Michael Kruse is a senior staff writer for Politico.

The tens of millions of Americans who watched The Apprentice on television have a pretty clear impression of what it’s like to be fired by Donald Trump. He’s seated in a big boardroom at a long table across from the anxious contestants. He’s scowling and stern. He has all the power in the room, and none of the doubt. The verdict drops like an ax. You’re fired.

This, on the other hand, is what it’s actually like: You, Bernard Goupy, have been the head chef for six months at Trump’s Mar-a-Lago Club in Palm Beach, Florida, where you serve a Caesar salad in a fancy bowl made from Parmesan cheese. Then one day, Trump stalks into the kitchen yelling about how one of his guests didn’t like the salad. And he angrily demonstrates the proper way to do it, throwing lettuce and tomatoes in a regular bowl and screaming that this is “how we make a Caesar salad where I come from.”


On TV, it’s hard to talk back to Trump. But in the kitchen at Mar-a-Lago, Goupy can’t resist. “I didn’t know you were the new executive chef,” Goupy tells the boss.

Trump, furious, storms off.

It’s only the next day that Goupy is actually fired—and not by Trump, but by the club’s general manager, who delivers the message that Trump doesn’t want to see Goupy around anymore.

When The Apprentice turned the celebrity real estate developer into a reality television phenomenon, it also brought into American homes an indelible image of Donald J. Trump as the ultimate arbiter. Of Trump as the decider. Of Trump as the boss.

The act of firing somebody is one of the hardest parts of being an executive—knowing who’s right in what role at what time, and who isn’t. The TV Trump made the dismissal of subordinates a personal signature, blending blunt authority with a theatrical version of how a man in charge behaves.

Of course, until this past year, Trump’s style and skills as a boss mattered mainly to his organization’s 22,000 employees and buyers of his 15 books, a mostly schlocky, often contradictory array of business tips and self-help pablum. But now, 12 years after his first televised firing—of somebody named David Gould, for not selling enough lemonade on the streets of New York—his executive style is suddenly a national security issue. Trump the tycoon is seeking to morph into Trump the president, largely on the basis of his record as a businessman.

Based on conversations with people who have worked for him, people who still work for him and a half dozen of his biographers, the reality of Trump as an executive—his methods and his manner—bears little resemblance to the man viewers saw on the show. Rather than magisterial and decisive, Trump the actual boss swings wildly between micromanaging meddler and can’t-be-bothered, broad-brush, big-picture thinker. He is both impulsive and intuitive, for better and for worse. He hires on gut instinct rather than qualifications; he listens to others, but not as much or as often as he listens to himself. He’s loyal—“like, this great loyalty freak,” as he once put it—except when he’s not.

His unpredictability in the boardroom is not a quirk but a hallmark, according to those who’ve worked with him for years. He is on the job around the clock, and expects those on his payroll to be the same way, but also resists a rigid schedule—he is, in other words, an unstructured workaholic. The way he manages his people and properties, too, is a reflection of his abiding conviction in the value of unfettered competition—between his own staffers, between himself and his staffers and vendors and contractors, and ultimately between himself and the rest of the world.

So how would the 26th floor of Trump Tower translate to the West Wing of the White House? How would the chairman of the Trump Organization perform as chairman of the United States of America?

New Window Photo Gallery: Donald Trump’s Entourage (Click to open) | Damon Winter/New York Times/Redux

Over the past year, Trump’s idiosyncratic management style has been sorely tested on the national stage, which came as no surprise to those who’ve watched him closely at his businesses. His tiny campaign team is in many ways a classic Trump operation, veterans of Trump world told me, staffed with fiercely loyal near-novice players handpicked for crucial roles by the man they call Mr. Trump. Just as classically Trump was his response to criticism of the team: He spent months brushing off and ignoring its increasingly embarrassing and well-publicized internal power squabbles. And he resisted repeated calls from inside his campaign—even from his own family members—to fire his fiercely loyal campaign manager Corey Lewandowski, eventually giving in only after his rise in the polls seemed to stall. Even then, sources told Politico, the firing was engineered by his adult children and executed by his son Donald Jr.

