Trump: Salesman-in-chief or chief executive?

Story highlights

  • Michael D'Antonio: While Trump excels at self-promotion, he has failed at managing multiple business ventures and his campaign
  • Opinion: Trump's mismanagement indicates that he'd make a poor commander-in-chief
CNN brings you the stories of Hillary Clinton and Donald Trump from those who know them best in two CNN Special Reports, "Unfinished Business: The Essential Hillary Clinton" and "All Business: The Essential Donald Trump." The documentaries air back-to-back starting Monday at 8 p.m. ET.

(CNN)The closer we get to Election Day, the more we must reflect on the type of presidency we can expect from the winning candidate. Will the country get the "Team of Rivals" described by Doris Kearns Goodwin in her book about Lincoln's cabinet or, perhaps, a collection of Yes Men of the sort who helped Richard Nixon self-destruct?

During his lurching campaign, Donald Trump has sought to reassure the nation that he "is going to get great people" to help him once he's seated in the Oval Office. The implication is that he will make up for his own lack of experience and expertise by creating a stellar cabinet and recruiting thousands of lower-level officials who will help him fulfill his pledge to "Make America Great Again."
    Michael D'Antonio
    Trump hasn't always been consistent on his need for great advisors. At some points along the way -- like when he said "my I.Q. is one of the highest" -- Trump has seemed dismissive of the need for counsel. This is, after all, a man who has said that his insights into military affairs come from "the shows" (read: TV news). And when asked whom he consults on foreign affairs, Trump said, "'I'm speaking with myself, No. 1, because I have a very good brain."
    So which Trump is the true Trump? The record shows it's the one who brags about his high IQ and has so little interest in competing ideas that his first choice is to consult himself. Indeed, in 2007, Trump told a TV audience that he preferred to hire good people but was wary of those who might be too smart. He said, "I hear so many times, 'Oh, I want my people to be smarter than I am.' It's a lot of crap. You want to be smarter than your people, if possible."
    Visit Trump's office, where he runs his real estate, hotel and licensing businesses, and you will see that he is the unrivaled smartest-man-in-the room. As his three adult children each explained to me, their father is one of the best marketing and development executives around, and they wouldn't presume to match his expertise. Top company officials who are not family members told me the same thing. But while Trump may have a particular gift for real estate and promotion, he has also shown that he struggles to both hire and listen to the best talent available to help him. He is more Tricky Dick than Honest Abe.

    Is this any way to run an airline?

    Of all the businesses Trump has tried to run, he was least equipped to manage the ill-fated airline he named the Trump Shuttle and operated from 1989 to 1992. Purchased from the now defunct Eastern Airlines, the shuttle connected New York with Boston and Washington on an hourly schedule. The shuttle took flight amid great fanfare as planes were repainted and outfitted in gold-colored fixtures and accompanied by a launch party that featured waiters dressed in tuxedos circulating with trays of champagne.
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    As Trump applied what he knew from the real estate business to his shuttle, airline veterans raised concerns. The weight he added to planes during renovations increased operating costs, as did his commitment to providing full in-flight meal service on trips that were no more than 45 minutes. He also violated a cardinal rule of the airline industry -- do not call safety into question -- by denigrating the rival Pan Am Shuttle as a money losing operation with old aircraft. The subtext was that the planes were in poor condition, and the company might not be able to afford repairs.
    The first executive Trump hired to run his shuttle, an industry veteran named Bruce Nobles, was ousted after about a year on the job, even though he had matched Pan Am's market share. (Trump wanted more.) When asked by The Daily Beast to comment on his experience, Nobles said, "I cringed every time he opened his mouth. He really didn't understand the business and at times he said things that really weren't helpful ... That was his style, and it really hasn't changed."
    Nobles' replacement, Richard Cozzi, was questioned by the press about whether he was running a real airline or simply treading water while a buyer was sought to take over an enterprise saddled with heavy debt. He insisted that he was operating the shuttle to make a profit, not prepare it for sale. However, he would last little more than a year himself as a former Eastern Airlines flight operations director Terry Hallcom was brought in to replace him.
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    The Trump Shuttle ceased operating roughly six months after Hallcom assumed his new position. It was taken over by Trump's lenders, who hired US Airways to run it. A few years later, US Airways reported it was profiting on this operation. Meanwhile, Pan Am executives said that their shuttle had made money throughout its competition with the Trump Shuttle.

    Who loses money on casinos?

