Commentary: What will be this year’s ‘October Surprise’?

The term “October Surprise” was first coined in politics in the summer of 1980 by William Casey, campaign manager for presidential candidate Ronald Reagan.

Casey was concerned that incumbent President Jimmy Carter would announce a hostage deal with Iran in late October, in the waning days of the campaign, and use that victory to defeat the Republican challenger.

More than four decades later, we know that Casey’s feared “October Surprise” never materialized, and there are still some conspiracy theorists who even believe that Reagan’s campaign secretly conspired with the Iranian government to convince them to wait till after the November election to free the 52 Americans who had been in captivity for more than a year. Ultimately, the hostages were released after 444 days, coincidentally on the day of Reagan’s inauguration in January 1981.

But the term “October Surprise” stuck in the minds of the media and voters alike. Every four years, political pundits speculate what might happen in the tenth month of the year that could tip the scales to one candidate or the other.

In 2016, Oct. 7 may have been the most shocking day of surprises in presidential campaign history. First, the Washington Post reported on a leaked 2005 audiotape of presidential candidate Donald Trump telling George W. Bush’s cousin in extremely crude terms what he could do (and presumably had done) to women: “Because when you’re a star, they let you do it. You can do anything…”

We all know how that monologue ended.

Later that day, Wikileaks released a trove of private emails from Hillary Clinton’s campaign chairman John Podesta, many of which made the Democratic Party nominee look bad – including excerpts from speeches she gave to Wall Street banks for high fees, a question that was leaked to her before a presidential debate and a contradictory stance on trade deals from the one Clinton was then espousing on the campaign trail.

In 2020, the New York Times sprung an October surprise on President Donald Trump, publishing a series of investigative articles about the incumbent president’s finances which revealed that Trump was $400 million in debt and had paid just $750 in federal taxes in 2016 and 2017.

The topsy-turvy 2024 race has already had a plethora of stunning surprises between July and September: a candidate’s meltdown on the debate stage, an unprecedented switch of Democratic nominees right before the convention and not one but two unsuccessful assassination attempts on the former president and Republican nominee.

What could possibly happen in October that might “surprise” everyone and change the course of a toss-up campaign?

Can Vice President Kamala Harris and President Joe Biden broker a truce between Israel and Hamas and Hezbollah, proving to voters she has the foreign policy diplomatic expertise the country needs?

Will there be a stock market crash (remember October 1987 and September 2008) or the declaration of a recession, which would cast a very negative light on the Biden-Harris administration?

Could Ukraine achieve victory by seizing more Russian territory to vindicate the Biden-Harris strategy of coalition building and loyally sticking by an ally against notorious Russian dictator Vladimir Putin, whom Trump has openly admired the past decade?

Will Trump’s pressure on House Speaker Mike Johnson to shut down the government without a spending bill lead to chaos and an economic downturn?

Or could some damaging personal revelation from Trump’s or Harris’ past – like former President George W. Bush’s youthful drunk driving violation in October 2000 (how quaint that all seems now) — tip the electorate towards one candidate decisively?

On the New York City front, there is a treasure trove of possible surprises ahead this fall: Will any City Hall employees be indicted by the many law enforcement agencies conducting raids and issuing subpoenas to Mayor Eric Adams’ top aides? Just how close will the path of corruption lead to Gracie Mansion’s doorstep?

With plummeting approval ratings and mounting legal woes, will Adams decide not to run for reelection? Will former Gov. Andrew Cuomo decide that he must run for mayor to keep the left wing of the Democratic party out of power?

One thing’s for sure: it will be a hair-raising, roller coaster ride of a month. Buckle your seatbelts and try to enjoy (or at least survive?) the ride.

Editor’s Note: City & State would like to invite readers to send in their predictions about what “October Surprise” might arise in the next month before Election Day. Scroll down or click here to submit your educated guesses. We will publish the most creative ones that are sent in by Sept. 30.