He did win the 2016 election, he just wasn’t selected by the “American voters”. Whether the alternative is better or not is irrelevant.
Back to the original statement “Americans chose him” is even further from that - “American voters” - as only a small portion of the American population actually voted for him.
Going back even further to saying DC doesn’t deserve representation for electing one anti-semite, I assume this was a joke, but to be clear there are states that have elected far worse.
It did start with jokes before we were all so serious. You’re exactly right that we can define this all kinds of ways to say “Americans didn’t choose.” Bill Clinton only got 43% of the 55% who turned out to vote in 1992. But Americans did choose him, even if the rules or turnout don’t reflect a popular consensus.