Donald Trump Will See You in Court
Donald Trump Will See You in Court
April 25, 2016

Donald Trump, who earned billions plastering his name on hotels and neckties, golf courses and steaks, portrays his career as an unrivaled winning streak that not only made him rich, but adored. As president, he says he’d use those same skills to cut good deals for the American people, too.

In reality, not all of Trump’s customers and business partners have come away praising his name, or his brand. Since 2000, Trump has been sued 72 times in federal court, more than some of his high-profile peers, in cases both serious and frivolous. Casino magnates Stephen Wynn and Sheldon Adelson have been named in 20 and 11 federal suits during that time, respectively. Real estate developer Richard LeFrak has been named in one case.

Trump gets sued simply because “he’s a tremendously successful business person who speaks his mind and doesn’t easily cave to threats and litigation,” said Alan Garten, general counsel for the Trump Organization.

The 72 cases count only federal lawsuits against Trump himself, not those filed against his companies. Include them—along with the many lawsuits Trump and his businesses have filed against others—and altogether Trump and his companies have either sued or been sued at least 1,300 times since 2000, a Bloomberg analysis of state and federal court filings from around the country shows. (Even that total falls short: Court documents on scores more lawsuits against Trump dating back to the 1980s are no longer readily available.)

Over 1,300 cases since 2000
Over 1,300 cases since 2000


Who sues Trump, whom does Trump sue, and why? Of the 1,300 cases Bloomberg examined, most were over mundane complaints—a casino looking to recover a gambler’s debt, a patron at one of his businesses who slipped and fell. These certainly show that Trump is a grievance magnet, but they otherwise don’t lend much insight into his legal strategy. Set those aside and you’re left with 203 notable—if not always serious—cases involving Trump and his companies (collectively, we'll refer to them as Trump's cases).

203 cases considered

Trump has been sued numerous times by unhappy condo buyers. And by Trump University students who felt they were duped. And by an actor who played the Phantom in the “Phantom of the Opera” over a canceled concert series. Trump has filed multiple lawsuits over alleged palm tree vandalism and twice sued over noise from airplanes flying near his flagship club, Mar-A-Lago in Palm Beach, Florida. He sued comedian Bill Maher over a $5-million wager. And he and his businesses have sued at least eight times to recoup royalties for licensing his name. Virtually no corner of his business has been spared from litigation.

Litigation spiked during the recession

One of Trump’s main businesses involves licensing his name to real estate developments, including hotels and condo buildings. Many of the lawsuits were filed as the U.S. fell into recession in 2008 and the real estate industry was in turmoil. At least two Trump-branded projects went under, spurring lawsuits from dissatisfied condo buyers.

Cases annually
Trump’s real estate battles

Legal battles over real estate deals make up about 45 percent of the lawsuits involving him and businesses. Many of the condo buyers who sued him said they bought units in buildings because of alleged shady sales tactics that led them to believe Trump had more at stake in the projects than just his name.

“The market crashed, like it did for a lot of other people,” Trump said in a 2011 Bloomberg interview when asked about a stalled project. “My name is on many successful deals.”

Among the more prominent real estate cases are multiple lawsuits against Trump over a failed resort in Mexico that bore his name. Approximately 200 people sued in a group case in 2009 to recover as much as $13 million in total deposits they made on condos in the Trump Ocean Resort Baja Mexico, a luxury beach-front property near Tijuana that was planned but never built. Trump settled his part of the case for an undisclosed amount.

Trump golf courses and resorts

Trump’s golf courses and resorts, particularly his Mar-A-Lago club, the 17-acre Florida estate he turned into a lavish private club, are among his most prized possessions. And he often goes to court over them. In addition to the airplane noise suits, he also sued the town of Palm Beach for fines he incurred when he installed an 80-foot flagpole on the club’s front lawn.

“The flag is not going anywhere,” he told the New York Daily News in November 2006, shortly before filing the lawsuit in January 2007, when town fines had reached $120,000. “And that’s final.”

