Yes, openssl is installed, but without the universal variant. Wine requires that openssl be installed with the universal variant, which is why MacPorts is trying to rebuild openssl now.
The log you attached says:
:info:build In file included from cryptlib.c:117:
:info:build ./cryptlib.h:62:10: fatal error: 'stdlib.h' file not found
:info:build #include <stdlib.h>
:info:build ^
:info:build 1 error generated.
stdlib.h is supposed to be in /usr/include. Are you sure you have installed the Xcode command line tools? They are required. Open Xcode.app, open its Preferences window, and check the Downloads tab.
P.S: Remember to use WikiFormatting when writing in Trac.
P.P.S: Note that port list doesn't do what you think it does.