Let me put it this way: if you look up Asphalt Poser Club or #whyIdontskateboard on instagram, you'll see all the egregious examples of brands trying to use skateboarding in their marketing. It's been going on for years and years, and it's not going to stop any time soon. To skaters, it's very obvious when they've just handed a skateboard to a model. This way, it's got a little bit more credulity.
At least they're supporting a real skater when they use the image. Yes, it's absolutely still culture vultures, but at least they're hooking up someone who skates all the time, and in return they get something that looks a bit more genuine.
To whoever said, "He's not going to convince me to buy a $400 beanie", they're not trying to. Skateboarders are nowhere near their key demographic. They're using skateboarding as an image to market to people who know nothing about skateboarding.
To whoever said, "Better this than a monster energy logo", exactly right.
tl;dr: More power to him, fuck it, get that cheque.