Five Things That Should Keep Trump Up At Night

Politically speaking, Trump has a lot going for him. Very early in the primary season, he is the runaway front-runner for the GOP nomination.  Wrapping this up early will save him a lot of money and allow him to aim resources at Biden, instead of at his fellow Republicans.

He is battle-hardened. He has already endured dozens of serious scandals that would have ended most candidacies – two impeachments, 91 criminal indictments, a videotaped incitement of insurrection, the “grab em by the” lady bits tape, dozens of embarrassing gaffes, a porn star hush money conviction, a sexual abuse conviction, popular vote losses in 2016, 2020, 2022, and 2023, etc. 

Despite all of those calamities and more, Trump somehow still has around 35-ish percent of voters consistently enthusiastic about him and another 15-ish percent of voters who currently seem willing to hold their noses and vote for him.

After all of that, it’s difficult to imagine what could cause Trump to lose much electoral ground in the next 10 months.

Moreover, Trump has the good fortune to be running against a politically wounded, gaffe-prone octogenarian who has had to endure post-pandemic economic headwinds throughout his term.

Add to that the very real possibility of a third-party candidate siphoning off anti-Trump voters from Biden, and it can’t be denied that Trump has one hell of a strong political hand. At this stage, he should be considered the favorite to win in November.

But if I were on Team Trump, these are five challenges that especially would concern me.

Surviving a Conviction(s)

A major conviction, especially on the insurrection-related charges, could weaken Trump with a block of undecided voters. The Washington Post recently reported:

“…election-day surveys showed 31 percent of Iowa caucus-goers and 42 percent of New Hampshire GOP primary voters said Trump wouldn’t be fit to serve as president if he’s convicted of a crime.

Those are big scary numbers, but I would add two caveats to them: First, with an army of Trump lawyers trying everything possible to delay proceedings, it’s going to be very challenging for prosecutors to get a conviction and subsequent appeals completed before the November election.

Second, I’d be surprised if even one-quarter of those people who today say a conviction would be a deal breaker for them would actually abandon Trump. After hearing Trump and his supporters endlessly claim how the conviction(s) was the product of a politically motivated witch hunt, I think many cynics will agree with that cynical argument.

Still, if even a relatively small fraction of that large block of conviction-sensitive voters abandon Trump because of a conviction(s), that could be decisive in a close general election.

Moving Beyond “The Base”

Also, Trump is currently weak with swing voters. While much is made of how loyal Trump’s base is, once the primaries are over the MAGA base is not anywhere near large enough to give Trump a general election win.  He needs to win over the non-affiliated independents, soft Democrats, and soft Republicans who will decide this election. Like Biden, Trump has a lot of work to do to win over those voters.

Trump should be very worried about his poor showing with independents so far. MSNBC’s data geek Steve Kornacki noted a remarkable 71-point difference between how New Hampshire independents voted for Haley by 21 points compared to how the state’s Republicans voted for Trump by 50 points.

Fox News exit polls in New Hampshire found that 35% of GOP vote primary participants, many of whom were independents, indicated they would be so dissatisfied if Trump won the Republican nomination that they wouldn’t vote for him.

Again, if even a fraction of that holds in November, that could seriously hurt Trump’s chances in battleground states.

The Economy, Stupid

Then there is the economy. The state of the economy has traditionally been very important to swing voters – independents, soft Republicans, and soft Democrats.  Up until now, that has helped Trump pull ahead in the polls.

But as pandemic-related economic challenges have eased, the economy under Biden has very quietly gotten robust – historically low unemployment, consistent economic growth, much lower inflation than earlier, interest rate decreases likely on the way, a historic boom for the stock market/retirement funds, wage growth outpacing inflation, and, at long last, increasing consumer confidence.  The United States under Biden has the strongest post-pandemic economic recovery in the world.

Even if that good economic news only neutralizes the enormous past advantage Trump enjoyed on this issue, rather than turning it into a strength for Biden, that could help Biden win over persuadable swing voters.

Doh! Roe!

Trump also continues to face tricky political winds related to abortion rights. Surveys show that two-thirds of Americans think the overturning of the Roe v. Wade decision that kept abortion legal and safe was a mistake. Meanwhile, Trump is out there telling anyone who will listen that “I’m the one who got rid of Roe v. Wade.”  That’s music to Democrats’ ears.

The 2022 elections showed how much Republicans’ post-Dobbs abortion bans have hurt Republicans, particularly in suburban battlegrounds where battleground state elections are often decided.

Now congressional Republicans are promising a national abortion ban. That just adds fuel to this fire.

That would also worry me a lot if I was a Trump supporter.

Trump Being Trump

Getting voted out of the White House and kicked off Twitter has made Trump’s outrageous behavior a bit less visible than it was when he had the presidential bully pulpit. To the extent that Trump has been visible, a lot of the news coverage has been focused on how resilient he remains with the relatively narrow band of Americans who make up his political base. That success appealing to Republicans has made Trump look, up until now, relatively strong and normal.

But in a general election campaign, Trump’s steady stream of outrageous comments and actions will once again be more visible. Trump can’t keep himself from sounding childish, bigoted, incoherent, unstable, and dictatorial. That persona led Trump to lose the popular vote by 3 million in 2016 and 7 million in 2020.

