A collage of William Bar shaking Donald Trump's hand, an October 2020 calendar, vials of vaccines, and a pigeon on top of a mailbox.

Election 2020

The October Surprise is Coming


There’s a long history of Presidential campaigns manufacturing an event timed to influence the outcome of the election. Undoubtedly, Team Trump is working on a host of dirty tricks to retain power.



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Since the invention of the telegraph in 1843, presidential campaigns have deployed opposition research a week or two before Election Day—far enough out to let the dirt spread far and wide, but close enough to November to deny the besieged opponent adequate time to respond. This autumnal dirty trickery is called, colloquially, “October Surprise.”

I said “since the invention of the telegraph,” but I was rounding up. The first known October Surprise was engineered by President Martin Van Buren, the Richard Nixon of his day, in the election of 1840. His party—the Democrats—had uncovered a (real) scheme whereby the opposition Whig party had paid folks from Pennsylvania to travel to New York and cast their ballots. Some proto-Roger Stone released this juicy tidbit to the press, which had a field day attacking the honor of the Whig candidate, William Henry Harrison. But the President’s gambit didn’t work. Voters cannily assumed that the cheating happened on both sides, shrugged off the charges, and voted the mendacious Van Buren out of office after a single undistinguished term.

The October Surprise makes for a nice media narrative—the mainstream press behaves as if there must be an October Surprise every election, like there must be a winner for Best Picture, and the Chris Cillizzas of the world invest much energy and ink in determining which mid-autumn event (Parasite or Once Upon a Time…in Hollywood) is the October Surprise.

Whether these bombshells make any real difference, however, is a matter of debate. Did rumors of African-American bloodlines cost Warren G. Harding any votes in 1920? Did LBJ’s peace plan spell doom for Nixon in 1968? News of a decades-old DUI charge against George W. Bush did not dissuade enough swing voters in 2000, alas. More recently, the Access Hollywood tape was dropped on October 7, 2016, only to be trumped, pun intended, by the Jim Comey memo, which Jason Chaffetz leaked to the media. One side out-October Surprised the other.

Ronald Reagan’s campaign manager William Casey is said to have coined the term “October Surprise” in 1980. That was the year of the Iran hostage crisis, a story that dominated news coverage for months, and rumor has it that Reagan’s team secretly negotiated with the Khomeini government for the hostages to be freed after his inauguration—thus denying President Jimmy Carter the “October surprise” of their release. But here’s the thing: after four years of malaise, stagflation, and oil embargoes, Carter wasn’t winning re-election even if he’d brought the hostages home safely. Reagan wound up winning 44 of the 50 states. I believe the political term of art for that is “ass-kicking.”

At the moment, the incumbent president, Donald John Trump, is heading for an Election Day rout. Biden will crush him. Think Nixon in ’72, Reagan in ’84, Meryl and Maks on Season 18 of Dancing with the Stars. Trump’s campaign is the Titanic, Jared Kushner’s at the helm, and the American people are the iceberg. Absent Russians hacking into our machines and changing vote totals, it would take a deus ex machina-level October Surprise to right the Trump ship this year. And I mean deus literally. Jesus would have to rise again wearing a MAGA hat to make this thing close.

But that doesn’t mean Trump, Kushner, Bill Barr, and the rest of the dirty tricksters won’t try. To neutralize the “surprise” element of “October surprise,” let’s look at some of the shit they might pull—and explain why it won’t work:

Dead Letter Office

The gambit: Trump’s crony in charge of the USPS, Louis DeJoy, lays waste to the post office, the better to sabotage the mail-in voting process. (You’re not gonna believe this, but DeJoy has a financial interest in the USPS going down the tubes).

The reality: There turns out to be just as many Republican mail-in voters as Democrats, and the dastardly scheme does nothing but screw up the many businesses that rely on mail, pissing off most of the country, who blame Trump.

The likelihood: It’s happening unless someone like Mike Bloomberg swoops in and saves the day. (Remember Mike Bloomberg? Short guy, used to be mayor of New York?)

The Battle of Antifa

The gambit: Bill Barr sends his DOJ stormtroopers into [checks list] Atlanta, Philadelphia, Milwaukee, Detroit, and other cities in other swing states, to gin up violence and vandalism.

The reality: This already failed in Portland, and also in Washington, where Barr’s Gestapo tear-gassed peaceful protesters so that Trump could have his picture taken in front of a church, holding up a Bible as if he did not understand how books work. Turns out, people trust moms and vets more than Barr’s goons.

The likelihood: They think the “Trump As Protector” narrative plays with suburban moms, so yeah.

Vote West, Young Man!

