Lucky Loser: How Donald Trump Squandered His Father's Fortune and Created the Illusion of Success

by Russ Buettner, Susanne Craig

From the Pulitzer Prize-winning reporters behind the 2018 bombshell New York Times exposé of then-President Trump’s finances, an explosive investigation into the history of Donald Trump’s wealth, revealing how one of the country’s biggest business failures lied his way into the White House

Soon after announcing his first campaign for the U.S. presidency, Donald J. Trump told a national television audience that life “has not been easy for me. It has not been easy for me.” Building on a narrative he had been telling for decades, he spun a hardscrabble fable of how he parlayed a small loan from his father into a multi-billion-dollar business and real estate empire. This feat, he argued, made him singularly qualified to lead the country—except none of it was true. Born to a rich father who made him the beneficiary of his own highly lucrative investments, Trump received the equivalent of more than $500 million today via means that required no business expertise.

For decades he squandered his fortunes on money-losing businesses only to be saved yet again by financial serendipity. He tacked his name on every building while taking out huge loans he’d never repay. He obsessed over appearances while ignoring threats to the bottom line and mounting costly lawsuits against city officials. He tarnished the value of his name by allowing anyone with a big enough check to use it, and he cheated the television producer who not only rescued him from bankruptcy but also cast him as a business savant—the public image that carried Trump to the White House.

Drawing on more than twenty years’ worth of Trump’s confidential tax information—including the tax returns Trump tried to conceal—alongside business records and interviews with Trump insiders, New York Times investigative reporters Russ Buettner and Susanne Craig track Trump's financial rise and fall—and rise and fall again.

Genres: Nonfiction, Politics, Biography, History, Audiobook, Business, Biography Memoir

528 pages, Paperback

First published September 17, 2024

Reviews

[John McDonald · Rating 5 out of 5]

Donald Trump is a liar, a con man, and a thug.

I have been reading about and following Donald Trump's disastrous financial decisions and schemes designed to con banks and individuals out of their money since the early 1980s. I thought I knew enough--maybe far too much-- about Trump.

I was wrong. This unique review of Trump, his father's own deceits, and Trump's absolute absence of self-awareness and inability to admit error or defeat was far beyond my expectatons.

This is what I learned about Trump, aspects of who he is, that this book clearly illustrates:

1. Donald Trump lies, often without knowing why or having to do so, and he lies so much that someone who wants to know the facts or the truth shouldn't believe anything he says.

2. Trump acts impetuously and without doing due diligence, probably because he is lazy and dislikes having to deal with details, even in making substantial financial decisions.

3. Trump is lazy.

4. Trump issues personal attacks against people to who tell him something is not working as Trump believes it should or who disagree with Trump's assessments.

5. Trump wages opposition by filing suit, even when there are no facts to support the allegations he makes in the lawsuit. As a consequence, virtually all the lawsuits he's filed in business matters have been dismissed.

6. Trump, the person the public sees, is the product of illusions Trump specifically creates or those who create illusions that benefit him: reporters who declined to challenge his assertions of wealth, property ownership, political matters. Television hosts who acted as sycophants rather than interviewers.

7. Trump engages in behaviors that are self-destructive, mostly in the long-term but just as frequently in the short-term.

8. Whatever wealth Trump claims is the result of the wealth built by his father, Fred Trump, over Fred's 40 or so years building apartments in Queens and Long Island with government-guaranteed loans or outright loans.

9. Trump has had tremendous luck that often salvages his disastrous financial decisions, but before he was able to develop product endorsements or licensing deals because of the huge popularity of the Apprentice, Trump was routinely bailed out by his father.

10. Trump has failed (by metrics we commonly use to judge failure in business) at virtually every business venture he has undertaken.

11. Trump may owe 100 Million Dollars or more in back taxes because of the illegal deductions he took and tax strategies (and undervaluations) he's engaged in.

12. Today, bankers decline to do business with Trump or lend him money.

13. If the authors are correct, any small, seemingly insignificant adverse event in the financing arrangements he made for his few remaining businesses will cause the collapse of what's left of the Fred Trump-Donald Trump empire.

