Wine: Could Not Initialize Graphics System. Make sure that your video card and driver are compatible with Direct Draw

For anyone else getting this problem when attempting to run older games on Wine - in my case this due to the graphics card not supporting the native resolution of the game (800x600) - you can check supported resolution types with:

xrandr -q

However you might be able to add custom resolutions as well.

Otherwise within the Wine configuration you will need to ensure 'Emulate a virtual desktop' is ticked and the appropriate resolution for the game is set.