Will Trump be able to adapt his eccentric executive style to the demands of this new arena? Will he even try? Throughout his career, according to people who know him, Trump’s ego has grown and his patience has dwindled, intensifying his tendencies toward imperiousness and impetuousness. Some close watchers of his business career see a distinct before and after, between the early Trump and the Trump who made a burst of bad decisions in the late ’80s and early ’90s, fueled by feelings of insatiability and invincibility, that changed both his business and personal lives.

“He went from one kind of person to another,” says Barbara Res, who was his project manager on Trump Tower and later played an important role in the refurbishment of the Plaza Hotel under Trump.

And what might surprise people most about Trump, Res said, is this: “He didn’t like firing people.”

I have never heard him say the words ‘You’re fired’ to anyone. He really doesn’t fire people. He makes it known he doesn’t want you there, and you move on.”

Yes, the man for whom “You’re fired” became such a pop-culture buzzword that he tried in 2004 (and failed) to trademark the phrase doesn’t actually fire many people, she confessed and others confirmed. Trump likes talking about how people are “fired like a dog”—he even used that line on the show—but he often leaves the deed to his deputies.

“I have never heard him say the words ‘You’re fired’ to anyone,” Billy Procida, a vice president for the Trump Organization in the early ’90s, told me. “He really doesn’t fire people. He makes it known he doesn’t want you there, and you move on.”

The Apprentice, people reminded me, was just a TV show.

***

Back in early 2004, before Trump was a potential leader of the free world, his executive philosophy was already coming under attack by management theorists. The Apprentice pitched business as conflict—a cutthroat, zero-sum, winner-take-all scramble. “Life’s a vicious place. No different than a jungle,” Trump explained to USA Today.

This did not sit well with actual business leaders. The co-CEO of Fortune 500 company Golden West Financial called The Apprentice “banal, manipulative, unreal.” The dean of the business school at the University of Tampa knocked what Trump was peddling on the show as “almost a feudal model of leadership.”

“He started screaming about my Caesar salad, and I said, ‘I didn’t know you were the new executive chef.’” —Bernard Goupy, former head chef at Mar-a-Lago “He came in and said, ‘Now I think is a good time to make a change.’ I said, ‘OK.’” —Bruce Nobles, former president of the Trump Shuttle “He went from one kind of person to another. ... We, at the office, didn’t like that at all.” —Barbara Res, Trump Tower project manager “He was hands-on in the sense of knowing what was going on. ... In terms of decision-making, he delegated a great deal to Barbara.” —John Barie, Trump Tower architect “He didn’t have to manage—we managed. ... It was my company that built Trump Tower. All the design decisions were made by me and my associates. Donald talked pretty.” —Artie Nusbaum, a higher-up at the main construction firm for Trump Tower Credit: Allan Tannenbaum/Getty Images; Robert Platzer/Getty Images; Bobby Bank/Getty Images; All others courtesy of subjects

Perhaps the highest-profile critique came from Jeff Sonnenfeld, an associate dean at the Yale School of Management, one of the nation’s top thinkers on corporate leadership. He hated The Apprentice. Sonnenfeld told Newsweek it was “vulgar,” less about business and more like “musical chairs at a Hooters restaurant.” He wrote in the Wall Street Journal that the contestants weren’t set up as teams but rather “circular firing squads—hardly the staffing pattern of an enduring enterprise.” He went on NBC and said the show was “being sold as the secrets of success. It’s not.”

Then one day that spring, in Sonnenfeld’s office in New Haven, Connecticut, the phone rang. The voice on the other end was immediately recognizable.

It was Trump. He wanted to talk.

“He thought that I was misguided and didn’t understand the reality of the way business works and what he was trying to do with the show, and that there were great lessons of leadership in every show,” Sonnenfeld says. He recalls telling Trump that “his lessons of leadership were a pretty dark view of humanity” and “that business isn’t about destroying your competition to succeed.”

Sonnenfeld remembers telling Trump he was being cynical; he remembers Trump telling him he was being “naive.”

Then Trump offered him a job. He was starting something called Trump University, Trump explained—and would Sonnenfeld like to be its president? Sonnenfeld said thanks but no thanks. He was happy with his position at one of the finest institutions of higher education in the world.

Sonnenfeld understood what Trump was trying to do: “He was going to try to drown the squeaky wheel with oil.”

