Photograph by Pari Dukovic for TIME

‘My Whole Life Is a Bet.’ Inside President Trump’s Gamble on an Untested Re-Election Strategy

June 20, 2019

‘My whole life is a bet,’ the President of the United States says, resting his forearms on the edge of the Resolute desk in the Oval Office.

It’s a steamy evening in mid-June, and Trump is facing a set of high-stakes tests around the world. Tensions rising with Iran. Tariffs imposed by India. Protesters flooding the streets of Hong Kong. But Trump is confident, ready to joust. He has invited a group of TIME journalists for an interview, blown past the allotted time and settled in for a wide-ranging discussion. Along the way, he orders a Diet Coke with ice with the push of a small red button set into a wooden box on the desk, and directs an aide to fetch a copy of a hand-delivered birthday letter sent from Kim Jong Un.

Politics is rarely out of mind for any man who wills his way into this rarefied sanctum. Especially not one who calls his campaign manager on many days by 7 a.m., and certainly not now, the day before Trump formally kicks off his 2020 re-election bid. So it doesn’t take much prodding for the President, a former casino magnate, to start making book on the sprawling field of Democratic challengers.

A “progressive” will probably win the primary, Trump predicts, running down the competition with evident relish. Joe Biden “is not the same Biden,” he says, adding later, “Where’s the magic?” Kamala Harris, he notes, “has not surged.” Bernie Sanders is “going in the wrong direction.” Elizabeth Warren’s “doing pretty well,” he allows, but Pete Buttigieg “never” had a chance.

Why? “I just don’t feel it,” Trump says. “Politics is all instinct.”

Trump in the Oval Office on June 17.
Pari Dukovic for TIME

Once again, Trump is putting his own instincts at the center of his campaign. The political mercenaries who tried to discipline his impulses in 2016 have been shown the door. The 2020 campaign is unmistakably Trump’s show. “We all have our meetings,” the President says. “But I generally do my own thing.” Campaign staff have been hired to follow Trump’s lead, and the President has made it known that when he tweets a new policy or improvises an attack at a rally, everyone had better be ready to follow along. “He blows the hole and everyone runs into the breach,” says an aide.

Gone is the rickety operation that eked out an upset victory over Hillary Clinton. In its place, advisers boast, is a state-of-the-art campaign befitting an incumbent President. Trump’s campaign is gearing up to spend $1 billion, and may well get there. His team has spent more money, earlier in the campaign, than any re-election bid in recent history. Campaign staff sit in slick offices in a glass-skinned tower overlooking the Potomac River in Arlington, Va. And Trump has won total control of the Republican National Committee, which fought against him for much of 2016.

Despite the trappings of convention, however, Trump has for the most part thrown out the playbook for incumbency. The last three two-term Presidents were lifted in important ways by a bipartisan message. Bill Clinton ran on the 1994 crime bill and tax reform. George W. Bush ran on keeping America safe in the wake of 9/11. Barack Obama reminded voters that Osama bin Laden was dead and General Motors was alive.

Trump, who lost the popular vote in 2016 and is the only President in the history of Gallup polling never to crack 50% approval, says he’s ready to defy that legacy. “I think my base is so strong, I’m not sure that I have to do that,” he tells TIME, after being asked whether he should reach out to swing voters. The mantra of Trump 2020 is “turnout, turnout, turnout,” as campaign manager Brad Parscale puts it. “People all think you have to change people’s minds. You have to get people to show up that believe in you.”

Insiders know it’s a tough path. In 2016, Trump flipped three Democratic bastions—Michigan, Pennsylvania and Wisconsin—by a combined 79,646 votes, capitalizing on Hillary Clinton’s liabilities and energizing disaffected voters. Trump drew an “inside straight,” says his 2016 campaign chief executive Steve Bannon. He can’t count on that luck in 2020. “You have to get every f-cking deplorable,” Bannon says, using his own Clinton-inspired term for Trump’s ardent supporters. “Everybody’s got to show up.”

