Eli Stokols is national politics reporter at Politico. Ben Schreckinger is a reporter for Politico.

What they heard as they ate deli sandwiches around Donald Trump’s hulking wooden conference table sounded like the businessman’s typical bravado. These 25 New York political operatives had come to ask him to run for governor. But Trump had another plan—a very specific plan—to run for president.

“You guys are going to be very helpful when I do the big thing,” he said, according to people who were in the room that day.


To the GOP county chairs and assemblymen there in Trump Tower’s glass-enclosed conference room overlooking Fifth Avenue and Central Park, Trump’s aspirations seemed far-fetched and the plan itself sounded downright implausible.

“He said, ‘I’m going to walk away with it and win it outright,’” a long-time New York political consultant recalled. “Trump told us, ‘I’m going to get in and all the polls are going to go crazy. I’m going to suck all the oxygen out of the room. I know how to work the media in a way that they will never take the lights off of me.’”

This gathering of New York’s political class was not held on the eve of Trump’s announcement. It was much earlier than that – 25 months ago, in the weeks before Christmas of 2013, a period well before most Americans and even many politicians were thinking about the 2016 presidential contest. Well before Trump would come to utterly dominate the GOP race from the very moment he declared himself a candidate.

In this meeting, Trump showed his cards, laying out the route he would take to tonight’s Iowa caucuses.

Notoriously frugal, Trump insisted he wouldn’t need to spend much money on paid advertising, drawing disbelief from the professionals gathered around his table.

“You can’t run for president on earned media,” one attendee recalled telling Trump.

The billionaire looked up, and paused for a long moment. “I think you’re wrong,” Trump said.

“Are you going to do all those little events at the Pizza Ranches?” another person asked, referring to the Iowa fast-food franchises that are a staple of presidential campaign stops.

“Maybe a little,” Trump replied. “But it’s really about the power of the mass audience.”

I’m going to get in and all the polls are going to go crazy. I’m going to suck all the oxygen out of the room. I know how to work the media in a way that they will never take the lights off of me.”

What sounded then like fantasy now looks like prophecy. Trump’s long-planned but largely improvisational campaign, propelled by a high-wattage personality, has him in position to win the Iowa caucuses, and perhaps steamroll his rivals on his way to the GOP nomination.

It couldn’t have worked for anyone else. Everything that explains the first-time candidate’s mind-blowing success—his uncanny ability to read and react to people and to bait his foes into positions of weakness, his eagerness to accept risk, and, above all, his ability to trust his gut to navigate the race while eschewing professional guidance—is the result of an entire career in the public spotlight and the ruthless worlds of New York real estate, media and politics.

“When he looks down his nose at the political consulting class, no wonder,” said veteran Republican pollster and Trump acquaintance Tony Fabrizio. “And I’m one of them!”

And yet, all Trump’s brash confidence obscures another truth: As much as he’s succeeded in consistently conveying confidence and strength, he, too, has been beset by the same uncertainty and self-doubt throughout the campaign that all candidates face.

COLD FEET

In the months before he entered the race, Trump’s then-advisers, Roger Stone and his young associate Sam Nunberg, proposed that the real estate developer and celebrity enter as late as possible, perhaps even skipping Iowa, and storm to the nomination a la Richard Nixon, who declared his candidacy for the 1968 Republican nomination on February 1 of that year.

Trump nixed that strategy in favor of a June entrance for two reasons. The first was that it would allow him to test the waters long enough to exit the race in time for the fall season of his reality show The Apprentice in case his campaign flopped.

The second was that Trump, an astute observer of the television industry, saw a news void he wanted to fill during the summer doldrums of the campaign — when most candidates are busy fundraising and building ground organizations.

But the entire thing almost didn’t get off the ground. A week before he took that slow escalator ride down from his office and into the presidential race, Trump was overwhelmed by what he was about to do. He got cold feet.

Donald Trump reportedly had second thoughts before he announced his candidacy on June 16 at Trump Tower in New York, pictured above. | Getty

Trump was in Aberdeen, on the east coast of Scotland, to open a new clubhouse for one of his golf courses when he called the man who would soon be his campaign manager, Corey Lewandowski, and said he wasn’t sure he wanted to go through with it. He told Lewandowski he wanted to put the announcement off for two weeks, according to two people with knowledge of the conversation.

One Trump confidant described the episode as “last-minute stage fright.”

“He was all over the map,” said another Trump intimate. “Totally out; delay it; do some events in the early states, but not others.”

