Timothy O’Brien

Timothy O'Brien, award-winning author, 2005 book, "TrumpNation: The Art of Being the Donald".
In TrumpNation, O’Brien said “three people with direct knowledge of Donald’s finances” estimated his wealth was “somewhere between $150 million and $250 million.” TrumpNation also cited Trump's own personal estimate of $1.7 billion to $9.5 billion.(1)

Trump sued O'Brien for $5 billion in damages for libel.(1) Discussed during the litigation was a Deutsch Bank 2005 estimate of Trump's net worth of $788 million.(2) In 2009, the judge dismissed the case. Trump appealed. Two years later, a three-judge panel affirmed the judge's decision.(1)

"There are parts of him that I really like", but, “he’s essentially a name-caller and a bully and a sort of P. T. Barnum of the modern era. . . . People who are really comfortable with who they are and what they’re worth don’t need to strong-arm people.”(1)
(1) http://www.nationalreview.com/donald-trump-tim-obrien-courtroom-story
(2) https://www.bloomberg.com/view/articles/2016-05-20/trump-s-financial-report-that-s-rich

Trump says "'I’m a great deal-maker.' And then the reality, the objective reality, is that he’s been a horrible deal-maker. His career is littered with bad deals."
http://www.politico.com/2016/04