(I contacted Trump’s spokesperson to ask about this incident, Goupy and other details in this story. Trump responded: “Management is an art that is very important to me. Having leadership skills and employees that love their work is one of the great joys of life.”)

Trump then invited him to play golf at his club outside New York. Sonnenfeld doesn’t golf, but his wife does, so he brought her along as well as a colleague, Barry Nalebuff, a professor of management. The three of them had lunch with Trump at an outdoor cafe at the club, and all three … kind of liked him.

“To my horror and amazement,” Sonnenfeld says.

“In person,” Nalebuff told me, “he can be incredibly charming.”

This was not the Trump seen on TV. And the business ideology Trump was promoting on his show—the corporate office as Survivor, as Lord of the Flies—was not the one and only Trump way. He had started differently.

Trump Tower opened in 1983. It was the first building Trump ever built more or less from the ground up. It remains the best building he ever built from the ground up. And people who worked with him at the time draw a picture of a boss who was receptive and open. Res calls him “very smart” and “very, very confident,” a leader who took into account the expertise of others. “He would listen to people,” she says. At least, sort of. Once she found the right combination of “flattering” him and “fighting” with him, “then he would see the light—he did ultimately listen to reason.”

“He had no choice but to trust us,” says John Barie, one of the top architects on the project. “Being new to the design and construction process, he was very much involved.” Barie told me he has fond memories of Trump and his wife at the time, Ivana, and the first of the three children they would have, Donald Jr., coming with a stroller to the job site on Saturday mornings. “He was hands-on in the sense of knowing what was going on,” Barie says. “In terms of decision-making, he delegated a great deal to Barbara.”

At a time when there were almost no women involved in the construction industry, Trump trusted Res to take charge. “He wanted me to be him on the job,” Res wrote in her book, All Alone on the 68th Floor: How One Woman Changed the Face of Construction. “He said I would be like a ‘Donna Trump’ and I would treat everything as if it were my project.”

The completion of Trump Tower also marked a new role for Trump himself—and created a new stage set for his ambitions. His father had never moved out of his drab Brooklyn office with fluorescent lights, aging cabinets and walls decorated with certificates and plaques. Donald, on the other hand, positioned himself high in the marble-and-glass environment of Trump Tower, behind an oversize desk in a suite with tall, wide windows and a lordly view of Manhattan.

On his walls, he hung magazines, slipped into gold frames, showing his face on the cover. Trump was the boss. And patterns began to show up.

***

One of them was his approach to hiring, a topic of obsessive interest to corporate leaders. Trump had his own views on this. “When I hire people,” Trump once told gossip columnist Liz Smith, “I interview them for 20 minutes, or 10 minutes, or three minutes, and I hire them.”

First impressions counted most. Trump had spotted Matthew Calamari at the 1981 U.S. Open tennis tournament when Calamari, a security guard, tackled a pair of heckling troublemakers. Trump loved it and offered him a job. Calamari started as a bodyguard. Today, he’s the Trump Organization’s chief operating officer.

“When Mr. Trump hired me he told me what he expected and that I would report directly to him,” Calamari wrote to me in an email. “I have never had to go from person to person to find out what my job was or communicate how I planned to handle any situation. He has excellent instincts when it comes to people, something I’ve noticed over the years. He has said that every hire is a bit of a chance, that people with great credentials may not work out whereas those with lesser credentials often prove themselves to have great merit.”

Offering a lot of opportunity to people with not a lot of experience earned Trump loyalty in return. “If you’re looking for someone to slam or slander Trump, you have the wrong guy,” Procida says when I call him. Procida never went to college, started his career as a builder of a small housing project in the Bronx and wrote fan letters to Trump—who hired him and made him a vice president.

“He gave me an opportunity as a 26-year-old to take on a very significant role,” Procida says, and “after working for him for that year, my career catapulted. … He let a 26-year-old uneducated kid go to Europe and Hong Kong and represent him. How ballsy is that?”

