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

Trendingnow

1

As Big Tech showers employees with perks to win the talent war, Nvidia built a nearly $5 trillion company by making people pay for their own lunch

2

Mark Zuckerberg feeds his cows macadamia nuts and beer to create the 'highest-quality beef in the world' on his $300 million estate in Hawaii

3

MacKenzie Scott alone accounted for one-third of America's $19.2 billion in megagifts last year

1

As Big Tech showers employees with perks to win the talent war, Nvidia built a nearly $5 trillion company by making people pay for their own lunch

2

Mark Zuckerberg feeds his cows macadamia nuts and beer to create the 'highest-quality beef in the world' on his $300 million estate in Hawaii

3

MacKenzie Scott alone accounted for one-third of America's $19.2 billion in megagifts last year
LeadershipDonald Trump

5 of Donald Trump’s craziest lawsuits

By
Ben Geier
Ben Geier
Down Arrow Button Icon
By
Ben Geier
Ben Geier
Down Arrow Button Icon
August 14, 2015, 1:11 PM ET
Republican Presidential Candidates Address 2015 Family Leadership Summit
Republican presidential hopeful businessman Donald Trump fields questions at The Family Leadership Summit at Stephens Auditorium on July 18, 2015 in Ames, Iowa. Photograph by Scott Olson — Getty Images
Add Fortune on Google for similar content.

Right now, Donald Trump is in the thick of the race to be the Republican Party’s presidential nominee, and despite all of the distractions—allegations of sexism against Fox News anchor Megyn Kelly, dust-ups with other candidates, getting into a spat with Senator John McCain—he is still leading in national polls.

Long before he was on the political stage, though, Trump spent plenty of time in another contentious arena—the court room. The Donald has filed many, many lawsuits over the years, but here are five of the strangest and most mystifying.

Trump sues Trump

NEW YORK - AUGUST 1987: Donald Trump, real estate mogul, entrepreneur, and billionare spends most of his day attending board meetings in which he manages the construction of his buildings in his offices on August 1987 in New York City. (Photo by Joe McNally/Getty Images)

In the 1980s, when Trump was in the relatively early days of his professional ascent, he sued another businessman who dared to have the same last name as him. Julius and Edmond Trump were trying to buy a chain of drug stores, and their business was called "The Trump Group." When Donald Trump found out — via a letter delivered to him that was intended for the other Trumps, according to Crain's New York Business — he went on the offensive:

A day after the letter was sent, Donald Trump’s lawyer, Roy Cohn, demanded that the Trump Group change its name by the following day or they would face consequences. A little while later, Donald Trump sued Julius and Edmond Trump in New York state court, alleging they were nothing but a pair of late-arriving immigrants trying to piggyback on his good name.

“Plaintiffs have used the Trump family name for 40 to 50 years in the New York area. More recently, the Trump Organization has come to stand for respectability and success across the United States,” the complaint read.

It went on: “The defendants are South Africans whose recent entrance in the New York area utilizing the name 'the Trump Group' can only be viewed as a poorly veiled attempt at trading on the goodwill, reputation and financial credibility of the plaintiff.”

The case took half a decade to resolve. It was eventually thrown out.

Merv Griffin

Donald Trump, left, gestures skywards as he explains the laser show and fireworks to entertainer Merv Griffin, before grand opening night of the Taj Mahal Casino Resort, in Atlantic City, N.J., on April 5, 1990. Griffin, who once owned the Taj Mahal, swapped it for the Resorts International Casino which was owned by Trump. (AP Photo)

In 1988, Trump sued Merv Griffin, talk show host and creator of game shows including "Jeopardy!" and "Wheel of Fortune." The suit stemmed from a deal over casinos in Atlantic City. Trump eventually sold his stake in the casinos to Griffin.

Trump sues Trump (Ivana this time)

Donald Trump and Ivana Trump, in 2001

Of course, some of Trump's lawsuits have been more personal. In the early '90s, he sued his ex-wife Ivana, accusing her of fraud and of breaking an agreement not to talk about their relationship, according to the Daily Beast.

