Why you should care

Because scorched earth won’t do the charred political landscape justice once the dust from Trump vs. Clinton settles.

In this installment of our special election series on Donald J. Trump, OZY reports on what the billionaire’s strategy might look like if he were to secure the GOP nomination — and take on Hillary Clinton. Stay tuned for more pieces as he continues his march to, perhaps, the Oval Office.

After all of the ink and pixels spilled on 2016 election coverage, Super Tuesday confirmed what the polls have been telling us for months: We are headed for a clash of the titans between Trump and Clinton. And if the numbers hold true again, it appears Trump will have an uphill, though not insurmountable, climb to best Clinton, and there’s a chance he could wind up one of the biggest losers in presidential history.

Or become President Trump.

Nobody thought he could win the Republican nomination either, and he might just be getting warmed up. “I haven’t even started with her,” the mogul said of Clinton in the last GOP debate. So what might it look like when he does and the Trump-branded wrecking ball hits the Democratic Party establishment?

Shrinking the Gap

On the surface, each candidate seems ideal for the other. Facing Trump means Clinton’s character and likability shortfalls are suddenly merely relative — only the Donald could convert one of the most polarizing figures in America into the “love and kindness” candidate. Facing Clinton allows Trump to continue his assault on money in politics, offers up a bounty of material to fuel his ad hominem attacks and helps turn out conservative voters who might otherwise sit on their hands. (Neither the Trump nor Clinton campaigns responded to requests for comment).

The early numbers give Clinton an edge. Aggregate head-to-head polls have Clinton beating Trump by 3 to 4 points, and Trump’s divisive message seems to have little crossover appeal. A recent Economiste numbers trending in his favor. First, there is his general unpredictability. Neither Hillary nor Bill Clinton, Trump fanboy Chris Christie has pointed out, “know the playbook with Donald Trump, because he is rewriting the playbook.” And it’s a playbook for a game that has no boundaries — everything is in play and one player is always on offense. “Trump does not play by any rules,” says Steffen Schmidt, a political science professor at Iowa State University, “and therefore Clinton cannot possibly prepare for what he plans to throw at her.”

Trump has telegraphed some of his lines of attack already. You can bet Clinton will feel the burn of her connections to Wall Street and the donor class far more from Trump than Bernie Sanders— if nothing else, says Northeastern University professor Daniel Urman, because Trump himself was one of those donors. “He can even show photos of Hillary and Bill at his own wedding as evidence that they had to do ‘donor service’ work.” And not only does such a gambit stoke a Fox News–watching base that is obsessed with the cadre of special interests surrounding the Clintons, but it allows Trump to cast himself in the role of Ross Perot or Michael Bloomberg, the self-financing billionaire who can appeal to independents (and even Sanders voters) fed up with Wall Street and money in politics.

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Fighting Free Trade

Trump will also likely channel Perot to do something no GOP candidate has been in a position to do for a long time: challenge the Democrats on free trade. It may have been Bill who was involved in the birth of the North American Free Trade Agreement and the World Trade Organization, but Trump will make sure Hillary carries that baggage, all while he preys on fears of immigrants taking U.S. jobs.

Such populist issues will be Trump’s best bet to appeal to working-class white voters in key upper Midwest and Rust Belt states. And it’s not unrealistic: a December survey of working-class households making less than $75,000 a year showed Trump with 38 percent support, more than Clinton and Sanders combined. And, if Trump does turn out large numbers of non-college-educated whites while holding traditional Republican voters, Jude Barry, a political consultant at Catapult Strategies, tells OZY, then Clinton will have to turn out Black voters at the same pace as Barack Obama — a big task.

Bringing Out the Baggage

Speaking of baggage, says Schmidt, expect Trump to embrace simmering Clinton scandals with her emails and Benghazi and to breathe new life into the skeletons languishing in the Clinton closet. He’s already accused Bill Clinton of having a “terrible record of women abuse.” Could a rehash of old Clinton scandals effectively neutralize Bill, keeping him on the sidelines as he was for Al Gore in 2000? Topping it all off, Trump’s vague policy positions make him remarkably flexible — get ready for the mother of all Etch A Sketch resets as he retools for Clinton.

To be sure, Democrats can take solace in a number of things beyond Trump’s alienating animus. This is not Bill and Hillary’s first trip to the rodeo, and if anyone can play hardball with a bully, it’s the Clinton machine. And, as Trump’s forays with Carly Fiorina and Megyn Kelly show, it will be harder for him to attack a woman, particularly in front of the general electorate. Then, there is the matter of money. “Fundraising is going to be the biggest challenge for Trump in the general election,” says Darrell West of the Brookings Institution. He’ll need more money to keep up with Clinton, and if he gets it from special interests, West says, “he will have to change one of the major narratives of his candidacy.”

And what a yuge irony that would be if the ultimate alpha-male Republican candidate and self-proclaimed “winner” and “really rich” guy loses in November to a woman … and a Clinton … and because he lacked sufficient funds. It’s going to get really ugly, though, before that happens, or before we inaugurate a President Trump. Seal your windows and hide your kids — there’s a firestorm coming to America.

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OZY2016

The route to the White House: news, stories and analysis from on and off the presidential campaign trail.