Beyond the people who always vote Republican, Trump won because his flagrant flaws could not win over enough people to vote Democratic because of their flagrant flaws. The appeal of Trump to many voters is well articulated in this WSJ 2020 opinion piece. The gist: “This is the voice of the resistance on the right. This sentiment has been building for decades. Its scale is suggested by the degree of Trump outrages these voters have been willing to discount on behalf of a larger cultural and political cause. What exactly is their problem? In our time, it takes the form of the left’s cultural triumphalism on matters of identity, race, gender and indeed assimilation, or “the American idea.” Basically, they think we are arrogant jerks who do not consider them or care about them.
To me, below are the central reasons Trump won.
Economic issues:
It was the Republicans to win as the party in power was being punished throughout Europe for inflation related to covid supply chain collapse and stimulus spending. I don't think that is fair or rational, but it's true.
Harris failed to say what she was for clearly and didn't defend Biden's economic policy, when it was quite defensible. Many believed that inflation was Biden's fault, which Kamala didn't even touch. Personally, I do not believe it was primarily his fault, and Biden did great compared to other leaders, but she didn't even make the argument.
She didn't criticize Biden's border policy at all, though it is the number one issue with voters. While she has endorsed his late-to-the-table reforms and the Congressional bill that Trump torpedoed, she needed to say he was wrong in his approach from the beginning, and she would not follow that path. She did say the latter, but she had to say the former.
Crime “reforms” of Democrats that have led to a decrease in prosecutions and an increase in retail crime in some localities. Plus Democratic states/cities not being able to make a dent in homelessness despite a flood of money to do so. Obviously, there is nuance in this area but the perception is - with reason - that Democrats have been worse about solving the issue. And the numbers say so. Together, New York and California have 250,000 homeless people out of 58 million people; Texas and Florida together have 54,000 homeless people out of 53 million.
“Woke” issues. They are all connected in a new dogma. Democrats are generally on board or tolerant of the new dogma; Trump is completely against it (and like the right in general, not in a nuanced way.)
Democrats going all-in for identity politics instead of for keeping the focus on the poor and working class across all demographic lines. This ended up pushing out, particularly, white men but also, to a degree, white women. (Think about that obnoxious "Karen" slur directed to white women.)
Democrats support of DEI, in which diversity only includes BIPOC groups , equity means equality of outcome, not opportunity and inclusion means inclusion of the same "diverse" groups - and specifically excludes Jews. Plus it doesn't work as done.
The rising anti-Semitism, particularly among youth, in which there is a double-standard seen, particularly, at the Universities. When protestors break the law and policy at colleges protesting the war, they are met with kid gloves. When someone says something racist, homophobic or transphobic, the response is met with quick and consequential condemnation.
Decolonization and the oppressor/oppressed narrative plus the white people bad/brown people good narrative. The best example of this woke nonsense is the non-sensical attack on Israel via a "decolonizing" lens and "white oppressor "lens. These attacks are incoherent on the face of them and make zero historical sense, but is part and parcel of Woke dogma.
Supporting - even over the objections of parents - youth gender transition in spite of the lack of scientific evidence that it is a sound practice and the fact that youth cannot reasonably consent to interventions that can or will lead to sterilization for females and inability to orgasm. When a person detranstitions, they are given no support and, in fact, attacked. A couple of left-leaning groups have sprung up to ring the alarm, but Democrats aren't listening (so far!) The groups are DIAG and LGBT Courage Coalition
Supporting anti-female policies of Title IX revisions to, effectively, change the point of the act from protecting women based on sex to gender, which, perversely ends up hurting females. (It won't survive Supreme Court scrutiny.)
Supporting homophobic and misogynistic policies of pushing trans ideology, which is attempting to erase sex and put gender in its place. (So, practically, there are no longer female spaces and kids who are most likely gay are being talked into changing sex.)
Supporting policies that encourage schools to lie to parents about their child's gender transition. And supporting anti-parent and family policies of creating "sanctuary states" for gender-confused kids due to the bans on all youth gender care in red states. Neither policy is right to my mind, but encouraging the breaking up of families has absolutely turned many Democrats to the right.
“ Nanny State” issues
The perception that Democrats were too rigid in dealing with Covid, particularly in terms of school closures. Plus that they tried to suppress the speech of those who didn't agree with the CDC. Plus they tried to shame (or force) people into getting vaccines, even after it was clear getting the vaccine was unrelated to the transmission of the virus.
Biden's administration attempt to suppress "disinformation", but it was always politically coded - disinformation was always on the right to the administration.
Obviously, the revoking of parental rights in trans matters is a major "nanny state" issue. Particularly egregious is teaching kids at a young age about gender as per gender theory (overthrowing the primacy of the sex binary for the gender "spectrum"). Since the theory is not accepted by majority of people in the US, it amounts to indoctrination by a special interest group in America and is completely anti-pluralistic. The same could be said about the troubling ethnic studies movement, which is trying to instill the anti-Western civilization and anti-Israel (anti-Semitic as well) post-colonial, oppressor/oppressed narrative to young kids.
I voted for Kamala because of the unique danger of Trump, but unless Democrats make a real break with woke ideology, there is a good chance I won't vote Democratic in 2028. I am a liberal. I believe in equal opportunity for all. I believe in free speech. I believe in diversity and inclusion of all. I believe we should help those in need. I believe that we should support the working class. I believe in pluralism. I believe in democracy. Basically, I believe in Martin Luther King's vision of America. But the current far left does not believe in these things. And Democrats haven't broken with the far left. We need to reject them, isolate them, and get our party back on the right path. Here's hoping.