Michael Kruse is a senior staff writer for Politico.

Earlier this month, 11 weeks after his inauguration, in the aftermath of bungled attempts at instituting a Muslim travel ban and “repealing and replacing” the Affordable Care Act, and in the midst of sinking approval ratings, steady reports of Russian influence on the outcome of last fall’s election, staff strife in the White House and growing inner-circle alarm that the first 100 days of his administration would be seen as a failure, President Trump sauntered to the rear of Air Force One to make sure the reporters traveling with him had the story straight. “I think,” he told them, “we’ve had one of the most successful 13 weeks in the history of the presidency.”

The following week, in an interview with Fox Business, he doubled down. “I don’t think that there is a presidential period of time in the first 100 days where anyone’s done nearly what we’ve been able to do,” he said.


And last Tuesday, in a speech in Wisconsin, Trump held firm: “No administration has accomplished more in the first 90 days.”

Critics have expressed amazement at this self-assessment. How, wonder people who are even fleetingly familiar with presidential history, can Trump look back at the past three months and seriously say they were the best ever?

To others, though, who have worked with him, have been watching him for decades and know him well, nothing could be more familiar. “I just shake my head,” former Trump casino executive Jack O’Donnell told me the other day, “and I say, ‘Well, that’s Donald Trump.’”

These three statements, 53 words in all, are potent shots of unadulterated, time-tested Trump—short, confident declarations of success, in spite of objective evidence of failure, uttered with total disregard for the parsing and fact-checking that constitutes so much of the coverage of him and his administration. Biographers, ex-employees, veteran New York City gossip columnists, public relations professionals and political operatives from both major parties say recognizing this well-established pattern of behavior—stumble, proclaim victory, move on—is imperative to understanding Trump.

He flopped as an owner of a professional football team, effectively killing not only his own franchise but the league as a whole. He blew up his first marriage, married his mistress, and then divorced her, too. He bankrupted his casinos five times over the course of nearly 20 years. His eponymous airline existed for less than three years and ended up almost a quarter of a billion dollars in debt. And he has slapped his surname on a practically never-ending sequence of duds and scams (Trump Ice bottled water, Trump Vodka, Trump Steaks, Trump magazine, Trump Mortgage, Trump University—for which he settled a class-action fraud lawsuit earlier this year for $25 million). Other risk-taking businessmen might periodically cop to falling short while pivoting to what’s next. Not Trump. He has dealt with his roster of losses largely by refusing to acknowledge them as anything other than wins.

More than a belief in the power of positive thinking or the casual audacity of a tireless salesman, Trump has perfected a narrative style in which he doesn’t merely obscure reality—he tries to change it with pronouncements that act like blaring, garish roadside billboards. Unrelenting in telling his own story, he has defined himself as a success no matter what—by talking the loudest and the longest, and by insisting on having the first word and also the last. And it’s worked. Again and again, throughout his adult life, Trump in essence has managed to succeed without actually succeeding.

This, not his much-crowed-about deal-making prowess, is Trump’s most singular skill, I’ve heard in more than a dozen recent interviews.

“He’s not successful at what he claims to be successful at,” said Tim O’Brien, the author of TrumpNation: The Art of Being the Donald. “He is, however, arguably the most successful self-promoter in United States business and political history. And that’s a form of success.”

“He knows of no other way,” former New York Daily News scribe George Rush said, “and that is to spin until he’s woven some gossamer fabric out of”—he searched for the right word—“garbage.”

Even his admirers, who dispute the notion that Trump has not accomplished important things in this first stage of his first term, grant that his ultimate success will depend in no small measure on his ability to convince people that he has succeeded. “I think by the power of persuasion he’s going to end up getting things done,” said Sam Nunberg, a political adviser early in his campaign who credits Trump with the appointment of Neil Gorsuch to the Supreme Court and a flurry of executive orders that have undone or loosened Barack Obama-implemented policies and regulations. “He certainly could sell ice to an Eskimo—and I mean that as a compliment. He’s the spinner of all spinners.”

And he’s only upped the ante over the past month.

“I don’t lose,” he told the Financial Times.