The key is making Trump’s instinct for America’s sore spots the engine of a political machine designed to inflame supporters. At its core, his campaign is a kind of a perpetual outrage machine. It uses algorithms—automated settings on Internet platforms like Google and Facebook—to place massive digital ad buys anytime Trump creates a firestorm. The cycle is simple: Trump says something controversial or offensive; that drives a surge of search interest in the topic; and that gives his campaign an opening to serve up online ads. The ads encourage supporters to text the campaign, take single-question campaign-generated polls, and buy Trump hats, yard signs, beer coolers and WITCH HUNT decals from the campaign online store, all of which rakes in voter contact data.

Never before has an incumbent President run a campaign this way. “It is a strategy built for the new partisan era,” says Princeton University presidential historian Julian Zelizer. “Candidates are always doing things to turn out their supporters. What has not been tested, at least in modern times, is a strategy in which all the rhetoric and all the policy is just tailored around the turnout crowd and there is no effort to go beyond it.”

Which brings us to the wager on which the gambler has staked a second term. Trump has already smashed the norms of American politics, remade the Republican Party into his cheering gallery and taken the national news cycle hostage. Can he win a second term on the basis that’s he’s governed in the first, by playing to his base?

Nowhere has the machine adapted to the President as it has in the Oval Office. Over the course of TIME’s 57-minute interview, the case for Trump’s re-election unspools through a series of set-piece requests made to his assistants. Pressed over his commitment to get the U.S. out of foreign wars, he has a ready reply. “We defeated ISIS,” he says. “Maybe you could ask somebody to bring me those maps,” he adds, speaking to one of his staff. Soon enough, an aide brings in three printed sheets showing the Islamic State–held territory in Syria shrinking to zero.

A coffee station at the Republican National Committee Annex in Arlington, Va., which also houses Trump campaign staff.
David Williams—Redux for TIME
Supporters gather in Orlando for Trump’s campaign kickoff.
David Williams—Redux for TIME

When asked whether the latest attacks against oil tankers near the Strait of Hormuz, which U.S. officials blame on Iran, threaten to draw America toward a new, dangerous intervention in the Middle East, he requests favorable data once more. “Do me a favor, will you get the information I had yesterday?” he says to an aide in the next room. “The companies, the countries that benefit from the strait? I want to show you something. China gets 60% of their oil there. Japan gets 25% of their oil. We get very little.”

Of course, ISIS continues to launch attacks. “We’ve taken back the caliphate,” Trump says. “That doesn’t mean one of the crazies doesn’t walk into a store all bombed up.” And it’s not impossible to imagine the world economy or the Middle East descending into chaos if Trump fulfills his wish “to get out” of the region. Even as he downplays Iran’s alleged attack as “very minor,” his outgoing Acting Secretary of Defense announced a deployment of 1,000 more U.S. troops to the Gulf to bolster U.S. installations against what the Pentagon calls an escalation of threats from Iran.

The core of Trump’s pitch — to voters as well as visiting journalists—is that there’s been great progress around the world on his watch. The collapse of Chinese trade talks — and a mounting tariff fight that the Oxford Economics research firm says will shave 0.3% off GDP in 2020 and potentially cost the economy $62 billion in lost output over the next year—is not a failure, it’s a success, he claims. “I give them a lot of credit, but we’ve helped create China. You look at what’s happened over the last period of time, and China wants to make a deal,” he says. “I’m very happy now collecting 25% on $250 billion, which is what we’re doing.” Few trade experts see Trump gaining the upper hand in his tariff battle, but in his telling, multiple countries are looking to make deals with the U.S., thanks to his unconventional approach. He lists some, only off the record, again calling for a document that provides rather weak support.

