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Trump: The Deals and the Downfall

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No figure has come to symbolize the excesses of the 1980s as vividly or as powerfully as Donald Trump. As master builder, as media star, as bestselling author, as conspicuously wealthy consumer, Trump reigned--until his spectacular collapse--unchallenged as a unique new breed of entrepreneurial superstar, one who was as confidently victorious on television and the podium of an endless string of press conferences as he was in the boardrooms and bankers' offices where he waged his epic battles, For all of the media attention that has been devoted to him, though, what do we really know about Donald Trump, apart from what he has carefully contrived to foster the myth of a self-made financial genius, a man whose extravagance was merely a perquisite of success?

In Trump: The Deals and the Downfall, the journalist most qualified to tell the story finally unravels the myth and revel as the truth behind the rise and fall of the remarkable mogul. For over thirteen years-from the time Trump was an audacious newcomer on the New York real estate scene--Wayne Barrett has scrupulously followed Trump's career, and has charted a pattern of backroom deals and the underside of Trump's own business practices--behavior nothing like the canny prowess celebrated in Donald's own autobiographies. The Trump we meet in this exceptional book is a man who, rather than a self-created millionaire, is in fact heir both to a substantial empire built by his equally rapacious father and to the Democratic machine connections that made the empire possible. Barrett's investigative biography takes us from the days of Donald's lonely youth to his brash entry into the real estate market, and to the still-secret machinations behind the major deals that made his name; from the initial triumph of the Hyatt Hotel to the successful purchase of the largest parcel of real estate in Manhattan, the West Side Yards; from the incomparably opulent Trump Tower to such contrasting showpieces as the Taj Mahal casino and the Plaza Hotel; from the extravagance of the $1,000 per-square-foot, unoccupied Trump Palace apartments to the extraordinary, desolate Palm Beach estate Mar-A-Lago.

Barrett's investigation of these deals provides not only a fascinating chronicle of Trump's own suspect business practices, but also a hair-raising account of the workings of power brokers in the heady and heedless money culture of the 1980s. Here is a detailed portrait of the forces that made a Donald Trump possible: the banks that advanced him staggering loans, at times based on misleading information; Trump family associations with mob-connected figures; and compromising alliances with governors, mayors, and perhaps his most powerful benefactor of all, the rogue lawyer Roy Cohn.

Most compellingly Barrett paints an unprecedently intimate portrait of Trump himself, a man driven by bravado, ambition, and an anxious ruthlessness to subdue his rivals and control his allies. We see him head to head with an opponent as powerful as Pete Rozelle, ingratiating himself with the brooding governor on the Hudson, and fueling the Drexel engine driven by Michael Milken with hundreds of millions in fees--paid, ironically, by gaming companies to fend off Trump takeovers. We look behind the headlines to explore his complicated emotional and business relationship with Ivana, and the use he planned to make of his mistress Marla Maples as a "southern strategy" in his contemplated presidential campaign. And through interviews with scores of adversaries and former colleagues we are given a privileged look at Trump the businessman in action--arrogant as often as he is brilliant, reliant on threats as much as on charm, and ultimately a cautionary tale: himself the victim of a career that will see no parallel in our lifetime.

492 pages, Hardcover

First published January 1, 1992

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698 people want to read

About the author

Wayne Barrett

24 books32 followers
Wayne Barrett was an American journalist. He worked as an investigative reporter and senior editor for The Village Voice for 37 years, and was known as a leading investigative journalist focused on power and politics in the United States. He is known as New York City's "foremost muckraker."
“Our credo must be the exposure of the plunderers, the steerers, the wirepullers, the bosses, the brokers, the campaign givers and takers,” Barrett once said to journalism students at his alma mater, Columbia University. “So I say: Stew, percolate, pester, track, burrow, besiege, confront, damage, level, care.”

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Displaying 1 - 21 of 21 reviews
Profile Image for Cecily.
1,329 reviews5,387 followers
will-not-read
June 16, 2022
An old book (1992), which seems not to have returned to prominence in recent years. Nowadays, it's all taking down Trump: The Art of the Deal, and recent exposés by the likes of Sarah Kendzior.