“It’s been very much misreported that we failed with health care,” he said in the Fox Business interview. “We haven’t failed. We’re negotiating …”

“We will be stronger and bigger and better as a nation than ever before,” he assured parents and their children by way of introducing them to the White House for the Easter Egg Roll. “We’re right on track. You see what’s happening.”

But what’s happening, many think, is that he’s failing, and that his transparent strategy to distract from his manifest lack of preparation is being exposed on this blinding-bright, highest-stakes stage. This is, after all, the hardest job Trump has ever had, and even he occasionally has alluded to that. “Nobody knew that health care could be so complicated,” he memorably said back in February as his reform efforts floundered.

In one significant way, though, Trump’s never had it easier. Attention is his oxygen, and always has been, and for most of his professional existence, especially before the hit debut of The Apprentice in 2004, he had to work for it. Now he doesn’t. He’s the president, which he views (not wrongly) as a kind of proof in and of itself of success. “I can’t be doing so badly,” he explained to a reporter from Time, “because I’m president, and you’re not.” And when he asserts his versions of reality, they come, unlike in the past, with an immense governmental apparatus to back them up and the inherent authority of the office he inhabits. Trump no longer can be ignored. He has to be listened to.

“He creates his own reality,” said Barbara Res, a Trump Organization vice president in the 1980s and ’90s. “He created the reality that he was this big, successful businessman, and now he’s creating the reality that he’s a big, accomplished president.”

“He’s gotten away with this game his whole life,” Florida-based Republican strategist Rick Wilson said.

It worked for him as a businessman, and it worked for him as a presidential candidate—and if it doesn’t work for him in the long run as president as well, it will be a first.



***

Trump has been preparing for this for a long time.

In 1983, in a bid to grow his fame, he bought the New Jersey Generals of the second-tier United States Football League. In three years, he plunged $22 million into the endeavor. Angling for a giant payday or a spot in the National Football League, he spearheaded with Roy Cohn an antitrust lawsuit against the NFL. It was defeated in court. The suit sought $1.69 billion. A jury awarded $3.76. The embarrassing outcome led directly to the demise of the USFL.

“We’re dead,” said the vice president of the team from Memphis, Tennessee.

“We lost,” said a spokesman for the team from Jacksonville, Florida.

No, Trump said. “We expect to win a total victory.”

A judge in an appeals court upheld the initial ruling and pinned blame on Trump. At one point, in what he wrote, he likened decisions made by the owner of the Generals and USFL officials to “suicide.”

Trump was undaunted. In 1990, when $3 billion of debt racked up in a willy-nilly late-’80s spending spree and through over-leveraged Atlantic City casinos caused a financial calamity that coincided with the high-profile implosion of his marriage to the mother of his first three children, he scoffed that any of it would be a setback. The coverage of his divorce, his affair and the negotiations surrounding his prenuptial agreement were making his name “hotter than ever,” he told a reporter from New York.

“The business has never been better,” he said to the Associated Press.

Everything was “running flawlessly,” he added in a story in the New York Times, which appeared under a headline that read, “An Empire at Risk … Debt Forcing Trump to Play for Higher Stakes.”

The Trump Taj Mahal casino filed for bankruptcy in 1991.

The Trump Castle and the Trump Plaza casinos filed for bankruptcy in 1992.

“I’m doing great,” he told the Times in 1993.

And he was right in that it could have been worse. Trump ended up not ever having to file for personal bankruptcy and escaping from his “blip,” as he would come to call his not-quite-Waterloo of the ’90s, because of family money and because the banks had lent him such staggering sums he was effectively too big to fail. The banks let him defer payments and put him on an allowance—of $450,000 a month. Trump then completed his comeback partly by going public with his casinos and shifting restructured debt to shareholders who would rue placing their trust in Trump. Nobody made much money off Trump in Atlantic City other than Trump himself.

“I’m intelligent,” he told a reporter from Fortune in 2000. “Some people would say I’m very, very, very intelligent.”

In 2004, after not quite a decade in which Trump Hotels and Casino Resorts failed to turn an annual profit, not even once, the company filed again for bankruptcy. Shares that had traded at more than $35 in 1996 now were at less than 50 cents. His casinos were $1.8 billion in debt. The business was in shambles. “The business has been great,” Trump told a reporter from the Washington Post.