Campaign manager Brad Parscale has designed an operation that’s responsive to Trump’s impulses.
David Williams—Redux for TIME

Eventually, Trump just cuts to the chase. “Look, I think I’ve done so much—could you bring me the list of things, please, give me four of them,” he shouts through the door. “I’ve done more in 2½ years than any President in the history of this country.” Three printed pages with 72 bullet points emerge: Economic growth is up, and unemployment has stayed at or below 4% for 15 months. He signed tax cuts into law, opened up Alaska’s Arctic National Wildlife Refuge to oil drilling, recognized Jerusalem as the capital of Israel, canceled the Clean Power Plan, withdrew from the Iran deal and the Paris Agreement, issued an order to make a space force the sixth branch of the military. He’s aggrieved by the perception that he doesn’t get credit for what he’s done.

The Oval Office isn’t the natural venue for Trump’s brand of politics. Campaigning is where he really feels at home. So Trump has merged the two to an unprecedented degree — filing for re-election on the first day of his presidency, naming a 2020 campaign manager just a year into his first term and banking at least $100 million for the effort so far. In June, an independent government agency found that senior White House adviser Kelly-anne Conway had violated a law prohibiting federal employees from engaging in partisan politics by repeatedly slamming Trump’s 2020 opponents in media interviews and on Twitter. (“Let me know when the jail sentence starts,” Conway scoffed in May.) Even as Trump sat with TIME, his Administration was tossing red meat out the back of the campaign wagon in the form of a pledge to deport “millions of illegal aliens” in the country.

The nerve center of the re-election bid isn’t Trump Tower, where campaign mail arrives and Eric and Lara Trump have studios for television hits, or even the Arlington office tower. The node closest to Trump’s brain is a narrow room with a single window two doors down the hall from the Oval, where Jared Kushner sits. The President’s son-in-law, a former real estate developer and onetime moderate Democrat, began pitching in with policy research on trade and taxes back in 2015, then took a behind-the-scenes leadership role that November after he saw Trump ignite a crowd in Springfield, Ill. By the end of the campaign, he had emerged as a kind of shadow campaign manager, guiding Trump where possible and reassuring worried Republicans on all fronts. He’s playing a similar role this time around, as an architect of the campaign and troubleshooter, talking nearly every day with Eric Trump, Republican National Committee chair Ronna McDaniel and Parscale.

Supporters attend a Trump rally held to announce his candidacy for a second presidential term, in Orlando.
David Williams—Redux for TIME

One of Kushner’s main projects has been populating the leadership ranks of the Republican Party with Trump loyalists. In February 2018, he and Eric Trump installed as head of the re-election effort Parscale, a lanky 43-year-old digital-marketing entrepreneur from San Antonio who engineered Trump’s targeted online-ad blitz in 2016. Parscale has hired about 60 staff and worked with the RNC to create an online fundraising platform, known as WinRed, to compete with ActBlue, the Democratic digital juggernaut. Drawing on his tech-startup background, Parscale is also developing a smartphone app that attempts to “gamify” Trump supporters’ engagement with the campaign by offering prizes. In exchange for getting friends to share their contacts, hosting Trump events in their home or knocking on doors, voters get perks like better rally seats, photos with the President, signed hats and other incentives.

Parscale, a 6 ft. 8 in. former college basketball recruit, sees his role as Trump’s facilitator. “He’s the real campaign manager, the real finance director, the real director of everything,” Parscale says. “My job is to build a team that’s ready to deal with whatever happens.”

More often than not, the President will go off-script, and a campaign official likens Trump’s knack for riling voters to an old night-fishing trick, shining high-power flashlights into the water to draw quarry to the surface. “The United States is a pond. The President is like the lights,” says the official, who requested anonymity to speak candidly. “If he’s not there, there’s no light, fish are deep, I need a really big lure, it’s expensive.” But, the adviser continues, when Trump lights things up with an issue like immigration or trade, it becomes easy to draw prospective voters out.

A rally in Grand Rapids, Mich., in late March offers a case in point. Trump issued an off-the-cuff threat to “close the damn border” if Mexico didn’t stop two large caravans heading toward the southwest border. The crowd erupted in cheers. Electrified by the response, Trump told aides he wanted to move ahead with a plan to close ports of entry. A series of three tweets were drafted to be released on Trump’s Twitter feed the next morning, announcing that large sections of the border would be closed the following week.

