Donald Trump's New York

As a newspaper reporter in 1980s New York, I did my best to avoid writing about Donald Trump—or any other celebrities. In practical terms, that meant staying out of the line of sight of the city desk as much as possible, which I accomplished by getting assigned to beats in City Hall and the courts.

But late one night, as I covered an important, dull meeting in City Hall, a public-relations person told me that Donald Trump was waiting to be interviewed. I was ushered into some office where he sat behind a small desk. He wanted to talk about his plan to renovate the ice rink in Central Park, a job the city government had dithered over for six years. I was struck by his piercing stare—looking not at me, but over my right shoulder, and seemingly far into the distance.

What I took away was that the stare was his “man of destiny” look, as if he were posing for a statue of the American entrepreneur to the rescue. His pose that night always seemed laughable until I realized recently that the joke was on me. For Trump’s destiny turned out to be large indeed: in that early venture into the civic arena, he was taking one more step in what Maggie Haberman’s smartly probing new book calls “The Making of Donald Trump.”

Haberman’s book is a devastating character study—all the more so because when she gets there after more than five hundred pages, she finds there is no “there” there for Trump. Or, as she explains in the book’s concluding passage, “ultimately, almost no one really knows him…. [H]e is often simply, purely opaque, permitting people to read meaning and depth into every action, no matter how empty they may be.” Donald Trump is all mirrors.

As a celebrity mogul, Trump made himself to order for an era when gossip was going mainstream in the news business. His gaudy glamour generated plenty of publicity; New York’s tabloid press in particular was an eager victim, and soon enough the national media was as well, even prestige outlets. And yet, he was something of a joke. When the notion of a Trump presidential run was floated in 1987, Garry Trudeau lampooned him in his widely read “Doonesbury” comic strip. His Trump character claims to have a rapport with the average voter, explaining, “I’ve spent my whole life with people of modest means.” A reporter asks in what capacity. “Evicting them. I’ve seen how these people live.”

Haberman was one of the few reporters to view the man seriously as a potential political candidate. She writes that after being taken in by one of Trump’s earlier feints toward running for president, in 2011, “Friends and sources in New York had mocked me as gullible for that coverage.” But she had taken note of the enthusiastic reception Trump had received from voters in New Hampshire and realized earlier than most that he was a viable candidate.

Haberman came onto the scene as a City Hall reporter in the late 1990s for the New York Post, the paper that served as Trump’s advocate in the gossip wars. She moved on to the paper’s tabloid rival, the New York Daily News, and then to Politico and the New York Times. With the scrappy resourcefulness of a New York tabloid reporter and the clout and perspective of the Times, she is ideally suited to deconstruct how Trump fabricated his persona and explain how his backstory shapes his actions on the public stage.

In Haberman’s telling, Trump’s story is built upon layers of falsehoods—it’s all a con. For example, she looks into a 1980 interview Trump did with the Times in which he describes his foundational experience of attending the ribbon-cutting ceremony for the Verrazzano-Narrows Bridge in 1964 at the age of eighteen. His tale was that he saw how Robert Moses, who oversaw the project, had cut out the bridge’s designer from getting any notice that day. Trump claimed to realize “then and there” that “I don’t want to be anybody’s sucker.” As Haberman reports, every detail in Trump’s story was wrong; in fact, Moses had amply praised Othmar Ammann, calling him “the greatest living bridge engineer.”

It’s a small matter, but it sets a pattern. Trump tells a reporter his ancestry is Swedish. (It’s German.) He posed as a publicist in phone calls to reporters. He falsely claimed to have made millions of dollars by selling his stocks just before the market crashed in 1987. He inflated the value of his financial holdings. He claimed after the 9/11 attack that he sent hundreds of workers to help clear the World Trade Center site, which Haberman could find no evidence for.

