Twin October Surprises (are they surprises if they're premeditated?):
In a case brought by the the Boston Globe, a judge will decide (at 9 a.m. EST) whether to lift gag orders on a case involving the nasty divorce of Mitt Romney booster and Staples kingpin Tom Stemberg and his ex-wife Maureen. Gloria Allred is apparently representing someone involved, probably Maureen.
Allred is brilliant and politically very canny—it's hard to believe she would bother unless what was in the papers, and what Maureen is dying to say, is more damaging than a garden-variety divorce or even an affair.
But we may never know, as there's a good chance the judge will deny this request.
The other surprise is one being perpetrated by Donald Trump. Less savvy politically, he's more focused on sensationalism, so it's not impossible to imagine he may really have something stupid, like the Obamas' divorce papers (which would not cause many waves unless they contained contradictory personal info or REALLY unsavory details of why they almost divorced).
However, since he has denied that it involved rumors that Obama sold cocaine in college by saying it's something that matters more to voters, I'm guessing he must have some damaging document. Perhaps he has dug up Obama's Columbia thesis and it's got alienating racial content or—gasp!—something that could be construed as socialism. Or maybe he applied for a grant and stated he was born out of the country, which would be cheating.
Whatever it is, and whatever Allred's got up her sleeve, this is high-stakes shit. If they unleash something lame, it could easily help the very candidate they intend to hurt. And if it's actually damaging, then we just spent two years and over a billion dollars only to have an election decided by a single piece of information purposefully withheld and released at the last possible moment.
Or both could fizzle and we'll be where we were, in a tied race/race tilting toward the president marginally where the electoral college favors the president so far.