None of the previous 44 presidents are listed as businessmen, though Andrew Jackson (1767-1845, president 1829-1837) cries out as Trump's prototype. Jackson's parents emigrated from northern Ireland. He was orphaned at 14, used his wiles to become a "frontier lawyer", and made a fortune in speculation of lands that by law were Cherokee, but which hungry settlers were stealing at gunpoint. That made him a gentleman plantation owner and businessman. (Think: Trump Towers, casinos.)
He despised President Washington for the Jay treaty (1795) during the Napoleonic war, which gave preference in (free) trade with Britain (it was, after all, controlling the oceans), and refused to go to his funeral, though he was already a rising star as Tennessee's sole congressman. (Think: Trump's tariff wars and McCain's funeral.)
The real losers were the natives on both sides. (Think: Standing Rock.) British strategy for decades had been to create a buffer state to block American expansion. The Americans refused to consider a buffer state and the proposal was dropped. Article IX of the treaty included provisions to restore to Natives "...all possessions, rights and privileges which they may have enjoyed, or been entitled to in 1811"--but the provisions were unenforceable. In any case, the British soon lost interest in the idea of creating an Indian buffer state and stopped supporting or encouraging tribes in American territory. I.e., the US won, as it gobbled up the nice bits of the rest of the continent.
Jackson milked the prestige of defeating both British and Spanish troops in Florida and New Orleans. Alexis de Tocqueville despised Trump (sorry, Jackson), later writing in Democracy in America that Jackson "was raised to the Presidency, and has been maintained there, solely by the recollection of a victory which he gained, twenty years ago, under the walls of New Orleans."
Jackson vs Trump
In describing Jackson, De Tocqueville eerily describes Trump. (I have inserted a few points for colour, though the reader can add his/her own examples for Trump):
*General Jackson is the agent of the state jealousies; he was placed in his lofty station by the passions that are most opposed to the central government. It is by perpetually flattering these passions that he maintains his station and his popularity.
*General Jackson is the slave of the majority: he yields to its wishes, its propensities, and its demands--say, rather, anticipates and forestalls them. ... General Jackson stoops to gain the favor of the majority;
(Jackson was famous for his people's inauguration ball, which a cross-section of US business types and their families stormed, climbing through windows and in their drunken debauchery, trashed the place. Think: Trump's embarrassing inauguration.)
*but when he feels that his popularity is secure, he overthrows all obstacles in the pursuit of the objects which the community approves or of those which it does not regard with jealousy.
(Think: Trump's transgender rulings.)
*Supported by a power that his predecessors never had, he tramples on his personal enemies, whenever they cross his path, with a facility without example;
*he takes upon himself the responsibility of measures that no one before him would have ventured to attempt.
(Think: North Korea.)