Anyway, apparently Barrett feared Trump's resurgence and tried to warn people. He also wrote critical investigations of Ed Koch and Rudy Giuliani
He died the day before Trump's inauguration.
Here's a 2017 Politico article about him: https://www.politico.com/magazine/sto...
Profile Image for Mark.
1,280 reviews150 followers
March 28, 2020
In the introduction to this book Wayne Barrett recounts a phone conversation with Donald Trump's press agent, who urged the author to drop the word "downfall" from the subtitle. Trump "will make a comeback," he advised, in words that twenty-four years later seem not just prophetic but an understatement. The comeback also has the effect, though, of preserving the relevancy of this book, as it offers readers an ability to assess its subject's early years using sources no longer available to authors today.

The portrait Barrett paints is not a flattering one. He traces the origins of the family's business empire to Donald Trump's grandfather, Fred Trump, Sr., who had accumulated several properties and mortgages before his early death from pneumonia. These his son Fred Jr. -- Donald's father -- transformed into a successful career as a developer, building homes and apartments in Queens and Brooklyn from the 1930s to the 1950s, Barrett emphasizes the role of connections in the development of the younger Fred Trump's business, seeing his ties with the Democratic machines in both boroughs as integral to his business activities.

Federal investigations in the 1950s brought an end to Fred Trump's activities as a developer, leading him to focus instead on managing his existing properties. Yet Donald exploited both his father's name and the network of contacts he developed to break into the Manhattan real estate market in the 1970s. Barrett goes into considerable detail about the evolution of each of Donald's deals, from his first major project in renovating the old Commodore Hotel to his long-term pursuit of the development opportunities available in the disused 60th Street railyards. Much of the profits gained from these projects were due to the extremely favorable terms Donald wrung from the city, thanks not just to his inherited connections but those of Roy Cohn as well, as the infamously corrupt attorney dealmaker emerges as a surrogate father to the young man.

Though Donald's early successes established him as a major figure in the New York region, it was Trump's involvement with the defunct United States Football League which brought him to the national stage for the first time. While Barrett probably overemphasizes Trump's role in bringing about the demise of the league, he makes it clear about how Trump's goal in using the USFL as a means of forcing himself into the more expensive National Football League did the struggling young league no favors. It was during this period in the mid-1980s that Trump also became involved in the casino industry in Atlantic City, where he sought to build up an entertainment empire far larger than could be viably supported by the market there.

Barrett also addresses Trump's emerging national image during this period, as it becomes key to his initial downfall. As he followed his father's career trajectory from development to ownership, he received tens of millions of dollars in loans from banks that he used to go on a massive buying spree. These loans were offered without even a cursory examination of Trump's underlying finances, as bankers were drawn less to a careful assessment of his assets and liabilities than a submission to the power of his personality and the glamour of his public image. The result was that by the end of the 1980s Trump was overleveraged, and Donald entered the new decade facing both the implosion of his heavily indebted empire and an embarrassing and costly divorce from his first wife Ivana.

