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

As a Manager, Donald Trump Encourages ‘Apprentice’-Like Rivalries

By
The Associated Press
The Associated Press
Down Arrow Button Icon
By
The Associated Press
The Associated Press
Down Arrow Button Icon
May 31, 2016, 6:14 AM ET
1991 Man of The Year Awards
Photograph by Ron Galella—WireImage

When Donald Trump acquired a pair of Atlantic City casinos in the mid-1980s, he pitted his managers against each other in a ferocious competition over everything from booking entertainers to attracting high-rolling gamblers.

That one of those managers was his wife, Ivana Trump, but didn’t earn her any slack.

“His tactic there, as our success surpassed the Castle’s in 1987, was to shove the Plaza’s performance in Ivana’s face, like a mirror, holding it up for her to see the reflection of a less than successful manager,” John O’Donnell, Ivana Trump’s rival in the casino wars, wrote in a 1991 book.

 

Trump’s penchant for encouraging rivalries is now roiling his presidential campaign just as he’s captured the GOP nomination, creating deep uncertainty among Republicans about his preparedness for a complex and costly general election campaign. The tensions boiled over last week with the abrupt ouster of political director Rick Wiley, who left the campaign after just six weeks.

Wiley found himself caught between Trump campaign manager Corey Lewandowski, one of the businessman’s original campaign staffers, and Paul Manafort, a veteran Republican hand who was brought in to bolster the operation in March. While Wiley was originally hired by Lewandowski, he aligned himself with Manafort’s vision of a more robust and expensive campaign operation—a vision Trump does not appear to have fully bought into. He also was seen as being unwilling to fill top jobs in battleground states with people close to Lewandowski, according to people familiar with the decision.

Wiley did not respond to requests to discuss his tenure with the Trump campaign. Trump aides would not make the candidate available for an interview, but they did not dispute the notion that the real estate mogul encourages internal competition.

“Of course there’s competition because you want the best,” Lewandowski said. “That’s the type of mindset you have to have in the federal government.”

Sam Nunberg, a former Trump aide who was fired last year, put the dynamic more bluntly: “He loves playing people against each other.” Still, Nunberg said he appreciated the competitive environment, crediting it with keeping staffers creative and committed to the organization.

But for other Trump aides, the businessman’s cutthroat style led to mistrust and paranoia

“You can’t trust the other guy’s people,” said Stuart Jolly, who resigned as Trump’s campaign field director after Manafort and Wiley were given more power. Jolly confirmed Friday that he is joining the pro-Trump group Great America PAC as its political director.

Some current and former Trump advisers blamed the businessman for withholding information about staff changes from his team, sometimes leaving them to learn about internal developments in the media. Some have taken to shopping negative stories about their rivals to the press in a bid to undercut each other in the eyes of the boss — even if the stories reflect poorly on Trump.

Even more concerning for Trump as he eyes a likely faceoff with Democrat Hillary Clinton is the uncertainty the internal friction has created about the direction of the campaign. People close to the campaign say there are major questions about battleground state hiring, voter-targeting efforts, and super PAC fundraising.

Those close to the campaign insisted on anonymity because they were not authorized to discuss the campaign publicly.

Trump turned his fondness for competition into ratings gold with his television show “The Apprentice,” where rival teams battled against each other to impress the boss. Those who failed were unceremoniously fired—a made-for-television version of events that sometimes played out in Trump’s real businesses.

In 1985 and 1986, Trump acquired full control of two Atlantic City casinos in quick succession. Ivana Trump was put in charge of one, named Trump Castle, while the other—Trump Plaza—was overseen by casino managers hired away from gambling titan Steve Wynn.

Castle and Plaza managers were expected to compete over everything from casino entertainers to which property bought more copies of Trump’s autobiography, “The Art of the Deal.”

The most heated competition of all: which casino could draw the high-rolling gamblers who would wager thousands of dollars per hand. By 1987, the larger and more luxurious Plaza was successfully wooing this small but elite set, aided by top-tier prize fights in the Atlantic City Convention Center next door.

Instead of allowing the Plaza to establish itself as the unrivaled venue for high-rollers in Atlantic City, however, Trump underwrote Ivana’s campaign to compete for them.

“If we presented a $100,000 player with a gold Rolex watch, the Castle gave him two,” O’Donnell wrote in his book “Trumped! The Inside Story of the Real Donald Trump — His Cunning Rise and Spectacular Fall.” In a 1997 interview, Trump said “the stuff O’Donnell wrote about me is probably true,” using an expletive to describe his former executive as a loser.

