I think I can say with complete assurance that Alexander Hamilton would have despised Donald Trump: his laziness; his lack of intellectual curiosity; his corruption; his empty egotism; his tinpot authoritarianism; and his lack of principles. To Hamilton, Trump would have been a third-rate version of Burr, who, at least, had a valid claim to be a war hero.
It has to be conceded, however, that the two do have some things in common: a New York background; a chip on their respective shoulders; a flair for publicity; and a taste for good-looking women. With Madison, however, Trump had absolutely zero in common. You can be sure that Madison would have despised him, too.
For the modest, reserved, hyper-rational Madison, the Trump parade would have been the last straw. It represents everything he feared and tried to prevent in American politics.