I see where you're going with this and I accept the possibility Trump is just clumsy and avoidant on the issue.
But you must be aware that there is a strong belief amongst MAGA types and deep conservatives in general that slavery was benign if not beneficial to those subjugated. D'Souza wrote a whole book about it.
They believe liberals exaggerate the bad parts of slavery due to irrational white guilt and black people agree because they are whiners and want reparations.
I strongly suspect this plays into Trump's rants regarding museums and history curricula.