More than 27 years before Donald Trump was elected president of the United States, Bruce Nobles, then the president of the Trump Shuttle airline, assessed with some befuddlement the business and managerial practices of his boss. Nobles had climbed a conventional corporate ladder at American, Continental and Pan Am, companies with org charts any MBA would recognize. The Trump Organization, on the other hand, was smaller, looser and much more freewheeling, and working for Trump, Nobles discovered, was a markedly different experience.
“It surprised me 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 delegation of authority and responsibility,” Nobles told a reporter from Newsday in the fall of 1989. “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.”
Mere months into Trump’s time as the owner of an airline—the purchase was finalized that June—Nobles already had concerns. Trump had overpaid with more than $400 million of borrowed money, he seemed most interested in cosmetic touches like the size of the “T” on the tails of the planes, and the debt service quickly became crippling. Once, Trump suggested cutting costs by flying with two pilots, not three, and Nobles had to tell him that would be illegal.
Trump’s appetite was greater than his ability to manage what he had acquired. Last week on the phone, as Trump passed the one-month mark in the White House and prepared for tonight’s speech before a joint session of Congress, Nobles told me that what he sees now is what he saw then. “His behavior to date,” he said, “is consistent with the behavior I saw 30 years ago.”
Trump’s company, despite his grandiose portrayals of a sprawling empire, always at base was a mom-and-pop entity, and what Trump managed throughout his lengthy professional career was principally a core group of barely more than a dozen executives housed on the 26th floor of Trump Tower. Until now. As president, Trump sits at the top of a massive bureaucracy not of his own making, a complex hierarchy designed to help him handle the most information-intensive, crisis-driven job in the world. He appears to be struggling to adapt. Hundreds of positions remain vacant, key posts have been declined by wary nominees, poorly vetted picks have withdrawn or been rejected, and the day-to-day functioning of the West Wing has become its own running news story. Trump has dismissed the accounts of turmoil as “fake news,” insisting his administration is running like a fine-tuned machine. But for those who have known him, studied him and worked with him the longest, the more pressing question is whether Trump will be able to scale up. Is his well-established idiosyncratic style as a manager suited for this monumental task?
“I don’t think there’s anything of scale that he’s had his hands on that he hasn’t made a hash of,” biographer Tim O’Brien said in an interview last week.
“Ramping up,” fellow biographer Gwenda Blair added, her tone dry, “is something he’s maybe not so good at.”
“When we worked together,” Nobles said, “he had three casinos in Atlantic City and he had the shuttle, and all four companies had their own operating systems, and I went to him and said, ‘Why don’t we combine these things?’ And he said, ‘No. I want those guys competing against each other. I think it will make all of them stronger.’ Any normal businessman I know would have said, ‘Let’s take advantage of the economies of scale here.’ He didn’t think like that.”
And as the ‘80s flipped to the ‘90s, the consequences of Trump’s unorthodox decisions were clear. “All those businesses are gone, of course,” Nobles said, “because they weren’t as successful as they could have been—and should have been.”
So while smart, experienced political professionals have called the start to the Trump presidency unprecedented in the annals of the office, it is not unprecedented in the annals of Trump. Trump has managed the Oval Office in Washington pretty much exactly the way he managed for on Fifth Avenue in New York, say people who worked for him at different points over the last 45 years as well as writers of the best, most thoroughly reported Trump biographies. In recent interviews, they recounted a shrewd, slipshod, charming, vengeful, thin-skinned, belligerent, hard-charging manager who was an impulsive hirer and a reluctant firer and surrounded himself with a small cadre of ardent loyalists; who solicited their advice but almost always ultimately went with his gut and did what he wanted; who kept his door open and expected others to do the same not because of a desire for transparency but due to his own insecurities and distrusting disposition; who fostered a frenetic, internally competitive, around-the-clock, stressful, wearying work environment in which he was a demanding, disorienting mixture of hands-on and hands-off—a hesitant delegator and an intermittent micromanager who favored fast-twitch wins over long-term follow-through, promotion over process and intuition over deliberation.