By this time, these predictable go-to tactics were bolstered by the success of his new reality show, making NBC all but an official PR partner. The network was portraying Trump to tens of millions of viewers in precisely the way he always had wanted to be seen—as one of the country’s premier managers, executives and entrepreneurs. But Trump, as ever, remained his own best, most committed publicist. Bankruptcy, he argued to the AP, is not a bad thing: “I don’t think it’s a failure. It’s a success.”

“You are what you think you are,” he wrote in his book called Think Big in 2007. “Oftentimes,” he added, “perception is more important than fact.”

Trump’s casino company filed for bankruptcy again in 2009.

“I never went bankrupt,” he said on ABC in 2011.

“I’ve done an incredible job,” he told The Atlantic in 2013.

And in 2015, of course, he announced he was running for president. “They all said, a lot of the pundits on television, ‘Well, Donald will never run, and one of the main reasons is he’s private and he’s probably not as successful as everybody thinks,’” he said in his speech at Trump Tower. “So I said to myself, you know, nobody’s ever going to know unless I run, because I’m really proud of my success. I really am.”

***

Can this work? Can Trump succeed even if he doesn’t succeed when he’s not the president of the Trump Organization but the president of the United States of America? In my conversations of late with people who have worked with him, studied him and know him well, opinions varied. Some said sure. Others said maybe. But nobody said no chance.

“Yes,” Trump biographer Gwenda Blair said matter-of-factly when I asked her the question. She’s seen it work too much for too long to dismiss the possibility.

“I can’t think of anything he hasn’t been able to spin into some kind of success,” said Res, the former Trump Organization vice president. “I’ve always said he must have sold his soul to the devil. Because he wins all the time. He always wins. He seems to get away with everything.”

Being the president is, though, so different from anything he’s ever done, many of the people I spoke with maintained, in terms of difficulty, scrutiny and accountability. The rules are different in this arena—or have been.

“Clearly you can campaign, and win, by being P.T. Barnum,” O’Brien said. “That’s because elections have become celebrity contests. But I think governing is different than campaigning.

“And I think the 100 days benchmark does matter for him,” he continued, “because he promised swift action: ‘I will come to the slow-moving, ossified bureaucracy that is Washington, D.C., and—presto—I will make it move quickly.’ Lo and behold, his 100 days have come and passed with no significant legislation. … I don’t know that he can get away with abracadabra for four years.”

“It’s true he has often been able to turn failure into success, or at least claim success,” longtime Democratic strategist Bob Shrum told me. But he stressed that the presidency is not the same: If Trump fails, Shrum said, “it will not be like the collapse of an apartment development in Puerto Vallarta. It’s not 200 people who lose their apartment deposits—it’s 24 million people who lose their health care. It’s not 500 people who lose their casino jobs—it’s millions of people who have been left behind and thought he was going to fix things for them.”

“We’re not even close to how bad it’s going to get,” said Wilson, the GOP strategist from Florida who’s been a vociferous Trump critic. “It’s going to get substantially more difficult to keep selling this crap. He’s not dealing with some random vendors in New Jersey. He’s dealing with the American people. But I will say this: His cult has shown a great willingness to be a cult.”

The degree of difficulty is higher, and so, without a doubt, are the stakes—but Trump has not altered his fundamental approach. He is doing what he’s done best. This is why people are starting to focus on his track record as a seller of success at least as much as an achiever of it. And if anybody can pull this off, if any person can get re-elected as president if the rest of these four years go something like the past three months, say Wilson and many others, it is him.

“It’s the unwillingness to lose,” said Nunberg, the former Trump political adviser. “I would be surprised if he doesn’t end up being very successful.”

In the political sphere specifically, said Tim Miller, who was the communications director for Jeb Bush’s 2016 campaign, “this has been tested at this point for two years, right?” And the upshot is clear: “His voters aren’t going to abandon him in the face of failure, as defined by the political elite, the media and pundits.”

PR professionals, too, seem skeptical that his failure in office necessarily would result in his failure at the ballot box come November 2020. They have been watching him work for decades with a mixture of horror and awe.

