Inside Some of Donald Trump’s Most Expensive Lawsuits

Over the decades, Donald Trump has used the legal system to get what he wants. 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 some of his biggest, most expensive lawsuits, including Trump’s huge legal battle involving his educational program (page 9).

1. She lost Miss USA and lost to Trump

Miss Pennsylvania Sheena Monnin competes in the Miss USA Pageant.

Miss Pennsylvania didn’t know she’d spend the rest of her 20s fighting Donald Trump. | YouTube

  • What happened: Trump sued a former contestant.
  • How much: $10 million

In 2012, Miss USA contestant Sheena Monnin resigned from her role as Miss Pennsylvania and took to Facebook, claiming the pageant was rigged. Trump responded on Good Morning America. “[Monnin] suffers from a thing called loser’s remorse,” he said. “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 Trump 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, Monnin filed a malpractice suit against her former lawyer. Although the details of the settlement are protected, she will not have to pay Trump any money.

Next: Who knew the American flag could cause so much trouble?

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