https://bugs.winehq.org/show_bug.cgi?id=41639
--- Comment #40 from Hugo hpessotti@gmail.com --- (In reply to Byeongsik Jeon from comment #39)
I think the XQuartz update is the right solution. However I think it is registered as a bug because it is not possible for some reason.
Problem is that XQuartz does not receive an update since 2016-10-29 (latest version is 2.7.11) and it is the only binary distribution of xorg that works well with the latest Mac OS X (Apple stopped shipping X11 with OS X 10.7 in 2011).
In fact, XQuartz dev already said that he wont release XQuartz anymore and recommends using macports (a kind of package manager that compiles everything in place) as a way to have the latest xorg-server on MacOSX.
However, macports it very little user-friendly and even Wine recommends using XQuartz because it is ready for installation and works out-of-the-box.
As a workaround, most of us just download XQuartz 2.7.9, which is bundled with freetype 2.6.3.