As news stories and web searches spiked, the campaign bought digital ads about immigration. Though the President later backed off the threat, his campaign kept the momentum going by spending $250,000 over the next nine weeks pushing out ads on Facebook and paying for clicks on Google Search. “The content we produce, the advertising we platform, there’s never been anything like it in politics,” Parscale says. “We have our own television show in a way.”

A clothing detail in Orlando for Trump’s campaign kickoff.
David Williams—Redux for TIME

Using such techniques, Parscale has built a list of 35 million voter contacts. The outreach has been churning for more than a year now. When Trump barnstormed Republican strongholds before the midterm elections, officials asked attendees to text wall or Trump to phone numbers plastered on signs and scoreboards inside the arena. Those cell-phone numbers, and other data collected through RSVPs, help the campaign construct a community-level map of energized supporters and prospective volunteers—a cohort they call “the Army of Trump.”

Since 2015, Trump has used rallies to serve up a potent cocktail of tribal resentment and rage. They thrill the President as much as anyone: talking to TIME in the Oval, he boasted of 120,000 people requesting tickets to his official re-election kickoff on June 18 in an Orlando arena. “This is the size of Madison Square Garden. I think it’s slightly larger,” he says. “It’s where the Orlando Magic plays. It is packed. We’ll have thousands and thousands of people outside.”

The familiar slogan has been updated—Make America Great Again has become Keep America Great—but the tone of the show has not. Trump promised in Orlando to build a wall to keep out dangerous “aliens” and called the Democrats’ immigration policies “the greatest betrayal of the American middle class and, frankly, American life.” The swamp in Washington still needs draining, according to the President, even though it’s now his bog. The crowd’s enthusiasm waned when he talked about his achievements, but it broke out in raucous calls to “lock up” Hillary Clinton when he mentioned her name. “Our radical Democrat opponents are driven by hatred, prejudice and rage,” he said in Orlando, pointing to House efforts to investigate his 2016 campaign’s ties to Russia and possible obstruction of justice by the President. “They want to destroy you, and they want to destroy our country as we know it.”

Jim Messina, who ran President Obama’s 2012 re-election campaign, says this approach helps Trump dominate the national conversation on issues, like immigration, that motivate his base. Democratic strategists worry that the Trump campaign will have the chance to spend tens of millions of dollars building a campaign in the field and defining his opponents for months, all while the Democrats are mired in a long and brutal primary battle.

What mystifies many is that Trump, a lifelong pitchman, has never bothered to sell himself to the broader public. “The thing they are not doing, which I think is really odd, is doing any sort of general-election messaging,” Messina says. “By this point [in the 2012 election], we were in the Midwest trying to tell the economic-recovery story, which you would kind of expect them to be doing right now. Instead every single thing they’re doing is about the base.” The problem with that, he adds, is the nation — including the battleground states that will decide the election — is growing more diverse every year, which sharpens Trump’s need to expand his coalition. “If you just do a base strategy, then you’re not going to be able to expand to any states,” Messina says. “And I think that is where this election is going.”

Supporters gather in Orlando for Trump’s campaign kickoff.
David Williams—Redux for TIME
A man dressed as Abraham Lincoln.
David Williams—Redux for TIME

There is, of course, a large section of the country, the government and its centers of power that have not bent to Trump’s politics. That can infuriate the President. Halfway through the TIME interview, the subject turns to special counsel Robert Mueller, who survived nearly two years of attacks by Trump and his allies to produce a damning 448-page document enumerating Russia’s efforts to help Trump win in 2016.

Some of the people closest to Trump offered damaging evidence. His former chief of staff, White House counsel, deputy campaign chairman, Deputy National Security Adviser, staff secretary, communications director and others testified under oath, at risk of prison time, to acts by Trump that Mueller said were designed to “influence” and “control” the probe. While Mueller declined to say whether those acts amounted to obstruction of justice, Democrats and at least one Republican say they did. Pressed by TIME about his aides’ testimony, Trump becomes angry. “It’s incredible,” he says. “With all I’ve done, with the tremendous success I’ve had, that TIME magazine writes about me the way they write is a disgrace, O.K.?”

