Automaton is a machine- such as a chess playing automaton- a machine that plays chess- Stalin can't be this.
Feminist- a person who fight for equality of genders and empowerment of women - no, Stalin was not famous for this.
Progenitor is the person from whom something originates, but Stalins' politics did not continue long (not until today and were changed) and his offspring isn't particularly famous
Misanthrope- a person who does not like other people. This seems to be fitting, as he killed many, including his friends (correct)