Yeah, to an extent, sponsors are always gonna be pushing to get the most out of their riders, but when you look at coordinated efforts that big name brands do now, it hardly seems like there was any sort of Wes Kremer "campaign" at all (those ads above are from his shoe ad in 2016), just someone who's always killed it coming through with a little something more that happened to give him the edge. Plus, wasn't DC broke as fuck at this point? And Sk8mafia definitely didn't have that kind of budget...
Leo Romero in 2010 was a good one. I'd say that was one of the last organic SOTYs, but he was always a Thrasher dude. Wes is San Diego, giving him the element of surprise.
Grant's win seems obvious in hindsight, but there were some debatable circumstances that year -- he basically dropped his first video part of the year when he won, which ended up being a teaser for his Nike part that the public hadn't seen yet. Plus, being from Atlanta, I'm not really allowed to say this, but 2011 could have easily gone to Busenitz.