The Miss Pennsylvania lawsuit wasn't the first time that Trump had experienced drama related to a beauty contest. In 2006, a vitriolic exchange erupted between the business magnate and talk show host Rosie O'Donnell, who likened Trump to a "snake-oil salesman" after he declined to dismiss Miss USA Tara Conner for her alleged substance abuse.
When Trump heard that O'Donnell -- whom he's dubbed "a real loser" -- had called his financial security into question, he threatened to sue her. Trump told People magazine: "You can't make false statements" and "Rosie will rue the words she said."
He never sued.
NEXT: Lawrence O'Donnell