As Trump’s organization grew, his interests expanded beyond Manhattan real estate. In 1983, he bought the New Jersey Generals of the United States Football League. In 1984, he opened his first Atlantic City casino. In 1985, he opened his second. The executive Mr. Trump had more and more staff to manage. But the Trump Organization never became a corporate structure in the traditional sense, with standard protocols or an accepted org chart any more complicated than Trump and everybody else. The Trump Organization, including the roster of subsidiary clubs, golf courses and licensing vehicles, last year had 22,450 employees, according to PrivCo. But key staffers on the 26th floor number around only a dozen—“a teeny operation,” author Tim O’Brien wrote in TrumpNation, “that catered to Donald’s zealousness and preference for quick decisions.”

He kept his door open, so people could come to him with ideas, as long as they made it quick, but also so that they could hear him when he wanted to be heard, which was almost always.

He didn’t dial office-to-office extensions. He didn’t use an intercom. He just yelled, for what he wanted and from whom.

His inner circle was loyal. Blanche Sprague, one of his key former executives, told me, “I don’t have any hatchety things to say—and I’m anything but a backside-kisser. I’m not that way. I say what I think.” She called Trump “very empathetic” and “one of the kindest, most considerate people in the world.”

George Ross, a former legal adviser for Trump and an executive vice president for his organization, told me Trump gives members of his staff “freedom of decision” and always “the ability to get his ear.”

“That’s why people work for him for decades,” Ross says. The list of long-timers includes people like Calamari; Norma Foerderer, his personal assistant, who died in 2013; Rhona Graff, his secretary, who declined an interview request; and Andy Weiss, an executive vice president, who also would not talk for this article. Now his three children from his first marriage work for him, too—Donald Trump Jr., Ivanka Trump and Eric Trump, who graduated from Penn, Penn and Georgetown, respectively, all with undergraduate degrees, like their father, not an MBA among them.

He motivated with praise, pay and fear—titles, too, calling deputies “executive vice presidents,” giving them an air of autonomy and authority. “The title,” Ross told me, “enables them to do things they wouldn’t be able to do without the title.” But any Trump Organization flow chart has just one person in charge.

“There was no formal business plan, no development strategy,” Gwenda Blair wrote in her book, The Trumps. “Instead Donald would come up with ideas, do the preliminary calculations in his head, then tell someone to get moving on it.”

“He says, ‘Go do it’—that’s the end of it,” Ross says.

“Or there’s hell to pay,” Procida says.

Illustration by C.J. Burton for Politico Magazine

The demands and the loyalty went hand-in-hand. Loyalty to vendors and contractors, on the other hand, even top-line partners, was a different matter. Artie Nusbaum, a higher-up at HRH Construction, the firm that coordinated the bulk of the work on Trump Tower, was reluctant in a recent interview to give Trump too much of the credit for his management of that career-making effort.

“He didn’t have to manage—we managed,” Nusbaum told me. “It was my company that built Trump Tower. All the design decisions were made by me and my associates. Donald talked pretty.”

In 1986, he says, Nusbaum joined with Trump to fix up Wollman Rink in Central Park, a simple job that Trump pitched as a publicity ploy.

“He said to me, ‘Artie, you’re going to get so much publicity out of this,’” Nusbaum said. “It’ll be the best thing that ever happened to you.” The rink rehab, which Nusbaum agreed to do at cost, generated headlines—for Trump. He didn’t talk about his partners, Nusbaum says. “There was no room on the hill for the two of us. He wanted to be king of the hill.”

It was the last time Nusbaum worked for Trump, he says.

They talked about an apartment building. “He said, ‘$30 million.’ I said, ‘$40 million.’ He said, ‘Goodbye,’” Nusbaum told me. “That is not negotiating. … A good negotiator negotiates. If you want to sleep with a woman, talk nice to her. You don’t say, ‘Hey, bitch, get in the bed.’”

Nusbaum concluded Trump was no longer the same guy he had been in the Trump Tower days.

“He thought he could do no wrong.”

***

On TV, as the centerpiece of The Apprentice, Trump’s firings were dramatic and sudden. Not so in real life.

In 1990, Bruce Nobles was president of the Trump Shuttle, which Trump had bought from Eastern Airlines and then renamed. “I went to him in the spring of 1990,” Nobles told me, “and said I thought I should leave.”

The economy was sinking, and so was his airline, beset with the hundreds of millions of dollars of debt Trump had taken on to buy it. Nobles had had it. “He and I had reached a point,” he says, “where we weren’t communicating very well.”

