• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia
Leadership

This Is Donald Trump’s Biggest Weakness

By
Pamela Kruger
Pamela Kruger
Down Arrow Button Icon
By
Pamela Kruger
Pamela Kruger
Down Arrow Button Icon
July 28, 2016, 11:01 AM ET

On Tuesday, Hillary Clinton made American history as the first woman to become a major party’s nominee for President of the United States. But the next day it was Donald Trump once again commanding media attention. “Russia, if you’re listening, I hope you’re able to find the 30,000 emails that are missing,” the Republican nominee said at a press event, seemingly urging Russian hackers to illegally obtain Clinton’s emails from her time as Secretary of State.

The statement ignited a firestorm. The Trump campaign insisted the presidential candidate had been misunderstood, and Trump later said he was joking. Still, many struggled to understand why Trump made the comment in the first place.

Trump’s former ghostwriter, Tony Schwartz, however, had no trouble coming up with a theory:

Why Trump’s extreme Russia remarks? Feeling small after two nights of strong Dem speeches. Incapable of measured reflection Just reacts.

— Tony Schwartz (@tonyschwartz) July 28, 2016

 

Schwartz, president of the Energy Project, a New York-based consulting firm, recently has emerged as a go-to expert on (and reliable critic) of Donald Trump. He shadowed Trump for 18 months while ghostwriting Trump’s first bestseller, the 1987 The Art of the Deal. Saying he had a “deep sense of remorse” for having helped propel Trump into stardom, Schwartz spoke publicly about Trump for the first time in a New Yorker article published earlier this month. Schwartz had written every word of the book, he claimed, telling the New Yorker it was a “nonfiction work of fiction.”

“I’m one of the very few people who really saw this man up close and isn’t constrained by a NDA [non-disclosure agreement],” he said in an interview with Fortune this week. “The reason I’ve chosen to come forward is I believe Trump is deeply unqualified and would be extremely dangerous as President by virtue of his easily aroused anger and thin skin.”

Below is a transcript of the interview, edited for length and clarity.

Fortune: What was the Trump empire like in the 1980s?

Schwartz: There wasn’t yet a Trump empire back then. It was a few guys in an office. He operated with a very small number of people. They worked on a small number of very high profile deals that he had made. The biggest of them were the Grand Hyatt and Trump Tower.

How did he become so successful in business?

He’s a person who pushes and pushes and intimidates and that is an effective strategy for getting things in the world in which he made his success. He’s a testament to the power of aggression in getting what you want in this world of real estate and construction. I see him as a bully. It’s fine to buy an apartment from a man like that, but not to vote for him for President.

What do you think Trump’s Achilles’ heel is?

When you needle him and when you make him feel either not valuable or important or smart or even good looking, he gets very, very reactive, and he doesn’t operate on rational terms. We’ve seen this in the presidential campaign.

Donald Trump’s vanity was basically all I saw of him. He was about Donald Trump all the time. And his interest was in knowing how you felt about him and whether you recognized that the last thing he said he did was even greater than the previous thing he told you about.

Trump has been accused of lying. What would you say is his biggest lie?

I genuinely believe his biggest lie is a kind of a broad one—which is that he knows anything about anything related to being President of the United States.

He has such a short attention span that he was, in my experience, unable to retain much information about any subject because he couldn’t pay attention for long enough to do that. It’s reflected in the severe limits of his vocabulary, the elementary nature of the sentences that he speaks, the lack of specificity he gives about anything he would do as President.

You’ve described him as this vain, self-centered person. But what about what his children? How do you explain the fact that people are so loyal to him?

Who says people are loyal to him? His kids are—they’re his kids. None of the people who were involved with the Trump organization when I was there are still there. That was 30 years ago.

I do not think Trump has friends. I saw no evidence of that. He had business acquaintances and relationships with people who worked with him.

Trump’s acquaintances were almost exclusively with wealthy people. This is not a guy who spent a moment thinking about the “people.” He wants to hang out with people he thinks are “winners”—people who have a lot of money and will tell him he’s the greatest.

Some people have questioned whether Donald Trump truly wants to be President. What do you think?

I did not think Trump wanted to be president based on what I knew of him—his short attention span, and desire to live in an unrestricted way. I assumed he recognized the job of president would require doing an awful lot of things he doesn’t enjoy doing. Running for president probably was a way for him to stoke his ego and get his voice out there, and he thought, the worst case is “I’ll build awareness for [the Trump brand].”

I’m guessing there came a point in the last several months when it dawned on him he could actually get elected, and the idea of that kind of power, reflected in the speech he gave at the RNC, suggests that yes, he does want to be elected president now. If, God forbid, he is elected, he’ll be looking for ways not to have to do the job.

