Why Did Trump Prevail Again?

Perspective from a chastened "never-Trumper"

Election 2024

WHY DID TRUMP PREVAIL AGAIN?

Perspective from a chastened “never-Trumper”

Greg Thomas

The people have spoken resoundingly: red over blue, Trump over Harris. As Van Jones said on CNN about the Democrats, “We got outflanked, outplayed, beat.” I had indications about Trump’s appeal even before 2016, but I couldn’t read the writing on the wall.

How I became a never-Trumper

During my teens and 20s, I was a student of self-help books. So, in the late ‘80s, I read Trump: The Art of the Deal. When my wife Jewel and I moved to New Rochelle in 2008, Trump’s The Apprentice was popular. I watched several seasons of that show because of the challenges of leadership and teamwork it displayed, as well as the drama of who’d be fired and who would ultimately win. Around that time, I got my first inkling of Trump’s appeal to Hispanics.

I hired a Lincoln Town Car to take me to the airport. The driver was a dignified Latino man, an elder, who had suffered a horrible tragedy. A decade before, his wife and children had been killed in a car accident. He told the story twice, on an agonized loop of painful memory, tears welling up in his eyes each time. Near the end of the drive, he told me that he was one of Donald Trump’s drivers. After one ride, he had asked, “Mr. Trump, why do you need to make so much money?” “So when times are tough, I have enough to survive,” Trump reportedly replied. Saving for a rainy day is a common refrain for those who grow up lacking money and is generally wise advice. A billionaire using it to communicate with one of his workers made me think of him as a sales and marketing guy with keen audience insight. His answer displayed how he could meet the psychology of his audience, in this case, an audience of one, his driver.

But I also thought it was cynical. A billionaire has much more than enough for a rainy day. Cynical insight likely also drove him to take out a full-page ad in NYC newspapers in 1989 calling for the reinstatement of the death penalty. This ad appeared not two weeks after a shocking assault on a young “white”¹ woman, the so-called “Central Park Jogger,” Patricia “Trisha” Meili, who was an investment banker. Five teenage boys—four of them “black” and one Hispanic, dubbed “The Central Park 5”—were painted as a wolf pack accustomed to “wilding” in Central Park. They were quickly charged with beating and raping Meili. In 2002, they were exonerated after a sick serial rapist, Matias Reyes, confessed to the crime. In 1989, however, Trump wasn’t content to let the criminal justice system take its course; he waded into this racially charged scenario, declaring his hatred for violent criminals and, by implication if not by name, for these young boys who, it later turned out, had been falsely accused and railroaded.

That put me on notice about Trump as more than a rich real estate mogul who knew how to play bankers and the media to his own benefit. What sealed my distrust and suspicions about Trump was his questioning of then-President Barack Obama’s legitimacy as an American and as President, that is, the infamous “birther” controversy. Obama’s administration ended up releasing Obama’s long-form birth certificate to tamp down the nonsense that Trump’s accusations had prompted. But that wasn’t the end of Trump’s racialized attacks: he also said that Obama played basketball too much and doubted he had the smarts to get good grades in law school, let alone serve as the editor of the Harvard Law Review.

Trump’s playing into racial stereotypes—insinuating that “black” people couldn’t be “real” Americans, and that they were only good at sports and not intelligent—was what tipped me into becoming a “never-Trumper” even before he decided to run for President. After Obama publicly mocked him at the 2011 White House Correspondent’s dinner, the night before announcing that Osama bin Laden had been killed, Trump was red-faced and humiliated. Some say that Trump began seriously charting a course to run for President that very night.

And now he is having the last laugh.

Democrats Miss the Boat…Again

I think it’s a mistake for Democrats to double down on Harris’s so-called race and her gender as the primary factors in her loss. Sure, those factors likely played a subliminal role for some, maybe even for many. But clearly, bread-and-butter pocketbook issues were predominant in the minds of most, with high inflation causing millions to look back fondly at the first three years of Trump’s first term—after he inherited an economy brought back from the brink of disaster by Obama following the 2008 financial crisis. Ten million immigrants flooding the southern border during the Biden administration was another black eye for the Democrats. My own mother spoke to me with resentment about the benefits illegal immigrants were receiving in NYC.

Let’s dig deeper into the claim that Kamala Harris lost due to her race and gender.

