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.