Trump wouldn’t let him go. “So I agreed to stay for a while,” Nobles says. For Nobles, when the firing finally came, it wasn’t a lambasting. It was a relief.

“In June, he came in and said, ‘Now I think is a good time to make a change.’ I said, ‘OK.’”

This parting of ways was a consequence of a stretch in Trump’s life in which his appetite overrode caution, and the executive instincts he considered so critical began to lead him astray. In 1988, basking in the success of Trump Tower, which made him a big deal in New York, and also the The Art of the Deal, which made him a big deal all over America, Trump was flaunting the new 281-foot yacht he called the Trump Princess. He bought the shuttle. He bought New York’s Plaza Hotel. He took control of a third casino in Atlantic City. He made the deals over the objections of his top financial advisers.

A lot of people observed a change in Trump during that period. “I think he’s had two very different management styles,” Wayne Barrett, the author of Trump: The Deals and the Downfall, told me. “Early in his career, I think he had a highly successful management style. He had key people around him who weren’t just sycophants. He had people, highly accomplished professionals, who worked with him on intricate details of projects.”



“He knows who to put in the game, when to put ’em in the game, who to give the ball to. … That’s what it takes to be a CEO, and he’s a very good one.” —Billy Procida, a former vice president for the Trump Organization

“I know Donald very well, and I believe if I was on a plane with him ... and if that plane started to go down, he’d figure out in five minutes how to fly it.” —Blanche Sprague, former Trump executive

“He has the ability to delegate authority to people he has full faith in and let them run with the ball. ... It would transfer beautifully [to the Oval Office].” —George Ross, Trump Organization executive vice president

“He has said that every hire is a bit of a chance, that people with great credentials may not work out whereas those with lesser credentials often prove themselves to have great merit.” —Matthew Calamari, chief operating officer of the Trump Organization

“He’s one of the best managers there is, in his own unique way.” —Sam Nunberg, former political adviser to Trump Credit: Allan Tannenbaum/Getty Images; Robert Platzer/Getty Images; Bobby Bank/Getty Images; All others courtesy of subjects

But by this point in his career, Trump had his wife, Ivana, running his Castle Casino Resort—never mind her lack of qualifications or experience running a casino. Then he brought her back to New York to run the Plaza Hotel. Res worked on the Plaza renovation with them, but working for Trump now was different than it had been on Trump Tower. She described an instance in which he had approved some marble because of its lower cost—but then erupted when he actually saw it.

“Donald took one look at this marble and started screaming at me,” Res wrote in her book. “He was shaking. ‘You did this,’ he said. ‘You bought this cheap shit and now you are making me look like a jerk. You’re no fucking good.’ I said, ‘Look, Donald, this is the marble you approved. It was cheap, you wanted to save money. Don’t blame me.’ It was like pouring gasoline on a fire. His face was red. His mouth was all twisted, and I thought to myself, ‘If he hits you, just take a fall.’”

Behind the business changes were personal ones. Trump had gone from being “a family man” to being “a ladies’ man,” Res told me. “We, at the office, didn’t like that at all,” she says. “It took him from being serious to not being serious.”

No episode better revealed Trump’s shift from a manager who depended on wise counsel to one convinced of his own infallibility than what happened in Atlantic City. After a helicopter crash killed three of his top casino executives, Trump had an idea, according to Jack O’Donnell, an executive at the Trump Plaza casino who wrote a book called Trumped!. Trump wanted O’Donnell to make one of the secretaries of one of the executives who had been killed an executive vice president.

“Jack, listen to me,” Trump told him, he wrote in the book. “I do this with people. I take people with no background and I put them in a position, and they perform for me. … I just know it. I have feelings when it comes to people. She can do this.” O’Donnell did not promote the secretary.

The first week of April 1990, the much-anticipated launch of the Taj Mahal went horribly—delays, malfunctioning slot machines, disgruntled customers. Trump biographer Harry Hurt, the author of Lost Tycoon, told me Trump “always takes virtually sole credit for anything good that happens and blames anything bad on ‘losers.’”

In this case, Trump went on CNN with Larry King to attempt to explain what he thought had gone wrong during the run-up to the opening of the Taj Mahal.

“I listened to other people,” he said. “I decided to listen to other people for the first time in my life.”

But in fact he hadn’t started listening. He had stopped.