    Like banks, casinos are home to large amounts of cash money. Whether you're talking about slot machines, blackjack or roulette, the odds always favor the house, and a well-conceived, well-run gambling hall should consistently make a profit.
    When Trump got into the casino business in Atlantic City, he didn't know anything about it. He didn't even like to gamble. Trump hired some veteran executives away from top casinos, but they were often exasperated by their boss. According to John O'Donnell, whom Trump recruited from the staff of the Las Vegas mogul Steve Wynn, Trump "did not understand gamblers. He could not comprehend that a person who comes thousands of miles to stand at a table and wager $10,000 over and over again on a throw of the dice is motivated by something other than money."
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    In a book that O'Donnell wrote about his experience as a Trump casino executive, he painted a picture of a boss who was not interested in cultivating high rollers by socializing with them and unaware of the need for the repeat business of everyday gamblers from New York City and Philadelphia. What Trump was interested in was the way his executives looked and dressed. O'Donnell wrote of how Trump warned his top men about the dangers of losing their hair, and recalled that he once told all the managers at the casinos that they should wear suits because "there are no sport coats in the Trump Organization."
    No matter what they wore, Trump's casino managers couldn't keep his gambling operations afloat while dealing with a mercurial owner who often refused their counsel. In a recent interview, O'Donnell recalled that Trump was so focused on short-term problems that he drew profits out of the casinos "on a monthly basis to services other debt." These withdrawals reduced the money available to maintain and market the casinos, which required constant reinvestment.
    As bankruptcy loomed, Trump began to blame his problems on two executives, O'Donnell's friends, who had died in a helicopter crash. "
    It was a convenient excuse," said O'Donnell, "that he could blame two dead men." O'Donnell added that this insult caused him to resign. Trump later called O'Donnell, "a third rate executive" and insisted that he had been fired.
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    Trump's casino adventures would amount to four big bankruptcies, which victimized employees, creditors and lenders. The failures suggest that the man in charge either failed to hire the right people to keep these cash machines running or wouldn't let them do their jobs. Either way, Trump's record in Atlantic City doesn't inspire.

    Trump as political manager

    Presidential campaigns are long, stressful affairs marked by surprises and crises that test a candidate's mettle. Though the campaign trail doesn't come close to the level of pressure felt in the Oval Office, it's long been considered a reasonable test. Watch a man or woman run for president, and you get a sense of how he or she might fare once elected.
    In Trump's case, we've seen a repeat of his performance as a businessman. As a public promoter, mostly of himself, he has done well. But as a manager of a complex enterprise that requires specialists and seasoned executives, he has struggled. The best evidence of his troubles can be seen at the very top of the campaign organization. Trump's first campaign manager, Corey Lewandowski, departed after accusations that he manhandled a female reporter. (Video supported the accuser.) His replacement, Paul Manafort, left amid revelations of his shadowy relationships with politicians abroad. Now Trump's third manager, Stephen Bannon, is dogged by controversies over his divorce, his voter registration and the inflammatory politics of the website he managed, Breitbart News.
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    Trump's style worked in the GOP primaries where he was rarely pushed out of his sound-bite comfort zone. Gifted as a solo performer, he stole the spotlight from the 16 others, playing with the media like an expert. But from the moment when he captured the nomination and lost the cover provided by all the others who crowded the stage, Trump has staggered from one problem to the next.
    The ultimate example of Trump's struggle to run a larger and more sophisticated campaign enterprise has been his bumbling over immigration. Trump, the solo performer, declared his candidacy with an anti-immigrant diatribe that included words like "rape" and "murder" and "drugs." He made the forceful deportation of 11 million undocumented immigrants the centerpiece of his drive for the Republican nomination. In recent weeks, he has expressed a desire to soften this policy, but then contradicted himself.
    Surrogates, who are supposed to faithfully represent the candidate's views, haven't provided any more clarity. Instead they have used salesmanship and buzzwords to insist a muddled argument is crystal clear. The silliest example was Donald Trump Jr.'s use of the term "baby steps" to justify the candidate's retreat from his promise to immediately deport millions.
    How did the Trump campaign get so confused on immigration? The problem started with the man in charge. In typical fashion, Trump recruited a seasoned advisor, Mark Kirkorian, who has studied the issue for 20 years. When asked to comment on the confusion over Trump's immigration plan, Kirkorian replied that the candidate does have a detailed proposal. He then added, "It's just that he's never read it."
    Remarkably, Trump has not improved management of his campaign with time. Politico reported that as of September 1, some campaign staffers don't know who makes decisions and what the overall strategy for winning is. Trump has spent precious time in states like Mississippi and Washington, where he is unlikely to affect the vote in November, and a campaign press aide recently sent key supporters an email asking them to cease accepting TV interview requests. In capital letters, Bryan Lanza pleaded, 'PLEASE DO NOT BOOK ON YOUR OWN."
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    But none of this should be particularly surprising. Trump has confessed that he isn't much of a reader and that he prefers to act on the basis of his instincts. He wants Americans to feel confident in those impulses, even though they are driven by a man with no political experience and a unique record of failures.
    The problems in the Trump campaign reflect the candidate's well-established style. Unable to trust those who know better, and unwilling to learn more about matters beyond his experience, the billionaire who would be president wants us to trust that he will run the country well. If we were electing a salesman-in-chief, Trump might be a good choice. But his record as a manager tells us he would make a poor chief executive, which is every president's primary job as leader of the most powerful and complex organization the world has ever known.