American voters elect the President and Vice President of the United States of America indirectly, through an arrangement known as the Electoral College system. The U.S. Constitution, in Article II, Section 1, Clause 2, as amended by the 12th Amendment in 1803, together with a series of implementing federal statutes, provides the broad framework through which electors are appointed and by which they cast votes for the President and Vice President. However, the Constitution says nothing about how the states should allot their electoral votes. The winner- take-all was the choice of the majority of the States. Presently, 48 states and the District of Columbia (Maine and Nebraska are the exceptions, having adopted the district system) have adopted the winner-take-all method of allocating electors. Under this method, the slate of electors, representing the presidential and vice presidential ticket that wins a plurality of votes in a state is elected on Election Day in November, and later meets in mid-December as the Electoral College to cast all of the state’s electoral ballots for the winning presidential and vice presidential candidates. This electoral system has proved undemocratic in modern time. The objective of this paper is to shed light on the limits of the American presidential electoral system which is no more in accordance with the ideals of the democracy today. Through historicism and Marxism theories, investigations have shown that some candidates can get a majority of the popular votes but fail under the winner- take-all conundrum. More importantly, the system has generated a dangerous geographical separation with red and blue territories in the same United States. The compromises and ideals of 1787 constitutional convention are rather outmoded for the 21st century democracy.