As Haberman makes clear, news media aided Trump’s distortions. In one case that says a lot, a New York Post reporter and his editors essentially made up the quote that provided one of the era’s more famous page-one tabloid headlines: MARLA BOASTS TO HER PALS ABOUT DONALD: “BEST SEX I’VE EVER HAD.” As Haberman recounts, the Post reporter had interviewed a friend of Trump’s girlfriend and later second wife, Marla Maples. The woman, who’d known Maples through an acting class they took, said Maples had boasted of the “romance” she had with Trump. “Uh, ‘romance’—you mean, sex?” reporter Bill Hoffmann asked. “Well, yeah, sex too,” she replied. “The best sex she ever had, I bet,” Hoffmann suggested. “Yeah,” the friend said, which became the basis for that immortal tabloid headline. Trump loved it.

Nineteen-eighties New York was a city trying to strut again after being crippled financially in the previous decade. Its racial polarization and fear of crime; its thirst for wealth and lost glamour; and the high-volume, over-the-top style of its leading public figures all weighed heavily in the baggage Trump unpacked in Washington. Like Mayor Edward Koch, Yankees owner George Steinbrenner (who inspired Trump’s famous “You’re fired” on The Apprentice, according to Haberman), and U.S. Attorney Rudolph Giuliani, Trump had the ability to get attention from a celebrity-crazed news media. He learned politics from his amoral fixer attorney Roy Cohn, and from observing one of the last of the city’s powerful county political bosses, Meade Esposito. “The dynamics that defined New York City in the 1980s stayed with Trump for decades; he often seemed frozen in time there,” Haberman writes. 

Much as he never really left New York, he’d never really left childhood either, in Haberman’s portrayal. As president, he’s subject to shifting whims and emotions like a three-year-old on a bad day, and just as suggestible and hungry for immediate gratification. “For dessert, Trump made sure to receive one more scoop of ice cream than his guests were served,” Haberman writes at one point. Trump advisors became his monitors: “By the spring of 2020, it had become clear to many of his top advisors that Trump’s impulse to undermine existing systems and bend institutions to his purposes was accompanied by erratic behavior and levels of anger requiring others to try to keep him on track nearly every hour of the day.”

Confidence Man is enriched with vignettes that illustrate its subject. A humorous one—it sounds like a Doonesbury cartoon—has Trump calling himself a “popularist,” even when Steve Bannon tells him the correct word is “populist.” More serious is that, according to Haberman, Trump told aides “I’m never leaving” the White House after he’d lost the 2020 election. Or, as she reports, Trump was much sicker with Covid than acknowledged: “The doctors knew exactly how sick Trump had been; without the monoclonal antibody treatment, the administration’s health officials believed, Trump may not have survived.”

The problem Haberman faces is that Trump’s character has already been so thoroughly exposed through his own bombastic actions on the public stage and the disclosures of former aides in memoirs and congressional testimony. Her great contribution is that the book shows how Trump’s New York experience set the context for his odd and sometimes dangerous presidential style.

It’s an important contribution, but one that has limits. Given the focus on his New York roots, I’d have liked a better sense from a Trump biography of where he got his affinity for white, blue-collar workers. His hectoring, needling, repetitive style of arguing politics sounds like one of the guys having at it in a Queens bar. Where did that come from? And why was Trump able to create a bond with what used to be called the workingman when so many other politicians couldn’t?

The other story I’d like to have read more of is Haberman’s. For doing her job as a reporter in a straightforward, honest way, she’s put up with an incredible amount of blowback from both Right and Left, and from Trump as well. Critics on the Right should realize that her sources of information are primarily Trump’s own aides, whose expressions of shock at the president’s actions create a chorus in the book, and often enough, apparently Trump, who just can’t stop himself from talking to the “third-rate reporter.” Critics on the Left: nothing in the book would have changed anyone’s vote if reported earlier. Haberman was masterful in managing her reportorial relationship with Trump & Co. for her newspaper readers’ benefit. The space and flexibility of writing her own book has allowed her to build on that.

Confidence Man
The Making of Donald Trump and the Breaking of America
Maggie Haberman
Penguin Press
$32 | 608 pp.