What The Real Winner Of The First Debate Can Teach Every Single Candidate (Including Trump)

Dan O’Donnell breaks down Milwaukee’s presidential debate and names a surprising winner who wasn’t on stage or getting interviewed by Tucker Carlson


Aug. 24, 2023
Perspective by Dan O’Donnell


The biggest winner of the first Republican presidential debate wasn’t on the stage.  He wasn’t in Milwaukee and no, he wasn’t on Twitter talking with Tucker Carlson.  He was somewhere south of Richmond continuing to take the world by storm.

And every single candidate on that stage desperately needs to learn from him.

Oliver Anthony, an unassuming singer-songwriter from Virginia, has the number one song in America—a monumental achievement for an unsigned artist made even more impressive by the fact that his “Rich Men North of Richmond” features no production whatsoever.  There are no flashy electronic drops, no synth backbeats, no harmonies; it’s just him and a guitar singing from the heart about the country he loves.



He didn’t accompany it with a slickly edited music video; he just had a local college radio station film him in a field.  In a country accustomed to YouTubers who now flawlessly mimic Hollywood from their bedrooms, Anthony’s video shouldn’t have worked.

But it did.  Flawlessly.  And not in spite of its imperfections, because of them.  “Rich Men North of Richmond” resonates so deeply because it is real.  It’s raw, emotional, almost guttural; just a regular guy with an old guitar and a powerful message about a country he sees slipping away.

Oliver Anthony is all of us because he could quite literally be any of us.  Without a multi-million dollar production budget or an army of publicists, his simple melody and honest, powerful message pierced the veil of political and corporate censorship and speaks directly to millions of people hurting in Joe Biden’s America.

It was fitting then, that the first question of Wednesday night’s debate was about his song.

“His lyrics speak of alienation, of deep frustration with the state of government and of this country. Washington DC is about a hundred miles north of Richmond,” said moderator Martha McCallum before playing a short snippet of the video. “Governor DeSantis, why is this song striking such a nerve in this country right now? What do you think it means?”

“Our country is in decline,” DeSantis answered automatically before launching into an obviously well-rehearsed attack on Bidenomics. “This decline is not inevitable, it’s a choice. We need to send Joe Biden back to his basement and reverse American decline.”



It was a good enough answer, and DeSantis had a good enough night, but did either it or him really stand out in any way? Did any of the candidates, other than perhaps Vivek Ramaswamy incessantly yapping like a chihuahua high on cocaine?

He, more than any other candidate, came across as a policy lightweight punching well above his weight class with a smug arrogance that belied the bumper sticker populism coming out of his mouth.  He tried so hard to be genuine, to be relatable, to be Oliver Anthony that he came across as the fakest candidate on stage, and it was apparent from his very first answer.

“So first, let me just address a question that is on everybody’s mind at home tonight. Who the heck is this skinny guy with a funny last name and what the heck is he doing in the middle of this debate stage?” he said, responding to moderator Bret Baier’s question about voting in just two presidential elections in his 38 years. “I’ll tell you, I’m not a politician, Bret, you’re right about that. I’m an entrepreneur.  “My parents came to this country with no money 40 years ago.

“I have gone on to found multi-billion dollar companies. I did it while marrying my wife, Apoorva, raising our two sons, following our faith in God. That is the American dream.”

Stephen Colbert pilloried this sort of pandering 19 years ago on “The Daily Show.”

“That’s why I believe in the promise of America,” he said, building to a thunderous finish to his faux speech. “Because I, the son of a turd miner, the grandson of a goat ball licker, could one day leave those worthless hicks behind while still using their story to enhance my own credibility!”

Ramaswamy’s reliance on such a familiar political trope left him open to the most withering attack of the night (even though it, too, felt practiced).

“I’ve had enough. I’ve had enough already tonight of a guy who sounds like ChatGPT standing up here,” an exasperated Chris Christie said after Ramaswamy used yet another cliché by claiming to be “the only person on the stage who isn’t bought and paid for.”

Christie then went in for the kill.

“The last person in one of these debates, Bret, who stood in the middle of the stage and said, ‘What’s a skinny guy with an odd last name doing up here’ was Barack Obama,” Christie said. “And I’m afraid we’re dealing with the same type of amateur standing stage tonight.”

It was so vicious and so effective because it was so accurate: Republicans spent eight straight years mocking Obama for his inability to speak without a teleprompter and then spent two straight hours regurgitating the same tired talking points about bringing back prosperity, restoring freedom, and standing up for the American people.

The voting public rejected that sort of thing seven years ago when it elected the only man who seemed to be speaking plainly and from the heart directly to them. Former President Trump was and continues to be a political phenomenon for the same reason that “Rich Men North of Richmond” is a massive hit: Because his is a message that is just unfiltered, unedited, unflinching him.

None of his Republican rivals—and, really, no one else in politics—has been able to replicate that. In every debate, every speech, every interview, Trump gives you Trump, warts and all. He is unapologetically himself, polls and consultants and concern for norms and politeness and even common courtesy be damned.

Americans really do value someone who “tells it like it is,” and even if their rational brains understand that he doesn’t give them the best chance of winning an election, their emotional connection to him won’t let them abandon him, no matter what he does. He is honest with them because he IS them, or at least he is what they envision themselves to be if they were in his place.

If they were, in other words, a rich man north of Richmond. This, more than anything else, is why ultimately Wednesday’s debate didn’t do much to change Republican primary voters’ minds. Those who support DeSantis as the most electable candidate will continue to do so. The one percent or so of voters mesmerized by Doug Burgum’s eyebrows will continue to be. Ramaswamy was so bad that his moment might be over, while Haley might have been good enough to jump from eight percent support to double digits.

No one, though, did enough or potentially could ever do enough to cut into Trump’s lead.  For a huge swath of Republican primary voters, he is their man and they will follow him anywhere—whether it’s to a Tucker Carlson interview airing opposite the debate or straight into what may be a general election debacle.

For better or for worse, he is the rich man they want north of Richmond.