No. of Recommendations: 3
Does he mean something like “I love people who have been poorly served by the educational system” (a somewhat sympathetic interpretation) or “I love my poorly educated supporters”?
I mean - obviously the latter? Right? There doesn't seem to be all that much ambiguity in what he's trying to communicate. There's a chunk of the population that's poorly educated, and he's expressing that he loves them. It's also pretty obvious that he's using that in a colloquial manner, not expressing romantic love or anything like that - the same way one would say, "I love the Yankees" or "I love the Irish."
In the context of the full quote, there's even less ambiguity:
"We won with young. We won with old. We won with highly educated. We won with poorly educated. I love the poorly educated."
He's just rattling off groups on an exit poll crosstab. Highly vs. poorly educated. He expressed "love" for the latter group. Doesn't seem too difficult to take his meaning. He's saying he loves that group of people.