The gambit: GOP moves heaven and earth to get Kanye West onto the ballots and into the debates, to play the Jill Stein/Ross Perot spoiler role.

The reality: Trump thinks that because Ye is Black, and also popular, he must, therefore, be popular with Black voters. The truth is that Kanye dominates the “white suburban teenager” demographic, and those kids can’t vote.

The likelihood: Although he was booted from the ballot in Illinois, and some of the signatures on his ballot in Wisconsin are of questionable authenticity, I doubt we’ve heard the last of Ye’s beautiful dark twisted fantasy of spoiling Biden’s run.

For Sale: Snake Oil

The gambit: Circumventing FDA approval, Trump signs an executive order allowing the Russian-manufactured novel coronavirus vaccine to be available in the States by Halloween.

The reality: The Russian “vaccine” turns out to be Stolichnaya. Even if scientists come up with a vaccine by the end of October, it won’t be ready for many months because of clinical trials.

The likelihood: пятьдесят пятьдесят

Flash Cash

The gambit: Trump works with Congress—as opposed to dashing off memoranda of questionable legality—to pass legislation to provide Americans generous unemployment payments, a moratorium on student loan and mortgage/rent payments, and protection from eviction.

The reality: He doesn’t understand how this even works. If we get financial help, it will clearly be because of Nancy Pelosi.

The likelihood: Doubtful.

Hunter Gathering

The gambit: Future felons Rudy Giuliani and Bill Barr, with an assist from Fourth of July Traitor Ron Johnson–all of whom have been busy for months trying to find manufacture dirt on Joe Biden–roll out “proof” that HunterBidenBurismaJoeBidenUkraineProsecutorZelenskyPartridgeinapeartree.

The reality: Anyone who believes this laughably and obviously desperate ploy is not voting for Biden under any circumstances—although the news media, having learned nothing since 2016, will both-sides it to death.

The likelihood: Mortal lock

Tara Reade 2.0

The gambit: Republican ratfuckers convince someone else to accuse Joe Biden of sexual assault.

The reality: The op—and that’s what it was, an op, exploiting #MeToo to benefit the rapist-in-chief—failed the first time, because the accusation was flimsy. If there was a credible sexual assault claim against Joe Biden, we’d know about it by now.

The likelihood: They’ll do it if they can find a willing accuser.

Kick the Bleep Out of the Veep

The gambit: If it’s Susan Rice, it’s the Clintons and Benghazi. If it’s Kamala, it’s that she’s a cop and also simultaneously wants to defund the police, like a Senatorial Schrödinger’s cat.

The reality: Have you seen the sycophantic mannequin they’re running? The handsome blue-eyed lickspittle who is guilty of most of the crimes Trump also committed?

The likelihood: Absolute. Which is likely why Biden is waiting to announce.

Change Horses

The gambit: Swap out Mike Pence for a shinier object, such as a Nikki Haley.

The reality: Trump and Pence are not just running mates; they are partners in crime. That makes for a messy divorce.

The likelihood: Small as Trump’s fingers.

Wag the Dog

The gambit: Trump finds a pretext to invade…I don’t know, Iran? Syria? Lebanon? Some country he doesn’t know the capital of and can’t find on a map.

The reality: Mobilizing for war won’t be popular during a pandemic, and being a wartime president means less time for golf.

The likelihood: Trump hates dogs, so no.

And if none of those things pan out, there’s always:

Caravan of Dreams

The gambit: Did you know that a gang called MS-13 has formed a caravan that is headed for the Texas border right now? Lock up your wife and children, we’re under attack!

The reality: The US is among the most dangerous places in the world with respect to COVID-19, with Texas and Arizona being particularly bad. No one’s coming here.

The likelihood: If they trot this one out, you know it’s all over.

Other than Russians hijacking the voting machines, accidental deployment of nuclear weapons, unforeseen natural disasters, or global extinction events, the only October Surprise I can think of that would really upend the election is if something happened to Biden. Joe needs to wear a helmet on his bike rides and keep on his mask and maybe just stay in his basement in mothballs, because we need him alive and coronavirus-free for the next 80-some-odd days.

More likely, the October Surprise will be the other way around: the Deutsche Bank documents reveal Trump as a money launderer for the Russian mob; DNA evidence in the E. Jean Carroll trial proves that Trump raped her; the NRA lawsuit takes down half the GOP, including Trump; further disclosures from the intelligence community show conclusively that Trump is owned by Putin; his status as a longtime confidential informant for the FBI is confirmed. So many shoes are going to drop, it’ll be like DSW up in here.

Bottom line: As long as we can fight voter suppression and our side turns up at the polls, Trump’s going to lose, and he’s going to lose bigly. Whatever October may bring, there won’t be any surprises in November.

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