I believe it will take a while for the general population to get tired of winning. Discounting the hyper partisans on both sides, the mellow middle is very happy right now. Very. Think of it......The Clinton years were pretty good, only when the GOP took over. Bush was ok and completely distracted the government with war. Obama said all his policies were going to be great for folks......he lied. Nothing he did really worked at all.
Along comes this brash guy nobody really likes. They are not sure what he says will come to pass, but he isn’t a crook, like Hilary, so let’s hire him. Turns out the guy is a first class ass, but everything he touches turns out to be true.
There is not one area where American life isn’t better under two years of Trump vs any of these other guys. The average guy has noticed. 2016 was close. This won’t be close.
“Tired of winning” in this context typically means a group of malcontents don’t think that the newly created wealth is tricking down to them fast enough, so the idea of electing Leftists to squeeze the sponge begins to appeal to them.
I don’t think we’re there yet.