Cover of Trump Nation by Timothy O'Brien
1. Too Famous?
In January 2006, Trump filed a $5 billion lawsuit against author Timothy O'Brien and his publisher for understating Trump's wealth. In his book Trump Nation, O'Brien reported that three people close to Trump had estimated his worth at between $150 and $250 million. Trump, who said he had told O'Brien that he was worth between $4 billion and $6 billion, claimed that O'Brien's low estimate had hurt his reputation and cost him specific business deals. Trump's suit was dismissed in July 2009, and his subsequent appeal failed in September 2011. "Essentially the judge just said 'Trump is too famous,'" Trump told Atlantic author William D. Cohan. " 'He's so famous that you're allowed to say anything you want about him.' Well, I disagree with that."
Miss USA competition photo
2. 'A Beautiful Young Woman Who Had Sour Grapes'
At the end of 2012, Miss USA contestant Sheena Monnin told the Pittsburgh Tribune-Review that she was "shocked" by an order to pay Donald Trump's company $5 million in damages. Monnin had claimed on her Facebook page that the pageant was "fraudlent," "trashy," and "rigged," because the five finalists were determined in advance of the pageant itself. The Miss Universe Organization -- which Trump owns in partnership with NBC Universal -- filed a suit, and won an arbitration award, against Monnin, and Trump himself called her "a beautiful young woman who had sour grapes because she wasn't a top-16 finalist." (Monnin notes that the ruling has not been confirmed by the court, and that her lawyers have submitted arguments for vacating the arbitration decision.)