Book Review: "Confidence Man: The Making of Donald Trump and the Breaking of America"

Maggie Haberman's book is a not particularly insightful, or unique, look at Donald Trump.

For a while during the darkest days of the Trump administration, I read every book I could get my hands on. I had a seemingly insatiable appetite for any sort of scandal-mongering account. It was as if I wanted to find some account which would provide a Rosetta Stone into how it was possible for such a madman to have control of our federal government…or perhaps I simply wanted to relish the sight of such obvious dysfunction, as if doing so would vindicate my revulsion for the man and everything he stood for.  

Then the 2020 election happened, and Trump was cast out into the political abyss (or so it seemed at the time). After that, my desire to read about him plummeted. After four years, I’d found that my appetite for insider accounts and gossip-laden tomes had been well and fully sated. And, unlike many in the political establishment, who have bemoaned the lack of books about the Biden Administration, I actually find it refreshing to have a man in the Oval Office who knows that the true role of a president is not to be in the limelight but instead to do the hard (if often unglamorous) work that we elected him to do.

Which is why, when I saw that the New York Times’ Maggie Haberman had a new book coming out that promised to be a tell-all volume about Trump the man and the political figure, I had some major reservations about whether I even wanted to read it. However, I am nothing if not consistent, and so I decided that I should give it a read, if for no other reason than that it might be the last book on Donald J. Trump and his hellish administration that I will ever force myself to read. 

In these pages, Trump emerges as a man quite thoroughly shaped by the New York City of his youth, one in which money–or at least the appearance of it–was the way to gaining political power and clout. Moreover, he was also formed by his father, Fred, and not just because he repeatedly did everything in his power to tear his son down and attempt to build him up in his own image. Given this toxic domestic and urban environment, it’s no wonder Trump grew into a man who believed that his own will was all that mattered, that all people, no matter their position or importance, are nothing more than things to be used. 

It’s often been said that Trump is a self-made man, and there is at least a glimmer of truth to that assessment, at least as Haberman tells it. He was able to leverage his name even when his own finances were in shambles, gambling (correctly) that many banks would bail him out simply because it was too expensive to do otherwise. Thus, through simple hubris and the complacency of others (who often went out of their way to mock him) Trump slowly but surely clawed his way into dominance, and he was able to further leverage his name, and his chameleon-like politics, to score a political and presidential win. 

Beneath it all, however, there was a yawning emptiness. As has been the case with almost every other person who has tried to profile Trump, Haberman sometimes struggles to give us a rich psychological depth, some missing piece of the puzzle that might help us make sense of the madman who very nearly upended the US constitutional order and initiated a true dictatorship. To some degree, this isn’t her fault, because almost every other person who has written a similar account has hit the same wall. The bottom line seems to be this: Trump is a narcissist and a cypher. He lacks almost all interiority (and, by extension, loyalty to anyone but himself), and this is what makes him so fascinating and so desperately dangerous. 

Those looking for more insight into the workings of the Trump presidency will not find much new in Confidence Man. In fact, the later parts of the book start to drag a bit, because we’ve already read so much of Haberman’s coverage of the Trump White House (to say nothing of the legions of other reporters who have already published tell-all books, most notably Bob Woodward). 

Nevertheless, at the end of the day, I do feel at least moderately rewarded for having read this book. Yes, she deserved the criticism she received when it was revealed that she did not reveal to the public Trump’s explicit statement that he had no intention of leaving the White House, even if he lost the election to Joe Biden. To my mind, though, the paradox of Confidence Man, and indeed any book that attempts to fully makes sense of Trump as a person and as a phenomenon, is simply this: no one book could ever hope to capture the full complexity of who Trump is and what he means to so many millions of Americans, some of whom continue to worship at his altar (even if, as seems to be the case, his political clout has begun to wane).

 At the same time, the utter vacuousness of the man, the lack of anything truly substantive to his psychology, means that Haberman’s book ends up falling somewhat flat. When it comes right down to it, I’m not entirely sure that there really is that much more to learn about Trump as either a man or a political figure, particularly in the aftermath of the recent midterm elections. Ultimately, books like Confidence Man show us much more about the state of contemporary political journalism than they do about the Trump phenomenon or America more broadly.

As vainglorious and fame-seeking as Trump is, he’s matched in that regard by Haberman herself, who ultimately becomes as much a character–and an enabler–of Trump as any of the cronies in the White House or at Mar-a-Lago. While I didn’t hate Confidence Man as much as I expected to, nor can I say that I would recommend it.