“I think he’s the same Donald Trump as the Donald Trump I knew when I was working with him,” said former Trump Organization executive vice president Louise Sunshine, who worked for Trump for 15 years starting in 1972. “Same management style. He’s always created competition and chaos.”
“I don’t think he manages,” said Artie Nusbaum, one of the heads of the construction company that built Trump Tower. “I think he just lets it all happen.”
“He gets an idea in his head and just says, ‘Do it,’” said Barbara Res, a Trump Organization executive vice president in the ‘80s and ‘90s. “There’s no direction. The idea isn’t built up or fleshed out. He just says, ‘Let’s do this.’ It’s like a stream-of-consciousness thing with him.”
“He’s not a great manager,” O’Brien said. “He’s a performance artist pretending to be a great manager.”
Trump was at his best as an actual manager, as opposed to as an expert brander or as an effective reality TV star, according to O’Brien, Res and others, more than 30 years ago—when he appeared to know what he didn’t know and hired people who could help him, and then let them do just that. This, they say, was the managerial style that enabled him to erect Trump Tower, which opened in 1983. But some five years later, when Trump’s fame spiked in the wake of the publishing of The Art of the Deal and he tried to branch out and scale up by buying with billions of dollars of borrowed money a third casino in Atlantic City, the Plaza Hotel in New York and the aging fleet of planes so he could own an airline with his name on it, the result was an all-but-fatal business failure. If not for family money, the fact that the banks were as beholden to him as he was to them and the canny wizardry of a lender-mandated chief financial officer—a position he had never had as part of his own staff—Trump almost certainly would have had to declare personal bankruptcy. He might have become ‘80s-era trivia instead of the 45th president.
Trump’s abilities as a manager have been a fixation for decades—for him and for others. The appraisals haven’t always been in agreement.
“Although there is a board room, there is no board,” Bill Geist wrote in a cover story in the New York Times Magazine in 1984.
The Trump Organization, longtime Trump attorney George Ross told the New York Daily News in 2004, “is a dictatorship, not a democracy.”
“He’s assertive, aggressive and very in your face at the same time,” Trump’s namesake son, Donald Trump Jr., told biographer Robert Slater for his book that came out in 2005. “He can be very scatterbrained when he talks to someone, but it’s all for a purpose. He can get people confused. But he ultimately gets what he wants.”
That hasn’t always been what his company needs. “Donald’s erratic temperament distracted everyone from business objectives,” Jack O’Donnell wrote in his book after he quit working as a casino executive for Trump, adding that Trump “did business almost entirely in the moment.” The Trump Organization, O’Brien wrote in his biography, “catered to Donald’s zealousness and preference for quick decisions.” Wrote Blair: “There was no formal business plan, no development strategy. Instead Donald would come up with ideas, do the preliminary calculations in his head, then tell someone to get moving on it.”
Trump, too, of course, has said many things about Trump, and about this.
“Trump does well with management,” Trump said in 1990 to a reporter from the New York Times for an article about his pending financial collapse.
“People rule in many ways,” he wrote in 1997 in The Art of the Comeback, opting for an interesting verb. “But whether through fear or respect, your opponents and even your friends must know they can’t push you around. If they can, you’re not the boss. They are.”
In 2004, in Think Like a Billionaire, he cited a book about narcissism. “A narcissist does not hear the naysayers,” he wrote, practically identifying himself as such. “At the Trump Organization, I listen to people, but my vision is my vision.”
All of this, of course, was said about Trump and by Trump in the context of Trump as a celebrity, pop-culture provocateur and private businessman. When he started running for president, though, and when he used as one of his main pitches his business and financial success, his managerial track record took on exponentially greater significance. If he wanted to be America’s first CEO president, what kind of CEO had he been? If he wanted to manage the country, how had he managed his company?
