The Washington PostDemocracy Dies in Darkness

Trump’s origins in a New York world of con men, mobsters and hustlers

In “Confidence Man,” Maggie Haberman puts special emphasis on Trump’s ascent in the late 1970s and 1980s.

(Illustration by Doug Chayka. Images: iStock; Bernard Gotfryd and Carol M. Highsmith Archive from Library of Congress; Bettmann/Getty Images; and Ron Galella Collection/Getty Images)

Maggie Haberman hails from a New York City very different from Donald Trump’s dominion of glitz and criminality, but she knows that dominion well. Raised in the household of a traditional shoe-leather New York Times reporter and a well-connected publicist, and now herself ensconced at the digitized Times, Haberman’s earliest assignments involved covering City Hall and its satellite ethical sinkholes for the New York Post and the Daily News. That singular education in New York corruption has stuck with her and sets her apart from her peers reporting on the Trump presidency and its seditious aftermath. It now distinguishesConfidence Man: The Making of Donald Trump and the Breaking of America” as a uniquely illuminating portrait of our would-be maximum leader.

With a sharp eye for the backstory, Haberman places special emphasis on Trump’s ascent in a late 1970s and 1980s New York demimonde of hustlers, mobsters, political bosses, compliant prosecutors and tabloid scandalmongers. This bygone Manhattan that Tom Wolfe could only satirize in “The Bonfire of the Vanities” is the fundament to any understanding of what makes Trump tick. “The dynamics that defined New York City in the 1980s,” Haberman observes, “stayed with Trump for decades; he often seemed frozen there.” Zombielike, he swaggers and struts and cons on the world’s largest stage, much as he did when gossip columnists fawned over him as The Donald; and he will continue his night of the living dead, with menacing success, until someone finally drives a metaphorical stake through his metaphorical heart.

The rote rap on Trump is that he was a bumptious, hyper-ambitious real estate developer from Queens who never earned the respect of the Manhattan society pooh-bahs and who vowed to beat them at their own game — a vow that eventually led him to the Oval Office, astonishing even Trump. That storyline appears in “Confidence Man,” but Haberman knows it is superficial.

For one thing, there were countless other outer-borough operators on the make in 1980s New York, one of whom Haberman astutely calls Trump’s “mirror image” despite their obvious differences: the Rev. Al Sharpton of Brooklyn, both men shameless headline grabbers who smeared opponents and basked in newfound glamour; they were slightly clownish intruders who refused, she writes, “to be thrown out of their new ring” by a disdainful city establishment.

Inside that cauldron of fakery, Trump, no rugged individualist, and padded with his father’s millions, gravitated to a specific milieu of arrivistes whom he equated with supreme power, class and ruthlessness. He held in especially high regard the bully George Steinbrenner, from the outer outer borough of Cleveland, and became a constant presence in the Boss’s Yankee Stadium box. (I’d not known until reading Haberman that Trump, a wimp when it came to sacking underlings, found his tag line for “The Apprentice” by impersonating Steinbrenner barking “You’re fired,” over and over, not least at the Yankees’ oft-discharged manager Billy Martin.)

Off to one side there was the raffish schemer Roger Stone, a well-digger’s son from Norwalk, Conn., who got his start as one of the political saboteurs for Richard Nixon’s 1972 reelection campaign, and whose Washington lobbying mega-firm (with Paul Manafort as one of his co-partners) came to represent the Trump Organization’s interests. From the outermost borough of Adelaide, Australia, there was the unscrupulous media mogul Rupert Murdoch, who had already turned the liberal tabloid New York Post into a right-wing scandal sheet and who in 1985 completed the acquisition of 20th Century Fox that would eventually give the world Fox News, commanded by another member of the New York gang, Roger Ailes. There was also the high-profile, media-savvy U.S. attorney Rudy Giuliani, from Brooklyn like Sharpton, and he and Trump would circle each other until they seriously hooked up some years later.

Trump’s chief mentor, and a consigliere to most of the big shots named above, was the legendary underworld and overworld fixer Roy Cohn. The pampered son of a kingpin in Bronx Democratic politics, long notorious for his McCarthyite Red Scare grandstanding, Cohn, as Haberman details, connected Trump with Stone as well as with organized crime while giving him master classes in high-stakes con-man strategy and tactics. Whenever Trump today intimidates the press with threats of retaliation, whenever he defends his aggressions by claiming to be the victim, whenever he calls his accusers (especially if they represent the federal government) life-destroying, treasonous “scum,” he is channeling his mentor, Cohn.

