http://bugs.winehq.org/show_bug.cgi?id=12044
--- Comment #38 from Sam Edwards CFSworks@gmail.com 2012-02-21 04:48:10 CST --- Dmitry,
I suspected as such. If you're interested, here's what I've learned so far:
Running with WINEDEBUG=-all,+font reveals that the init_freetype function actually gets called right before the crash. (Perhaps something more serious happens and Wine attempts to re-init to recover?) I even ran all of the output through a '| grep init_freetype' for good measure and found that the only situation where Wine attempts to re-initialize FreeType is where GMod attempts to render the toilets -- and not just as a killicon: I have modified ingame objects (e.g. Wiremod screens) to use this font and the same thing happens whenever any of them attempt to display "9" (the codepoint of the toilet)
If you want to try digging around a bit, the reinit-and-crash seems to be caused by: trace:font:GetGlyphOutlineW (0x110c, 0039, 0006, 0x33c16c, 972, 0x33bd90, 0x33c190) The font is a TTF with SHA1=83edb89c48e1c72995cd04bf3f9f088d2382b725 (can be found if you run a Google search for "Headhumper.ttf" - though its original filename is "HL2MP.ttf")