Author’s note: In response to Schwartz’s public comments to the New Yorker and others, Donald Trump’s lawyer has sent Schwartz a cease-and-desist letter and demanding the return of all royalties. Trump has claimed that Schwartz is a disgruntled former partner. Fortune reached out to the Trump campaign and will update this post if it receives a response.

About the Author
By Pamela Kruger
See full bioRight Arrow Button Icon

Latest in Leadership

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Fortune Secondary Logo
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • World's Most Admired Companies
  • See All Rankings
  • Lists Calendar
Sections
  • Finance
  • Fortune Crypto
  • Features
  • Leadership
  • Health
  • Commentary
  • Success
  • Retail
  • Mpw
  • Tech
  • Lifestyle
  • CEO Initiative
  • Asia
  • Politics
  • Conferences
  • Europe
  • Newsletters
  • Personal Finance
  • Environment
  • Magazine
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
  • Group Subscriptions
About Us
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • Pinterest icon

Latest in Leadership

Aerie built a $2 billion brand by rejecting Victoria’s Secret’s old playbook. Now it wants to win the AI backlash.
C-SuiteRetail
Aerie built a $2 billion brand by rejecting Victoria’s Secret’s old playbook. Now it wants to win the AI backlash.
By Phil WahbaApril 30, 2026
1 hour ago
Google Cloud revenue is now 18% of Alphabet’s business. Is this the beginning of the end of Google’s search identity?
Big TechGoogle
Google Cloud revenue is now 18% of Alphabet’s business. Is this the beginning of the end of Google’s search identity?
By Alexei OreskovicApril 29, 2026
6 hours ago
A man in a suit and tie
InvestingMeta
Meta just bumped its 2026 capex forecast up to as much as $145 billion for the AI boom—and investors flinched
By Amanda GerutApril 29, 2026
9 hours ago
teri
BankingBanks
Exclusive: America’s largest Black-owned bank launches podcast with mission to unlock hidden shame holding back generational wealth
By Nick LichtenbergApril 29, 2026
9 hours ago
pete hegseth
PoliticsIran
‘A strategic blunder’: Democrats confront Hegseth as the Iran war’s price tag hits $25 billion
By The Associated Press, Ben Finley, Stephen Groves, David Klepper and Konstantin ToropinApril 29, 2026
11 hours ago
Jamie Dimon says bureaucracy sinks companies and the solution may be getting rid of the ‘jerks’ who don’t want to solve it
C-SuiteJamie Dimon
Jamie Dimon says bureaucracy sinks companies and the solution may be getting rid of the ‘jerks’ who don’t want to solve it
By Marco Quiroz-GutierrezApril 29, 2026
12 hours ago

Most Popular

Apple cofounder Ronald Wayne—whose stake would be worth up to $400 billion had he not sold it in 1976—says that at 91, he has no regrets
Success
Apple cofounder Ronald Wayne—whose stake would be worth up to $400 billion had he not sold it in 1976—says that at 91, he has no regrets
By Preston ForeApril 27, 2026
3 days ago
‘Take the money and run’: Johns Hopkins economist Steve Hanke on why the UAE quit OPEC
Energy
‘Take the money and run’: Johns Hopkins economist Steve Hanke on why the UAE quit OPEC
By Shawn TullyApril 29, 2026
1 day ago
‘The cost of compute is far beyond the costs of the employees’: Nvidia executive says right now AI is more expensive than paying human workers
AI
‘The cost of compute is far beyond the costs of the employees’: Nvidia executive says right now AI is more expensive than paying human workers
By Sasha RogelbergApril 28, 2026
2 days ago
Jamie Dimon gets candid about national debt: ‘There will be a bond crisis, and then we’ll have to deal with it’
Economy
Jamie Dimon gets candid about national debt: ‘There will be a bond crisis, and then we’ll have to deal with it’
By Eleanor PringleApril 29, 2026
21 hours ago
‘They left me no choice’: Powell isn’t going anywhere—blocking Trump from another Fed appointee
Banking
‘They left me no choice’: Powell isn’t going anywhere—blocking Trump from another Fed appointee
By Eva RoytburgApril 29, 2026
13 hours ago
More than two-thirds of U.S. schools say they’re unable to afford the cost of student free lunch—and MAHA’s dietary guidelines may make it worse
Economy
More than two-thirds of U.S. schools say they’re unable to afford the cost of student free lunch—and MAHA’s dietary guidelines may make it worse
By Sasha RogelbergApril 29, 2026
23 hours ago

© 2026 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.