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“I love the poorly educated” is unusual because it defines a huge group of people primarily by a deficiency: what they lack educationally. trump's statement can be interpreted charitably as an expression of solidarity with people who lack formal education, but the wording is sufficiently strange that it's also reasonable to question what exactly he meant.
Really? It doesn't seem that difficult to parse. Not all that much different from Joe Biden saying, "I love the Irish," or George Bush saying "I love the folks in the military."
I don't know that "poorly educated" is all that weird a term, either. Sandel used it in the quote I took from his article, which was an article entirely in support of the less educated.
One can question whether Trump is sincere in this expression of love, but I more often see that quote presented in a context where it appears that the expressed sentiment itself is somehow problematic.