In contrast, Malto's decision to sign with Nike will surprise few observers. (Indeed, rumors of Malto's imminent shift had been flying for quite some time.) And today's top-skateboarder does not have to tread as lightly when he steps outside the sport's more traditional pastures.

"It's been some interesting and pleasant conversations," says Kaspar van Lierop, Nike SB's Global Sports Marketing Manager.

"Normally it starts more informal, and then gets more serious in the end. But this was more the other way around," observes Lierop, who hails from Holland and has himself been a skateboarder for 18 years.

"It's been a total pleasure working with Sean, I have to say. He's super-grateful, super-talented at skateboarding," he adds. "What I have noticed with him is he likes to think along with what we're doing. He's really interested in sports in general, basketball particularly. When it comes to commercials that we produce, whether it is skating or other categories, he's really interested. It's not like, 'Hey, I like the shoes. Let's go skate.'"

In terms of the anatomy of the contemporary skateboard deal, how important has secrecy been to the Malto negotiations?

"Skateboarding is growing up, getting more serious, more organized," continues Lierop. "Which is both good and bad. These days everyone is working with pretty serious agents and contracts, so it's a little more serious then back in the day. Just legally you have to be careful. It's not just one person in the company, like, 'Hey, let's sign this dude.' More people within the company have to be aligned. We just want to come out with the news when it is fully done. It's not a secret now."

Generally speaking, Malto's shift is the kind of news that skateboarding pundits, both amateur and professional, often live for. Does Lierop himself spend much time agonizing over how the chattering classes/forums will perceive Malto's momentous decision?

"If someone does not have respect from the core, if he's not delivering raw street footage, that is when we lose that credibility," says Lierop. "That core community are the ones that help you get there. And those are the ones that could eventually get you down from that spot. Yes, we dip into a broader audience. But we try to make sure that that message is as core as it can get. Yes, there are people who might not be agreeing with our strategy, who we're adding on. It would be really hard to create a team where everyone is stoked on every single person."