Trump settled the case, agreeing to replace the flagpole with a shorter one and to move it.

He also sued neighbors of his Doral golf course in Florida, accusing them of vandalizing “aesthetically pleasing and expensive” palm trees and other plants he installed on the edge of the property, blocking their view of the course. Five cases are still pending.

Campaign lawsuits

Trump has been involved in at least three suits stemming from his campaign for president, which include one over protests in front of Trump Tower. A spokeswoman for the Trump campaign did not respond to requests to comment.

Labor disputes

Trump has been sued a handful of times over employment practices, with plaintiffs citing alleged discrimination. This includes a case where a Mar-A-Lago chef claimed he was fired in favor of someone younger. Trump said he was fired for being a “terrible” chef. Trump settled the case.

Licensing deals gone wrong

Trump will gladly affix his name to a number of products, but Trump will go to court if he feels the terms of a deal aren’t met. An unusual licensing case involved a Trump University student who sought to market on Trump's TV show, “The Apprentice.” Trump sued over the name, and the case ended in a settlement with the student agreeing not to use Trump’s name.

Bankrupt casinos

Trump’s former casinos in Atlantic City, including Trump Taj Mahal, filed for bankruptcy in 2004 and 2009. As a candidate for president, Trump’s opponents have suggested that the bankruptcies are indicative of a reckless businessman. He defends them as a common business practice, and has said he was smart to take advantage of corporate bankruptcy law.

Suing beauty contestants

Trump has filed multiple suits over the Miss Universe pageants, which he no longer co-owns. In one case, a contestant, Sheena Monnin, said in a Facebook post and on the “Today” show that she thought the Miss USA contest was fixed, and said that the organization was “in many ways trashy.” Trump sued, and countered Monnin on “Good Morning America,” saying she suffered from “loser’s remorse.” Trump won the case.

Trump also recently settled another case filed against Univision, which decided not to broadcast the pageant after Trump called illegal Mexican immigrants criminals and rapists.

Trump University

Trump is currently facing a series of lawsuits over Trump University, in which he’s accused of misleading marketing practices for real estate seminars. Students said they paid as much as $34,995 for the program that was pitched as an apprenticeship led by Trump’s handpicked experts. The venture was a scam, according to a suit by New York Attorney General Eric Schneiderman. Trump says they were legitimate courses and students raved about them.

Case types
What can we learn from Trump’s many legal clashes? He gets sued far more often than he sues.

Trump and his companies have been the defendant in almost 70 percent of the 203 cases Bloomberg analyzed.

“When you have the name recognition that he has, there is always going to be someone gunning for you,” Garten said.

Plaintiff / Defendant
Trump settles cases. A lot.

One of Trump’s signature lines in campaign speeches is that he doesn’t get sued a lot, because he rarely settles. But, in fact, he settles many lawsuits. Of the cases in which the outcome is on the public record, 59 have been settled, or 35 percent. He was sued in 36 of those 59 cases. An additional 23 cases were withdrawn by both parties (he was the defendant in 21 of these cases). While the terms of those cases aren’t public, a withdrawal often indicates that the parties settled outside of court.

Some settlements were resolved with “other people's money,” including cases where a project's developer paid legal claims, Garten said.

When Trump loses, it’s often when he goes after someone else.

Trump has lost in court 19 times. In 10 of those cases, Trump or his companies were the plaintiff.

But when he wins, someone was usually coming after him.

In general, Trump can hang his ‘Make America Great Again’ hat on his success rate in the courtroom. He and his companies won in 42 cases, compared to the 19 he lost. And in those wins, he usually deflected a challenge from someone else. He was a defendant in 33 of those 42 wins.

“Mr. Trump is without question an aggressive business person who is willing to stand up for what he believes in,” Garten said. “He’s not willing to walk away or cave when someone is trying to take advantage of him.”

You may or may not want to see Donald Trump in the White House, but you sure don’t want to see him in court.

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