He has a general interest in history but is very convinced of American exceptionalism. He hates the actual america that really exists but is unable to let go of the mythology of america as a "land of the free". Thoughts?
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Lies My Teacher Told Me (PDF) might be less confrontational and could get past his defenses better
My dad had a copy of that in the bathroom growing up. He also had anti-bush magnets all over the fridge.
Depending on how deep he wants to go, The Two Faces of American Freedom by Aziz Rana is an incredible book, but it's not pop history, it's harder to read. However it is accessible compared to some other academic history works I've seen.