One of the entertaining aspects of the Donald Trump 2016 experience has been the remarkable incompetence his campaign demonstrates on a fairly regular basis. One of the primary sources of Trump’s appeal is supposed to be his famous business acumen and managerial skills – he’s going to go to Washington and clear out all the hapless dopes and losers who’ve been fumbling about and making bad deals. But that message is constantly undermine as his campaign organization keeps stepping on rakes and face-planting, screwing up in ways that are both relatively harmless and potentially catastrophic.

We were treated to another example of minor incompetence earlier this week as Politico reported that it had gotten a hold of an email Trump’s campaign sent to the Republican National Committee requesting some opposition research on Hillary Clinton. That email ended up in Politico’s hands because one of Trump’s communications staffers accidentally sent it to a Politico reporter who has the same first initial and surname as the RNC research staffer. It’s a small foul-up in the larger galaxy of ineptitude that is the Trump campaign operation, but it did give a hint as to how Trump is going to go after Hillary.

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The research Trump’s team requested has to do with the Whitewater real estate deal, a throwback Clinton scandal from the ‘90’s. If you’re unfamiliar with the bewilderingly complex details of the scandal, don’t concern yourself too much. The important things to know about Whitewater are that it was the starting point for the manic and obsessive investigations by congressional Republicans that culminated in Clinton’s impeachment proceedings, and that years of investigation into Whitewater found no actual wrongdoing on the part of either Bill or Hillary. As Politico noted, Trump’s team wanted information on Whitewater as quickly as possible to fold into their anti-Hillary talking points.

As a political weapon, Whitewater is a dud. Greg Sargent writes at the Washington Post that Republicans tested out Whitewater as an anti-Hillary message during her 2000 campaign for the Senate and it flopped badly. If voters back then didn’t give a damn about the ginned-up and inscrutable “scandal,” there’s no reason to believe they’ll be more receptive to it 16 years later. But I don’t think Trump and his people are planning to bore people to death with the details of a failed real estate deal from the late 1970s. They likely have something different in mind.

My guess is that Trump and his people are going to try and create a sort of scandal fog around Hillary, and that Whitewater plays a part in doing that. Whitewater alone doesn’t do any damage Clinton, but if you casually include Whitewater as part of a litany of Clinton “scandals” (alongside Vince Foster, Travelgate, Rose Law Firm, Troopergate, Benghazi, emails, and the like) it starts to take on a hint of menace. You’re creating the impression of rampant malfeasance without actually having to assert or document any wrongdoing. Trump’s already started doing this – in an interview with the Washington Post he said: “It’s the one thing with her, whether it’s Whitewater or whether it’s Vince [Foster] or whether it’s Benghazi. It’s always a mess with Hillary.” He’s not making an allegation and he’s not diving into the details, he’s just saying the words and nudging his audience towards the conclusion he wants them to reach.

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It’s a brash move by Trump, but if he really wants to get into a “scandal” fight with Hillary, he starts at a distinct disadvantage. The Clinton scandals are, by this point, eye-glazingly familiar to anyone who’s paid even cursory attention to politics over the past 25 years. They might not know the precise details of Whitewater or Travelgate or Benghazi, but they know of them and they’re priced into their existing knowledge of Hillary Clinton. On the other hand, Trump’s many, many, many, many, many, many, many scandals are still relatively unknown to the electorate. They represent a fine opportunity to educate the voting public on Trump's various failings, both personal and professional. Indeed, there’s a hard-to-miss irony in Donald Trump, a man who has cocked up more than his fair share of real estate deals, targeting Hillary Clinton over Whitewater.