Highly visible “Trump being Trump” news coverage is great for Trump when the task at hand is appealing to the Republican base. But a constant stream of Trump outrageousness doesn’t always help him with more moderate swing voters. Moreover, his undisciplined stream-of-conscious blathering keeps him from repeating the most persuasive anti-Biden messages and pro-Republican messages.

Again, Trump is far from politically weak. He is rightfully favored to win in November. But if I were a Trump operative, these are five things that would certainly keep me up at night.

12 thoughts on “Five Things That Should Keep Trump Up At Night

  1. Re: “Even if that good economic news only neutralizes the enormous past advantage Trump enjoyed on this issue, rather than turning it into a strength for Biden, that could help Biden win over persuadable swing voters.”

    So how do Biden’s comms people get people to a) notice, and b) care that these economic improvements are things they should care about?

    I’ve been saying for months that even though the stock market’s great, employment #s are robust, and inflation’s trending downward, this election might be decided on where gas and food prices are in Oct./Nov. IMHO, it’s where today’s electorate’s head is at, on politics: How much did my Dorito’s cost and what was the price at the pump when I bought that bag of chips?

    • Great question, Kevin.

      Trust me, I am discouraged by the same thing. However, I have been encouraged to see that consumer confidence has recently reached a two year high, even at a time when the news coverage of the economy seemed overly dour to me.

      https://www.reuters.com/markets/us/us-consumer-confidence-perks-up-december-2023-12-20/

      As interest rates finally begin to decrease in the coming year and news coverage of improving numbers continues, I hope that consumer confidence number will continue to improve.

      Also, I hope that some of that $117M that Biden has on hand will be used to get that story told. With so many people not following the news, well-targeted paid messaging is going to be necessary.

      People who are still really struggling aren’t going to buy this. But that’s not everyone. Biden needs consumer confidence improvement, not unanimity.

      • Copy that.
        To your point about paid media, i do hope the targeting is solid.
        Say that as I still think back to the 2016 primary when I received emails inviting me to be an early member of the Cruz Crew. Yes, that was “Ted” Cruz.
        I think their targeting was a bit off, though I did enjoy messing with their and costing them money retargeting me by putting t-shirts in the shopping cart, then x-ing out. 🙂

  2. What are you hearing or reading that makes you believe Trump is favored to win in November?l

  3. I think that – as usual – you nailed the salient details of the situation.

    Between the MAGA faithful and the hold-your-nose crowd he has 45 percent baked in. Maybe a conviction would change that assessment. So too might a health event or some Trumpian faux pas of unimaginable awfulness – something like a thirty-second rant caught on video of him talking about he really feels about his supporters – but absent that he’s trying to get enough support to flip Arizona, Georgia, Michigan, Pennsylvania and Wisconsin. I think North Carolina might be in play as well this time.

    Could he do it? Hell, yeah. Especially if Biden has a health event or there’s something awful on his watch – an attack, a border event – that gets laid at his feet.

    Cut away all the BS and here’s the issue: either Joe Biden or Donald Trump will be sworn in next January 20th. Anyone who cares about which octogenarian stands on the east front of the capitol to take the oath of office better do everything in their power to get their guy elected because right now it’s a jump ball.

    • Yeah, those of us who are unenthusiastic about Biden don’t really have the luxury of being unenthusiastic about Biden. The stakes are too high. So, speak out, donate, volunteer…

      • 100 percent. I’m rapidly coming to believe Joe Biden is the Rodney Dangerfield of American politics; no matter what he does – and his record is remarkable over the first three years with a closely divided Congress and the ugliness that is Trump – he gets no respect.

        Including the possibility – however faint – of border/immigration reform. There is not a more divisive, difficult, dysfunctional issue in American politics and yet there’s real negotiations happening to resolve it. Yes, it’s been declared DOA by Speaker Johnson and the House Freedom Caucus and yes, it is making the leftmost wing of the party gag just on the rumors of what might be in there but it’s as close as we’ve gotten in a couple of decades and back when I was in politics a good deal was defined as something that made both sides unhappy so again, there’s a there there.

        If there’s anyone in the Wry Wing universe who know the arcane rules of the House better than me (not a big bar to clear), I’d love to know if such a bill – assuming it passes the Senate – could be brought to the floor on a discharge petition or another mechanism to force a vote.

        And if it can, is there a 218+1 coalition of Republicans and Democrats to pass it? That strikes me as a high hurdle as nearly all Republicans are going to be – what’s the technical term? – chickenshits about bucking Trump and a good chunk of Dems on the left – far more than the squad – won’t be able to swallow a bill praised so orgiastically by Thom Tillis and Jim Lankford.

        • My lack of enthusiasm is not about Biden’s policy accomplishments. In that sense, he’s the most successful POTUS in my adult lifetime (might be an argument for LBJ, but I was a kid then). I’m just not enthusiastic about his skills using the bully pulpit and the political weakness and potential vulnerability that comes from his age.

          But I’m over it. I’m all in. If you can’t be with the one you love, honey, love the one you’re with.

        • OK, I claim no arcane knowledge here, but if the Senate were to pass it, couldn’t they attach it as an amendment to a must pass funding bill that would then have to go back to the House? I expect that the House would vote to pass it without the amendment, sending it to reconciliation, but at least they’d have to vote on it….

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