Over the decades, Donald Trump has used the legal system to get what he wants. But that doesn’t mean things turn out in his favor. According to USA Today, Trump has been involved in at least “3,500 legal actions in federal and state courts during the past three decades. They range from skirmishes with casino patrons to million-dollar real estate suits to personal defamation lawsuits.” And these don’t even count the suits levied against Trump since his presidency.
There’s simply too much to review, so we chose 18 of his biggest, most expensive lawsuits, including Trump’s huge legal battle involving his educational program (page 9).
1. Trump vs. Miss USA contestant (2012)
- What happened: Trump sued a former contestant.
- How much: $10 million
In 2012, former Miss USA contestant Sheena Monnin resigned from her role as Miss Pennsylvania and then took to Facebook, claiming the pageant was rigged. Shortly after, Trump appeared on Good Morning America and said, “[Monnin] suffers from a thing called loser’s remorse.” He went on to say, “She lost, and if you looked at her compared to people who were in the top 15, you would understand why she was not in the top 15.” A couple days later he sued her.
Strapped by student loans and living expenses, Monnin spent the rest of her 20s trying to pay for the legal fees necessary to defend herself. The court eventually ruled that she pay $5 million for defamation, which she could not afford. In 2013, she filed a malpractice suit against her former lawyer. Although the details of the settlement are protected, Monnin will not have to pay Trump any money.
Next: Who knew the American flag could cause so much trouble?