The matter of how the U.S. President is to be selected was a tough nut for the delegates in the Constitutional Convention in 1787 to crack. Mason observed the following in convention, “In every Stage of the Question relative to the Executive, the difficulty of the subject and the diversity of the opinions concerning it have appeared.” The alternative proposals centered around the Congress, State legislatures, the governors, the people, and electors designated for the specific purpose as the possible determiners. Although the delegates were men of considerable experience, their best judgments about how the alternatives would play out were subject to error as well as the confines of their times. In re-assessing the Electoral College, we could do worse than adjust those judgments and rid them of circumstances pertaining to them that no longer apply. For example, the Southern States no longer have slaves, so the question of whether those States would be disadvantaged by going with a popular vote no longer applies; the alternative of going with the popular vote nationwide no longer suffers from that once-intractable pickle. Yet lest we rush headlong into a popular vote without respect to the States, we are well advised not to dismiss the points made by the convention delegates, for we too are constrained by our times, and we may thus not be fully able to take into account points that have been forgotten.
The full essay is at "The Electoral College."
1. James Madison, Notes of Debates in the Federal Convention of 1787 Reported by James Madison (New York: W. W. Norton, 1966): 370.