Overall Barrett's book is a damming autopsy of Trump as a person and as a businessman. While the author's biases occasionally shine through, the sheer amount of detail he uses, based on an examination of the enormous amount of filings, financial records, and lawsuits produced over the course of his subject's activities, makes it difficult to disagree with the substance of his assessments. It is a book that should be read by everyone interested in learning about Trump's early career in business, one that offers some food for thought for readers today in considering what he might do should he win the highest office in the land.
Profile Image for Andie Rix.
14 reviews7 followers
August 4, 2016
Barrett very detailed in his description of the antics of the young Donald Trump. A great exposition of a very little man.
Profile Image for Marianne Markkanen.
159 reviews
February 21, 2017
Anybody who voted for Trump should read this. It is terrifying, the bankruptcy, over borrowing, narcissistic, misogynistic behavior that should worry any American who supports this President.
Profile Image for Mary .
126 reviews
May 10, 2017
When I read the obituary of investigative reporter Wayne Barrett earlier this year, I found out about this book, which is a must-read for critical thinkers in these times. The exposition of all the deals and cons perpetuated by Donald Trump throughout his career are as exhaustive as they are detailed. Given the litigious nature of the subject, it is remarkable that Barrett was never sued, but that also attests to the absolute veracity of his research.
Profile Image for Valarie.
189 reviews14 followers
May 21, 2017
I liked the book, but found it kind of a slog, mainly because I lived through much of this and didn't really need all the minutiae of every deal. It also ended a little too soon -- I would have liked to know more about the "reinvention" (which my version of the book actually promised) because it's the reinvention that is at the center of all of his current troubles. But I'm glad I stuck through it, if only to have a solid example that his behavior is a feature and not a bug.
Profile Image for Gregory Gentry.
Author 1 book5 followers
July 7, 2025
Fascinating glimpse into Trump and his behavior pre politics. spoiler: Nothing has changed.

Side note, the new cover and tag line for this book are terrible. They do not do the text justice, and make it appear as a cheap tabloid hit piece instead of the detailed, nuanced piece of investigative journalism it actually is. I read the 1st edition, and never would have bought it if I'd stumbled across the current printing.
Profile Image for Haroon Haider.
56 reviews2 followers
March 31, 2023
A gripping and comprehensive account of the life and business dealings of Donald Trump, written by investigative journalist Wayne Barrett. With a keen eye for detail and a wealth of insider knowledge, Barrett exposes the truth behind Trump's claims of being a self-made businessman and real estate developer, revealing instead a man who relied heavily on manipulation, deceit, and connections to achieve his success.

Barrett's investigative biography traces Trump's life from his lonely childhood to his entry into the real estate market and beyond. Throughout the book, we are given a detailed insight into Trump's personal and business relationships, including his complicated emotional and business ties with his first wife, Ivana, and his mistress-turned-second wife, Marla Maples. Barrett also sheds light on Trump's reliance on questionable characters from the mafia and city politics, as well as the back room deals behind his New York, Atlantic City, and Florida projects.

What makes this book so compelling is Barrett's ability to paint an intimate portrait of Trump himself. He depicts Trump as a man driven by bravado, obsessive self-regard, and an anxious ruthlessness to subdue his rivals and seduce anyone with the power to aid his empire. We see Trump head to head with powerful opponents, ingratiating himself with brooding governors, and fueling the Drexel engine driven by Michael Milken with hundreds of millions in fees.

Perhaps the most important message of the book is the cautionary tale it presents. Through interviews with scores of adversaries and former colleagues, Barrett offers a privileged look at Trump the businessman in action - reckless as often as he is brilliant, reliant on threats as much as on charm. Ultimately, the book begs the question, "is this the man we want to lead the world?"