“The great lesson of Trump’s career is that what goes around does NOT come around, not even a little,” Eric Dezenhall, the CEO of Dezenhall Resources in Washington and one of the country’s experts in crisis and damage control, wrote to me in an email. “It is wrong to hold him to the same standard as other presidents. The pundit consensus is that if he fails to deliver on jobs and key legislation that he will be punished for it. Wrong. His main mission is to vex the political and media elite, period. It’s essentially a mandate to entertain. If he does that, most of his supporters—and the people who will never admit they are his supporters—will be satisfied for quite some time. If he fails to deliver in other areas, well, that’s the fault of the deep state or some other villain. There is always the possibility that his run at the tables will end at his presidency, but I’m not so sure.”

The question of whether Trump can use his usual M.O. to similar effect in this new, infinitely more important role raises a basic question: Success as defined by whom? Because the truth is there is nothing absolute or agreed upon here. Assessments of presidents aren’t unilateral or fixed. They shift over time, depending on who’s writing them, when and why. And the group that traditionally has the first crack at it, the people who have penned the initial reviews for many of Trump’s 44 predecessors—the press—Trump has spent most of the past two years trying to delegitimize. And with a significant portion of the electorate, it has worked. He’s never waited for others to write his own history, and he’s not waiting now. After saying in his announcement speech two Junes ago that he would “do various things very quickly,” like “repeal and replace the big lie, Obamacare”—“mark my words,” he said—Trump this week denounced on Twitter “the ridiculous standard of the first 100 days.” It “doesn’t matter,” he told reporters.

Eventually, of course, there will be a longer list of campaign pledges kept or not kept, and more and more actual numbers, hard statistics, showing his success or failure on health care and crime and infrastructure improvements and tax reform and wages and jobs and on and on—all of which voters can use to gauge his performance. But will they? And which voters? Because this, too, is part of Trump’s unwavering conviction in his ability to control the narrative.

“I inherited a mess with jobs, despite the statistics, you know, my statistics are even better, but they are not the real statistics because you have millions of people that can’t get a job, OK,” he said in his recent interview with Time, appearing to reference the sustained job growth the country experienced under Obama while simultaneously using this bewildering, punctuation-free sequence of words to shift blame and cloud facts.

His most zealous fans, a base that has polled consistently somewhere south of 40 percent, will believe him, and in him, forever, argued many of the people I talked to. So how many independents and moderates or on-and-off, in-and-out voters, then, can he keep convincing? How many of the people in places like Ohio and Pennsylvania and Michigan and Wisconsin, the people who in the most purely mathematical sense made him the president—how many of them will get the jobs he promised throughout the campaign? Will their lives get measurably better? Will it matter? It’s impossible at this point to say for sure.

Past presidents, including some seen as the best presidents, have conceded failure and expressed contrition when that’s what was called for. “The power of the presidency is often thought to reside within this Oval Office, yet it doesn’t rest here. It rests in you, the American people, and in your trust,” Ronald Reagan said in his 1987 apology for his role in the Iran-Contra affair. “Your trust is what gives a president his powers of leadership.” Watch what Reagan said that night and try to imagine Trump doing the same. Almost everybody I talked to agreed: He will never fail and say so. He is absolutely and unquestionably going to try to do what he’s always done. It’s what’s gotten him here, say the people who know him the best.

O’Donnell, the head-shaking former casino executive, recalled the week in April 1990 in Atlantic City when Trump’s Taj Mahal rushed to open to create cash flow to start servicing the suffocating debt Trump had taken on to make the $1.1-billion project happen. The staff was unprepared and overwhelmed. Machines malfunctioned. Customers fumed. “This is a lot of baloney!” shouted one woman. “We came all the way from East Orange.”

“It was just a disaster,” O’Donnell said. “A monumental failure.”

Trump’s prized casino, which he had billed as “the Eighth Wonder of the World,” would be open for barely more than a year before filing for bankruptcy.

Trump, though, went on CNN in that summer of 1990 and told Larry King it was “doing great” and described it as “a tremendous success.” He explained that the chaotic launch only looked like a failure because it was actually exactly the opposite. So many people were gambling so much money, he insisted, the machines simply couldn’t handle the demand. “They blew apart,” Trump said to King. “They were virtually on fire.”

O’Donnell remembers watching the interview aghast.

“If you or I were sitting there,” he told me, “we would have trouble staring into the camera and lying. He doesn’t.”