Re: More detail please
With enough resources you can compromise the USB key itself to attack the system
Don't you need to modify hardware to do that? If it is even theoretically possible for software to remotely hack a USB flash storage device connected to a standard PC to make it act like a keyboard when connected to a different standard PC, color me shocked (and I'd like a link, please)
If you can leave USB keys laying around the parking lot and they're dumb enough to use that in the air gapped system, then they probably have so many other security failures you don't need this attack. If you're able to do a black bag job and break in to swap out the USB keys they use on the air gapped systems with one that's been modified, then you might as well just go directly to the air gapped system and do what you please.