Can Trump Whitewater-Raft His Way to the White House?

In an ironic twist, the Republican nominee—the author of many a failed real-estate deal—is trying to use the Clintons’ bad 1978 land purchase against Hillary Clinton

Hillary Clinton arrives at a courthouse in D.C. to testify before a grand jury on matters related to Whitewater in 1996. (Charles Tasnadi / AP)

Suddenly it looks like the presidential campaign could turn into a referendum on the 1990s. No, that doesn’t mean you get to vote your opinion on Third Eye Blind. Instead, Donald Trump seems to be determined to dredge up the detritus of the decade to attack Hillary Clinton.

Democrats knew what they were getting with the Clintons—an incredible political powerhouse, and a perpetual whiff of scandal. What they didn’t know, and still don’t, is how bad it will be this time, and how much it will matter.

Now comes one of the first tests. On Monday, Trump released a short video highlighting accusations of rape lodged against Bill Clinton by Kathleen Willey and Juanita Broaddrick. Attacks on Bill Clinton’s scandals are certainly fair game—the former president will find plenty of defenders, but his behavior will not. Whether they will work is a different matter. Hillary Clinton is trying to strike a delicate balance, reminding people why they liked the Clinton years without running as a nostalgia candidate, but she is ultimately the candidate—not her husband. The attacks could also simply remind people of Trump’s own checkered past as both a friend of the Clintons and a subject of sexual-harassment allegations. (I write in more depth about the risks, rewards, and lessons of this strategy here.)

On Wednesday, the Trump campaign inadvertently tipped off reporters that they’re planning to go in on the Whitewater scandal next. While emailing the Republican National Committee to “work up information on HRC/Whitewater as soon as possible. This is for immediate use and for the afternoon talking points process,” a Trump spokeswoman accidentally copied in Politico reporter Marc Caputo rather than Trump aide Michael Caputo. While it’s somewhat surprising that the Trump campaign (especially veteran aides like Paul Manafort) don’t have oppo research on Whitewater at hand, it makes sense that this would be where Trump hits next.

At this point, people under 30 are asking, “What is Whitewater?” (And those older than 30 may well be asking, “What was Whitewater, again?”) The name refers to a failed development in which Bill and Hillary Clinton invested in 1978. In the end, they lost $40,000 on the deal. (Money management has never been a strength for the Clintons, which might be why they’ve been so eager to make lots of dough since 2001.) Whitewater’s developers were James and Susan McDougal; James had worked with Bill Clinton in Arkansas government. The McDougals were later convicted of fraud, and the man who gave them a $300,000 loan claimed Bill Clinton had pressured him into making it. Three separate investigations concluded there was no evidence of criminal wrongdoing by the Clintons.

This might seem like an open-and-shut case, except that the Ken Starr’s independent-counsel investigation into Whitewater was later expanded to included several other tangentially related scandals in the Clinton years, including “Travelgate” and “Filegate,” both adopting the post-Watergate naming convention for controversies. Most importantly, Linda Tripp gave Starr tapes of conversations with Monica Lewinsky that led to Bill Clinton’s impeachment. Confused yet? (Here’s an old Washington Post explainer that is as clear as anything on this could be, which is to say moderately so.)

Needless to say, there’s hypocrisy in Donald Trump—who has four times had to declare corporate bankruptcy after unwise business decisions—criticizing someone over a failed real-estate deal. In theory, that could be damaging to Trump, though he seems immune to the normal rules.

Moreover, and more disturbingly, Trump is showing a willingness to engage with much darker and crazier elements. Trump decided in an iterview to resurface the thoroughly debunked (and truly disturbing) claim that the Clintons had their friend Vince Foster, an old law colleague of Hillary’s and then White House deputy counsel murdered. Foster’s death was a suicide. Trump of course brought Foster up in his classic I’m-not-saying-I’m-just-saying way: “I don’t bring [Foster’s death] up because I don’t know enough to really discuss it. I will say there are people who continue to bring it up because they think it was absolutely a murder. I don’t do that because I don’t think it’s fair.”

It might seem easy for the Clinton campaign to dismiss all of this as either old news or lunacy but for some uncomfortable coincidences. Like, for example, the news on Monday that Terry McAuliffe, a longtime friend and confidant of the couple and now the governor of Virginia, is under investigation by the FBI and Department of Justice over questions of whether he accepted illegal campaign donations during his campaign for governor. He’s another ’90s connection—“the Macker” was a top Clinton fundraiser back then, and those links helped him become chair of the Democratic National Committee in 2001. There are more recent links, too: McAuliffe’s time at the Clinton Global Initiative apparently plays a role in the investigation (though there’s no implication of impropriety at CGI or its parent, the Clinton Foundation—at least on this matter). When the story broke, McAuliffe said he’d cooperate but had not been contacted, a statement he made through his campaign lawyer Marc Elias. Elias just happens to have another full-time job at the moment—as general counsel of Hillary Clinton’s presidential campaign. All of this makes it hard for Clinton’s team to dismiss it all as crazy raving or expired gossip.

Trump may remember the Clinton campaign’s 1992 theme song, courtesy of Fleetwood Mac. But so far, he’s taking the different tack. To paraphrase: Don’t stop talking about yesterday.