Can Donald Trump win again? I doubt it

By Matthew Gagnon

Tuesday evening, former president Donald Trump announced what we all knew he would announce, confirming that he would in fact be running for his old job again in 2024.

“America’s comeback starts right now,” Trump said during the speech. “In order to make America great and glorious again, I am tonight announcing my candidacy for president of the United States.”

The speech itself was fairly pedestrian, predictable and full of the usual Trump rhetoric. Watching it, I felt like I could more or less have written the same speech if somebody had asked me to predict what I thought he was going to say. In other words, I didn’t feel anything particularly new or different watching the speech.

That may not sound important, but go back to 2016 for a moment and ask yourself what allowed Trump to catch fire and win the presidency in the first place. A big part of it was “newness,” or the sense that we had never seen anyone like this before, and had not heard a candidate speak like he did before. 

Last weekend, Dave Chapelle hosted Saturday Night Live and during his monologue explained this phenomenon better than anyone I had seen previously. Chapelle, who is a Democrat, explained that he knows why Trump was appealing because he lives among the “poor whites” in Ohio who are Trump’s base, and who still adore him. 

“The reason he’s loved is because people in Ohio have never seen somebody like him,” he said. “He’s what I call an honest liar.”

Explaining what he meant by that, Chapelle brought up the first debate, in which Trump claimed that the system was rigged and his opponent Hillary Clinton disputed it. He continued, “and the moderator said, ‘Well Mr. Trump if, in fact, the system is rigged as you suggest, what would be your evidence?’ Remember what he said, bro? He said, ‘I know the system is rigged because I use it.’ […] No one had ever seen anything like that. No one had ever seen somebody come from inside of that house outside and tell all the commoners we are doing everything that you think we are doing inside of that house.”

Obviously, Chapelle was playing it all for laughs, but as is typical with him, he was delivering a serious message amidst all the jokes. Trump was different. The house Chapelle was referring to was what you might call “the establishment” or just generally the world of the elite, the powerful, and the wealthy.

In essence, what was new and different about Trump was that he came from that world but had apparent contempt for it, and started telling people who suspected that the system was corrupt and rigged that it was in fact corrupt and rigged. 

Then he won the presidency. 

The sentiment that elected him in 2016 was one of frustration, and interest in overturning the table, breaking through the wall, or draining the increasingly proverbial swamp. People had more or less had enough of the “same old same old” establishment hack politicians and were willing to take a flier on a guy who offered something different. Trump won because he was able to build a coalition of disaffected blue-collar, working-class people with more traditionally Republican suburban center-right voters, and ride that coalition to victory.

But is that still possible today?

The country has changed a lot in six years. It has lived through four years of his administration, and opinions about him have hardened in both directions. The country has lived through civil strife, a worldwide pandemic, massive economic turmoil, and brutally disruptive and divisive elections. And we’ve now seen that in three successive elections, 2018, 2020 and 2022, the coalition that brought him to the White House in 2016 is not together anymore.

Can he rebuild it?

I’m fairly unconvinced of that. To win a general election, he is going to need to convince a lot of people who took that flier on him in 2016, and have since had more than enough of him, to step into the Delorean, gun it up to 88 miles per hour, and go back in time, and take a flier on him again. 

I have little doubt he can recapture some of those people, but he would need all of them and more to realistically be able to win in 2024. I’ve been involved in politics far too long to ever say that it is impossible. But, in a Republican Party that has developed a strong group of next-generation national leaders including Ron DeSantis, Glenn Youngkin, Tim Scott, Kristi Noem and many others, the question today ultimately has to be: would somebody else have a better shot at doing it?

Matthew Gagnon of Yarmouth is the chief executive officer of the Maine Policy Institute, a free market policy think tank based in Portland. A Hampden native, he previously served as a senior strategist for the Republican Governors Association in Washington, D.C.