What Will This Year’s ‘October Surprise’ Be?

Sometimes that’s easy. For instance, one can safely predict that Donald Trump isn’t going to win his “absolute immunity” case before the Supreme Court, just as surely as he wasn’t going to lose the case brought against Colorado for barring him from the ballot there.

But it feels unfair to ask Jonah and the rest of the gang to go on guessing what will happen in a modern presidential campaign, when insanely destabilizing “October surprises” have become standard procedure. The only safe prediction in 2024 is that the race will be upended by something completely unpredictable.

It wasn’t always that way, dear reader. I am an old-ish man, yet the only meaningful October surprise of my lifetime until 2016 came when word leaked before Election Day 2000 that George W. Bush had once been arrested for driving under the influence. In the end, that might have tilted enough votes to Al Gore to spoil an otherwise clear-cut victory for the Republican, plunging the country into the nightmare of a contested election.

Imagine: Within living memory, before Americans got comfortable with coup plots and porn-star payoffs, something like a youthful DUI arrest was scandalous enough to endanger a candidate’s presidential chances. Things are different now.

Part of the reason there have been so few meaningful October surprises is that few presidential contests over the last 40 years remained close enough to be scrambled by one. From the start of the Reagan Revolution in 1980 to its demise in 2016, only the two races won by Bush 43 were tight on Election Day. Barack Obama and John McCain might have ended up in a dogfight if not for the financial crisis that struck in the fall of 2008, but I doubt it. Disillusionment with Bush was so broad and excitement for the first black president was so high that I suspect Obama would have won comfortably regardless, if not quite as comfortably as he did.

With that as context, let me ask: Do you fully appreciate how bananas the last two presidential cycles have been with respect to October—or at least election-year—surprises?

In both races, not one, a computer that may or may not have contained evidence of the Democratic nominee’s criminality surfaced weeks before the vote, in bizarre circumstances.

In 2016, the FBI reopened its “Emailgate” probe of Hillary Clinton at the eleventh hour after it stumbled across communications from her on a device belonging to former Rep. Anthony Weiner, whom it was investigating for, er, sexting a 15-year-old. That surprise might have cost Clinton the election. Four years later, a laptop allegedly belonging to Hunter Biden turned up at a random Delaware computer repair shop containing emails implying corruption by Joe Biden. Intelligence experts rushed to reassure the press that the laptop was a Russian disinformation operation. Oops: It wasn’t. Biden held on to win by the skin of his teeth.

Those weren’t the only surprises in 2016 and 2020, though. In both races, not one, a hugely influential Supreme Court justice up and died in the thick of the campaign.

Neither was an “October” surprise, strictly speaking. Antonin Scalia passed away in February of 2016 while Ruth Bader Ginsburg passed in September of 2020, but their deaths very well might have decided the outcome of each year’s presidential race. For Republicans, filling the Scalia vacancy was a compelling reason to set aside their misgivings about Trump. For undecided voters fresh off of watching Amy Coney Barrett’s light-speed confirmation, thwarting a further conservative takeover of the court might have made the difference for Biden in swing states he won by razor-thin margins.

In the Trump era, when every presidential election is 50-50 and no one trusts anyone, October surprises seem not just likely but unavoidable. And so while it’s unfair to ask Jonah or anyone else to anticipate how freakishly strange 2024 might get, it’s an understandable question. There will be some unexpected jolt to the campaign, one assumes. We might as well start speculating about what it’ll be.

I have a prediction.

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It’s tempting to assume that an October surprise will matter less this year than in previous cycles because of how well the public already knows both candidates and how strongly it feels about them. If you’re voting for Biden, the election is about democracy or abortion or climate change; if you’re voting for Trump, it’s about inflation or immigration or “retribution.” There isn’t much room politically for an October surprise to matter.

It’s tempting to believe that. But it’s wrong.

The opposite is closer to the truth. Because so many Americans doubt that either candidate is fit for office, a sudden jolt to the race near Election Day could tilt them decisively toward one or the other. Look no further than last week’s verdict in Manhattan for evidence that certain “disengaged voters” who currently favor Trump will reconsider if met with a big enough “surprise.” According to New York Times political analyst Nate Cohn, a small but meaningful share has already switched to Biden following Trump’s conviction:

There’s also anecdotal evidence that “double haters” have been moved by the verdict. When political consultant Sarah Longwell interviewed a panel of nine two-time Trump voters who have since soured on him but are leery of supporting the president, she found post-verdict that five are now leaning toward voting for Biden.

An October surprise will matter, maybe more than it ever has. So what’ll it be?

