I think this is probably because hackers in younger generations never experienced the beast that was Microsoft in the 90s and have seen the progression of MS as one from "company that makes boring and/or bad OS" to the embrace of FOSS that's been happening recently.

I'm personally super interested in tech and hacking history, so I've read all the war stories, the pleas on FOSS homepages, the rants on sites like jwz's, books like Microserfs, etc. But even the most talented hackers who are 16-24 right now probably see Microsoft as "the Xbox company."