Trump keeps winning because the Left is not listening to many valid concerns of the Right. Their failure to listen lost them 2016, and it is why every left-leaning news source (NY Times, etc.) was completely blindsided by Trump’s win.
The Left needs to realize that most American’s don’t like extremes. Most Americans do care about border security. (Every neighbor of mine who voted for Hillary tells me that they care about border security.) Most Americans don’t want radical rapid cultural change in their lifetime, and so they want sensible limits on visas and legal immigration, especially from nations that have very different cultures.
The extremism of the Left is what has empowered the Right. If the Dems want to win in 2020, they need to stop “shifting left” and listen to what most Americans want. Otherwise, we will see more of Trump and his ilk, and will sit by while our environmental progress is reversed, the rich get richer, and big corporations take over even more.