https://bugs.winehq.org/show_bug.cgi?id=57050
--- Comment #10 from Rafał Mużyło galtgendo@o2.pl --- Is that 32 or 64 bit executable ?
If the former, you should look at VmSize for the process - the limit is quite low and if you hit it, you'll likely get an OOM crash regardless of having more free memory.