[jimktrains2]

> It’s absolutely wild to me that, with the benefit of 2020 hindsight, we’re still drawing conclusions about the public based on the fact that the person who earned by far the most votes of any candidate in the race still technically lost the election.

You're forgetting that we're not as a single, monolithic country; we're designed to be a union of (mostly) independent states. It is those state who select the head of the executive however they see fit individually. There is nothing stopping a state from issuing electoral votes by percentage and not by winner-take-all.

Since the Civil War and especially with the expansion of the commerce clause, we don't act quite like (mostly) independent states any more, but those basic premises and rules are still there. To be honest, the system works much like it's intended to -- the rural/agricultural states maintain some power even though since they're rural there are fewer people. This isn't inherently bad; however, I'd argue that making the number of people represented by a single representative essentially unlimited instead of having a bounded maximum like initially designed is the root of our problems. It's possible for states to gain or maintain population and loose representatives and electoral votes under the current system, which is the main issue.