Blizzard is going to release Diablo 2 Resurrected this year, but unfortually it doesn't support macOSX anymore, what a pity. According so many reviews released until now, it's really a re-maked version as original D2, nothing improved significantly except graphics.
So, if you still want to play it on latest macOSX Catalina with old D2, there is a WAY by special version of wine. After and at Catalina, the system disables the execution of 32bit codes, but D2 is total a 32bit executable, so it wouldn't be able to run by standard wine at Catalina.
From here
https://github.com/Gcenx/homebrew-wine
Install special version of wine with commands
brew tap gcenx/wine
brew install --cask --no-quarantine wine-crossover
Prepare your Diablo 2 on OSX, open Terminal, runs
$ wine32on64 ~/Downloads/Diablo 2/Diablo 2.exe -ddraw
It seems that only DDraw is working perfectly from wine, the D3D or OpenGL has texturing issue, the sound works well.
Wish this reminds your good memory from past time :)