Yes. Rubygems is the project that was run as amateur hour, not Debian.
EDIT: And before anyone mentions it: http://marc.info/?l=openssl-dev&m=114652287210110&w=...
EDIT: And before anyone mentions it: http://marc.info/?l=openssl-dev&m=114652287210110&w=...
About 1.9.3 and 1.9.1 are you sure that it isn't about this issue described here: http://stackoverflow.com/questions/8564210/why-are-we-instal... ?
Godspeed Leader Nussbaum! I hope that your first action is to find a replacement for whoever was responsible for the debian-ruby disaster.
It is nice to rely on system-packages, but if you depend on certain versions of certain packages you might see problems with that approach.