americanna:
One particularly interesting answer: Alexander Hamilton!
“Alexander Hamilton makes the top of my list, simply because of his apparent hypocrisy. He argued and fought for American rights, and once independence was achieved, he wanted to make the United States a country similar to Britain, dominated by a ruling political and financial elite where the people had little voice in the government. He opposed the addition of the Bill of Rights to the Constitution and even suggested breaking up the large states into smaller entities so they could not challenge the national government’s power. He frequently expressed his admiration for the British system of government. If he liked it so much, and tried to recreate it in the United States, why did he bother to support the Revolution in the first place? - Jim Piecuch”
https://allthingsliberty.com/2014/12/strangest-founding-father/
That’s the opinion of one contributor to the excellent Journal of the American Revolution. Other scholars name other patriots. Another scholar looks at Hamilton’s attitude to Britain–especially as compared to Jefferson’s. First, he detailed how the tobacco planters of Virginia were chronically in debt to British (English & Scottish) merchants–and, thus, resented them. He continues:
To add insult to injury, the British had invaded Virginia late in the war. Marauding soldiers had destroyed crops and livestock, including Jefferson’s own, torched the state capital at Richmond, and carried off hundreds of slaves to be set free. Virginia’s Anglophobia, and view of itself as the innocent victim, deepened. After the war, it was only natural for Virginians to use the loss of the slaves as an excuse not to pay their prewar British debts, totaling £2.3 million in 1790. What made Virginia distinctive, however, was that although it had suffered much, it had contributed relatively little in blood and treasure to the national cause, or even to its own defense. Virginians like Henry “Light Horse Harry” Lee (the father of Robert E. Lee), and John Marshall (the future chief justice), not to mention Washington, served with distinction in the Continental Army and became leading Federalists. But the efforts of Governor Jefferson to organize resistance at home had been notably ineffectual, provoking calls for an investigation into his conduct.
A discerning European visitor, seeking to explain the Anglophilia of Federalists like Hamilton in the mid-1790s, observed that “resentments do not subsist when you have won. Satisfied pride reserves no desire for revenge.” Whether or not Talleyrand realized it, the same psychological principle applied in reverse to Virginia. There people did not have such a clear-cut sense of having won. The struggle for independence from the economic coils of the Mother Country continued after 1783. Nor could one really say that Virginia’s pride had been satisfied or its honor vindicated by its wartime performance. Hence the chip on the shoulder that Virginians carried vis-à-vis the British – let us call it the “Virginia syndrome” – and their recurrent urge to strike another blow.
Harper, John Lamberton. American Machiavelli: Alexander Hamilton and the Origins of U.S. Foreign Policy
Harper does not see Machiavelli as a demonic plotter, but as a lover of freedom showing how it can be subverted. And he traces Hamilton’s reputation as it waxed, waned & has waxed again–usually in opposition to Jefferson’s.