Going after a Miss USA contestant

LAS VEGAS - JUNE 3: Miss Pennsylvania USA Sheena Monnin competes during the 2012 Miss USA pageant at the Planet Hollywood Resort & Casino on June 3, 2012 in Las Vegas, Nevada. (Photo by Isaac Brekken/Getty Images)

In 2012, Sheena Monnin, a contestant in the Miss USA pageant, owned by Trump, claimed that the entire contest was rigged. Trump, naturally, sued her. He called her "a beautiful young woman who had sour grapes because she wasn’t a top-15 finalist,” reports The Atlantic. This one Trump actually won. He was awarded $5 million in damages.

Trump vs. The Chicago Tribune

The Willis Tower sign.

In the 1980s, Trump had plans to build a tower in Manhattan that would be taller than the Sears (now Willis) Tower. When a writer for the Chicago Tribune expressed doubts that would happen, Trump sued the newspaper. At the time, Trump hadn't even hired an architect yet, according to the Daily Beast.

About the Author
By Ben Geier
See full bioRight Arrow Button Icon
Add Fortune on Google for similar content.

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

U.S. Treasury Secretary Scott Bessent
EconomyDebt
AI’s $2.2 trillion deficit fix is already half fake, economists say
By Tristan BoveJuly 2, 2026
9 hours ago
Mark Zuckerberg, wearing a white shirt, smiles. He is standing in front of a crowd.
SuccessMark Zuckerberg
Mark Zuckerberg feeds his cows macadamia nuts and beer to create the ‘highest-quality beef in the world’ on his $300 million estate in Hawaii
By Sasha RogelbergJuly 2, 2026
11 hours ago
Chris Hulatt co-founder of Octopus Group
SuccessHow I made my first million
A 2-year taste of the office was enough to make 3 grads quit. Now they run a $13.2 billion investment firm: ‘We didn’t want a traditional job again’
By Orianna Rosa RoyleJuly 2, 2026
12 hours ago
Woman taking photo in scenic landscape
Successlifestyle
Americans are escaping the U.S. for New Zealand where house prices have hit a new low—but only wealthy Americans with $3 million spare can invest
By Emma BurleighJuly 2, 2026
13 hours ago
Jason Lemkin
Successwork-life balance
This investor won’t back startups unless staff are in the office 6 days a week: ‘Not because I don’t have empathy, because they’re going to fail’
By Preston ForeJuly 2, 2026
13 hours ago
The true cost of Donald Trump’s $2.2 billion year
NewslettersCEO Daily
The true cost of Donald Trump’s $2.2 billion year
By Diane BradyJuly 2, 2026
18 hours ago

Most Popular

As Big Tech showers employees with perks to win the talent war, Nvidia built a nearly $5 trillion company by making people pay for their own lunch
Big Tech
As Big Tech showers employees with perks to win the talent war, Nvidia built a nearly $5 trillion company by making people pay for their own lunch
By Marco Quiroz-GutierrezJuly 1, 2026
2 days ago
Mark Zuckerberg feeds his cows macadamia nuts and beer to create the 'highest-quality beef in the world' on his $300 million estate in Hawaii
Success
Mark Zuckerberg feeds his cows macadamia nuts and beer to create the 'highest-quality beef in the world' on his $300 million estate in Hawaii
By Sasha RogelbergJuly 2, 2026
11 hours ago
MacKenzie Scott alone accounted for one-third of America's $19.2 billion in megagifts last year
Success
MacKenzie Scott alone accounted for one-third of America's $19.2 billion in megagifts last year
By Sydney LakeJune 25, 2026
8 days ago
Today, Emily Blunt is worth $80 million thanks to her Hollywood career—but she actually wanted to be a UN Spanish translator on $80K
Success
Today, Emily Blunt is worth $80 million thanks to her Hollywood career—but she actually wanted to be a UN Spanish translator on $80K
By Orianna Rosa RoyleJuly 2, 2026
21 hours ago
Americans are escaping the U.S. for New Zealand where house prices have hit a new low—but only wealthy Americans with $3 million spare can invest
Success
Americans are escaping the U.S. for New Zealand where house prices have hit a new low—but only wealthy Americans with $3 million spare can invest
By Emma BurleighJuly 2, 2026
13 hours ago
Current price of oil as of July 2, 2026
Personal Finance
Current price of oil as of July 2, 2026
By Joseph HostetlerJuly 2, 2026
14 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.