skateboarding was always a bit political in a way that it's something that is or was illegal in many public spaces, like graffiti or smoking weed, and often occured together with them. it was seen as a lower class/low life sport in the public eye for long and associated with punk or rap subcultures. so for most non skaters it was probably always seen as some sort of center left subculture. at the same time, within skateboarding, right wing stereotypes were pretty rampant especially in the 70s and 80s as we now see and find out. it also seems that many skateboarders past their 40s turn into the same conservative types they hated when they are young, which is also nothing unusual. companys putting out racist graphics for laughs or shock value. even if a company isn't overtly political in their messaging or graphics, people will analyze products, videos or read interviews with riders and kind of put 2 and 2 together.
there are also graphics that are clearly about political issues. real-hanging klansmen, alien workshopXinfowars collabo, dollarlave and anti hero making fun of capitalism(depressed officeworker, monkeys in suits in front of flip charts), duane peters doing hail trump decks, stuff jason jessee did with the driven.
imo skateboarding as a whole is operating pretty much in the spectrum of libertarianism and anarchism. in the sense that the industry is pretty libertarian but often wants to come off as vaguely anarchist. i'd say it's inherently libertarian in that there's a wide range of views from individuals within the industry. the views probably haven't changed that much, the internet just makes them more visible, so now we know how some pros think politically and take that into account in our opinions.
i would say there is definetly a good deal of racist skatepros outthere and many who seem politically illiterate. i can't think of a single big name pro that is really far left or radical left though. one thing that is pretty much exclusive to america it seems is displaying patriotism in graphics, see all the american flag designs you got. i'm in gay europe and in most european countries waving the flag is not really a normal thing to do. well, especially in germany. you just don't run the flag at all except when there's a big soccer game or something. and it's not because the flag is bad or racist, it's just that flagwaving is so much a thing of right wing weirdos that nobody does it just to not get associated with them. lately they've been switching to the reichsflag though overhere.
so there's all kinds of political tension within skateboarding, which imo makes it impossible for skateboarding as a whole to be totally non-political. we will always be affected by laws concerning public places and skateboarding has it's own progressive movements within that are often opposed by those who don't want things to change at all, so it's a whole political microcosm.
that said, trying to have your real life views align with those of any company you support is mostly fruitless imo. i personally would never buy stuff from a brand whose boss is an outright racist or support a skater that promotes hateful thoughts, and i can make that choice. it would be different if i was forced to buy this stuff, but i can simply opt out of supporting or promoting the brand.
social progress or regress in the skatescene depends on locality and demographics so they are not the same anywhere. in germany we have some board brands that have antifa and/or anticapitalist messages, but that is because antifa and anticapitalism don't have the stigma here that they have in the usa. we even used to have center right politicians openly sympathize with antifa because opposing fascism and authoritarianism is a big unifier here after being ruled by fascists and authoritarian socialists respectively.
in the end skateboarding follows capitalist/neo-liberal logic in terms of how it adapts to social or political change. there's a spectrum around the center where anything goes, extremists are usually shunned on both sides of the spectrum and often remain alone, and social progress means more ways to market shit to people. corps generally don't support social causes because they are nice, they just turn social movements into sort of focus groups they cater and sell stuff to. i think this is what is mostly happening in the skateboarding industry in regards to social progress.