If race were the predominant factor, then how could Barack Obama have been elected to two terms? If gender was the main reason Hillary Clinton lost in 2016, how could she have won the popular vote? Even Bill O’Reilly admits that if Michelle Obama had run, she would’ve had a much better chance of overtaking Trump than Harris. Al Sharpton’s intersectional “because she’s black, Asian, and a woman in a multiethnic marriage” falls flat. It relieves the Democrats from looking in the mirror to take responsibility and accountability for becoming a party run by coastal elites looking down on those less educated than themselves; a party that hectors people into using “Latinx” to de-gender the Spanish language when Latinos and Latinas themselves aren’t down with that re-frame; a party that released directives at the end of Obama’s second term giving transgender students right of access to bathrooms, locker rooms, and participation on athletic teams corresponding with their claimed gender, but in the eight years since has not adequately addressed some parents’ concerns and perceptions that trans women may have an unfair advantage in women’s sports.

Further, Democrats haven’t reckoned with the social and cultural damage done in 2020 and beyond after George Floyd’s murder. Riots in cities were called “peaceful” as footage of burning stores and police stations played in the background. BLM morphed from a movement declaring that black lives indeed matter to a golden egg for its leaders to buy expensive homes while not providing significant assistance to victims of police brutality. DEI became all the rage in corporate America while college faculty and scientists were compelled to sign highly ideological diversity statements as a condition of being hired.

So, Biden’s administration not only bungled the exit from Afghanistan, over-heated the economy during the pandemic, resulting in inflation, and sat by idly as millions of immigrants streamed in without permission from other countries, but they had the nerve to gaslight the nation regarding Biden’s capacity to run for a second term. Are you going to believe us or your lying eyes? they seemed to ask U.S. citizens, most of whom had already thought for several years that Biden was too old to run again. The Biden administration hid him from public scrutiny for as long as possible, and then his campaign refused to have Harris face interviews until the second month of her run.

When Harris finally began doing interviews, her unwillingness to separate herself from Biden and explain why exactly she had changed from her far-left positions in 2019 and 2020 was telling. Not being forthcoming on these matters allowed voters to presume, not without basis, that she would continue the same status quo Democratic party approach that many Americans felt was ineffectual and out of touch with working- and middle-class concerns.

I was given an opportunity to see much of this as long ago as 2016, but I didn’t take it. Jewel and I still lived in New Rochelle, NY back then. I called a taxi. An older “white” man picked me up and we began discussing the contest between Hillary Clinton and Donald Trump. He said he felt that Trump cared for struggling working people like himself. I couldn’t believe my ears. “Do you really think he cares about you? He doesn’t; he cares about himself,” I declared. The gentleman was quiet for the rest of the trip and likely went on to vote for Trump. To him, I was likely just another dismissive Democrat who wouldn’t even take the time to ask why he felt that way.

I should have paid more attention—the Democratic party should have paid more attention—to voices like his. I failed to grasp that the other side of “Trump cares for me” is “the other side doesn’t care for me.” Until the Democrats recalibrate their messaging and policies to reach people like my two drivers, and until they gain some insight into Trump’s appeal among the demographic groups that chose him over Harris, they are guaranteed to remain in the wilderness of discontent and election failure.

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Greg Thomas is CEO of the Jazz Leadership Project, a firm that uses the principles and practices of jazz music to enhance leadership success and team excellence in organizations such as JPMorgan Chase, Verizon, Center for Policing Equity, TD Bank, and Google. He is Co-Director of the Omni-American Future Project and Co-Editor of The Omni-American Review. In October 2021, he co-produced the two-day broadcast, "Combating Racism and Antisemitism Together: Shaping an Omni-American Future," which may be viewed here and here. He blogs at Tune In To Leadership, where a version of this essay originally appeared. He co-authored Reimaging American Identity with his partner, Jewel Kinch-Thomas, and Amiel Handelsman. He is currently working on his memoir, The Making of An Omni-American: My Journey from Race to Culture to Cosmos. He has published previously in the Journal of Free Black Thought here, here, here, and here.

1. I put racial terms like “white” and “black” in scare-quotes, because I do not believe race is real. See my post on this topic in the Journal of Free Black Thought, “Deracialization Now.”