Comment by amlib

It ran fine as in not crashing, but you were limited to dx8 or maybe dx9a feature set which limited many visual effects and there were significant performance issues originating from wine's reliance on translating dx to opengl, lack of offloading cpu grpahics "command lists" (or whatever it's called) to a deditacted thread and the disjointed state of linux graphics at the time... It took until about 2013 for wine staging to run hl2 properly with multi core rendering and with all bells and wistle, but performance was still inferior.

I think linux graphics were only good when paired with the right version of red hat and nvidia drivers on a supported workstation dedicated for running proprietary 3d/vfx software packages as an alternative to the aging SGI workstations. Every other use case was pretty rough... until about 2017 when things began to change massively, and finally now, where you can actually get better experiences than freaking windows on most use cases.