MS removed 16-bit support on 64-bit Windows. Linux and WINE can run older Windows programs than Windows can! So, if Microsoft is the polar opposite, then Linux must be the stratospheric opposite.

64-bit Windows 10 can run WINE too so that point goes to Windows again.

As far as I know, Windows 10 does not support 16-bit segments at all, so Wine on Windows 10 would be unable to execute 16-bit code. I don’t know to what extend 64-bit Windows supports segmentation at all.

Linux, in contrast, gives complete control of the LDT except that the LDT may not contain call gates, long mode segments, or anything with DPL != 3.

Making this work safely, especially on x86_64, is a real PITA, so I can’t really blame MS for declining to support it.

Do you realize that Windows 10 can run Linux aswell? Also Windows 10 NTVDM (NT Virtual DOS Machine) has an unofficial port to 64bit.

Windows 10 can run Linux in a VM (e.g. Windows Services for Linux, which is a VM these days), and it can run DOS or Windows 3.1 or whatever else in a VM as long as you have virtualization enabled. What it can't do is run native 16-bit segmented code as a regular user mode process. Linux can.

The NTVDM port appears to be a legally dubious emulator.

Apple can afford to do that, and still retain royal customers. The lock-in is too real.

Microsoft on the other hand has to keep literally everyone happy (90% of the world not on Linux or Mac). Ofc, they can't abandon backwards compatibility.

I am not complaining - as a Windows user i am quite happy Windows runs old software.