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Trump's Never Managed to Be a Manager

Timothy L. O'Brien is the executive editor of Bloomberg Gadfly and Bloomberg View. He has been an editor and writer for the New York Times, the Wall Street Journal, HuffPost and Talk magazine. His books include "TrumpNation: The Art of Being The Donald."
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"I realized that America doesn’t need more 'all-talk, no-action' politicians running things. It needs smart businesspeople who understand how to manage. We don’t need more political rhetoric -- we need more common sense. 'If it ain’t broke, don’t fix it' -- but if it is broke, let’s stop talking about it and fix it. I know how to fix it." --Donald Trump, "Crippled America"

When Donald Trump strides onto the stage at Cleveland's Quicken Loans Arena Thursday night to accept the Republican Party's presidential nomination, he'll complete the penultimate step on an improbable journey toward the White House.

He'll also have the opportunity to define his qualifications to hold the world's most powerful political office. His close friend and fundraiser, Colony Capital CEO Tom Barrack, told a CNN reporter at the convention that he expects Trump to drive home his prowess as a business executive and to demonstrate "how good he can be when he's in the saddle."

While many of Trump's bona fides have been hard to pin down -- how conversant and informed he is about, say, foreign, monetary, fiscal, health, education, immigration, regulatory and defense policies -- we actually do know a lot about his capacity to manage a business.

Trump has run the Trump Organization for decades from Trump Tower, 26 floors above Fifth Avenue in Manhattan. The Trumps ascended to that aerie in the 1980s from less glamorous space on Avenue Z in Brooklyn, where Trump and his father, Fred, managed a valuable portfolio of middle-income housing. While the family business has a tonier address now, it's still a small shop despite the Trumps' inclination to paint the operation in Fortune 500 hues and to exaggerate, often by thousands and thousands of people, the actual number of employees who work there.

“People thought we were this humongous firm with billions of people,” a former Trump executive, Blanche Sprague, once told me. “In the New York office, there were only about eight or 10 close ‘executives’; the rest were secretaries and accountants and everybody did everything."

The Trump Organization doesn't appear to have grown much since I last checked in several years ago. It has contractors and others on its payroll, of course (and used to add its Atlantic City employees to its ranks when trying to top lists of New York's biggest private employers), but as Politico's Michael Kruse recently noted, "key staffers" at the Trump Organization "number around only a dozen."

The Trump Organization juggles a handful of tidy golf courses. It processes paperwork associated with its management, development and ownership of a clutch of valuable skyscrapers and retail spaces. But first and foremost, it's a licensing machine that serves as the promotional springboard for someone who's been more entertainer than executive.

What the Trump Organization isn't is a complex bureaucracy with a huge budget, public accountability and legions of employees with a global footprint and a multi-faceted mission. In other words, it's nothing like the federal government -- and nothing during Trump's tenure there or elsewhere has prepared him to take the managerial reins in Washington.

"I couldn’t stand to see what was happening to our great country. This mess calls for leadership in the worst way. It needs someone with common sense and business acumen, someone who can truly lead America back to what has made us great in the past. We need someone with a proven track record in business who understands greatness." --Donald Trump, "Crippled America"

Trump doesn't have a "track record in business" that's persuasively "proven."

The creature of his father's, bankers' and bondholders' funds, Trump binged in the 1980s and melted down in the 1990s. Along the way he trashed his chances of being a top-tier Manhattan developer and then tumbled through a series of casino and hotel bankruptcies.

Trump's Atlantic City casinos were the largest and most challenging enterprises he ever had his hands on, and he larded them with debt, churned through managers, made tactical and strategic blunders and foisted the wreckage on the workers, vendors and investors who depended on him.

When I was writing a book about Trump more than a decade ago, I talked to Marvin Roffman, a prominent gambling-industry analyst. (The book, "TrumpNation," published in 2005, provoked a libel suit from Trump that was later dismissed.)

“I’ve met with hundreds of the top corporate executives," Roffman said. "The number one decision I make is on management, the people who run these companies. If you get a bad guy in there, they can take down major companies, giants can come tumbling to their feet... . Donald’s troubles, aside from the financing, are from the management. I really don’t think that Donald understands the day-to-day skills needed to run a casino." (Trump got Roffman fired after the analyst made the mistake of accurately predicting that Trump's gambling empire would become a smoldering mess.)

Those same shortcomings also upended Trump's brief foray into professional football, when his inability to control costs were coupled with strategic and managerial lapses that helped doom the nascent United States Football League in the 1980s.

“In business, cooperation is essential to success.” --Donald Trump, "Midas Touch"

Trump doesn't have a reputation in the business world as the Grand Collaborator.

He's had some joint efforts that have gone well – as when he and NBC paired up to conquer reality TV with "The Apprentice." (The partnership eventually unraveled because of the network's apparent discomfort with Trump's attacks on Mexican immigrants.)

Meanwhile, high-profile joint ventures with the likes of Chicago's Pritzker family, the company that once owned Holiday Inns, other USFL owners, his bankers and the governments of New York and Atlantic City, all ran aground and became unfriendly or litigious.

“My attention span is short.” --Donald Trump, "Surviving at the Top"

This is true.

“I don’t think Donald has the patience, or the interest, or the attention span to be a hands-on operator,” the late Al Glasgow, who worked for Trump as a consultant, told me several years ago. “He’s just a deal maker. He blows in and then he moves on to the next deal.”

Impatience hasn't always hurt Trump. Rapid-fire deal-making has allowed him to pounce on undervalued properties, like a tower at 40 Wall Street that may turn out to be one of his best investments. But his lack of focus has doomed some of his most important businesses.

A distaste for sweating the details or worrying about negative consequences also helps explain Trump's ability to float past his own setbacks. That survival instinct allowed him to become comfortably wealthy again by the early 2000s, when he traded empire-building for celebrity. But it hasn't produced a disciplined, restrained and astute corporate titan.

"Do you know your 'why' behind your 'what?' You have to have a good reason for doing what you’re doing, because people connect with the why." --Donald Trump, "Midas Touch"

One of the questions of this political season is the "why" behind the "what" of a Trump presidential bid. Until recently, Trump has run his campaign on a shoestring budget while relying on a staff as small as the Trump Organization crew.

The campaign has lurched from one sensation to the next, kept aloft by Trump's ubiquity on social media, his guerrilla takeover of the GOP debates and his appeal to a certain swath of the electorate. But none of those things mean that Trump's campaign has been well-managed.

Trump has said that he might drop out of the race even if he's elected in November. A New York Times report yesterday said that he had been fishing for a vice president who could essentially run the government for him -- suggesting that he's willing to license his name to the White House rather than focusing on the nitty-gritty of a management challenge like the presidency. If that's true, then it proves the point of one of Trump's other bromides:

“Building a brand may be more important than building a business.” --Donald Trump, "Midas Touch"

This column does not necessarily reflect the opinion of the editorial board or Bloomberg LP and its owners.

To contact the author of this story:
Timothy L. O'Brien at

To contact the editor responsible for this story:
Jonathan Landman at