The moment provides a glimpse into why the Trump re-election operation runs on perpetual outrage. Those closest to him know a conventional campaign couldn’t regulate a man who scorns political and ethical norms and is unable to let challenges to his authority pass. He isn’t faking his outrage—about the media, the Mueller report, his opponents—and that anger, whatever its ultimate source, is politically powerful. “Nobody has been treated as unfairly as Donald Trump,” the President says.

That in turn means that Trump’s team may not have much choice in the kind of campaign it runs. “A unique challenge Trump’s campaign will always have is Trump is not tethered to the campaign,” says Robby Mook, who managed Clinton’s 2016 presidential bid. “He is going to go out and do whatever he does every day. So his campaign will have to figure out, strategically and tactically, how to cope with that.” The machine that Kushner and Parscale have built is designed to harness the power of Trump’s grievance message, which resonates with tens of millions of voters. “He’s not pivoting,” Kushner tells TIME. “The President is who he is and doesn’t pretend to be anything else.”

But they also recognize they need to do more. The campaign is knocking on doors in African-American enclaves in Florida and North Carolina to talk up the landmark prison-reform law Trump signed in December 2018. It’s also testing how to pitch Latino voters in New Mexico and Nevada on Trump’s Chinese tariffs. “The No. 1 issue driving Latino voters to like him and support him is his fight against China,” a senior campaign official says, adding that the campaign is working to figure out why that’s an animating issue.

A man, with 'Trump 2020' painted on the sides of his head, attends a Trump rally in Orlando.
David Williams—Redux for TIME
David Williams—Redux for TIME

But cranking the outrage machine for so long may make it hard for voters to hear a subtler frequency. Privately, some Trump advisers say they need to do a better job touting the President’s record, especially on the economy. But can that message break through the pain Trump’s tariffs have caused for many voters? And in the meantime, a large chunk of the campaign budget is still being spent on hot-button topics like immigration. “They are trying to say they are running a normal campaign and doing outreach,” says Messina, who now tracks ad buys for his consulting firm. “It’s all show.”

For the moment, polls show Trump trailing the Democratic front runners in some key states. Trump is being briefed on polling data at least twice a month, and in the past few weeks has been requesting more granular breakdowns, according to a former adviser who speaks to Trump. “He’s aware that he’s not beating any of the major candidates right now one-on-one nationally,” the adviser says. He fired some of his pollsters after internal surveys were leaked showing him trailing Biden.

Trump himself doesn’t seem to know whether he can really beat the odds. Still fuming about Mueller, Trump keeps coming back to the investigation and makes contradictory claims about its effects. “Based on the economy, I should be up 15 or 20 points higher,” he says, but “the thing that I have that nobody’s ever had before, from the day I came down the escalator, I have had a phony witch hunt against me.” Minutes later, he asserts the opposite. The Mueller probe “turned out to be an asset,” he says, “because it’s really energized our base like I’ve never seen before.”

There’s no question Trump has significant advantages as he looks ahead to the re-election fight, beginning with time and money and the biggest megaphone on the planet. In his position, most incumbents would appeal for four more years by pledging to unite the country. Casting this approach aside makes him “historically unusual” for an incumbent President, says Timothy Naftali, former director of the Richard Nixon Presidential Library and Museum. “He basically wants to beat the house, politically, again.” Whether he wins his bet or not, Trump’s campaign will test the power of outrage. —With reporting by Tessa Berenson, Massimo Calabresi, Edward Felsenthal and Abby Vesoulis/Washington

Correction, June 20:

The original version of this story contained a photo caption that misstated the location of Trump’s re-election campaign headquarters. They are in New York City, not Arlington, Va.

Trump officially kicks off his re-election campaign on June 18 at a rally in Orlando’s Amway Center.
David Williams—Redux for TIME

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