Election memo: Trump's Hillary Problem

Harris still has the edge in the final week, because Trump has a Hillary-sized pundit-class problem

Photo of then-Democratic nominee Hillary Clinton in November 2016 by Gage Skidmore, via Wikimedia Commons. Graphic by Tom LoBianco/24sight News.)

*** Paying subscribers to 24sight News got first look at this yesterday, as a thank you for supporting independent journalism. Now it is out from behind the paywall, as a public service. Thanks all. More coming tomorrow AM, household emergency at moment (all is fine, but I’m a one-man band and family always takes priority.)

You don’t know what you don’t ask about.

That was one of my big lessons from 2016, when I was working in the trenches at CNN covering the election which stunned everyone — even the winner, Donald Trump.

It spurred a cottage industry of introspection at how the professional pundit class — from White House veterans to cable stars, and all manner of reporters of campaign consultants in between — could have whiffed so badly in the predictions game. It even catapulted Trump running mate and Big Tech protégé J.D. Vance into the mainstream with his explainer book “Hillbilly Elegy.”

It also helped sharpen my senses as a reporter on what indicators to watch for in elections, and which pollsters perform well and which ones not so much. (Ask any old statehouse veteran, and they’ll tell you who the tune into and tune out based on any given pollsters style of sampling and questioning.)

So for my second election memo (you can read the first one here, a very back of the envelope deal which evolved from talks with friends and laypeople) I’m digging into the unseen of 2024. And based on all my reporting, it looks like Donald Trump has a Hillary Clinton 2016 problem: the public indicators used by most are not catching a widespread wave of anger and resentment, creating a false sense of confidence.

1. Women voters are angry, and engaged

There’s a ton of anecdotal evidence about this out there, and certainly plenty of polling and, based on who you’re listening to, a fair amount of wishcasting. But I think the quiet women vote is real.

Here’s why:

In my talks with veteran Republican campaign hands, I have heard a good amount of backlash to Trump and Republicans coming in from women they’re pinging — be it for GOTV, small-dollar fundraising or other GOTV. In some cases women in the burbs have even taken the step of writing back with nastygrams.

Trump has spent a lot of time distancing himself from the Supreme Court he filled with anti-abortion conservatives who ended five decades of federal protection for abortion access. He’s disavowed the Project 2025 playbook written by his top aides with an eye on his return to the White House.

But his rallies, his podcast interviews, his performance onstage with Harris in their lone debate have displayed an intent focus on winning over working class men — to the chagrin of appealing to women.

Add to that the fact that what may have been reservations about Trump in 2016 after the Washington Post published the Access Hollywood tape where he bragged of grabbing women by the “p***y” were hardened into confirmations of Trump’s attitude toward women based on both actions in office and a raft of further scandals, many adjudicated, including in the historic first criminal conviction of a former president.

And after close to a decade of dominating the national debate, that behavior has been cemented as gospel among many women voters. As many have noted, the Dobbs decision was a historic reversal of rights for a singular group of Americans — and not quickly forgotten. (And Harris’s campaign certainly grasps this, running on reminders of threats to abortion access and reproductive health.)

2. Trump’s MAGA world sounds overconfident, but behaves insecurely

Trump’s hardest of hardcore supporters are loud, and on occasion threaten violence against others if they don’t think they’re voting for Trump. That’s still stunning in America, even after the January 6th insurrection and a 2020 race which was filled with political violence.

And stunning grabs headlines and attention. Boring does not.

A steady theme I’ve noticed in almost a 10 years now of covering Trump is deflating enthusiasm this time around. People leaving rallies and events early (this is not new this year, it’s just getting more attention closer to the election.)

MAGA and Trump, in the broader public, has the feel of disco. One day it’s everywhere, then one day it’s not.

In reality, the cultural zeitgeists shift and move quietly over time, until someone smart latches on to one and they catch fire — like when Trump tapped into global nationalist populist outrage which had been growing steadily for decades after the Cold War’s end.

But that was almost a decade ago.

Trump’s super-MAGA Madison Square Garden rally, which some have likened to the 1939 American Nazi rally, bears hallmarks of over-confidence. Trump wore the colors of a radical white nationalist militant group, the Proud Boys — perhaps he was trolling, perhaps he was signaling his allegiance. We’ll never know because he’s not a reliable source of information on the record. (Under oath is different.)

But the person who stole the show was a Texas comedian who pounded away at Latinos before declaring Puerto Rico an island of “garbage. That pronouncement spurred damage control from Trump’s campaign and top Republicans in a way I haven’t seen since the Tea Party era. Actions are always the clearest sign of a campaign’s internal assessments.

Trump has been saying that he’s already won the election (which is clearly inaccurate) but his well-coordinated RNC team of blue-chip lawyers have been preparing for an election loss quietly in the states, planning to challenge election results akin to the slapdash efforts after 2020 which fueled the January 6th attack on the Capitol.

And Trump’s communications director felt it would be beneficial to show billionaire Jeff Bezos’s supplication to Trump after Bezos nixed an endorsement for Harris in his newspaper — real power does not announce itself.

3. The old indicators are stuck on Trump

I still remember watching the 538 polling dial move from almost 100 percent chance Clinton won to a clear victory for Trump, on election night in 2016. Some, especially on the left, have internalized the trauma of that loss into believing that

I don’t see it that way, because it assumes that pollsters live in a static profession and don’t adjust for changes in demographics and voter behavior. That’s silly thinking of course, because a professional who’s career is based on accurately gauging public sentiment will always (or should always) adjust and calibrate. And I know plenty of good pollsters who have done that.

Similarly, over close to a decade now, covering the ins and outs of Trumpworld has become an almost singular focus of national political reporting. It has become the establishment model of coverage, and Trumpworld figures old and new are now establishment sources and influencers.

One reason Trump was missed early in the 2016 cycle was because of a heavy reliance on longrunning GOP sources who were 100 percent convinced there was no way Trump could ever win. And coverage reflected that. Now Trump, his campaign and his GOP have enjoyed the benefit of an aura of inevitability which used to be applied to Clinton. The Trump teams focus on, and success, in pressing the establishment and legacy media mirrors that of Clinton from eight years ago.

But the groundswell of channeled rage seems to be from the pro-democratic coalition — the American grouping of everyone from disaffected conservatives and old establishment Republicans, to the hyperonline left. Call it “Blue Anon” or some other term, but the rebellious rage has solidified on the left and jelled in a way that the tea party-turned-MAGA used to boast when it was out of power.