This would actually be a lot easier if it were a court. A waiver to USCIS is done at the whim of the officer assigned to it. They could give me a pass, or they could deny it, which would be left on my application that I was refused entry and that would make any future attempts that much more difficult.

I've been told by three different lawyers that this this not something that would be extremely difficult to get into a court, and there is no case law in this area to draw from.