Maybe a spare tire ?
He's probably pumping the spare tire
This way you can lift the wheel up and let it bounce a little bit after you pump it up. So it's worth it.
Could be trying to determine where the air is escaping from if it has been deflating.
I guess that is his winter set that just came out of the trunk
Spare or maybe the bead broke. Won't fill without taking it off.
Nope, that’s how you do it. Take the wheel of to pump it up.
Maybe just changing tires