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

My copy of the book.

Far from being an autopsy, Maggie Haberman’s 2022 book about Donald Trump, Confidence Man: The Making of Donald Trump and the Breaking of America, is more an origin story of not just how Donald Trump came to hold the most powerful job in the world, but of those along the way who toiled the American cultural and political soil to make it manifest.

I’ve avoided the myriad Trump books coming out, both amid his presidency and in the aftermath — primarily because I don’t have much interest in what I was already closely following in real time — but when I saw Maggie had a book about Trump coming out, I knew I was going to read it. She was the indispensable New York Times White House reporter during the Trump years, partly owing to her time covering Trump prior to his candidacy announcement in 2015 (she followed him to New Hampshire, for example, when he was considering a presidential run in 2011), meaning she understood Trump and the New York City milieu he came out of better than most other reporters, and partly owing to her dogged fearlessness as a reporter. Through the Trump years, Maggie faced harsh criticism from both sides: Trump and Republicans who thought she was a Clinton ally and emblematic of the “fake news” mainstream media, and Democratic pundits and activists who viewed Maggie as soft-peddling Trump’s views (and concealing others) in order to continue gaining “access” to him. The former isn’t even worth addressing in any serious way; as for the latter, Maggie had access to Trump, I think, because Trump was familiar with her prior to 2015 and so, he’s a moron who thought he could flatter his way through an interview, even with someone like Maggie. But also, Maggie’s so-called “access journalism” broke newsworthy stories again and again concerning the Trump White House.

But this isn’t a book about Maggie — although I sensed a level of self-reflection, self-deprecation and an almost you’d-miss-it-if-you-weren’t-paying attention dry humor peppered through the book I appreciated — it is about Donald Trump, who for more than four decades managed to project his way to success, or in one of understanding Trump’s thinking, “positive think” his way to success. From his burgeoning days as a scion of one of New York City’s real estate families under the tyrannical and demanding shadow of his father, Fred Trump, Trump preoccupied himself more with the appearance of success, branding and marketing rather than anything of actual substantive success. Importantly, though, to achieve that, he a.) needed his father’s help in money and connections to the inner workings of New York City government and politics, but crucially with people thinking he didn’t need his father’s help, i.e., that he was self-made; and b.) needed the help of the aforementioned government relationships his father or he cajoled or bullied into reality, but again, with people thinking he was self-made all the way rather than another crony capitalist businessman.

His management style reflected his penchant for branding over substance: He blustered (bullying is another word one could use) his way through things he didn’t know and his Trump Organization operated more like Trump Disorganization, as one individual referred to it back then. And when he would fall into financial troubles only a few years before his father would succumb to Alzheimer’s in the early 1990s, Fred was back again to bail him out, as were some choice banks.

The throughline in all of Trump’s dealings, with government regulators and lawmakers, with competitors and consumers, with bankers and his own family members, was to be the “Confidence Man,” even if he had no idea how to actually run a profitable casino, or Cold War politics, or how to exist within a successful marriage that didn’t end with him having an affair and turning the affair into more publicity.

Maggie’s book is brilliant in laying out the above case and showing how everything Trump was and tried to be in the 1970s and 1980s continued into the 1990s, the early 2000s and despite a few start-and-stop flirtations with running for office, finally culminated with his bid for the presidency in 2016 and his shocking win. And then, once he was in office, how he continued to operate as if he was still in 1970s New York City running his namesake organization. He’s not a man who has changed, or was cowed or humbled by the office of the presidency, in terms of his comportment or management style — at his most basic level, Trump is still that ego-driven, insecure boy seeking approval from his domineering father, it’s just now, the wider public are surrogates for his father; and I’m not trying to be an armchair psychologist, only that it is clear throughout his life, Trump has sought external validation in everything he does and only cares about himself in order to achieve it — the only thing one can say that changed with Trump are some of his more Democratic-leaning perspectives he voiced in prior years (and donated money toward candidates who espoused similarly) because he understood the direction the Republican Party was moving in the 2010s and he capitalized on it as yet another branding opportunity. That is, he attached his name to the rising anti-elite, nativist and populist attitudes overtaking the base of the Republican Party, primarily, but not only, as a reactionary movement against the first black president, Barack Obama.

Trump never cared about policy, even one of his most identifiable policy positions of building a wall on the Southern border only made sense to him because he connected with it on the fundamental level of being a “builder,” but he didn’t care about any of the nuances and complexities around immigration. He never cared about functionally being president, only that he was president as another vehicle for fame and fortune. From New York City and New Jersey to Washington D.C. over the last four decades, that has always been the motivating factor for Trump: what pushes the brand forward.

