This is now the third presidential election where Trump is the Republican nominee, and each race has been unique. In 2016, he was the outsider who appealed to the forgotten voter. In 2020, we had the pandemic, which upended everything. In 2024, Democrats swapped their candidate in the final lap. Despite the differences in these elections, with each one I’ve found myself asking the same question: Does Trump really want to win?
The obvious answer is, “Of course he does; why wouldn’t he?” But let me explain why I keep asking myself this question.
In 2016, Trump’s campaign began as a long shot. Many, including myself, questioned if he was serious or just using the campaign as a platform to boost his brand. The way he bulldozed through the Republican primary was nothing short of remarkable. At the time, I wasn’t happy about his entry into the race and hoped that upon winning the Republican nomination he’d start acting more presidential. He didn’t, of course.
It made me wonder if he really wanted to win.
Somehow, it worked. Trump's authentic brashness resonated with voters compared to Hillary’s diabolical phoniness. Still, his victory never felt like the result of a calculated plan — it felt like Trump accidentally found himself winning the race.
By 2020, Trump had the power of incumbency, a strong economy, and a dedicated base. He was cruising to reelection. And then the pandemic hit. While the lion’s share of the criticism of his handling of the pandemic was entirely partisan, he did leave himself a wide-open target. Instead of letting health experts lead the daily COVID briefings, he took center stage, putting himself in a position where his lack of medical expertise undercut the authority he was trying to project.
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And then there were the debates. Trump’s performance in the first debate against Joe Biden was widely criticized. Instead of presenting himself as a competent leader ready for a second term, he interrupted, talked over, and antagonized Biden to the point where even his supporters were left wondering what the strategy was.
It made me wonder if he really wanted to win.
Now, in 2024, we’re seeing some of the same patterns. Trump remains wildly popular with his base, but his campaign seems stuck in the past. During the primaries, he attacked fellow Republicans rather than focusing on Joe Biden or Kamala Harris. His failure to move past the 2020 election hasn’t helped him. As much as I've grown to like JD Vance, in light of the fact that at the time Trump announced his running mate, it was looking increasingly likely that Joe Biden was going to be forced out, I think there were better options for a running mate. But perhaps even more troubling is Trump's lack of focus during interviews and particularly the debate. Frankly, I don’t think Trump prepared for his debate with Kamala Harris at all. These are major unforced errors.
It makes me wonder if he really wants to win.
I want to believe running for president is more than just Trump seeking adoration from large crowds, but time and again, he makes decisions that seem baffling for someone who is serious about the election and committed to victory. I've been saying for months that if Trump wants to win the election, he needs to run a disciplined campaign, and he hasn't been.