The call from Lewandowski’s mercurial new boss threw the operative — sitting back at Trump Tower in New York — for a loop, according to both Trump insiders. Lewandowski had uprooted from New Hampshire and been working since January to build Trump a campaign infrastructure, which included some of the earliest staff hires of any campaign-in-waiting in Iowa and New Hampshire.

But, just as he would when facing a tough decision in the months to come, Trump worked through his discomfort quickly. Whatever doubts plagued him in Scotland, by the time his plane returned home from the country of his mother’s birth, now just days before the planned announcement, Trump had resolved to push ahead. “How can I not give this a shot and let these politicians ruin the country?” a third confidant recalled an apprehensive Trump saying the day before he announced.

Lewandowski disputed this version of events, saying the June 16 launch date was decided on May 9 and that Trump never wavered from it.

Trump’s 2016 kickoff foreshadowed exactly how nontraditional his campaign would turn out to be.

INSULTS, UNSCRIPTED

Trump, according to those who have known him for years, has never relied on scripts, talking points or a teleprompter. During his 14 seasons on The Apprentice, Trump would tell producers, “I don’t work with scripts.” He was content to glance quickly at the bullet points on a notecard. “In these scenes for the show, it was very intimate and he’d be eye to eye, face to face with these contestants and looking to get reactions and reading their facial and emotional reactions,” said another Trump ally. “It’s what he does now, but just in front of larger crowds.”

On the day of his announcement, his staff distributed four pages of polished, prepared, remarks. In them, he stated he was running in the tenth sentence. But instead of following the plan, Trump spoke for 15 minutes before announcing, “I am officially running for president of the United States.”

In a moment that’s been scrubbed from Trump’s official video of the event, the house speakers began playing him off with Neil Young’s “Rockin’ in the Free World” before the real estate mogul signaled for the music to be cut off. Rather than leave the stage, he spoke off the cuff for another 30 minutes, and said: “When Mexico sends its people, they’re not sending their best. They’re not sending you. They’re not sending you. They’re sending people that have lots of problems, and they’re bringing those problems with us. They’re bringing drugs. They’re bringing crime. They’re rapists. And some, I assume, are good people.”

Trump didn’t foresee the furor his Mexico comments would generate; it was a reaction that built slowly and broke into a fever pitch in early July. But even if he didn’t predict what exactly would kick off the media frenzy, he had planned all along to offer the media a candidacy it couldn’t resist covering.

“Immigration was always at the top of everything he said,” one Trump confidant said. “He’d been saying it for years: ‘We need a wall, we have no borders, we don’t have a country.’ He was just incredulous about it.”



Cable networks were immediately riveted by Trump, whose every move was seemingly broadcast live. Hordes of cameras and reporters scrambled to follow him from one sensational campaign stop to the next, including a tour of the Mexican border at Laredo, Texas in July.

After weeks of dominating the political news cycle thanks to an uproar around his immigration comments, Trump sparked another controversy so large it had Republican leaders certain this would be the end of their unwelcome front-runner. After Fox News anchor Megyn Kelly asked Trump during a debate some tough questions about his penchant for insulting women, Trump shot back, saying Kelly chose that line of questioning because she “had blood coming out of her eyes, blood coming out of her…wherever.”

Like the Mexican controversy, Trump’s feud with Kelly and Fox was unplanned. But unlike with that first episode, his team was eager for him to walk it back. Lewandowski and Trump’s daughter, Ivanka, prepared memos outlining various ways to ease off the Kelly story. But Trump wouldn’t relent; he doesn’t do damage control.

“In all these cases, he’ll take the memos people put in his hands and listen to people’s comments, but he’s still going to do his own thing,” said a source close to Trump’s inner circle. “On some things, Corey is the last arbiter of charting the final course, but most of it is Donald.”

Trump had worked months earlier to establish what his team thought would be a strong, supportive relationship with the television network that has become so central to Republican messaging. Before his candidacy, he had been appearing regularly on Fox and enjoyed a friendly relationship with Fox News chief Roger Ailes. The two had dined together several times.

Trump and Lewandowski entered the race with an impression that Fox would be friendly to Trump’s candidacy, according to Republican consultant Cheri Jacobus, who entered into talks with the campaign for a communications role last spring.

At an interview at Trump Tower in May, Jacobus said Lewandowski predicted a rosy relationship with Fox and suggested Trump could eventually help her land a contract with the network. A source at Fox said Trump did not have any influence over such decision-making. “He basically indicated that their press strategy was Fox — that they had Fox. I said, ‘I don’t think Roger Ailes operates that way,’” said Jacobus, a longtime Fox guest. Instead, she responded that the network’s CEO gives individual hosts the freedom to go their own way.