14. Illusion. Trump is built and exists on illusion. The irony of his business success, the lie, really, became real when the producers of the Apprentice realized that Trump was not operating a worldwide property business, as he proclaimed, but a family-run business, which operated in offices that were cramped, cluttered, and not suitable to the image the producers wanted to portray. They spent millions creating a boardroom, which Trump did not have, and an image that attempted to portray Trump as an imaginative, tough businessman.

15. Trump deceives his business partners and others for no apparent reason. The authors cite an example of the German owner of 40 Wall Street, an entrepreneur who made a vast fortune in shipping and real estate, visiting Trump at his Trump Tower apartment to discuss Trump's intent to buy 40 Wall. Hanging in the apartment were what Trump stated were original French impressionist paintings which the owner carefully scrutinized. As the visitor positioned a camera to capture a photo of one of the paintings, Trump stuck his hand in front of the lens and said, "please, no photos." The visitor apologized and put the camera away. Later, he told the person who escorted him that the paintings were faked, forgeries, and that he had seen the original in a museum in Hamburg.

16. Those who do business with Trump are screwed by Trump. He does not live up to contracts, deals, or conditions of loans. Whatever promises he makes, he breaks.
One of the funnier anecdotes the authors reveal is one involving Mar-a-Lago. Trump bought MAL after visiting it, but, as was his habit, refused to do any due diligence and ignored obvious problems because he was so enamored of his decision to own the property. Trump bought the property and moved in. Once he had moved in, he began to notice the noise from jet aircraft flying over or near the property throughout the day and part of the night. MAL was in the flight path of a local airport. Trump was furious and demanded that the flight path be changed. He was told that was not going to happen and he sued. That case was quickly dismissed.

There are example after example of this sort of deceit by Trump, all designed to make him appear to be something he isn't. Donald Trump has had luck on his side, but he now has exhausted what business people--outside television--value most: trustworthiness and integrity.

My personal opinion is that the lies and the lack of integrity in all that Trump does will bring him down eventually. He has no chips left to play with or reserve of goodwill to ease the pain he feels or inflicts. The gods in ancient Greek mythology decreed that those who act with hubris-those humans who act as though they are gods when in fact they are merely mortal-inevitably will meet their downfall because of their deeds and misdeeds. Trump surely is a candidate for the punishment the Greek gods reserve for those who act with hubris in defiance of their mortal being.

[Sharon Orlopp · Rating 3 out of 5]

I listened to Lucky Loser: How Donald Trump Squandered His Father's Fortune and Created the Illusion of Success on audiobook. It's a well-researched book regarding Trump's childhood and adulthood, particularly around finances, investments, real estate, and taxes.

It illustrates the difference between what Trump's actual tax returns indicate versus the image he portrays.

[C · Rating 5 out of 5]

The definitive guide to Trump’s monetary endeavors. As someone who read “All in the Family,” “Apprentice in Wonderland,” and “Tired of Winning,” I think I’m well positioned to posit that this is the one to read for enlightening the faces of his finances in 528 detailed pages.

[Carolyn · Rating 4 out of 5]

Uggghhh.
If only Trump voters would read books like this…..
Well-researched and well written, eye-opening. All the usual things. Sometimes I lost focus when they described certain financial, tax and real estate machinations, but it was still well done and should be read by all voters.

[Margaret Shumaker · Rating 5 out of 5]

Fascinating and eye opening

This book illuminates in detail everything you need to know about Trump the businessman. There's a lot of smoke and mirrors, shades of the emperor's new clothes. The details about Fred Trump were new to me, I had not realized how wealthy Fred was and how often he bailed out his son. The discussion of his tax returns explains a lot, no wonder Trump didn't want them released.This book is well written and well researched and it is chilling to think such a fraud, A very dangerous fraud, could be elected again. We should be very worried.

