Tomorrow I will commit a long overdue version bump of openssl (1.0.0a).
Recent Portage versions had non-functional preserve-libs functionality,
which causes this upgrade of openssl to severely BREAK YOUR SYSTEM.
(Portage won't work any more)
Make sure you upgrade Portage to version 2.2.01.16706 or above before
you upgrade your openssl, or you'll have to hack some files to get
yourself going again (like I had to when I found out).