Welcome to The Trump Files, an ongoing and irregular series where I read about the 45th President. With so many books out there about him, The Trump Files is a project where I’ll read the books for you and suggest if they’re worth your time or if they don’t add to the conversation.
Confidence Man - Maggie Haberman (Penguin Press, 2022)
A slippery one. Part biography, part political history, part first person account, Maggie Haberman’s book Confidence Man is a lengthy account of Donald Trump's life and presidency, but it never really figured out what kind of book it wants to be. Is it a biography? It starts that way but trails off, almost losing interest in the 1990s. Is it a behind the scenes account of the Trump years? Maybe - but then why the focus on his early years? And what about Haberman’s frequent first-person interjections, is this her memoir of covering Trump?
Haberman’s been writing for the New York Times since 2015 and previous to that, she worked for Politico and two other NYC dailies. She is someone who knows her beat of New York City well; she’s able to draw on connections and sources to build up a timeline of 1970s New York and its heated, often contentious political scene. And as part of the team covering Trump’s presidency, she won a Pulitzer Prize in 2018 and was a finalist two other times. It’s no wonder the jacket blurb from Axios reads “This is the book Trump fears most.”
But here’s the rub: Confidence Man is a book with a lot of facts and gossip, but it doesn’t add much to the conversation for longtime Trump-watchers. It lays groundwork for a damning case, but never really pulls the trigger. And throughout, Haberman occasionally slips into the first person like she’s trying to settle scores. More on that in a second.
Confidence Man is essentially split into two halves. The first is an account of Trump’s rise in New York in the 1970s and 80s, his business failings in the 1990s, and rebirth as a TV personality in the 2000s. Haberman moves briskly, but takes readers into a shadowy world of long-gone people like Roy Cohn and Ed Koch, and a insular and corrupt world where kickbacks are common, political infighting the norm, and where properties can sit undeveloped for years. But before you know it, maybe 150 pages have gone by and you’ve finished reading about the first half of Trump’s life.
When Trump was elected in 2016 it came as a shock to many. I remember pundits were saying he couldn’t win and even the self-proclaimed Dirtbag Left guys at Chapo, who made their bones by thumbing their nose at establishment journalism, were surprised. Maybe Trump didn’t expect to win, either - only he knows for sure. But he did win and in the next four years, America shifted to the right. As The Nation’s Jeet Heer so aptly pointed out, Trump made the subtext into spoken text. Between stacking courts with right-wing judges, blanket bans on Muslims entering the country, and that wall he was always trumpeting, a lot of things that were simmering under the surface erupted into the surfice.
Haberman’s book covers this and more - the insults he threw at Barack Obama over the years and the way he fumed with Obama threw them right back at the 2011 White House Correspondents Dinner; a flirts with running in 2012 and again in 2014. And finally his 2016 campaign that landed him the Presidency. But so much happened in those four years that to keep this one at a manageable length - and it still runs almost 600 pages - she has to move at a brisk pace, meaning events are glossed over or omitted entirely. People like John Bolton flit in and out of the narrative, never really sticking around long or having their motivations explained. There’s precious little on Trump’s foreign policy: his summit with North Korea in 2020 is barely mentioned, while the Abraham Accords are limited to a single page. Instead we get stuff like this:
“In early April, The New York Times published a long story I had worked on with five colleagues that held Trump accountable for his handling of the pandemic. He and his advisers did not like the article, which appeared under the online headline HE SHOULD HAVE SEEN WHAT WAS COMING: BEHIND TRUMP’S FAILURE ON THE VIRUS, and, instead of rebutting it on it’s merits, set out to retaliate in a unique way.” (pg 421)
She then includes an account of Trump taking her appearance on a podcast out of context, I guess something that stuck in her craw.
These little asides, and there’s a lot of them, don’t really do anything to add to the story except to perhaps show that Haberman had a lot of access and that Trump read her reporting. In a book that teeters between a biography and a political history, they feel out of place and give Confidence Man a weird sort of tension - it takes readers out of her narrative and into her reacting to events rather than just reporting on them.
In sum, there’s some interesting stuff here and a few things I didn’t know - like Trump suggesting his Vice President should be killed during the Jan. 6, 2021 riots. But a lot of it will be familiar to those who paid close attention from 2012-2022, and even it still feels like some big things got missed (qanon, for example, gets one singular mention). Confidence Man is maybe a good place to start when looking into Trump, but it’s hardly the definitive read - or, as the jacket copy suggests, one that he should fear. Instead it fails to stand out from the crowded pack of Trump books and ultimately never even knows what it wants to be.