[Petter Deregren · Rating 5 out of 5]

Okay, so. Anyone who knows me, is very aware that I despise Trump. Even so, my knowledge has been limited to watching reports and exposes of the last ten years or so of his abominable entry into American politics. However, after reading this book, I feel very enlightened, and seeing how much of his image was built on sand, if not clouds, really makes me angry that it wasn't called out earlier. The man is a narcissist who lies without compulsion, with confidence, and reacts aggressively to being called out. He has no conscience, and the amount of lives he has ruined through his utterly callous actions devoid of empathy over the course of his life can be counted in tens of millions, if not more. The man is, and always was, a fraud, a failed builder, an attention-hog, and yes; a Lucky Loser.

[Clif Hostetler · Rating 3 out of 5]

This book charts the origin and rise of Trump’s real estate business, and how it evolved into monetized television celebrityhood which in turn created sufficient name recognition to enable election as President of the United States. Though his business record is riddled with numerous and repeated financial failures hidden behind a public veneer of success that only a privately owned company can maintain, the American public proceeded to conflate those apparent trappings of wealth with their wish to believe that people of high status can be trusted. Thus while this book provides a lengthy account of numerous business and media happenings, its overarching message ends up being a spotlight on the gullibility of the American public.

Donald Trump has often claimed that his business was started with a “small” loan of $1 million loan from this father. Research for this book has determined that he received the equivalent of more than $400 million from his father. This influx of his father’s money covered repeated money losing projects and purchases. Then after that source of support was exhausted he was able to receive additional funds from the Apprenticeship shows and sponsorship deals fostered by the resulting exposure. But those sources of income were still insufficient to prevent him from proceeding to file for Chapter 11 bankruptcy protection six different times.

Some of the resulting settlements of those bankruptcies resulted in casinos or hotels continuing to operate under the Trump name but with his ownership interest reduced or nonexistent creating the false perception of ownership where none existed. Ironically one of his most lucrative businesses was one where in he had 30 percent interest which he unsuccessfully sued its management three different times trying to prevent them from doing certain property sales or swaps which increased value and income. One of those swaps that Donald tried to prevent yielded him as much as $185 million tax free. It almost seems that the best advice turned out to be the opposite of what Donald wanted to do.

The following is an excerpt from near the end of the book in which the authors summarize the “lucky” part of Donald Trump’s life:

Good things happened to Donald Trump. He did not earn most of those good things. He was born, he was discovered by a revolutionary television producer, and he was pushed into an investment against his will. And from those three bits of good luck came the equivalent today of more than $1.5 billion. That sort of tailwind could paper over a litany of failure and still fund a lavish life, and there is no evidence that in 50 years of labor Donald Trump added to his lucky fortunes. He would have been better off betting on the stock market than on himself.

The following except from early in the book says that Trump characteristics apparent early in his career were much the same as in his later political life.

Our reporting shows that the character traits that would become most identified with Donald Trump during his presidency were set in his early twenties through his relationship with his father. His instinct to fight everything without regard to cost or time or further reputational harm, to file lawsuits more like an angry trust funder than a businessman weighing risks and reward. His de facto definition of loyalty as a one-way street. His tendency to see himself as a victim of jealousy and unfairness. His belief that his instincts, which typically meant his desired reality, were superior to any reasoned analysis by experts. All of it emerges in his relationship with a doting, if cold, father.

The following is a NY Times articles about one of Trump's business failures and explains a continuing grudge he has against Columbia University.
Decades Ago, Columbia Refused to Pay Trump $400 Million

The following link is to article about Trump suing authors and publisher of Lucky Loser.
Trump Sues Authors and Publisher of ‘Lucky Loser’

[David · Rating 4 out of 5]

I've stopped after finishing chapter 21 only because of the results of 11/5/24. For me there's just no point in reading this kind of stuff anymore.

I had always been morbidly curious about Trump's actual background and I think the authors did a good job of presenting his history. Any book on this subject that isn't a hagiography has the same guy at the center. This is no different. But what it also brings is the story of how his father, Fred, built the business and created a pathway for his second son's success. Once that's established the authors detail his many business failures. It's quite remarkable in the worst ways.

