Walter Russell Mead, a political historian at Bard College in New York compares Trump to a composite of presidents Andrew Jackson, Franklin Delano Roosevelt and Ronald Reagan (see video "Thoughts on Trump"). What Mead sees in Trump is Jackson's fiery nationalist "anger", Roosevelt's allowing his cabinet and department heads to fight it out with him as "arbiter" and Reagan's supply-side economics. But academics are particularly unsuited to understand someone coming from the business world, let alone the brutal municipal politics of real estate development.
It is probably better to compare Trump to the ideal typical role of a real estate developer than any past presidents; although if one is going to make such a comparison Teddy Roosevelt would be more apropos. And in reverse, Trump is no Valentinian I, Aaron Burr, or Robert Moses.