Written by New York Times reporter Maggie Haberman, Confidence Man: The Making of Donald Trump and The Breaking of America examines the life and career of real estate mogul Donald Trump and his rise to the United States presidency. Having covered Trump for over 20 years through a variety of publications, it would be safe to say that Haberman knows more about the one-term President than just about any other journalist, making her the perfect person to write so expansive an exploration of Trump.
This would be the fourth book I’ve read detailing the Trump presidency (no, I’m not sure why I’m doing this to myself either). While I initially did not have an appetite for more literature written about the 45th President beyond Bob Woodward’s trilogy, this one got me with the promise of shining a light on Trump’s upbringing and his life prior to announcing his intentions to run for President in 2015.
Before he was thrust into politics, I knew very little about Trump other than his appearance in Home Alone 2, his wildly popular TV show, and his sporadic appearances in WWF/WWE over the years. So getting a blow-by-blow account of his formative years was something that piqued my interest.
With Confidence Man, Maggie Haberman’s intention is to unearth an explanation as to why Trump is the way he is by looking at how Trump largely getting what he wanted throughout his life made him narcissistic, irrational, impossible to work with, and hopelessly inept for the job at hand when he was elected President in 2016.
If like me, you followed his presidency closely in real time or read any of the Woodward books, there isn’t much new here with regards to the last seven years, but what really shines is the first half showcasing his pre-political life that highlights his questionable business practices. Haberman gets into the weeds by showing Trump’s seemingly unending quest to be embraced and loved by the public despite his abhorrent behavior at every turn.
A classic narcissist throughout his life, Trump feels like he’s the best of us and is owed this adulation, so any time he doesn’t get his way, he tries to completely annihilate his detractors and bury the truth over and over again. Throughout the book, Haberman goes through the countless court cases and persistent legal threats Trump levies against anyone who stands in his way. The man is obsessed with image and celebrity despite framing himself as a man of the people, a blatantly obvious con that for some reason seems to trick so many into supporting him.
If you’re looking for a book that constructs a framework of Donald Trump’s personality and actions, I can’t imagine a better read than Confidence Man. While the Woodward books are about as deep a dive you’re going to get into the minute by minute actions of the Trump administration, Confidence Man paints a more complete overall image of the man himself.