My only nitpicks were a number of typos throughout along with the several times the authors unnecessarily dunked on Trump for some stupid thing or other. It seemed gratuitous.

I felt the book largely delivered an interesting background that felt different from much of the rest of the books I've read on the subject. If you have the stomach for this kind of thing I'd recommend it but I'd more highly recommend for readers to find a book about something else altogether.

[Megan · Rating 5 out of 5]

Some inevitable questions nearly every person - myself included - asks before reading this book are: “is it truly worth reading? There’s so much out there on Trump already and I’m sick of hearing about his delusional tirades. Is there anything new I can possibly learn from this latest investigation into his life?!”

The answers to both questions are YES, it is worth reading this one and YES, you will learn so much new information that has never been publicly disclosed until now. Lucky Loser is a scathing indictment of Trump’s “business acumen”, which, in reality, is simply a carefully crafted illusion. One which, by all accounts, should have been shattered a long time ago.

The authors succeed where others have failed because they approached the mythologizing of Trump from an entirely new angle than works of their predecessors. Instead of reiterating the chaos he’s already caused and backing up evidence with his former inner circle (individuals which the MAGA crowd will simply dismiss as traitors), they instead focus on his entire life, personality, and his business projects (all cons, all failures) before he ever ran for office.

As it turns out, while many of us have long been aware of Trump’s business failings, and how many Americans were tricked into believing he was a successful, ruthless CEO and entrepreneur (thanks to the onset of reality TV and Mark Burnett’s unique ability to shape individuals into any role he needed them to play) - we still didn’t realize the full extent to just how much he’s been given, how much he’s squandered every opportunity, and incredibly, how he’s been rescued from ruin each and every time.

To begin with, many of us who (thought we) knew better scoffed at his remark that his father gave him a “small loan of a million dollars.” We weren’t scoffing for the appropriate reason, it turns out. We simply accepted that as more or less close enough to the truth and claimed that a million dollars was far from a “small loan.”

Actually, had those of us who scoffed really thought into it, we would have realized that the problem wasn’t the idea of looking at one million dollars like it was nothing. The problem was looking at one million dollars like it was something anyone could easily turn into a billion dollars (in other words, yes, it’s certainly a privilege, but it’s extremely rare to find individuals who can increase their wealth a thousandfold).

That’s because he never actually helped the incredibly successful businesses Fred Trump, Sr. had built to grow at all. When it’s instead revealed that his father - also a conman, but at least one with some degree of morals and loyalty (although very little of the former) - contributed well over $400 million - $400 million in 1985 being roughly equivalent to $1.165 billion dollars today - to lay the groundwork for his son’s image of future success, it makes a lot more sense how DJT continued to fail in his expenditures, yet could still claim with some credibility he’d been successful.

This was thanks the fact that his father bankrolled his ridiculous, often entirely unrealistic ambitions, only to buy him out somehow before he lost too much. He could still dress and act the part, which, as Trump himself maintained, “image and the illusion of success are everything.” If he was still driving brand new cars worth half a million dollars, buying multimillion dollar mansions and walking around with supermodel girlfriends, how could the public at large possibly see him as a failure?

The business community knew better, as well as the banks, who refused to lend him money after he repeatedly defaulted on loans he’d “given his word” he’d pay back (even Deutsche Bank, which had a reputation for taking on high-risk clients and projects, eventually had enough and refused to continue lending to him). There was complete shock - followed by intense ridicule - from top business executives when Trump was first declared The Apprentice’s “make-or-break careers” star CEO.

Even while the team producing the show knew Trump had greatly exaggerated the extent of his success and his knowledge of business, they still weren’t prepared for the reality they encountered when first stepping into Trump’s main offices. It was taken for granted that their set would already be provided - a huge business building, filled with busy personnel, ringing telephones, executive suites with expensive furniture - customary of any relatively successful CEO, let alone one who had been a household name for the better part of two decades.