***

The Taj Mahal filed for Chapter 11 bankruptcy protection in 1991. The Trump Plaza Casino filed for Chapter 11 bankruptcy protection in 1992. Trump spent the rest of the decade changing the nature of his business. Less building and buying. More branding and boasting. He talked about running for president. He wrote a book called The America We Deserve. He remained well known, and people kept talking about his hair, but his fame had plateaued.

Until 2004.

“Do you believe this?” Trump said to Larry King on CNN on February 27 of that year. He was a star.

“Donald, Donald …”

“Can you believe what’s happened?”

“What …?”

“I go into the boardroom, I rant and rave like a lunatic to these kids, and I leave and I go off and build my buildings. And then it gets good ratings, and they pay me,” Trump said. “I mean, can you believe this?”

He was on the cover of Newsweek. “The World According to Trump,” the headline read. “Just a decade ago, he was a punch line, a combed-over relic from the decade of greed. But he’s back, and bigger than ever …”

In The Apprentice, Trump now had a prime-time showcase. In a shark-tank setup, contestants had to scramble doing tasks like trying to sell stuff for the highest profit at a flea market, restoring and renting apartments, pulling rickshaw shifts and persuading people to buy Trump’s new “Trump Ice” bottled water—all leading to one winner at the end, who would be rewarded with a $250,000 job working for a year for Trump.

“Good lessons of leadership were violated in the show,” says Sonnenfeld. “Each show was more horrible than the week before.”

“The Apprentice was great entertainment and lousy leadership,” says Dave Ulrich, a business professor at the University of Michigan and a leadership expert who has written 23 books. “Relishing ‘firing’ 19 people to hire one is awful leadership.”

The show, however, cemented Trump’s nationwide image as a man in charge—and in classic Trump style, that image was ascending precisely as his actual casino company was collapsing. The last week of March, auditors at Ernst & Young warned investors in Trump Hotels & Casino Resorts of their “substantial doubt about the Company’s ability to continue.” The publicly traded company, operating Trump’s three Atlantic City casinos, was $1.8 billion in debt. In August, it would announce plans to file for Chapter 11 bankruptcy protection, the third time for Trump; shares, valued at $35.50 eight years earlier, traded at less than 40 cents.

To the public, it didn’t matter. In the middle of April, 28 million people watched the finale of the first season of The Apprentice—16 contestants scrambling to earn Trump’s favor to land a job in Trump Tower.

In 2004, Trump put out three books: How to Get Rich; The Way to the Top; and Think Like a Billionaire. Not everything in them was standard executive coaching.

“Find a receptionist who can speak English,” he told readers in How to Get Rich. “We had a breathtaking European beauty out front who could easily rival Ingrid Bergman in her heyday, but I discovered that her ability to recognize well-known people in the United States was limited to myself and maybe President Bush. … But you should have seen her. What a knockout.”

“Treat each decision like a lover,” he said in Think Like a Billionaire. “Sometimes you’ll think with your head. Other times you’ll think with other parts of your body, and that’s good. Some of the best business decisions are made out of passion.”

In How to Get Rich, he wrote: “A visitor in my office once mentioned that the goings-on there reminded him of a family fight in progress. I will admit that the volume level gets high now and then, and he wasn’t far off in his assessment. But if you want smooth sailing every day, move to the Mediterranean.”

In Think Like a Billionaire, he cited a book titled The Productive Narcissist, which “makes a convincing argument,” Trump wrote, “that narcissism can be a useful quality if you’re trying to start a business. A narcissist does not hear the naysayers. At the Trump Organization, I listen to people, but my vision is my vision.”

And in How to Get Rich, he wrote a whole section called “The Donald J. Trump School of Business and Management.”

“Good people equals good management and good management equals good people.”

“Surround yourself with people you can trust.”

“Remember that your organization is your organization.”

About firing, he wrote next to nothing.

***

Nobody like Trump has run for president before—certainly not for the nomination of a major party, and not so successfully. Late last summer, a little more than two months into his campaign, Trump was asked by a reporter from Bloomberg Businessweek to name a leader he looks to for advice on how to manage his company. “Me,” he said. Asked this past March on MSNBC to name some people he talks to for foreign policy counsel, his answer was the same. “I’m speaking with myself,” he said.

