If this was ANY other right-wing asshole, I would say "yeah, that's the only way to construe that insult."
But it's Trump. And he's a moron. And that's way, way, way, way, way, way, way, way, way, way, way, way,way, way, way, way, way, way, way, way,way, way, way, way too nuanced a joke for a moron like him to think up, even if it's not that nuanced or witty at all. I doubt he even knows what the Trail of Tears is. He was probably making a really forced and lame reference to her trailing him in votes or some shit.
Trump: he's a racist piece of shit, but let's not pretend he has any more than the intelligence of an eight year old.