The most tumultuous possibility is a health crisis for either candidate. Biden wouldn’t recover politically from one; doubts about his physical and mental fitness run too deep for a trip to the hospital to be successfully “messaged” away. Trump would fare better unless his crisis was plainly debilitating, partly because the public has more confidence in his baseline health and partly because his lunatic fans would insist that Biden had him poisoned or whatever. But it would hurt him, surely, by demonstrating that the health gap between him and Old Man Joe is smaller than we thought.

The political dynamics of another Supreme Court justice keeling over would favor Democrats, especially if the deceased were a Democratic appointee. It’d be 2016 in reverse. At the time, Republicans couldn’t bear the thought of the great Scalia’s death producing a 5-4 liberal advantage on the court. Eight years later, Democrats are facing a 6-3 conservative advantage that probably won’t be undone for a generation and might not be undone for two generations if it slips to 7-2.

Nothing would get disaffected progressives to set aside their qualms about voting for Biden like the near-term prospect of Supreme Court Justice Aileen Cannon would. Given what happened in 2016 and 2020, if I were Sonia Sotomayor or Elena Kagan I’d go get that check-up at the doctor’s office that I’ve been putting off.

Both of those are what we might call “actuarial” October surprises. But what about more foreseeable ones?

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An obvious potential surprise is Trump being convicted in one of the three remaining criminal cases against him, but that’s a longshot that’s getting longer by the day.

The prosecution in Georgia, for example, is frozen indefinitely as an appellate court considers whether Fulton County District Attorney Fani Willis is too unethical to remain in charge. And the classified documents case is going nowhere as future Justice Cannon takes her sweet time moving forward, lately having paused to determine whether Special Counsel Jack Smith was lawfully appointed or not.

The pace of the third prosecution, related to trying to overturn the 2020 election, depends in part on how the Supreme Court rules on Trump’s “absolute immunity” claim. If it sends the matter back to the lower court to determine which of his acts at the time were “official” or not, that’ll slow things down enough to ensure that that one won’t make it to a jury before November either.

But if it does, and Trump is convicted? One would hope that would be the end of his presidential chances. Disengaged voters and “double haters” have already inched away from him after seeing him convicted on minor charges in New York; a jury verdict finding him criminally at fault for his coup plot four years ago might send undecided voters fleeing.

On the flip side, if a New York appellate court ends up overturning Trump’s conviction in Manhattan before November, that might be the end of Biden. Undecided voters might treat it as confirmation that Trump was right all along about Democrats waging illicit “lawfare” against him on trumped-up charges (no pun intended). The backlash would be fatal, especially after Team Joe spent so much time and energy hyping the fact that his opponent is a “convicted felon.”

Another “surprise” possibility: What if a well-timed “deepfake” of either candidate saying something outlandish and disqualifying emerges?

Don’t laugh. Biden has already been the victim of one during this campaign and his aides have used the prospect of it happening again as an excuse to suppress the audio of his interview with Special Counsel Robert Hur. Phony yet convincing audio and/or video of politicians caught in compromising situations will have “October surprise” potential in American elections forevermore. And in a race in which voters already doubt the fitness of both contenders and deeply distrust non-aligned media sources, it’s easy to imagine them lending undue weight to a “scandalous” recording that surfaces just before Election Day.

Imagine a tape of Biden struggling to remember his own name in a meeting with a foreign leader. Or envision the probably mythical audio of Donald Trump saying the N-word on the set of The Apprentice appearing after nine years of liberals trying and failing to verify that it exists. The country would divide instantly and bitterly over whether either recording was a high-tech dirty trick or shocking confirmation that the other side’s candidate is even less suited to being president than they assumed.

As a bonus, if the target of the deepfake ended up losing the election and then the nature of the fakery were exposed, his supporters would insist that the outcome had been effectively “rigged” and should be treated as illegitimate. It would be the “Hunter’s laptop” fiasco on steroids. Public faith in the integrity of American elections, already distressingly weak, would soften further.

It’s such an obvious and easy way to set Americans at each other’s throats that one wonders why Russia or China wouldn’t do it.

I think we’re likely to see a deepfake or two, or 10. But that’s not my prediction.

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No, my prediction is this: At some point before November, intelligence sources will allege that Trump has been privately lobbying foreign leaders to undermine Biden’s policies.

“Biden’s policies” are America’s policies so long as he’s president. In better days, it would have been an unholy scandal for a presidential candidate to secretly undercut American policy abroad during a campaign for the selfish end of gaining an electoral advantage. But as we saw with the case of George W. Bush’s DUI, Things Are Different Now.

