****Writer’s Note: If you enjoy the blog check out my interview with Maggie Haberman on WDEV radio , or on our podcast, Vermont Viewpoint, available wherever you get your podcasts. 

The New York City of my youth was an inhospitable place. To a kid from the Jersey Shore who could see NYC in the distance, the city was a place that had pro hockey games and boxing fights. The 80s and 90s were about garbage strikes, government incompetence and bankruptcy. Fathers commuted there. It wasn’t a place where people actually lived.

Back then, the city was governed by a byzantine system of political clubs. These clubs were run by “party bosses’’ whose power came from doing favors and getting people jobs within a town or a borough. The most important of these bosses was a man named Amadeo Henry “Meade’’ Esposito. The grandson of Italian immigrants, Esposito acted as the chairman of something called the Kings County Democratic Committee, which made him the most powerful man in New York.

These committees are difficult to explain. They’re not the mafia, though they dealt with them. Think of them as social clubs where you hung out with your friends from the neighborhood. You went to the club house offices to learn about job openings, attend social functions and meet people. Pretty soon money began to change hands, job connections were made, conflicts were mediated and all between the most powerful men in the city.

People like Esposito grew in influence over time and eventually wielded immense power in Brooklyn, dispensing favors and acting on  the right side of the law - mostly. 

If you wanted to be a judge or city councilor or even get a job in Brooklyn in the 1970s, you had to know someone who knew someone who knew Esposito. In those days, the line between the criminals and the politicians was very thin, and Esposito straddled it every day. He used this power and connections to shape a New York made from dealmaking, political power in the back room, special deals for favored friends and intimidation. To get a sense of this New York City, watch the movie “Serpico’’ where Al Pacino is ostracized for being a lonely honest cop in a corrupt police department. 

It is this New York into which Donald Trump was born and learned the values - or lack thereof - he took to the White House. 

These lessons and this New York are wonderfully captured in Maggie Haberman’s excellent book -  “Confidence Man - The Making of Donald Trump and the Breaking of America.’’

I had the great pleasure of interviewing Haberman this past Monday for the radio show Vermont Viewpoint on WDEV. She is a Pulitzer Prize winning reporter for the New York Times, and a two-time Pulitzer finalist for her coverage of COVID and the January 6 riot. 

Oh, and she is from New York and lives in Brooklyn. This is important. It makes her, by far, the best journalist to write about Trump. Because to do it well, which she does, she has to write about where Trump comes from. New York in the 70s; a complicated, unique, corrupt place that can only be truly understood if you’re from there. 

Haberman’s book functions almost as a travelog of New York in the 70s and 80s. There is Gay Talese, the 21 Club, the Cuomo family, Mayor Ed Koch, Al Sharpton before the diet, Studio 54, the Village Voice, Robert Moses, Roy Cohn and, of course, Donald Trump. 

“In many ways Trump is preserved in amber liquid,’’ Haberman told me. 

What she means is that Trump came of age in the 70s and 80s and hasn’t changed since. In order to develop real estate projects, which Trump did with his father Fred, you had to speak the language of people like Esposito. It was a world of shady tax breaks, lobbying, threats, blackmail and corruption of all kinds. These were the tricks of the time, and Trump remains a product of that time. 

Trump’s life - as Haberman told me - isn’t entirely a lie, but is filled with exaggeration. He learned early on that public relations was critical to creating a facade, a reputation for wealth and success. 

“He ultimately realized that he could win as much press for projects that he never completed as those he did,’’ Haberman writes. 

Trump closely identified with Roy Cohn, the lawyer to the red-baiting, Communist hunting Senator Joe McCarthy. Cohn gave Trump two separate bits of advice that would define his presidency: 

1. “Never give in.”

2. “Everything can be treated as a transaction,’’

It is HERE we can find the central theme of Trump and the answer to the question we’ve all asked ourselves since his election: 

How did we get here?

Trump did not create the tribalism, hatred and anger of modern day politics, Haberman says, he just surfaced what was there and used it to his advantage. 

He is just the latest character to take advantage of the opportunities wrought by first radio, then network television, then cable TV, then the Internet, and finally social media. These tools allow him to treat government service as a transaction, a brand-building exercise and a grift. 

Trump’s rise to the presidency began with the Apprentice TV show, which elevated him from a second rate real estate developer of failed Atlantic City casinos to a household name. The Apprentice pitted contestants against each other to win a job at Trump’s organization. At season’s end, someone would win and be hired. 

When it came time to film the show, producers couldn’t use Trump’s actual buildings because they were too threadbare. Instead, they were forced to build a special set with a big, important looking chair for Trump.

The show, aired in 2004, and dominated television ratings and framed Trump as a successful business executive. And it was all fake.

And yet...

Following Trump through Iowa on the 2016 presidential campaign, Haberman was taken aback when a voter told her why he supported Trump. He said, “I watched him run his business.’’ Never mind that it was on TV. The grift had worked! Trump was sworn in as president a few months later. People believed the story. 

Other Trump books disclose the frightening scenes that occurred on a daily basis within the Trump White House. Haberman’s book has these scoops as well. She has photos of Trump tearing up government documents and flushing them down the toilet. She describes the casual racism and misogyny. She reveals his obsession with looking the part when selecting staff only to then turn on them when not shown sufficiently loyalty. 

Trump is the kind of guy you would never want to be in a room with. It is a testament to Haberman’s professional dedication to journalism that she ventured to Florida three times after his loss to Joe Biden to interview him for the book. 

Haberman’s other key takeaway (one that I agree with) is that Trump doesn’t think strategically; he just wings everything, throwing chum in the water to see what will happen. 

She wonders aloud whether Trump is actually guilty of a conspiracy to foment the riot on Jan. 6, dubious that he is capable of such multi-dimensional thinking. 

Haberman is a reporter and proud of it. When it comes to the key question of the last decade with Trump - “How did we get here?’’ she resists playing armchair shrink. Instead she prefers to stay on her turf, reporting the WHAT of Trump and the WHY. 

When I asked in our radio interview what might have happened if the Jan. 6 rioters had actually reached Mike Pence and House Speaker Nancy Pelosi, she demurred, not wanting to breach her journalistic guard-rails. 

And she is right to do so. We want Haberman right where she is, getting us the facts on Trump, not speculating about what might happen next. For me it is a refreshing reminder of journalism that informs, complete with context and nuance. 

The larger question of how a thrice-married, porn star paying, election denying, shady character from Queens could actually become president of the United States and what that says about our country is something she leaves to us… the voters.

It is the question we have to answer … and fast.