Instead, they came across a handful of rooms, mostly barren of furniture and personnel. Given the timeframe, they didn’t have time to find a new CEO to who worked so well with the producers and the scripts on such short notice (especially given that most successful CEOs didn’t want any involvement in the world of media). So instead, they went to work creating what they’d expected to see: a boardroom in a shiny, modern building, sleek lobby, elevator - presumably leading from the lower level personnel offices to the executive suite, along with hired extras to show how busy the company was (sometimes even staff from the show would have to step in to play these parts).

And so began another lucky period for Donald Trump, one in which the media again made him appear as someone entirely different from who he really was. Time and again, this happened in the past as well, due to three factors whose impact cannot be overstated: first, his father’s repeated financial backing and support for all projects - and even more important, backing out and saving his son when it became apparent that once again, another business venture of his was doomed to fail (all that mattered was saving Donny, not the contractors, the shareholders, the co-founders, the workers).

The second factor necessary for his attempts at success (turned illusions of success) was his father’s large network of loyal friends in high places that he’d accumulated over a long period of time as he built up the business. Politicians who could sign for permits no one else would, mayors who would look the other way at skirting some regulations. They would all take Donald under their wing as a favor to their lifelong friend, Fred.

Lastly, the media would continue to be complicit in hyping up Trump’s image as a successful real estate developer. He would repeatedly be offered spots on the old show, Lifestyles of the Rich and Famous, which was one of the first of its kind in giving “ordinary citizens” a peak behind the curtain of how the fabulously wealthy lived and spent. While many celebrities and businesspeople wanted no part of a show they considered tacky and intrusive, Trump was one of the few who jumped every time at the chance to show off.

For some reason, the media perpetuated his lies by never thinking to question his net worth - a figure provided to them only by Donald himself. Even magazines as trustworthy as Forbes simply took Donald’s ridiculously overstated claims of his net worth as an objective fact. All of these revelations make it all the more preposterous for Trump to play media victim now.

However, after reading how his father, father’s friends, and all those around a young Trump encouraged (at worst) or simply ignored (at best) the behaviors and trademark attitudes which would come to shape Trump’s business career and his own perception of himself, it’s not as difficult to believe anymore that he really does see himself as a constant victim.

A victim of vicious reporters or competitors who portrayed him unfavorably out of jealousy or unfairness, his constant belief that giving up wasn’t an option, no matter how ridiculous or costly a lawsuit might have been - this was encouraged by attorney Roy Cohn, to never stop fighting, as it would make one look weak - even as it cost very real financial damage as well as damage to his reputation as a serious businessman.

While this last trait I mention certainly isn’t the last of behaviors/attitudes ingrained in him, it’s certainly one of the most important: at the very beginning of his career, he was more prone to at least hearing out experts and their case for or against certain projects or aspects of the projects he’d dream up. Over time, he began to take the approach that “anything with his name on it” was already a success, and his “initial gut instinct” was always superior to expert advice.

It’s not exactly hard to imagine, then, how he’d behave if he were to become President. Which is exactly what this book allows you to determine from a seemingly endless trove of indisputable facts. I understand why many people felt the book was a bit too detailed by appearing to mention every aspect of Trump’s business ventures. This is one of the few cases where I’d argue it was necessary to include all of this information - given the continued support for Trump in spite of all the obvious lies and cons, it’s a unique case given how it’s almost, if not completely, without precedent.

One thing I did find unfortunate was the book’s title: Lucky Loser. There’s more than enough information for the objective reader to reach this conclusion. Calling the subject of the book a loser in the book’s title isn’t exactly the best way to convince Trump supporters and those on the fence that your book is objective and mostly without bias - which, of course, is who you’re ultimately hoping to reach most. I wish they hadn’t made that mistake.

That being said, I still feel everyone should read this book. If you consider yourself truly open-minded, then you should be willing to listen to SOME criticism of your preferred candidate. This book isn’t as blatantly partisan as others - especially not while presenting Trump’s business and personal failures in light of objective legal discoveries. It’s also important to note that most - if not all - information presented is decades old, and at the very least, before any outcry of bias or misinformation campaigns targeting conservative politicians.

