• 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

Karen Carter
C-SuiteFortune 500 Power Moves
Fortune 500 Power Moves: Which executives gained and lost power this week
By Fortune EditorsApril 17, 2026
32 minutes ago
The power has swung back to employers—and workers are paying for it in benefits, flexibility, and leverage
Workplace Culturecompany culture
The power has swung back to employers—and workers are paying for it in benefits, flexibility, and leverage
By Marco Quiroz-GutierrezApril 17, 2026
2 hours ago
Jack Dorsey, the CEO of Block
SuccessLayoffs
Twitter cofounder Jack Dorsey breaks down his thought process when he laid off 40% of his Block staff because of AI
By Emma BurleighApril 17, 2026
3 hours ago
She learned accounting before she was a teenager. Now she’s bringing Wall Street to the blockchain
NewslettersMPW Daily
She learned accounting before she was a teenager. Now she’s bringing Wall Street to the blockchain
By Sheryl EstradaApril 17, 2026
4 hours ago
Pope Leo XIV waves
SuccessWealth
Pope Leo warned the world is in ‘big trouble’ if Elon Musk becomes the first trillionaire
By Preston ForeApril 17, 2026
9 hours ago
The first wave of bank earnings shows why ‘resilience’ is Wall Street’s favorite word
NewslettersCEO Daily
The first wave of bank earnings shows why ‘resilience’ is Wall Street’s favorite word
By Diane BradyApril 17, 2026
10 hours ago

Most Popular

A world going broke: IMF says America's $39 trillion national debt is actually a global problem—and AI may be the only rescue
Economy
A world going broke: IMF says America's $39 trillion national debt is actually a global problem—and AI may be the only rescue
By Nick LichtenbergApril 16, 2026
23 hours ago
Pope Leo warned the world is in ‘big trouble’ if Elon Musk becomes the first trillionaire
Success
Pope Leo warned the world is in ‘big trouble’ if Elon Musk becomes the first trillionaire
By Preston ForeApril 17, 2026
9 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
Environment
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
2 days ago
MacKenzie Scott is bypassing the Ivy League and rewriting the $79 billion higher ed playbook by giving to HBCUs and community colleges
Politics
MacKenzie Scott is bypassing the Ivy League and rewriting the $79 billion higher ed playbook by giving to HBCUs and community colleges
By Sydney LakeApril 16, 2026
1 day ago
Germany already told its workers to ditch four-day weeks and work-life balance. Now the government wants to cut their pay for calling in sick, too
Success
Germany already told its workers to ditch four-day weeks and work-life balance. Now the government wants to cut their pay for calling in sick, too
By Orianna Rosa RoyleApril 16, 2026
1 day ago
Current price of oil as of April 16, 2026
Personal Finance
Current price of oil as of April 16, 2026
By Joseph HostetlerApril 16, 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.