A Timeline of the 23 "October Surprises" of the 2016 Election…
In years past, presidential campaigns typically only had to worry about a single so-called “October surprise” with enough firepower to potentially knock them off the the path to 270 electoral votes – George W. Bush’s secret DUI arrest and Mitt Romney’s “47 percent” video, for instance. But this year, instead of a landmine hidden somewhere in those 31 days, we’ve essentially had an advent calendar: a new October surprise for almost every day of the month.
https://www.rollingstone.com/politics/politics-features/a-timeline-of-the-23-october-surprises-of-the-2016-election-191857/
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"Trump managed to lose $916 million in 1995"
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New York’s attorney general’s office ordered Trump’s personal charity – which the Washington Post had reported was soliciting donations in the state illegally – to cease fundraising in New York immediately.
3.2005 hot-mic recording that featured Trump bragging about trying (and failing) to sleep with Access Hollywood host Nancy O’Dell
Shortly after the release of the “Trump tape,” WikiLeaks began releasing emails hacked from Clinton campaign manager John Podesta’s personal email account.