The “October surprise” is a staple of American elections, but they rarely live up to their billing. There have been some notable ones, of course, such as the eleventh hour release of George W. Bush’s 1976 DWI arrest in Maine mere weeks before voters went to the polls. Bush still won, but his previous 5 point lead in the polls shrank to the photo finish we wound up with. For the most part, however, many of the promised shock and awe moments of October have failed to deliver.

Could this year be different? John Fund at National Review put on his thinking cap yesterday and sees at least the possibility of both major party candidates bracing for some unpleasant and potentially game changing surprises in the final stretch.

Could the presidential election be decided by two competing “October Surprises” based on leaked information?

One from WikiLeaks could involve the deleted e-mails from Hillary Clinton’s private server and could be related to the FBI’s ongoing investigation of the Clinton Foundation. Another could involve the leaking of confidential tax-return information regarding Donald Trump, who has steadfastly refused to release his returns even as he demanded to see the returns of people seeking to be his vice-presidential running mate.

Speculation about possible October surprises is rampant here among political observers covering the Democratic convention.

John is right about this being a hot topic in the media cloakrooms at the moment. I was talking to him at an RNC event last night as well as a number of other journalists covering both campaigns and it was being brought up frequently. The big ticket item right now is the promise from Julian Assange to deliver even more goodies on Hillary Clinton which he assures us will wind up with her being arrested. Obviously the Wikileaks mastermind loves to pump up his own importance and draw attention to his website, but if he actually has the rest of Clinton’s deleted emails or more information on the Clinton Foundation, he may be sitting on some real political dynamite. As to Clinton literally being arrested… recent history shows the unlikely nature of that claim, but he could erode enough independent support for Clinton to tip the scales.

What of Trump’s tax returns? There’s no sign that he’s planning on putting them out in the public sphere before November and there must be a reason for it. Possibilities include things as benign as simply not wanting reporters pawing through his personal finances or a revelation that his total net worth isn’t quite what he claims on the campaign trail. Neither would be a necessarily disqualifying factor in the minds of voters. Keeping his taxes under wraps isn’t standard practice for a politician these days, but then Trump doesn’t do much that anyone would consider “standard” anyway. But what if it’s something more? Aside from some business dealings with unsavory characters I’m not sure what his tax forms could reveal. If it was anything patently illegal then we could assume that the government would already be all over him. That remains one of the known unknowns in the race.

So will this be the year of the real October surprise? In any other cycle I’d be highly skeptical, but the way this election is rolling out I’m not discounting anything. Both Donald Trump and the Clintons have long, complex histories involving vast amounts of money and contacts from around the globe. Who knows what may turn up? Either way, we should only have a few months to wait at the most before we find out.

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