A post on the official Wineskin website notes that there is a bug in OS 10.8.2, and is urging users not to upgrade:
for now if you want to use Wineskin, do NOT upgrade to Mac OS X 10.8.2. I have not narrowed down the issue, but Apple has totally and thoroughly messed something up that completely breaks anything that seems to be doing a resolutoin change and 3D graphics, or some combo… but basically all games will break. For now just don’t upgrade… there is something going on that needs to be narrowed down and Apple needs to fix it.
Wineskin is used to run some Windows applications and games on the Mac. Although typically used by people doing unofficial custom ports, some official Mac ports on Steam use it too. The problem seems to be due to a change made to the X11 Window System by Apple.
UPDATE: A new version of Wineskin is available that should rectify compatibility issues with 10.8.2