[Dick Heimbold · Rating 4 out of 5]

I listened to the book on Trump called Lucky Loser. It added a lot of detail to what I already know of his family life and wildly played business games. There is a lot of coverage of his father Fred, a hard driving apartment complex developer, who was a detailed planner and tough, tight-fisted director of his construction projects. Turns out Donald Trump was anything but a detail manager but preferred relying on his first instincts rather than the advice of any kind of expert. Donald was a schemer and liar from an early age. In military school for the yearbook picture, he borrowed another cadet’s jacket because it had a lot more medals than his. As businessman he jumped into a lot of businesses that failed, but his father always bailed him out. He took credit for his father’s considerable success, often bragging they were his own projects. He benefited by his father’s good relations with lenders and New York politicians. He ventured into casino management, with calamitous results and had to sell his yacht, mansions, sports team, airline, etc. to service loans and prevent forced bankruptcy. His appearances on the Apprentice TV show saved him from complete financial collapse. For the Apprentice, Mark Burnett, the producer who invented the wildly popular show Survivor, portrayed Trump for the national audience as America’s most successful businessman—setting the stage for his entry into national politics. The show flourished and made a lot of money for Trump. The timing was fortunate for Trump because the inflow of new money helped stave off creditors after him for past business failures.

Throughout his life he was always boastful, an exaggerator and habitual liar. Roy Cohn helped to harden his personality with advice never to admit mistakes and always seek revenge for slights large or small. Accordingly, his habit of suing became his modus operandi in thousands of cases. It instilled fear into those victims who didn’t have the time or money to slug it out in the legal system. Trump University was described in detail as an example of where a sleazy venture of his failed and for which he had to pay a 25-million dollar fine. There were many examples of Trump chiseling on deals to get more money or some other advantage out of them. There were examples of him shortchanging working men and women to whom he owed wages or payment for services. He was, it seemed, constantly probing the boundaries of legality and custom to punch through and gain some kind of advantage for his lifelong drive to make money—whether by tawdry schemes and grifts e.g. sneakers, bibles, baseball-type cards, political memorabilia or by grander schemes such as running golf courses, clothing branding or housing construction.

A central driving force throughout Trump’s life has been to be in the public eye and adulated, but short of that, to be frequently noticed in the media, even if not adulated. He always wanted to dominate or claim to dominate “like never has been done before,” at whatever he was up to.

The title Lucky Loser refers to several lucky breaks in Trump’s life of ill-fated ventures in the business world and political world that were saved by something outside of his ability to manage these ventures. For example, the authors cite Fred Trump’s largess in several cases that bailed out son Donald’s money-losing activities and consequent economic collapse. Also, with timely coincidence, The Apprentice TV show provided needed cash flow when Fred faded from the scene because of age—another stroke of good fortune. Fox News and social media are portrayed as perfectly suited for a conspiracist and aggressive liar such as Trump to hammer away continually misinformation to denigrate the press, government, and his enemies, and by so doing build a MAGA army capable of getting him elected president once—and then rising in insurrection with an assault on the nation’s capital when he failed to be elected the second time.

At the end of the book that was published in September 2024 the Trump drama is not completely played out. Not known is what the future holds. Will Trump win the election and have destiny smile on him again, with an opportunity to void federal criminal cases against him? Will the large civil penalties levied against him be reversed on appeal? Will the newest grifts continue to keep him in the black, the 100,000-dollar watches, the NFTs, the crypto scheme? Who knows? Looks to me like the upcoming election is the key. Winning could get him out of a lot of legal trouble and supercharge his grifts. Not winning could make him The Big Loser.

[Ellyn Ingalls · Rating 5 out of 5]

Please Read this book!!

For anyone who has not yet made a decision on the 2024 US election- a lot of this info was readily available pre 2016, but mainstream media didn’t bother to emphasize it.
Here is the book that tells you everything you need to know about trump- backed up by pages and pages of pre-internet FACTS. (For those fake news, must be AI fans. Nope, I saw a lot of this with my eyes when it was happening. Yes. I’m old…)
Please read this book. Thank you!!