For instance, here’s something that I dare say wouldn’t have flown during the 2000 election.

If you’re an American with enough juice abroad to get an American hostage released, you don’t refrain from using that influence until you get something that you want in return. Doing so has the air of a ransom demand, don’t you think?

In effect, Trump is lobbying Russia not to release Evan Gershkovich before November 5. He’s actually trying to extend the Wall Street Journal reporter’s captivity because he sees a benefit to himself in doing so. The possibility that Ronald Reagan’s campaign did something similar in 1980, conniving to delay the release of Americans held hostage by Iran until after the election, was so politically explosive that the matter is still being litigated more than 40 years later. Now here’s Trump conniving in plain sight.

If he’s willing to do that publicly, what is he doing privately?

With any other politician, it would feel unfair to speculate without evidence about them exploiting the foreign relationships they’ve built to undercut U.S. foreign policy. But in this case, character is destiny. Trump has done this before, after all: When he leaned on Volodymyr Zelensky in 2019 for information on Joe Biden in exchange for duly appropriated American weapons, he was subordinating the country’s interests to his personal interests. Electoral considerations inevitably influence a president’s policy choices, but only one president has been so brazen as to use official policy to try to extort an ally for oppo research on his opponent.

He has no qualms in principle either about accepting foreign help to win an election. In 2016, Trump half-joked at a press conference that Russia should “find” Hillary Clinton’s missing emails and publish them. The same year, his campaign eagerly promoted material lifted by Russian hackers from computers owned by Democrats like John Podesta and laundered through Wikileaks. Although it came to nothing in the end, his son and other staffers sought Russian assistance in the election at a meeting at Trump Tower.

Trump is amoral, transactional, and desperate to regain the presidency in order to thwart the remaining criminal prosecutions he’s facing. Because there’s no civic priority that he holds more dearly than his own aggrandizement, there’s nothing to dissuade him from reaching out to Russia or China or whoever with offers of favors when he returns to office in exchange for them making trouble for Biden now. Remember, even with respect to an issue like immigration about which he really does care, he was willing to sabotage congressional efforts to ease the crisis at the border because he feared losing his electoral advantage on the issue.

The idea that an American citizen shouldn’t undermine his country’s foreign policy wouldn’t even cross his mind.

In early April, the New York Times reported that Trump had recently spoken by phone to Mohammed bin Salman, Saudi Arabia’s de facto ruler, although the topic of conversation is unknown. Maybe they were just catching up. Or maybe Trump reminded him that rising oil prices are bad for an incumbent president in an election year. Or, maybe, they chatted about something else: “News of their discussion comes at a time when the Biden administration is engaged in delicate negotiations with the Saudis aimed at establishing a lasting peace in the Middle East,” the paper noted.

If Trump doesn’t want the border tightened until he’s president or Evan Gershkovich freed until he’s president, it would stand to reason that he wouldn’t want an Israel-Saudi peace accord signed until he’s president either. How would America react if it discovered in October that he had talked the Saudis out of making peace because he feared that doing so would help Biden?

A few weeks ago, NBC News published a report describing apprehension among U.S. officials that North Korea is preparing to “potentially take its most provocative military actions in a decade close to the U.S. presidential election, possibly at [Vladimir] Putin’s urging.” Russia doesn’t need any encouragement from Trump to spring an October surprise on Biden, no doubt regarding it as payback for the president’s support for Ukraine. But Trump is, of course, friendlier with Putin and Kim Jong Un than Biden is, and as president, he’d be far less likely to intervene in both countries’ spheres of influence.

He’d be the direct beneficiary of the October surprise they’re allegedly planning. What, precisely, would stop him from reaching out to either country and pledging his gratitude in advance if they decide to follow through on it?

An allegation before Election Day from U.S. intelligence that Trump had egged on some foreign malefactor to cause problems for America would explode like a grenade in the middle of the campaign. It would be a rerun of the Russiagate saga of 2017, except with suspicions of the other party’s malevolence an order of magnitude higher now than they were then. Outraged Republicans would insist that “the deep state” had unleashed its biggest hoax yet on Trump. (Unless Trump turned around and confirmed that he’d done it, I mean, at which point Republicans would pivot instantly to arguing that he’d done nothing wrong.) Democrats would counter that here was the smoking gun proving once and for all that Trump has been colluding with the international order’s most degenerate strongmen to empower authoritarianism globally.

It would be bedlam, unthinkable in any other era yet quite imaginable this summer or fall, I think. I’m already counting the hours. Things are different now.

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