It doesn’t prevent the damage and it only contributes a negligible amount of cushioning (unless one lands on the wrong part of the deck and it snaps, which would absorb some of the energy). Skaters get hurt and bruise their heels on a regular basis, and more serious injuries are also common. Impact dispersing shoes and insoles are also very popular in skating for this reason (and they tend to become more popular when doing huge stairsets/drops becomes trendy).
Skateboarders rely on their leg muscles and a lot of practiced technique to crouch and absorb the impact as they land. They have to do so while landing straight and keeping their balance so they can roll away and not slide out and lose control. If they do not roll away from it on the skateboard successfully, they will often be forced to try and run or dive roll out of it to try and absorb the horizontal momentum they had.
The approach speed (and therefore horizontal momentum) is really only needed to clear whatever object you’re trying to jump over (commonly stairs). It also helps to have some speed when rolling away, as it makes it less likely that a small crack or other obstacle will catch your wheels enough to jar you off-balance, which happens easily if you’re moving at a crawl.
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