Early in the campaign, in the first week of September of 2015, when his candidacy was garnering undeniable support but still was considered primarily a through-the-roof-ratings curiosity, Max Abelson of Bloomberg Businessweek took it seriously. “Trump is selling himself to America as the king of builders, a flawless dealmaker, and masterful manager. But he isn’t really any of those things,” Abelson wrote, describing not so much a builder and a buyer—at least not for a long time—but rather a landlord, a licenser, a marketer and “a golf bigwig” who “controls the teensiest details, rejects hierarchy, and picks top deputies by following his own recipe for promotion.” Trump’s “corporate leadership,” he concluded, “is a kind of teenager’s fantasy of adult office power.”
Throughout the rest of the campaign, the subsequent litany of stories in the major mainstream press scrutinized Trump’s array of less sterling business ventures, ranging from his late ‘80s mania to his more recent flops and duds and worse, like his “university,” his mortgage company and his impossibly leveraged casinos—the only public company he had ever run, and a rolling, unmitigated failure for everybody but himself. “The money I took out of there was incredible,” he said last summer, while those who had invested in him were left losers. Trump has built with ballyhoo and hocus-pocus more than he has with concrete and glass, according to the reports, especially since his initial efforts to expand caused the Trump Organization to teeter toward ruin. He consistently has managed his image more effectively than he has managed his interests. Trump as a business boss was a show long before Mark Burnett gave it a name and put it on the air.
“Management is an art that is very important to me,” Trump told POLITICO last summer, and loyal former and current employees said then in interviews with me that his management style would work wonderfully in the White House.
“It would transfer beautifully,” said Ross, the attorney and a longtime executive vice president.
“He’s going to pick great people and let them do their job,” former Trump Organization vice president Billy Procida said. “He’s going to do what he does—crisis management and strategic direction and then negotiations at a high level. Him and Putin will become best friends. He will disarm people. He’s disarming. I have seen him walk into rooms where people were ready to kill him, community groups, politicians, contractors—and within five minutes, he has people eating out of his hand. He’s a charming son of a bitch, he’s a tough son of a bitch, he’s a smart son of a bitch.”
“Mr. Trump’s energy and remarkable work ethic,” said Matthew Calamari, who started working for Trump in 1981 as a bodyguard and is now the Trump Organization’s chief operating officer, “will make for an easy transition.”
He has filled a fraction of the hundreds of important Senate-confirmed jobs necessary to make the federal government work. He has signed in staged ceremonies a flurry of executive orders that have felt at times raced-out and slapdash, including the immigration travel ban that has sparked nationwide protests and panic—the revised version of which has yet to be released but will assuage, he assures, the objections of “so-called” judges. He has ousted his first national security adviser in the midst of the ongoing flaring of the Russia scandal, and he has watched a potential replacement for the job beg off for personal reasons, which most likely means he didn’t want to be personally subjected to the evident chaos inside the White House. In early-morning and late-night Twitter posts since his inauguration, he has attacked Nordstrom, the city of Chicago, Chuck Schumer, “low-life leakers” and “so-called angry crowds” of unsettled constituents. He has declared the press not only his “enemy” but “the enemy of the American people,” dismissing coverage he doesn’t like as “Fake” the way he labeled previous obstacles “Little,” “Lyin’” and “Crooked.” He has held a news conference in which he ranted and raved while insisting he wasn’t “ranting and raving.” He has had his press secretary do the same.
That tense Sean Spicer news conference, in fact, on the first full day of the Trump presidency, is what convinced one veteran former Trump Organization employee that there would be no new White House Trump.
The fact-free pushback, the picture props of the inauguration crowds on the Mall, “denying the obvious”—for this person who knows Trump well, it was a telltale collection of Trump trademarks, a through-line from the 26th floor to the West Wing. “And that set the tone for what this administration will be,” he said.
Nobles, the former Trump Shuttle president, said the cross tweets littered with capital letters and exclamation points transport him to Trump Tower and the late ‘80s.
“None of us like to be criticized. I’ve never met anybody who does, but some of us handle it better than others—and Donald doesn’t handle criticism at all,” he said. “He just has to fight back when he’s criticized.”
