Trump vs. Rosie O'Donnell
Trump has long traded barbs with Rosie O'Donnell. In 2006, O'Donnell accused Trump of being a "snake-oil salesman."
"Rosie's a loser, a real loser," Trump responded, threatening to sue her. "I look forward to taking lots of money from my nice fat little Rosie," he told People.
Years later, when O'Donnell announced her engagement to Michele Rounds, Trump lashed out on Twitter. "I feel sorry for Rosie's new partner in love whose parents are devastated at the thought of their daughter being with @Rosie--a true loser," Trump tweeted. Although the two made nice briefly after O'Donnell suffered a heart attack, their public spats continue to this day.