In politics as in business, Donald Trump’s most important strategist has turned out to be … Donald Trump. “I’m the strategist,” he told New York magazine in April.

His energy, intelligence and instincts have gotten him further than anybody could have imagined when he got into the race in June 2015. But many of his other managerial calling cards—his impulsiveness, his affinity for broad-brush thinking over nitty-gritty policies, his preference for a small staff, his taste for internal competition and a kind of creative chaos, his reflexive reliance on blind loyalists instead of more disciplined surrogates, his reluctance to cede control, things that are all there in the history of his corporate ups and downs—have started to undermine his run.

With less than a month before the convention, he still had a skeletal campaign, with numbers unheard of these days for a major national bid: 70 employees to the Clinton campaign’s more than 700. Relative to his opponent’s operation, his fundraising, his advertising and his ground game lagged exponentially behind. His thoughts on the sort of sophisticated data work necessary to get out the vote bordered on open disdain.

For more than a year, the Trump campaign has run much the way the Trump Organization has run for roughly four decades, relying on a handful of trusted loyalists, often without obvious qualifications—like press secretary Hope Hicks, a former model and public relations hand with no prior experience in politics; like Katrina Pierson, his cable-ubiquitous national spokeswoman, a Tea Party activist from Texas; and like Lewandowski, whose previous experience as a campaign manager consisted of a long-ago and failed reelection effort for a U.S. senator from New Hampshire.

When Hicks accidentally sent a Politico reporter an email thread revealing the campaign’s intention to bring up Clinton’s Whitewater history, Trump didn’t fire her. When Pierson defended a controversial tweet of hers from 2012 (“… Obama’s dad born in Africa, Mitt Romney’s dad born in Mexico. Any pure breeds left?”) by telling CNN, “I myself am a half-breed,” Trump didn’t fire her.

And after Lewandowski was charged with misdemeanor simple battery for pulling a reporter away from Trump—charges that were later dropped—Trump didn’t fire him either. “I don’t discard people,” he told reporters on his plane. “I stay with people.”

Until late June, that is. With his showings in national polls against Hillary Clinton slipping, and with bad news cycles reaching an alarming level, he listened to the urging of his children and fired Lewandowski. Or at least had someone do it for him. It was shades of Bruce Nobles of the Trump Shuttle: Lewandowski told CNN his firing was a “nice conversation.” And Trump himself, uncharacteristically silent after the news broke, emerged late in the day to pronounce Lewandowski “a good man.” “We’ve had great success,” the boss allowed.

This is a guy who’s spent his entire career operating by the seat of his pants. If it involves bureaucracy, putting teams together and effectively negotiating with large numbers of people, he’s not good at it. He’s bad at it.”

In some ways, Trump’s executive style reflects that of some successful presidents. Bill Clinton was charismatic and freewheeling, armed with innate abilities to win a room and be charming and disarming one-on-one. Franklin D. Roosevelt, considered one of the most effective presidents ever, often pitted aides against each other—“getting advisers to argue with each other, and then they’d have to come to him,” as presidential historian Robert Dallek describes it.

But unlike them, Trump arrived in politics with a management approach built entirely outside the demands of public life. The tight structure of the 26th floor at Trump Tower, where Trump’s lieutenants are all always just a shout away, may have suited his personal taste and his deal-centric business. But this model has seemed increasingly ill-suited for a modern presidential campaign. Until late March, when Trump hired GOP campaign veteran Paul Manafort—at the insistence again of his children—no one on his staff had the slightest experience with growing an operation like that virtually overnight. Manafort was the kind of expert that Trump once listened to when he knew he was out of his depth. But Trump initially rejected Manafort’s counsel in favor of Lewandowski, the crew-cut former state police officer who called him “Sir” and “Mr. Trump” even outside his earshot. Lewandowski’s ouster was a victory for Manafort’s faction, but it served only as a reminder that something about the way Trump runs his small shop had created the problem in the first place.

Back in 1989, Nobles, the president of the Trump Shuttle, talked to Newsday about working for Trump. “It surprised me as to how much of a family type operation it was, instead of a business kind of orientation where there is a structure and there is a chain of command and there is a delegation of authority and responsibility,” he said. “As the organization gets bigger, and it seems to be getting bigger all the time, he’ll have to do a better job of actually managing the place as opposed to making deals.”