Haberman offers plenty of material about how these men did it all with virtual impunity. Of course, there would be the occasional fines and sealed judgments — and Cohn was disbarred weeks before he died of AIDS, abandoned by Trump, who knew the score on being heartless. But as Haberman describes, Trump went to great lengths to square himself with a paragon of the city’s power elite, the longtime Manhattan district attorney Robert Morgenthau, including making generous donations to Morgenthau’s pet charity, the New York Police Athletic League, the one charity commitment, Morgenthau would joke warmly, that Trump could be counted on honoring. Not until Cyrus Vance Jr., who had a fine pedigree but was no crusader, succeeded Morgenthau in 2010 did Trump and his properties, after Vance backed off for years, finally face serious investigation by the D.A.’s office — and even then, prosecutors on the case quit in protest when Vance’s successor suddenly seemed to drop it.

“Confidence Man” likewise enlightens about the massive oversights by the press and the broader world of publishing, especially in New York, not simply in failing to expose the corruption that Haberman catalogues but in creating and then abetting Trump’s celebrity. There were certainly exceptional naysaying reporters, notably Jack Newfield’s protege at the Village Voice, Wayne Barrett, who, at Newfield’s urging, dug deep into Trump’s shady dealings. Barrett’s and the Voice’s condemnations sparked a brief aborted federal investigation, but they weren’t about to shake the inertia at the most influential outlets, topped by the New York Times. Neither did the late lamented Spy magazine’s bull’s-eye satirical shots at the “short-fingered vulgarian” provoke inquiries, although they did provoke Trump to threaten lawsuits and are said to anger him to this day.

Indeed, the higher- as well as the lower-end media became Trump’s vehicles, sometimes absurdly. Haberman relates, for example, how in 1984 Cohn, the grand wizard of press manipulation, placed a profile story in The Washington Post’s Style section, followed up independently by another piece in a magazine called Manhattan, Inc., that — though skeptical and even arch about Trump — fed impressions that the brash young dealmaker might seriously serve President Ronald Reagan in top-level arms-control negotiations. Much later, in 1997, when Trump had fallen into one of his disastrous business troughs, a New Yorker profile, though as unguarded as any such piece was likely to be, helped advance his latest comeback. More famously, the queens of tabloid gossip, Cindy Adams and Liz Smith, aided by the New York Post’s garish Page Six, rendered Trump an epic figure. Long before “The Apprentice” completed his makeover as America’s fantasy mogul, driving the phony image to the credulous beyond the Hudson, the publishers, editors and scribes of the Manhattan press, forgoing the facts, had crowned him the king of New York.

Some of the episodes in Haberman’s later chapters on Trump’s presidency have already stirred controversy. Beneath the buzz, though, many of the richest storylines from the Trump White House, as reported in “Confidence Man” and elsewhere, have a distinctly New York ring. “Where’s my Roy Cohn?” Trump snapped in 2018, in anger at his attorney general, Jeff Sessions, the very conservative former senator from Alabama, who had recused himself from the Justice Department’s investigation into Russian interference in the 2016 election and whom Trump eventually ousted.

Before he was twice impeached, Trump found his man, yet another New York mouthpiece, William Barr, who as attorney general happily did Trump’s bidding in, among other things, lying about the damning Mueller report on the Russian interference — until Trump lost reelection and Barr, well-schooled in transactional loyalty and with his reputation as a supposed “institutionalist” tarnished, declined recruitment into Trump’s coup and at the last minute jumped from the sinking ship. The manic and often antic crimes of Stone, pardoned and unpardoned, add another layer of continuity, a louche link with the old Cohn-centered netherworld.

Haberman’s contribution in “Confidence Man,” though, is much larger than its arresting anecdotes. Later generations of historians will puzzle over Trump’s rise to national power. The best of them will have learned from Haberman’s book that none of it would have been possible but for a social, cultural, political, media and moral breakdown that overtook New York beginning in the 1970s, a fiasco of trusted institutions that, having allowed the Trumpian virus to grow, failed at every step to contain its spread, then profited from, aided and even cheered its devastation.

“It’s up to you, New York, New York,” runs the song that became a city anthem in these years, and so it truly was up to sophisticated, cosmopolitan New York with respect to checking Trump. But New York blew it on every level — and alas, even with “Confidence Man” in hand as a guidebook to that failure, it may be too late to start spreadin’ the news, with American democracy now at stake.

Sean Wilentz, a professor of history at Princeton, is the author, most recently, of “No Property in Man: Slavery and Antislavery at the Nation’s Founding.”

Confidence Man

The Making of Donald Trump and the Breaking of America

By Maggie Haberman

Penguin Press. 597 pp. $32

A note to our readers

We are a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for us to earn fees by linking to Amazon.com and affiliated sites.

Loading...