Hamilton was perhaps the most brilliant, articulate, accomplished, and farsighted of the Founding Fathers. As well-educated as Adams and Jefferson, he matched their classical scholarship while adding deep practical knowledge of finance, economics, technology, government administration, and business management. He was also the most modern of the founders, a wonk like O’Neill who knew how to run the numbers, and did, producing significant technical reports on such subjects as banking, retiring the national debt, and creating incentives for entrepreneurs. His fertile mind was always racing, devising new plans and financial schemes: The cerebral Hamilton invented sophisticated managerial systems of accounting, planning, and control, some of which are still in use. Moreover, like O’Neill, he had courage, ambition, energy, and a willingness to sacrifice personal financial gain to serve his country. A principled and loyal patriot, as a young man serving in the Revolutionary Army he demonstrated great promise as a leader. Subsequently, he became the second most powerful man in America, developing the best resume to succeed Washington and Adams as president (and he was said to be even prettier than John Edwards). Hamilton is today remembered as “the father of American capitalism,” having won the great ideological battle with Jefferson to create the economic system we enjoy today.
But Hamilton never became president because he was insecure, insensitive, opinionated, verbose, compulsive, headstrong, belligerent, proud, and lacking in self-awareness and self-discipline. He was a martinet, and an overstretched, overreaching micromanager. Brilliant in staff support to Washington, he was ineffective when operating on his own. A solo practitioner of the art of leadership, not only would he not tolerate fools, he wouldn’t belly up to the bar with lesser intellects who might have become allies and followers. His charm was reserved for the ladies, and therein lay a great weakness: a sense of invincibility that led him to believe he could get away with anything. When a marital infidelity became public knowledge, he compounded the problem, ham-fistedly turning what might merely have been an embarrassment into an act of self-destruction.
Hamilton thought of himself as the paragon of virtue but, in fact, often acted without integrity: He treated those who disagreed with him as disloyal, and went for their jugular. It was not enough for him to win every argument; it was necessary for his opponents to lose, and even better for them to be humiliated publicly. “The intellectual spoilsport among the founding fathers,” as Chernow puts it, he seems never to have considered that he could be wrong about anything. A contemporary cited his “pertinacious adherence to opinions he had once formed.” This arrogance made him a lightning rod for criticism. Hamilton did not understand the need to nurture relationships, and his insensitivity turned former friends and colleagues into foes: For all their differences, Madison, Jefferson, and Adams found common cause in a distrust of Hamilton.
As a leader, Hamilton was a realist, believing men were basically bad: selfish and dishonest. He had no faith in “the people” and no interest in presenting them with hopeful, inspiring visions of a better tomorrow. Hence, he tried to lead without listening to the needs of followers. A generous and feeling man in private, he was all head and no heart in public affairs. Caught up in the minutiae of details and facts, he lost sight of the central task of leadership: creating followers. According to Chernow, Hamilton believed it was only necessary to be “right” on the issues:
Hamilton lived in a world of moral absolutes and was not especially prone to compromise or consensus building. Where Washington and Jefferson had a gift for voicing the hope of ordinary people, Hamilton had no special interest in echoing popular preferences … he lacked what Woodrow Wilson defined as an essential ingredient for political leadership: “profound sympathy with those whom he leads — a sympathy which is insight — an insight which is of the heart rather than of the intellect.”