Jesse,
I taped tND latenight @ BB Kings a few years ago - I had a large backback on a luggage cart cause I had 2 SLAs (Portico and AD1000). The cop made sure I had a ticket before letting me through the barrier, and he looked in my bag, but he had no problem letting me roll through. I figure there are so many cops and entry ways into Times Square that if one of them says no you can just walk a few blocks and try someone else. I say go for it.