O’Brien, the biographer, says that never happened, even as the Trump Organization grew and changed. “This is a guy who’s spent his entire career operating by the seat of his pants,” he told me. “If it involves bureaucracy, putting teams together and effectively negotiating with large numbers of people, he’s not good at it,” he has concluded. “He’s bad at it.”

There’s another view, of course, and it comes from his loyalists.

“He has the ability to delegate authority to people he has full faith in and let them run with the ball,” Ross insists. “It would transfer beautifully” to the Oval Office.

At least in this way, Trump has a certain hint of the presidential: There’s an undeniable cult of personality that surrounds any president, according to Dallek, and Trump already has his. Disagree with his policy proposals, or question how he might handle the inevitable crises that cross the president’s desk, but Trump’s longest-serving soldiers believe that if there’s a crisis, the person they want facing it is Donald Trump.

“I know Donald very well,” Sprague told me, “and I believe if I was on a plane with him, and I’ve been on a plane with him—for long trips, to Japan—and if that plane started to go down, he’d figure out in five minutes how to fly it. He’d say, ‘Blanch-aaay’—that’s what he called me—‘Somebody has to find a way to fly this plane.’ I would have no fear. And I’m not an idiot. So that’s what I think."

***

Which brings us back to that theatrical act for which Trump is so known: firing people. When the plane is going down in the White House, so to speak, that often means someone close to the president is soon going to be looking for a new job. Harry Truman relieved General Douglas MacArthur of his command in Korea for bucking the president’s authority, a deeply controversial move. Bill Clinton let go of his first chief of staff, boyhood friend Mack McLarty, after his administration got off to a rocky start. But delivering the pink slip has bedeviled some presidents, too. George W. Bush praised his FEMA director, Michael D. Brown (“Brownie, you’re doing a heck of a job”) only days before he was fired amid the disaster of bungled Hurricane Katrina relief. And Bush famously held on to Defense Secretary Donald Rumsfeld for too long as the Iraq War descended into quagmire territory. Jimmy Carter fired four of his Cabinet secretaries in the summer of 1979, late in his one term, and it gave the public the impression his administration was in shambles.

Could Trump actually let people go, overcome his loyalty to the people who have pledged loyalty to him? If his image-conscious children aren’t pushing him to act, can he do it on his own?

Sam Nunberg thinks so. “He’s one of the best managers there is, in his own unique way,” Nunberg says.

Nunberg has some authority on this question: He’s been fired by Trump, twice. The first time was in early 2014 for his role in coordinating access for what turned into a searing BuzzFeed profile of Trump. Nunberg was hired back a little more than a month later, he said—then fired again last summer, after Business Insider dug up some old racist but mostly unhinged Facebook posts from several years ago in which Nunberg called Al Sharpton’s daughter a “n----!” and Obama “a Socialist Marxist Islamo Fascist Nazi Appeaser.”

“He called me up and fired me,” Nunberg told me, after he finished up with the Sunday morning shows. “He said, ‘Everything will be OK. I’ll give you a letter of reference.’”

Like Lewandowski, who loyally toed the Trump line after being shown the door, Nunberg was booted—but not very far. It’s possible to see Trump’s delegated half-firings as their own kind of technique, one that wouldn’t pass muster at a big company, and would be out of the question at the top levels of government, but keeps a sense of loyalty alive in the small operations that Trump is used to.

Nunberg worked for Trump for more than four years. I asked him what he had learned from the Republican Party’s presumptive presidential nominee.

“A couple things,” he said. “The first is never make people your heroes. Because you’ll always be disappointed. It’s a hard life. The second thing is, basically, always be concerned about yourself, frankly. Don’t count on the loyalty of others.”

Still, he said, he intends to vote for him.

Why?

“Well, I’m a Republican—and I think he’d be a good president.”

Weeks later, though, Trump sued Nunberg for an alleged breach of a non-disclosure agreement—essentially, for not being loyal—a case of a self-described multi-billionaire trying to squeeze a former employee out of $10 million.

I called to ask if this changed things for him.

“No, not at all,” he said. “Look, this is Donald just being Donald. Welcome to Trump world.”



Annabelle Timsit contributed reporting.