying his shirts anymore and the market will already be flooded with similar shirts. He will have no recourse against other printer making "parody" NSA" t-shirts. It is all total nonsense.