We got here by putting two of the most hated people in the country on the ballot against him, twice.
One was actively hated for decades by the ultra-powerful evangelical voting bloc and hardly loved even by her own party, then another who couldn't be more closely affiliated with the incumbent during a period of high inflation (globally) that ousted incumbents in virtually every election (globally) that year.
These are especially doomed against a completely amoral propaganda machine that's willing to say, in private, that the candidate is "a demonic force", while in public doing everything they can to get him to power (see: Tucker Carlson). Earning legitimate democratic victory against people who are quite literally and explicitly bad-faith actors is very hard.
And lastly, Roy Lee, Marc Andreessen and their ilk are nothing like the people who you're referring to. Being a low-status, cheating, amoral loser like Roy Lee is completely distinct from being a lower- or middle-income American worker.