He wants people to think athletes pay attention to what he says. So when athletes get butthurt and scream back at him or try to "ether" him, it gives Skip literally the exact thing he wants.

There's no point to it, really. Obviously Sherman is better at life than Skip. Everyone knows that. Saying it aloud and getting mad at Skip on TV just helps Skip win.

In an ideal world, everyone fucking ignores Skip and his bullshit, he goes off the air, and life goes on. Then Skip loses.