When Trump doesn’t get his way, such as unfavorable press coverage in the 1980s about his business endeavors or his Forbes financial listing and 2017 when [insert myriad Trump administration scandals], or when he loses a parcel of land he sought as a real estate developer and loses the 2020 presidential election to Joe Biden (or the Republican Iowa Caucus to Ted Cruz), Trump’s responses have always been the same: 1.) Lash out and portray himself as the victim, even if the result was his fault; 2.) Threaten and bully the people he thinks are responsible, up to and including his vice president Mike Pence; and 3.) Seek to sue the person or persons responsible. If there is another major throughline of the book (and there are many), it is that Trump is one of the most litigious Americans in the latter half century. To think of how many cases have been tied up in the courts, the wasted dollars and manhours, especially in the last seven years, because of Trump’s frivolous lawsuits is nothing short of astounding. And especially from the 1980s through to the early 2010s, he knew exactly what he was doing: Wasting the time and money of the person he sued, exhausting them into submission.

But one cannot extricate the story of Donald Trump from the story of America itself and that is the reason Maggie’s subtitle’s second half reads “the breaking of America.” American culture has always been rather fond of celebrities, especially the myth-making around masculine, self-made rich men. Donald Trump is not masculine, not self-made and he greatly exaggerates his riches, but that didn’t detract from the myth-making. That myth-making reached its zenith with the advent and popularization of his NBC show The Apprentice. What is particularly funny about the myth-making around the show, with many to choose from, is that Trump is famously adverse to interpersonal conflict (he’s an appeaser when faced with conflict just to survive the confrontation) and yet, he was known for “firing” people due to the show. Again, it was a faux-projection of toughness and masculinity. That boardroom toughness also extended to the so-called “locker room” talk with the Access Hollywood tape, Trump’s exploits with Marla Maples, and of course, the Stormy Daniels affair. Which, I must admit, so much happened during the Trump campaign for president and his actual time in office that I had actually forgotten about the Daniels scandal until Maggie talked about it in the book. In fact, when considering a run for office, Trump was most worried about the women in his life being uncovered. Alas, none of it mattered. Because as one cannot extricate an American culture that venerated celebrity from the making of Donald Trump, and one likewise cannot extricate an American culture that looked the other way when powerful men used their positions of power to sexually assault and harass women from the making of Donald Trump. Not only was Donald Trump a Frankenstein creature of such a culture, but it also, obviously, said something about the state of the political culture specifically in the United States that something like the Access Hollywood tape, which would have been disqualifying for a politician of any kind, much less the presidency, not even one election cycle prior, was not an impediment at all. He won the presidency, myriad warts and all. If anything, the “warts” were celebrated among the most hardcore of Trump’s base; they were part of the appeal!

Politically, I feel it is perhaps almost forgotten about that Trump began his rise in Republican politics based on birtherism, i.e., alleging that the first black president of the United States wasn’t actually born in the United States. Again, in a vacuum, that is abhorrent on its own and a reflection of Trump’s lack of character, but within the context of the American right, it also reflects something rotten that such a fringe belief was able to herald its purveyor into the mainstream. I also believe that Trump purposefully avoided running in 2012 because he didn’t want to run directly opposite Barack Obama. He knew he would be outmatched by him, whereas he felt he could take on Hillary Clinton in 2016 because she was a woman and a Clinton at that.

Perhaps the biggest paradox about Trump is that he seems by all accounts the most transparent human being who has ever been in the human eye. He seems easy to figure out, and allies and dictators the world over alike figured him out, too, to flatter him and cajole him to get what they wanted, as one example. But as Maggie ends her book noting, Trump is actually an opaque person, in that nobody really knows who he is. She alluded throughout the book that Trump is a deeply lonely person and I think that tracks alongside the idea of him perpetually seeking external validation. His opaqueness stems from the fact that Trump can say something like “there are very fine people on both sides” in regards to what happened in Charlottesville, and both sides, as well as those ostensibly in the middle, can hear it differently. Transparency isn’t tantamount to Trump being the “leaker-in-chief,” as Maggie calls it at one point; or to put it a different way, Trump isn’t the “most transparent president ever” because he regularly took questions from the media or was a leaker for his own purposes. Transparency isn’t treating the world stage both in grandiose measure and intimate measure as a therapist’s couch; transparency is letting people behind the work, behind the persona. Trump doesn’t do that. There is a thought in professional wrestling, of which Maggie rightly uses that analogy with Trump a few times in the book, that some wrestlers are always working the marks and as such, are unreliable narrators. Trump is that. He’s never not working the marks. Sometimes you have to wonder if Trump is a mark to himself (another thought in professional wrestling is the wrestler working themselves into a shoot, as in, believing their own hype).

I devoured Maggie’s book over the last three days because it is exceedingly readable and punchy in a way that doesn’t make her long trek through Trump’s life coming up in Queens to the Oval Office laborious because she is connecting the dots of what “made” him. I also think her book will rightly go down as an important record of one of the most consequential men in modern American history. To understand how we reached the brink of American democracy and a failed peaceful transition of power on Jan. 6, 2021, one must read Maggie’s book, not only to see how Trump was made, but to understand the American cauldron he came out of.

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