In an October filled with surprises, can President Trump still win?

It didn’t take long for this election’s first official October surprise to occur. Less than 22 hours into the new month, President Donald Trump tweeted that he and his wife, Melania, had tested positive for COVID-19.

That came just five days after a late September surprise, publication of a newspaper report with private details from Trump’s income taxes, showing that he avoided paying large sums of income taxes in recent years, legally but politically damaging nonetheless.

Who illegally released private IRS tax records remains an unanswered question. But just hours later, if you can believe it, Democrats were running TV ads about it.

Before that came a videotape with former Vice President Joe Biden appearing to call members of the military “stupid bastards.”

And you can pretty much count on more such attempts to influence the November presidential election’s outcome, although the sources will likely be masked to make verification difficult.

Some surprises are, in fact, coincidental but impactful. In October 1964, the Soviet Union’s leader, Nikita Khrushchev, was overthrown, and Communist China detonated its first nuclear bomb, both of which helped create a landslide victory for President Lyndon Johnson over conservative hawk Barry Goldwater.

News consumers, however, should be aware that most of these domestic surprises are engineered and carefully timed by operatives from one side or the other to affect voters’ decisions.

Oh, and spoiler alert, the surprises are not always true or in context. Politics, especially at the presidential level with all the powers, influence and money at stake, is not beanbag, as they say.

The full tape of Biden’s military comment to troops in 2016, for instance, shows he was attempting to joke and bond with them through a profane insult.

But given the ubiquity of cellphones with video, wise politicians, even when passing casually through pre-lockdown ropelines, need to be wary. And so do U.S. voters, whose short attention spans and pre-set partisan beliefs make them especially susceptible to malevolent misdirection and edited excerpts.

And while Russian collusion with the 2016 Trump campaign turned out to be false, foreign meddling in our elections continues. During George W. Bush’s 2004 reelection campaign, media reported that Saudi officials had cut the price of oil to help ensure their friend’s reelection victory.

Perhaps you recall the Iranian hostage crisis, which occurred mainly during the 1980 election year. More than 50 Americans were held by revolutionary forces in Tehran for 444 days.

Iran considered releasing them in the fall but decided that might help President Jimmy Carter’s reelection campaign. So, they postponed the release until minutes after Ronald Reagan took the oath on Jan. 20, 1981. Years later, the same administration was caught illegally selling anti-tank weapons to Iran for use in its war against Iraq’s Saddam Hussein.

The timing of these October surprises, even if true, strikes some of us as dirty pool, sitting on important or at least negative information until it can do the most damage or, in the case of book authors such as Bob Woodward, help boost sales in a heated election season. Journalism schools can debate the ethics of that, if they still do such things.

Remember the notorious “Hollywood Access” tape from October of 2016? A reporter from the Washington Post, which had already made its Trump antipathy well known, received a phone call from an as-yet unidentified person asking if he’d like to see a previously unreleased videotape.

That decade-old tape contained audio and video of then-private citizen Trump talking crudely with an entertainment reporter about grabbing women’s private parts.

It was a bombshell that rocked the political world just one month before the presidential election involving a female Democrat. Democrats and quite a few Republicans denounced Trump for days, demanding he withdraw.

As you may have noticed, Trump won anyway because for just enough voters in just the right electoral places, he gave voice to the outrage against a bipartisan Washington establishment that had played voters for years with empty promises.

That was also an early sign of Trump’s, well, surprise immunity to such surprises in any month of the calendar so far.

During the heated Democratic primary season of 2008 between Barack Obama and Hillary Clinton, the media were fed videotapes of Rev. Jeremiah Wright’s anti-Semitic and anti-American sermons in his Chicago church where the Obamas were parishioners.

In politics, you don’t release all the damaging evidence at once. So, drip, drip, more such tapes came out, forcing Obama to awkwardly claim he had no memory, must have been absent on those Sundays and, eventually, to renounce Wright.

The term October surprise entered America’s political parlance in 1980, meaning an event designed to affect a November election’s outcome. But the public relations tricks had been going on since the 1840s when Democratic incumbent Martin Van Buren tried to ensure reelection by timing mid-October news of the arrests of Whig opponents for state voter fraud. It didn’t work.

Then, there was the October surprise that shaped the historic presidential race of 2000. Days before the Nov. 7 election, a prominent Maine Democrat told a reporter that George W. Bush had been arrested there for drunk driving 24 years earlier.

Bush, who had been leading in Maine polls, confirmed the incident.

Bush strategist Karl Rove said keeping that arrest hidden was the worst mistake of the campaign, and Bush ended up losing Maine to Al Gore.

Well, you say, who cares about an October surprise in little old Maine? But had Bush captured that state’s four electoral votes, there never would have been a Florida recount, no hanging chad fights and no bitter, month-long legal fight ending in the Supreme Court.

This story was originally published October 6, 2020 at 6:00 AM with the headline "In an October filled with surprises, can President Trump still win?."