28. In both the 1888 and 2000 presidential elections, the candidate who received the most popular votes lost the election. Why?
From Quiz The Electoral College: How it Works
Answer:
Electoral votes are not allocated in direct proportion to state populations
In the 1888 election, Grover Cleveland won the popular vote over his opponent, Benjamin Harrison. In the election of 2000, Al Gore was the popular vote winner, receiving half a million more popular votes than his opponent, George Bush. But both Harrison and Bush won the electoral vote and the presidency. These anomalies were the result of the way in which the Electoral College system allocates votes to states.
If every vote cast by the general public had the same proportional influence in the Electoral College, the winner of the popular vote would always be the winner in the Electoral College. But simple arithmetic shows that this is not the case. Each state casts as many electoral votes as it has members in Congress. Although representation in the House of Representatives is based on population, every state has two senators, regardless of its population. This results in a disproportion between a state's population and its influence in the Electoral College, which is especially apparent when comparing small and large states.
For example, in the election of 2000, California voters cast approximately 10,800,000 popular votes for president and cast 54 votes in the Electoral College. Wyoming voters cast about 213,000 popular votes and three electoral votes. So California cast one electoral vote for every 200,000 popular voters, while Wyoming cast one electoral vote for every 71,000 popular voters, giving each Wyoming voter almost 3 times more influence in the Electoral College than each California voter. Although the disproportion rarely affects the outcome of a presidential election, the possibility remains that it may have that effect from time to time, as it did in the elections of 1888 and 2000.