Wow! That's a great idea! It's a tight squeeze even with towels though. My bag is 6'2 with a 6'1 board in it. If it doesn't work out too well, I have another board and lesson will be learned.

Should I check it at the ticket counter or attempt to bring it through TSA and check it at the gate? Any recommendations?

If I miss the morning flights, I'll need that night ride! haha