Another poster quoted Wikipedia somewhere here; MS implicitly acknowledged Wine's existence back in 2005 when they added a check for some of Wine's registry keys which would disable Windows Update if it found them. And in 2020 MS filed an Amicus brief in that Google/Oracle lawsuit in support of free re-implementations of APIs, citing Wine as a positive example.
While I am still wary of Microsoft after their previous anti-competitive behaviors, I think they've taken a more pragmatic view of late, and realize that projects like Wine are actually good for their platform as a whole. I expect if Wine/Proton did not exist, we'd see more (for example) Windows-only games ported to macOS or Linux. With Wine/Proton, those ports are mostly not necessary, and Microsoft gets to say that Win32/DirectX is something of a cross-platform gaming "standard".