Just after WWII who hated the nazis and saw the Russians as our greatest threat. How he could avoid that mindset or hearing about this from everyone he encountered growing up when he did is a mystery to me.
I didn't experience WWII, but I sure knew who the nazis were, that was one of the basic facts of history that you learned in school. And the Russians scared me to death, I'm old enough to remember Khrushchev and my kindergarten class cowering in the school basement as part of some drill.
As for Trump's mob ties, you're right, he was obviously a very poor student of their behavior as he was for everything else. Back in the day, they operated as a kind of underworld that was tough to infiltrate, those who gave things away came to a bad end - they hardly announced their nefarious intentions on national TV! 
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