Hi, It looks like libwine or libwine-development should be a dependency of winetricks, since winetricks doesn't appear to run without wineserver, and wineserver is part of libwine. See this page for the package info: [0].
It looks like you can trace the dependency chain from wine to libwine on Wheezy and earlier releases, but starting with Jessie, libwine is no longer part of the recursive dependencies of wine. For now, installing libwine should fix the issue. [0] - https://packages.debian.org/search?suite=stretch&arch=any&mode=path&searchon=contents&keywords=wineserver Cheers, Joseph