The relevant error in the log is:
---> Applying patches to openssl
---> Applying /opt/local/var/macports/sources/rsync.macports.org/release/ports/devel/openssl/files/patch-Makefile.org.diff
DEBUG: Environment: MACOSX_DEPLOYMENT_TARGET='10.6'
DEBUG: Assembled command: 'cd "/opt/local/var/macports/build/_opt_local_var_macports_sources_rsync.macports.org_release_ports_devel_openssl/work/openssl-1.0.0b" && /usr/bin/patch -p0'
patching file Makefile.org
Reversed (or previously applied) patch detected! Assume -R? [n]
Apply anyway? [n]
Skipping patch.
1 out of 1 hunk ignored -- saving rejects to file Makefile.org.rej
Please clean openssl and try again:
sudo port clean openssl
If it fails again, attach the main.log file whose location it will print out.