[Repurposed HackerNews comment]
OS/2 was a genuinely great OS in its time.
OS/2 2.0 was released in the same month as Windows 3.1. In that era, it was so much better, it was embarrassing.
(Linux 1.0 would not be released for another 2 years yet, and v1.0 of native BSD on x86 — BSD/OS from BSDi, i.e. still commercial — for another whole year. Yes, it was possible to run pre-1.0 versions of both — BSD/OS 0.3 came out in April 1992 as well — but pre-1.0 Linux was very sketchy and very hard work.)
If IBM had let Microsoft make OS/2 1 a 386 OS (x86-32) instead of a 286 OS, the IT world would have turned out very differently. An OS/2 1.x in 1987 that could multitask DOS apps would have been a big hit.
I suspect Windows 3, FreeBSD etc. and Linux would never have happened. Perhaps the GNU Project would have adopted the BSD-Lite kernel, as it did evaluate but foolishly discarded.
But saying that, OS/2 2 was still a 1980s-style OS, a nightmare of vast config files, special drivers that cost money and came on floppy via international post, building custom modified boot floppies so your hard disk or CD drive controller would be recognised and real major pain.
The desktop was very powerful but very weird and kinda clunky. It's no coincidence that nobody has ever re-implemented the OS/2 Workplace Shell on Linux. Lots of other 1980s OSes — Acorn's RISC OS; Classic MacOS; AmigaOS; NeXTstep; CDE; yep, all of those exist or existed. WPS? Yeah, no thanks.
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