This paper discusses didactics of history teaching in Latvia during Stalin’s regime found in “How One Must Teach History” and since 1991 found in “How to Teach History” by examining traits of authoritarianism and democracy in history teaching and the books’ usefulness to teachers. Results show history teaching under totalitarianism was severely prescribed with virtually no room for critical discussion. Post-1991 democracy indicates that critical discussion of history can occur, but the text is superficial and lacks examples to assist teachers unaccustomed to such teaching.