[Ari Damoulakis · Rating 2 out of 5]

If they had bothered to make the book shorter and not had such long, boring sections and details about Donald’s father and his scandals, if they made that section smaller and really concentrated on Donald, maybe more Americans with really short attention spans might have bothered reading this book and, of course I’m exagerating, but we wouldn’t be in this mess today.

[Emma · Rating 4 out of 5]

So apparently he’s even dumber than I thought he was🤣🤣🤣🤣🤣🤣 & some could argue that it all comes down to his (definite) daddy issues…

LONG REVIEW (for me):
4.5⭐️ rounded down because it was super dense & loooong & not all of it was necessary, but a really fascinating read about the entire Trump dynasty.

It read a bit different than most things about Trump because it focused less on the insane shit this man is constantly doing & more on the making of his empire & brand. He truly is the beneficiary of a lifetime of lucky breaks & wealthy saviors who were charmed by his odd, yet clearly powerful, form of charisma.

It also made me feel a sort of empathy for him because his dad enabled a lot of this behavior as a child & with the right resources (read: money) at his disposal, he has been able to become more volatile and egocentric without being checked or facing any consequences. I wonder what he would’ve become if his father hadn’t created a fantasy world for him where he is the King & his circumstances (again, read: money) will always work in his favor, because it’s created the Trump we have… & I think that guy sucks.

[Olivia Robinson · Rating 5 out of 5]

Well, I picked the wrong time to start this book. It is deeply researched and very well written- and made me want to scream daily. I plan to now start a mystery novel where the criminal is punished for his crimes.

[Lori · Rating 5 out of 5]

RTC

[Jude Mercer · Rating 5 out of 5]

It’s even worse than what I expected. Trump is truly one of the worst businessmen ever. He was always what he showed us as President - an inept, corrupt, arrogant liar and cheat. I blame Mark Burnett for the Apprentice. Without that, maybe his problems would have caught up to him instead of fueling years and years of fraud masked by celebrity. Regardless, anyone that still supports Trump knowing what this book lays out…

[Michele · Rating 5 out of 5]

Ross Buettner and Susanne Craig worked for years to uncover the story behind the mirage of Donald Trump's financial acumen. Employees and institutions working with Trump were obliged by NDAs or firmly warned not to divulge any information to The NY Times reporters. Even the banks who had been repeatedly defrauded stayed mum. Buettner and Craig persisted, and at last discovered a gold mine. Mary Trump and her brother had sued the survivors of Fred Trump Sr., including her aunts Marianne and Elizabeth, and her uncles Robert and Donald, for their fair share of the family estate. With the help of Craig in particular, Mary began to understand that the discovery given to her during the lawsuit was now her property. She was not under any legal obligation to keep it secret. She took possession of the "receipts," hauling the papers out of his office in a truck, and eventually turned much of the material over to the authors to help them explain the Trump organized crime syndicate.

This is a story of the family dysfunction, the particular psychopathologies of Fred Jr and Donald Trump, and the multi-generational crime spree perpetrated by them since Fred Sr arrived from Germany with his wife, Elizabeth. Senior died a young man, and Elizabeth became the genius behind the first generation of Trump fraudsters. Her right hand man was son Fred Jr., who could not refrain from defrauding everyone from the lowliest laborer to the federal government. He was the kind of guy who would pick up nails from a construction site so they could be re-used. His library had no books. When the kids came for dinner (a command appearance on Wed. nights), they ate dinner and went home after an hour. Table talk always resulted in arguments, with Marianne playing the part of nosy buttinsky and Donald the jokester. The rest of the family was of little account and got little notice. Fred Jr was headlong into fraud in every business realtionship he had. He chose to partner with men who small enough not to interfere, or even always understand, what he was up to. Those who did understand were paid off, in kind so it could be hidden from Uncle Sam. I would love to see an estimate of how much money the Trump crime family has stolen from the US governments (states and federal) since WWI. If any body tells you Trump crimes. had no victims, just think of the millions they didn't pay in taxes. They stole that from all of us. I don't care if Deutschebank would rather not o into it. I'd like my money back.

