Electoral College = Minority Rule

Answer- 113,999,959 or 114,000,000 loser vs 41 winner

Question- What is the largest difference in voter margin possible when the winner of the Electoral College loses the popular vote.

As we sit and ponder how one candidate
who received nearly 5 million more votes than
the other candidate can win by just the narrowest
in the Electoral College.

The answer is rather simple if one looks at the mathematical foundation
of the system used to elect our president.
It could be a whole lot worse.
Is it easier to get the support of 41 people or 114 million people?

The mathematical structure of the Electoral College makes this a reality;
Unity=loser Division=Winner

The above scenario is based on the following set of assumptions:
The winning candidate gets the support of 1 voter from each of the
41 smallest states. Putting them at 282 Electoral Votes
The losing candidate gets the support of 100% of registered voters
from the 10 largest states putting them at 256 Electoral Votes.

Seems outrageous? That is a emotional value judgement, it wouldn't
carry much weight in front of SCOTUS.
This particular scenario is an extremely unlikely one,
but there is a whole lot of grey area in-between.

Remember:
1. The SCOTUS is dominated by "Originalist" who claim to stick
to the text of the Constitution vaguely tempered in some way
by their own individual interpretation of the mores during the
time the Constitution was written.

2. The Constitution does not dictate that Electors are selected
by means of the popular vote. So in theory a state could assign
one person to decide who their Electoral votes will go to or simply
have such extreme voter suppression that only one person is qualified
to vote.

3. The Constitution does allow states to select their Electors via
popular vote if they chose to. (Most states do that now, but it is not
required).

Conclusion: based on this, someone like Trump is simply a product
of the Electoral System under which someone like him prospers. There will
be others like Trump even if he loses this particular election because
the mathematical structure of the Electoral College favors dividers over
uniters.

That is why phrases like: Southern Strategy, Red States vs Blue States,
Coastal Elites, Fly-over country, "we're a republic not a democracy",
systemic racism, gerrymandering, small state senators, the 2nd amendment,
pro-life, etc, etc have featured so prominently in our political discourse.

Our country has gone through many decades where the winner of the overall
popular vote has usually ended up as the winner of the presidential
election. This is because most states select their Electors via popular vote
and only practice minimal voter suppression strategies, but this is a rather
naïve approach. Once more candidates for elected office see the advantages
of gaming a poorly designed electoral system this will get worse.

If I wanted to game the system; my bedrock policy would be to tax the
10 largest states and give that money to the 41 smallest states (including DC)
(or alternatively you could do the opposite).
But before that, I'd make sure I belonged to the party that controlled the
majority of small states. That party would then get the legislatures of each
state to decide where its Electoral Votes would go rather than the popular vote
or practice extreme voter suppression. If you think about it the Republican party
is well on its way to achieving this goal.