Biographer Michael D’Antonio concurred. “The combativeness is a constant,” he said.
“And the way he’s running people ragged—that, I think, is classic Trump,” he added. “When you look at the people around him, when you see how exhausted they seem to be, that is something he’s always done.”
D’Antonio is far from a Trump booster—he said last year he thinks he has attention-deficit disorder—but he said last week he actually has been “favorably impressed” with some of Trump’s foreign policy hires, mentioning secretary of defense Gen. James Mattis and Lt. Gen. H.R. McMaster, the new national security adviser.
“To me,” D’Antonio continued, “it looks like he’s actually recognizing that there’s stuff that he doesn’t know and that’s where he should find some well-qualified help—and he’s actually doing it. They seem to be more experts than loyalists, and that’s a little fresh twist on his usual way of doing things.”
For Sunshine, that much is reminiscent of how Trump was before the early ‘90s crackup, before The Art of the Deal, going back to his more focused, more disciplined years building Trump Tower. “He used to have very competent, very capable, intelligent, positive voices around him,” Sunshine said.
These days, though, watching from her home in Florida, she pinned the blame for Trump’s topsy-turvy first month as president on a few of his closest aides. “Just listen to Kellyanne Conway. Just listen to her. You want to put a grapefruit in her mouth,” Sunshine said. “And Steve Bannon—he’s living in another world. And look how many people who are around Donald are Bannon people. Like Steve Miller.”
Procida, meanwhile, last week raged into the phone about the first month of his former boss’s first term.
“He’s trying to pick the right people and let ‘em do their job—that was always his No. 1 thing—and the problem is he hasn’t been able to get his people in. He’s really getting sabotaged at every turn,” Procida said, lashing out at what he views as obstructionist Democrats and meddlesome media. “I want him to be able to do his f—ing job. You want him to be able to do his f—ing job, whether you like him or not, right? And if you hire me to be the point guard of your basketball team, are you really going to shout at me all the f—ing time while I’m dribbling the ball up the court?”
Procida stopped to catch his breath.
“If he could just put f—ing blinders on …”
But that’s just it, according to many people who have worked for him over the years. Trump so seldom can.
“I remember one day we were trying to save the company,” one longtime former inner-circle employee told me, recalling the Trump Organization’s struggle in the early ‘90s to stay afloat, “and he walks into a meeting and says, ‘Let’s buy the New Jersey Nets.’”
Buying a professional basketball team would have been a stock Trump tactic, the person pointed out, a big, splashy story, a way to get reporters to write about something other than his financial travails, a conscious distraction meant for public consumption—a surface-level “fix” to a deep, systemic problem.
“I just said, ‘Uh, Donald …’”
Some question whether the real victim of the distractions isn’t Trump himself and what he says he wants to accomplish.
“I think there’s some serious managerial work to be done for him to fulfill his campaign promises,” said O’Brien, the biographer. “I think in order to scale up in anything, you have to have a strategic vision, a creative perspective about what you want to accomplish, and then you have to wed that to intellectual and managerial discipline, and that requires patience and perspective and an ability to delegate. And everything I’ve said in the preceding sentence are not attributes of Donald J. Trump.”
Different management styles have worked, and not worked, in the White House. And nobody ever has been fully prepared to be president. Presidents have said that. Presidential historians have said that. But according to O’Brien, who’s been reporting on Trump since the early ‘90s, the challenge for him is particularly steep: “He now needs to build a global network that is completely unlike anything he’s built or relied on before. This isn’t just about a modest course correction. This is about getting an entire personality transplant.”
Will the weight of the job lead to an altered, more sober, more regimented approach to management—a different Trump?
“Will he evolve?” Nobles said. “Good question.”
Another former employee answered it. “I don’t think he’s ever going to evolve on managerial style,” he said. “On policy and strategy, he may change, but he’s never going to evolve in how he does things and runs things. Because that’s what got him to the Oval Office.”