Blue Maniac
Alzheimers sufferer
Arsene Wenger played for Strasbourg and made appearances in the UEFA Cup. A little bit better than a conference player if you ask me.
Plural?
EDIT: And I'm sure Mourinho played for a top division Portuguese side at some point as well, even if it wasn't for long.
Belenenses, where it quickly became obvious that he wasn't very good. Then he became a teacher.