https://bugs.winehq.org/show_bug.cgi?id=42389
--- Comment #3 from fjfrackiewicz@gmail.com --- (In reply to Tim Nightingale from comment #0)
Created attachment 57191 [details] screen dump of wine and winecfg calls after a fresh macports installation
Nothing I can think of will persuade wine 2.0_0 installed from Macports to start. Previous versions have worked fine. I have completely removed my entire Macports installation, the ~/.wine directory, and any other traces of wine I could find, restarted my machine and rebuilt from scratch.
I've attached a screen dump, lightly sanitised, of my first attempt with a fresh wine installation to start a Windows Setup.exe program that's given me no problems in the past. My wine installation also fails on standards such as Notebook.exe.
I've tried the OSX 2.0 .pkg installation direct from winehq.org and that works OK.
I'm running macOS Sierra 10.12.3, Xcode 8.2.1 with all the normal bells and whistles, and xQuartz 2.7.7 on a MacBook Pro (Retina, 13-inch, Early 2015).
By the way, can you try this version of Wine straight from WineHQ's MacOS download page:
https://dl.winehq.org/wine-builds/macosx/i686/winehq-devel-2.0.pkg
and see if it still crashes?