On if his personal items like his wallet, key fob or something said "Kip Hawley is an Idiot!" inside the CLEAR plastic bag.
If he really wanted to make a 1st amendment issue... that is what he needed to do. The TSA wouldn't have a leg to stand on. Just wondering on your thinking on that.
Of course remember what I went through taking a 1-way from Detroit Metro to La Guardia, with a license plate, an MSP State Police hat, 4 - 3/8" long license plate screws and a flat blade screw driver in his bag. Along with reading materials related to computer security and a Subway sandwich.
Remember, I was down to mah skivvies before given the "OK". And just made last call for my flight. Noticing my 4 screws (yeah deadly weapons there) and screw driver (believable to be a deadly weapon as it has a "blade") were gone.
So, your thoughts on it being an item inside the bag with the statement on it, would be a good thing.