After eliminating his final competitors in early May, Trump knew that he needed a crash course on what lay ahead. This was how he came to sit down with Karl Rove.
Trump didn’t particularly like Rove, either. He found the “architect” of George W. Bush’s winning campaigns to be haughty and condescending. For much of the past year, Trump had raged against Rove when reading his columns in the Wall Street Journal, many of which were pitilessly critical of the GOP front-runner. On numerous occasions, Trump reached out to a mutual friend, the casino magnate and GOP megadonor Steve Wynn, asking him to relay his displeasure to Rove.
In early May, Rove’s phone rang. “Karl, kiddo, I talked to Donald and he wants you to write something nice about him,” Wynn said. “He won the Indiana primary. Can you write something nice about him?”
“As a matter of fact, I just got done writing a column, and I said some nice things about him,” Rove replied. “Would you like to hear it?”
Rove read portions aloud. He said that Trump had “bludgeoned 16 opponents into submission” and “rewrote the rule book,” beginning the column with a blunt declaration: “No one has seen anything like this.”
Wynn approved. But the next morning, he called Rove back. Trump hated the column. Rove had castigated the candidate for his endless string of insults, called the JFK–Rafael Cruz talk “nuts,” and written, “Trump’s scorched-earth tactics have left deep wounds that make victory more uncertain.”4
Wynn read Rove the riot act on behalf of his friend. But then he added something surprising: Trump wanted to sit down to talk strategy. “He says he wants to meet with you and get your advice,” Wynn told Rove. “He knows you did this twice.”
A few weeks later, on May 23, Rove surveyed the nine-hundred-square-foot living room of Wynn’s apartment in New York City. The setting was fabulous: Situated on the thirtieth and thirty-first floors of the Ritz-Carlton Hotel, the ballroom turned domicile featured, among other things, fifteen-foot cathedral ceilings, a library, a media room, and a private terrace overlooking Central Park South. Rove had arrived two hours early, wanting to keep the meeting private and avoid the media scrum surely accompanying Trump. Yet the candidate arrived by himself, right on time, without any entourage or fanfare. He, too, seemed intent on secrecy.
Trump and Rove had met before: In 2010, Rove traveled to Trump Tower to solicit funds for his super PAC, American Crossroads. He walked out with a $50,000 check. The small victory earned Rove some ribbing from Steven Law, a former Mitch McConnell aide and American Crossroads’ president. “Congratulations,” Law told Rove. “I think you’re the first Republican I’ve ever known to get a check from Donald Trump.”
There wasn’t much foreplay when they sat down across from one another inside Wynn’s opulent living room. Trump asked Rove what he needed to know. Rove, in firehose fashion, launched into his lecture on the contours of the Electoral College.
“You have to have a strategy to get to 270. We had several paths to get there,” Rove began. “We had the traditional battleground states, which were Florida, Ohio, New Hampshire, Iowa, New Mexico, Colorado, Nevada, Michigan, Pennsylvania, Wisconsin, Minnesota. And we had four battleground states that had traditionally been carried by Democrats: Arkansas, Tennessee, Kentucky, and West Virginia.”
“West Virginia?” Trump interrupted. “I did really good in the primary there. I can win West Virginia—that’s a big Republican state.”
“Well, in 2000 it wasn’t,” Rove explained. “Bob Dole had lost it by fifteen points four years earlier. The last time it had gone for Republicans in an open-seat presidential race was 1928, and it took nominating a New York Catholic to bring all the Methodists and Presbyterians and Baptists out of the hills and hollows of West Virginia to vote Republican.”
Rove worked his way around the map. When he reached the West, he focused on four states, Montana, Nevada, Arizona, and Oregon, explaining that Bill Clinton and Al Gore had each carried at least one of them. Trump, Rove said, would need to win at least two—and probably three—to stand a chance in 2016.
“Oregon? I can win Oregon,” Trump said excitedly. “I did really good in the primary there.”
“No, you can’t,” Rove cautioned. “In 2000, we had Ralph Nader on the ballot there, and he had a real following in Portland and Eugene; the state had just elected a Republican U.S. senator; they had Republican constitutional officers; they had a Republican majority in the statehouse; and we still lost it by half a point. Since then, it’s gone hard left. The last time we won a statewide race was 2002; we hold no constitutional offices; and we’re down to less than a third in the statehouse and a third in the state Senate. There’s no way you can win Oregon.”
Trump smirked. “I don’t need to,” he said. “I can win California.”
“No, you really can’t,” Rove chuckled, wondering whether the candidate was being facetious. Judging from Trump’s expression, he was not. “You’re down seventeen points in the RCP average,” Rove told him. “It’s a giant suck of time and money. There’s no way you can win California.”
Trump was growing irritated. “Well, I’ll win New York.”
Rove sighed. “No, you won’t. Bernie Sanders got more votes by himself than all the Republicans combined. Two and a half times the number of people voted in the Democrat primary than the Republican primary. You’re losing to Hillary by twenty-six points in the RCP average, and it’s a waste of time. If you spend a day trying to win votes in a place like California or New York or Oregon, it’s a day you can’t spend trying to win votes in Pennsylvania or Iowa.”
Trump looked puzzled. “I can win Iowa?”
“Oh yeah,” Rove cooed, building the candidate back up after tearing down his illusions. “You didn’t win the caucuses, but those farmers in the western part of the state, they hate her guts. And there are a bunch of blue-collar workers in the eastern part of the state that are worried about their jobs. You can win Iowa. But not if you’re spending your time in Oregon, California, and New York.”
Trump turned to Wynn. “Why aren’t people in my campaign talking to me about this?”
(Three days later, Trump gave a speech naming the “fifteen states” that he would campaign in. Among them: New York and California.5)
As the conversation progressed, Trump grew less defensive. He seemed to recognize that Rove, however patronizingly, was trying to help him succeed. Trump’s clutch of advisers talked little of long-term strategy or historical voting trends; mostly, they urged him to concentrate on animating the base with his rhetoric and policy positions. He had long dismissed the complaints from his adult children that Corey Lewandowski, the campaign manager, was doing him a disservice. But now, as he soaked up a briefing of unprecedented depth, Trump was beginning to wonder.
The meeting spilled into its third hour. Rove coached Trump on everything he could think of, from campaign finance to parochial swing state policy disputes. When the conversation turned to Pennsylvania, Wynn complained about Chinese steel, and Trump sounded off on the country, saying the United States should never have allowed it to join the World Trade Organization. “Actually, we should have,” Rove corrected him, “because that binds them to an international set of trading norms, and if they violate them, we can take action in front of the WTO. It takes a little time to do it, but in 2015, the Obama administration filed like one hundred and fifteen actions against China and other actors, and if history is any guide, we’ll win almost every one of those actions and recoup money for affected industries.”