I think about this quite often. OS/2 was amazing. It deserved to win. Honestly, the biggest problem at the time was that Microsoft was much more a bunch of cowboys, while IBM insisted on near perfection. The two sides simply couldn’t agree on anything. Microsoft’s “quality” was focused on being “hardcore” where they wanted things to be lean and quick, quality be damned. IBM was more focused on having very few bugs. If that meant it required more hardware, that simply served their bottom line.
Sadly that means over a quarter century of windows on ARM and it's still not right. Sigh.