Designing the presidency
Wilson has been variously called by scholars the "principal architect of the executive branch", "probably the single most important author of Article II", and the man whose "conception of the presidency...was in the final analysis the presidency we got". Using his understanding of civic virtue as defined by the Scottish Enlightenment, Wilson was active in the construction of the presidency's structure, its power, and its manner of selection. He spoke 56 times, calling for a chief executive who would be energetic, independent, and accountable. He was the first to propose a unitary executive (a proposal which initially provoked concern—having only recently won independence from the British Crown, many delegates were concerned vesting executive power in a single individual would lead to monarchy), and was its strongest proponent. Rival proposals included a triumvirate or leaving the composition of the executive to the legislature. Wilson, however, maintained that a single chief executive would provide for greater public accountability than a group and thereby protect against tyranny by making it plain who was responsible for executive actions. He also submitted that a singular chief executive was necessary to ensure promptness and consistency and guard against deadlock, which could be essential in times of national emergency. Wilson's unitary executive was ultimately adopted by the convention.
The executive as well as the legislative power ought to be restrained. ... The restraints on the legislative authority, must from its nature, be chiefly internal; that is, they must proceed from some part or division of itself. But the restraints on the executive power are external. These restraints are applied with the greatest certainty, and with greatest efficacy, when the object of restraint is clearly ascertained. This is best done, when one object only, distinguished and responsible, is conspicuously held up to the view and examination of the publick [sic]. . . . In planning, forming and arranging laws, deliberation is always becoming, and always useful. But in the active scenes of government, there are emergencies, in which the man, as, in other cases, the women [sic], who deliberates is lost. Secrecy may be equally necessary as dispatch. But, can either secrecy or dispatch be expected, when, to every enterprise, mutual communication, mutual consultation, and mutual agreement among men, perhaps of discordant views, of discordant tempers, and of discordant interests, are indispensably necessary? How much time will be consumed! and when it is consumed, how little business will be done! When the time is elapsed; when the business is finished; when the state is in distress, perhaps on the verge of destruction; on whom shall we fix the blame? Whom shall we select as the object of punishment?
One of the issues that most divided the convention was the method of selecting the president, with Wilson observing that the issue had "greatly divided" the Convention and was "in truth the most difficult". For his part, Wilson forthrightly supported the direct election of the president through a national popular vote. He believed that a popular election would make the presidency accountable to the people, and he believed more broadly that direct elections would make each branch of government "as independent as possible of each other, as well as of the states". This proposal, however, was received with decidedly mixed opinion, in part because some delegates wanted the selection of the president to be insulated from the popular will and in part because it would not count southern states' slave populations towards their voting power (which had been the major concern leading to the infamous Three-fifths Compromise). In an attempt to accommodate these objections, Wilson proposed selection by an electoral college, which would divide the states into districts in number proportional to their population, from which voters would choose electors who would in turn cast ballots for the president on their behalf. But this, too, was initially greeted unenthusiastically.
The proposal that at first received the greatest traction was one that Wilson disliked: selection by the legislature (Wilson had tried to accommodate the desires of these "congressionalists" in his electoral college proposal by including a contingent election, which would hand the selection of the president to Congress if no candidate received a majority of electoral votes). Yet further discussion uncovered consequences of legislative selection that many delegates considered objectionable; in particular, they worried that if the president was allowed to seek a second term (a widely supported notion), then legislative selection would make the president dependent on the legislature for re-eligibility, imperiling the principle of separation of powers.
Deadlocked on the method for selecting the president, the issue was ultimately left to the Committee of Unfinished Parts (also referred to as the Committee of Postponed Parts or the Committee of Eleven), which near the end of the months-long Constitutional Convention was tasked with resolving the remaining unfinished portions of the constitution. It was in this committee that an "eleventh-hour compromise", as Supreme Court Justice Elena Kagan has described it, was struck, which settled on the use of an electoral college very similar to the one Wilson had earlier proposed. The committee constructed a complex structure that, with few alterations, would become the Electoral College. In this system, each state would be awarded a number of electors equal to its number of House Representatives and Senators (this encoded within it the Three-fifths Compromise, boosting the slave states' representation in the Electoral College above their voting populations). Each state's legislature would decide upon the manner in which that state's electors would be chosen, and the electors would cast votes for the presidency. In the case that no presidential candidate received a majority of electoral votes, a contingent election would be triggered, handing the selection of the president to the Senate. After the Committee released their proposal, and at Wilson's urging, the contingent election was shifted from the Senate to the House of Representatives. With this alteration, the Electoral College—embodying a "web of compromises" that functioned as a "consensus second choice, made acceptable, in part, by the remarkably complex details of the electoral process"—was accepted by the convention.
Wilson believed that the moderate level of class conflict in American society produced a level of sociability and inter-class friendships that could make the presidency the symbolic leader of the entire American people. Wilson did not consider the possibility of bitterly polarized political parties. He saw popular sovereignty as the cement that held America together linking the interests of the people and of the presidential administration. The president should be a man of the people who embodied the national responsibility for the public good and provided transparency or accountability by being a highly visible national leader, as opposed to numerous largely anonymous congressmen.