In sum, this books is a must-read for anyone interested in understanding the man who has become one of the most polarizing figures in American politics. With Barrett's extensive research and insightful analysis, readers are given a nuanced and multifaceted portrait of a complex and controversial figure. Barrett's book is an excellent addition to any reader's library, and it will undoubtedly be remembered as a definitive work on the life and legacy of Donald Trump.
42 reviews
May 31, 2017
Quite a history of Trump's business dealings. Explains a lot about how he thinks and why he finds people checking on his "facts" to be troublesome. At times, you think it is just too much, and want to put the whole book down, but the entire history is important.
Profile Image for Paul Fox.
97 reviews3 followers
January 15, 2019
If many had read this book before 2016 we would have saved ourselves a lot of anguish and pain!
Profile Image for Yves.
38 reviews1 follower
March 20, 2022
Wayne Barrett wrote about Trump before most people knew the name that would soon be written across New York. Before The Apprentice rehabilitated his image and before his own Presidency destroyed it (again). Barrett's writing is engaging and thorough. It's too bad that he died before he could write a sequel. Trump ran a few more cycles of deals, downfalls, and reinventions. What fascinated me is how Trump was able to work deals with banks that made him "too big to fail" so that they ended up supporting his lifestyle and failed businesses rather than writing off his $100 million loans. Trump enabled Ponzi schemes that worked as long as those around him were getting paid; like when loans were pawned off to Japanese banks, who were blinded by the show, and didn't see the mess backstage. The book ends in the early 90s, just as his casino career was imploding but before Mar-a-Lago, his golf course foray, Miss Universe ownership, and The Apprentice.
54 reviews2 followers
February 13, 2023
I understand why this is lumped in with the other anti-Trump books but imo it makes him look like the genius he claims to be. The financial stuff is beyond me and boring, as others have pointed out, and an edit would be wise. I'm glad I stuck with it as there are some interesting tidbits scattered throughout and at the end.
Profile Image for Barrett Benton.
2 reviews1 follower
January 15, 2024
A certain amount of this book came to me as no surprise, since I'd been following the author's writings since he wrote a column for the Village *Voice* decades back. Having this book at hand, nonetheless, makes for amazing study: whatever you know - or think you know - about Trump, Barrett sets more than a few matters straight, and explodes more than a few myths along the way.
Profile Image for Sara Cochran.
71 reviews4 followers
August 4, 2019
Important information but hard for me to read. Financial stuff is pretty boring even when it shows a lifetime of corrupt practices.
Profile Image for Mel Bontje.
Author 2 books11 followers
January 3, 2026
Interessante stukken over de invloed van Roy Cohn.
Profile Image for James Crabtree.
Author 13 books31 followers
September 27, 2016
I received this book as part of a Goodreads Giveaway.

You would think that a book written by a Village Voice journalist (sic) and recommended by Democracy Now! would be free of bias, providing an untarnished look at Donald Trump from an objective standpoint... but you'd be wrong.

That was sarcasm, for those leftists who had their sense of humor removed before the Fall of the Berlin Wall.

Wayne Barrett is proud of his investigation into Trump's business dealings in the 1970s, before he was a household name. Barrett's articles got him banned from doing interviews with Trump for several years and the author claims that Trump offered to get him an apartment in NY as some sort of bribe. Since Barrett didn't take him up on his supposed offer, maybe it happened... and maybe it didn't.

The book uses the term "Trumpian" and it may be that he invented this term since this is a recycle of a book he originally published in 1992, which is all the more remarkable since this was in the days when Trump wasn't considered an "enemy of the people" by the democrats, who gladly accepted his money in charitable and political efforts (same thing in the case of the Clinton Foundation).

The big problem seems to be that Trump made money and he has a brand. The author goes into detail about business dealings which took place over 25 years ago and makes accusations of "rigging," bribery and other questionable practices (the book is absent of any references, so just like the apartment deal we have to take Barrett's word for it). Even the index of this book is a bit shy at 26 pages, considering the book is 445 pages of long, drawn-out discussions of Trump's real estate and other business dealings. If you feel you HAVE to read this book, buy the 1992 edition for 1 cent... there is nothing new here.
239 reviews5 followers
March 22, 2017
Barrett, an amazingly talented investigative journalist, started his 1992 expose with this 1914 quote from Dreiser's "The Titan"- "Frank Algeron Cowperwood does not believe in the people; he does not trust them. To him they constitute no more than a field upon which corn is to be sown, and from which it is to be reaped. They present but a mass of bent backs, their knees and faces in the mire, over which as over a floor he strides to superiority. His private and innermost faith is in himself alone."

I suspect more people should have read this book.



1,004 reviews1 follower
February 6, 2017
Trump: The Greatest Show on Earth: The Deals, the Downfall, and the Reinvention by Wayne Barrett is an interesting story of Donald Trump. The author has a slight bias but the information is very interesting.

I received a copy thru a Goodreads Giveaway.
2 reviews1 follower
February 11, 2019
Save yourself and don't read this one. Incredibly detailed but unless you are obsessed with him and want to know everything you could about everyone ever connected to him, skip this. Forced to stop after halfway. (YEAH, that bad! )
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