if the tire is rolling freely and not being propelled, then rolling is going to be slower than falling because it will get slowed down because it touches the road. Air still provides some slowing (like when a cold wind blows and you feel it on your cheek) but far less than the road would, even a steep one.
If you kept making the hill steeper and steeper, making the tire go faster and faster; eventually it would be straight up and down and the tire would only be falling like if you dropped it from an airplane.
Because the air slows a falling thing down just a little bit, there is a limit to how fast a tire can fall to the ground. That speed is the limit of how fast it could possibly roll down a hill, but probably not quite that fast because of the road slowing.
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