A third of Republicans support Donald Trump.
Photograph by Scott Olson — Getty Images

Long before he was on the political stage, the real estate mogul spent plenty of time in another contentious arena—the court room.

By Ben Geier
August 14, 2015

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

Donald Trump, August 1987, New York City
Photograph 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
Photograph by Charles Rex Arbogast — AP

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
Photograph by The LIFE Picture Collection/Getty Images

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)
Photograph 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.
Photograph by Scott Olson — Getty Images

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.

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