When Plaza managers pleaded to Trump that the competition between his two casinos was ill-advised, Trump mocked them.

“What are you worried about Ivana for,” he told one executive, according to O’Donnell’s book. “She’s just a woman. She can’t take the business.”

The competition described by O’Donnell led to an ill-advised, $70 million addition to Trump Castle, dubbed “The Crystal Tower,” and continued even after Trump sent Ivana back to New York and three of the Plaza’s top executives died in a helicopter crash.

Within weeks of the accident, Trump’s Castle team launched a surprise raid on Trump’s other casino: It’s top executive leased office space directly above the Plaza’s marketing department, offering the Plaza team raises of up to 30% to defect.

About the Author
By The Associated Press
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
  • Future 50
  • World’s Most Admired Companies
  • See All Rankings
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
  • Editorial Calendar
  • Press Center
  • Work At Fortune
  • Diversity And Inclusion
  • Terms And Conditions
  • Site Map
  • About Us
  • Editorial Calendar
  • Press Center
  • Work At Fortune
  • Diversity And Inclusion
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • Pinterest icon

Latest in Leadership

People protesting against tax giants.
PoliticsTaxes
How a free tax filing system from the government went from 296,000 users to zero in just one year
By Catherina GioinoApril 15, 2026
8 minutes ago
Boss has lunch with her workers outside
Successcompany culture
A $24 billion Dutch lender is cutting its workforce—and to get the remaining staff on board, the CEO is having sandwiches with them
By Emma BurleighApril 15, 2026
3 hours ago
Sal Khan
SuccessEducation
This CEO has teamed up with Google, Microsoft, and McKinsey to build an AI degree that could rival Harvard—and it will only cost $10,000 to attend
By Preston ForeApril 15, 2026
3 hours ago
Why insurance giant Travelers’ CTO is placing fewer, bigger bets on AI
NewslettersCIO Intelligence
Why insurance giant Travelers’ CTO is placing fewer, bigger bets on AI
By John KellApril 15, 2026
3 hours ago
horowitz
AIdisruption
a16z’s Ben Horowitz sees ‘AI anxiety’ consuming Silicon Valley founders. Workers’ fear of something else is killing adoption
By Nick LichtenbergApril 15, 2026
3 hours ago
Jeff Bezos pledged $10 billion for climate change. With the 2030 clock ticking, his wife, Lauren Sánchez Bezos, is leading the charge to spend it
EnvironmentJeff Bezos
Jeff Bezos pledged $10 billion for climate change. With the 2030 clock ticking, his wife, Lauren Sánchez Bezos, is leading the charge to spend it
By Sydney LakeApril 15, 2026
4 hours ago

Most Popular

Billionaire philanthropist MacKenzie Scott has donated again—a week after gifting millions to a college, she's just given $70 million to Meals on Wheels America
Success
Billionaire philanthropist MacKenzie Scott has donated again—a week after gifting millions to a college, she's just given $70 million to Meals on Wheels America
By Fortune EditorsApril 13, 2026
2 days ago
Retirees are facing a $345,000 bill they never saw coming — and most aren't prepared
Commentary
Retirees are facing a $345,000 bill they never saw coming — and most aren't prepared
By Fortune EditorsApril 14, 2026
1 day ago
Palantir CEO says working at his $316 billion software company is better than a degree from Harvard or Yale: ‘No one cares about the other stuff’
Success
Palantir CEO says working at his $316 billion software company is better than a degree from Harvard or Yale: ‘No one cares about the other stuff’
By Fortune EditorsApril 14, 2026
1 day ago
Warren Buffett’s first tax return showed $7 owed to the IRS. The then paperboy and former Berkshire Hathaway CEO is now worth $143 billion
Success
Warren Buffett’s first tax return showed $7 owed to the IRS. The then paperboy and former Berkshire Hathaway CEO is now worth $143 billion
By Fortune EditorsApril 14, 2026
1 day ago
Anthropic is facing a wave of user backlash over reports of performance issues with its Claude AI chatbot
AI
Anthropic is facing a wave of user backlash over reports of performance issues with its Claude AI chatbot
By Fortune EditorsApril 14, 2026
1 day ago
He was coding at 12 like Elon Musk and became one of Google’s youngest-ever CMOs—but now says Gen Z is better off ice skating than learning to code
Success
He was coding at 12 like Elon Musk and became one of Google’s youngest-ever CMOs—but now says Gen Z is better off ice skating than learning to code
By Fortune EditorsApril 14, 2026
1 day 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.