Do we actually know why Ray left? I’ve not heard that he was fired.
We don't know exactly what happened beyond the sequence of events and some posts from Winninger.
1) In October 2022, Dan Rawson suddenly arrives at WotC, from Microsoft (like most Hasbro execs), with the title Senior Vice President of Dungeons & Dragons. His background is extensive experience in converting MS customers from buying specific products, like, say, Office 2016, to subscription-based online services like the subscription version of Office 365.
2) A few days later, Ray Winninger suddenly "doesn't work at WotC anymore", and his Executive Producer of D&D position
seems to be empty. People assume that Rawson is simply taking over that role as part of his SVP deal.
3) Ray Winninger makes some Tweets/statements (I forget which), which vaguely imply he wasn't anticipating/planning this, and isn't exactly delighted about it, in a professional way.
4) Following the OGL controversy, in early 2023, suddenly there's a new Executive Producer of D&D, Kyle Brink, who manages to both help and hurt the situation with various comments. He implied he's going to be communicating about D&D more in future, as Winninger did, but AFAIK, it's been 9-10 months and that hasn't happened (feel free to correct me but I think the last public statement he made was about Dark Sun being "problematic").
Muddying the waters way further, Kyle Brink's LinkedIn (which I won't link in case there are any weirdoes here) shows him as having been Executive Producer of D&D (the exact same title as Ray Winninger) since
July 2022 - three months
before Ray Winninger left! Obviously it's possible to have more than one executive producer, but... that certainly didn't ever seem to be the case previously, and no announcements re: Brink being made into that position were made. Indeed, Winninger seemed to be trucking along as EP of D&D. Winninger's Twitter posts after July don't change in style or nature about D&D products up into September - he certainly was still acting like he was EP of D&D. That could merely be professionalism, of course - maybe he was training up Brink as a successor, or on gardening leave*. But what's odd is that in his handover he doesn't mention Brink at all, doesn't mention D&D has a new EP (indeed WotC didn't announce or mention that either), yet did talk about and praise most senior members of the D&D team. Notably a number of the people he specifically praised just got laid off, of course.
A lot of this is probably down to Hasbro/WotC's very peculiar corporate culture. It seems like they are very loath to announce staff changes below the highest executive level, unless there's a gun to their head, even if they're really significant ones for the potential direction of a major product. They inarguably actively cover up staff changes extensively, too - the biggest example is that Ray's original hiring, with was like, many months (maybe over a year, I forget) before he was seemingly allowed to "break cover" and say he'd replaced Mike Mearls, even though we all knew someone had to have, and his LinkedIn then had backdated how long he'd worked there (the latter is hardly unheard-of, I still need to update my LinkedIn with my current job title for example - but it is peculiar with such a big and frankly prestigious role). I work in corporate environments, at multi-billion-dollar places, and to me, this seems fundamentally odd - normally someone becoming an EP like that would be publicised in some way - at least when the previous guy left! A press release for the industry press or something. Just the guy announcing it on Twitter. I'm not sure what this cloak and dagger is about, but some corporations are just weird.
Anyway, that's as much as I know.