Donald Trump’s visage hovers over the road, just north of a large shopping complex in West Des Moines, Iowa. | M. Scott Mahaskey/POLITICO

According to Jacobus, Lewandowski countered by producing a printout of an email from Ailes to Trump, offering to be helpful in any way that he could. A source at the network said that it is not uncommon for Ailes to sign emails by offering a helping hand, but that it would be a mistake for that to ever be interpreted as helping a political candidate with editorial coverage. Lewandowski also told Jacobus that Trump would give his first big post-announcement interview on the network to the mogul’s friend, Bill O’Reilly. Jacobus said that move could miff Sean Hannity, who traditionally scored the first interview with candidates. Trump went ahead with his O’Reilly interview on the night of his announcement. Hannity brought Bush — at the time the much bigger get — on the same night.

The belief that Fox was supposed to be in his corner may have contributed to Trump’s vivid and enduring rage at Kelly for the tough questioning of him at the first debate.

Stone, a close confidant of Trump’s for 30 years, departed the campaign in the aftermath of the candidate’s suggestion that Kelly asked tough questions because she was menstruating, giving Trump's comments as his reason for leaving. But those who know Stone said the operative was also frustrated by a general lack of influence with a candidate who served as his own chief adviser.

“He is his own strategist. He is his own message maven. He is his own publicist,” Stone, who has continued to serve as a surrogate, said of Trump.

CALCULATED BLUSTER

That the media saturation was driven by controversies that led to widespread condemnation of Trump in the mainstream press and by pillars of the Republican Party didn’t matter to Trump. His team knew that the more Republican voters got to see of Trump the politician, the more they would like him.

They knew because they’d studied the polls.

When Trump first surged to the top of the Republican pack just weeks after his announcement, pundits pointed to Trump’s terrible favorability numbers to argue that his support had a hard ceiling and that other candidates would overtake him when the sprawling 17-member Republican field thinned. Indeed, Trump walked into the contest with a poll showing only 16 percent of Republicans viewed him favorably while 65 percent viewed him unfavorably.

But when Trump touched off controversy, his favorability skyrocketed, and by mid-July that same ABC/Washington Post poll found that 57 percent of Republicans viewed him favorably.

If you don’t have the same risk tolerance, he’s got you beat before you’re even in the game.”

It was an unprecedented jump. “I’ve never seen a candidate who’s so well-known who was able to suddenly turn around people’s opinions of him,” Monmouth University’s director of polling, Patrick Murray, told Politico last summer.

Pollsters were dumbfounded. Trump wasn’t. He had been testing his ability to turn his favorability numbers around for four months already. His team studied a PPP poll from February 2014 that showed Trump’s favorability rating 21 points underwater with Iowa Republicans. But by April, as he made appearances and courted local politicians while testing the waters ahead of a formal announcement, he had pulled even.

Trump’s team, said one insider, knew that “once you approached the national media it would work that way as well.”

And it has.

Not apologizing has only bolstered a candidate who appeals to voters fed up with political correctness and establishment niceties. Many of Trump’s most controversial statements and proposals, in fact, have been validated by the polls. And just as significant as the media oxygen they’ve sucked up, Trump’s most outrageous comments have baited his opponents into reactions he has strategically exploited.

It was, for instance, Trump saying that Hillary Clinton got “schlonged” in losing the 2008 Democratic primary and his calling her “disgusting” for using the bathroom during a debate that prompted her to call out his “sexism.” That, in turn, is what he cited as his reason for focusing again on Bill Clinton’s sex scandals, which he claimed are “fair game” because Hillary was attacking him.

His proposed ban on Muslim immigrants after the ISIL-coordinated attacks in Paris and San Bernardino drew condemnation from many of his rivals and top Republican leaders in Washington for going “too far” and being antithetical to “American values.” But for many primary voters suddenly fearful of the real possibility of more terrorist attacks on American soil, it was those other candidates who didn’t seem willing to go far enough to keep them safe.

“Most campaigns aren’t so secure as to make such declarative statements or shrewd enough to understand where it’s going to go,” said an operative close to the Trump campaign. “If you don’t have the same risk tolerance, he’s got you beat before you’re even in the game because you’re not willing to risk the way he is. These other guys—they have a lot more to lose than he does. They’re afraid to take the stands he does.”

“No one is going to out-Trump Trump,” this insider said.

Trump has been confident of that much all along.

Asked by Politico in July whether he thought Hillary Clinton or Jeb Bush would be a worse president, the mogul paused in the back seat of his black SUV at the Texas-Mexico border and said only, “Trump will be the best president.”

This article has been updated.