Donald was the mini-me to his criminal father. He began building with loans from his Dad, put into effect all the illegalities he was taught growing up, and eventually spent not only his part of Fred Jr's estate, but also stole very liberally from the shares of his siblings, and all of the money bequeathed to his niece and nephew by Fred Jr. . He bought off his siblings by including them in the profits of criminal schemes. Marianne finally broke with Donald, but only after a lifetime of participation in his crimes.

Trump survived his first wave of banruptcies thanks to the theft of his father's life's work. He survived the second wave courtesy of Mark Burnett and The Apprentice, from which he derived big money, but perhaps more importantly, was also able to build a facade of competency that obscured his real nature and still has people believing he is fit for anything but hawking cheap sneakers and bibles.

This is not a book I loved reading, but one I think is important.

[Melissa · Rating 4 out of 5]

He's dumber than I thought, wow. It's very...sad, anger inducing, frustrating, infuriating, unbelievable, that he was able to con soooooo many people. It's more a statement of how gullible people can be than it is about his stupidity. These other people have no excuse! They actually had a brain, maybe still do, and went against their better judgement to get in business with him. There are stories of people refusing and letting their better sense take the lead and say no, while too often people threw money into losing propositions. He had no idea what he was doing and just assumed things would work out, which they didn't. People lost so much in his schemes!!!

His father didn't correct him when he made mistakes, that cost millions! If Fred had just explained the concept of buy low, sell high, things would have turned out differently. Instead, Fred patted D Trump on the back when he bought high, lost everything, and had it foreclosed on. And when The Apprentice went to his office, the condition was so awful! It was in terrible, TERRIBLE, condition with mildew smells, and damaged furniture. They had to construct a fact office set on a different floor. Everything was on one floor, the elevator rides were fake according to the book. Never seen the show, so now idea.

I started this before the election results, and was so sad while I worked to finish it. Read this if you want to be more depressed about who will be in the White House.

[Peter · Rating 5 out of 5]

Will the real Donald Trump please stand up? Who is the real Donald Trump? Is he, as Churchill might say, an undecipherable riddle wrapped in an enigma? OR is he

‎ ‎ ‎ ‎ ‎ ‎• the über-businessman he presents in The Art of the Deal (1987) and Think Like a Billionaire (2004)?
‎ ‎ ‎ ‎ ‎ • the clever geopolitical strategist of his ghostwritten election year books Save America (2024) and Great Again (2016)?
‎ ‎ ‎ ‎ ‎ • the cruel and vengeful creature seen by his niece Mary L. Trump in Too Much And Never Enough (2020) and Who CouldEver Love You (2024), and by her cousin Fred C. Trump III in All in the Family (2024)?
‎ ‎ ‎ ‎ ‎ ‎• the mentally unstable figure seen by psychologists and psychiatrists in the volume The Dangerous Case of Donald Trump edited by Brandy X. Lee (2017)?
‎ ‎ ‎ ‎ ‎ • the reprehensible, venal and duplicitous autocrat seen by investigative reporters in Maggie Haberman's Confidence Man: The Making of Donald Trump and the Breaking of America (2022), Bob Woodward in Fear (2018) and Lucky Loser: How Donald Trump Squandered His Father's Fortune And Created the Illusion of Success (2024) by Russ Beutner and Susan Craig?
‎ ‎ ‎ ‎ ‎ ‎• the recently emerged babbling idiot seen by millions as he does "the weave" to spice up his rhetoric?

‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎‎ Two observations jump out from the above list. First, Donald Trump inspires long subtitles. Second, he seems to enjoy hurting people, either by acts of petty revenge or by anti-social acts like cannonballing guests at his club's swimming pool. One wonders if he also tears the wings off flies or focusses the sun's rays on ants.

Oh! You haven't read Lucky Loser? Perhaps that's because it was just released. So, let's look at this very meaty addition to the Trump story.
‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎‎ Among its other contributions, Lucky Loser subtly suggests a new interpretation of the Trump psyche as a split personality. When Trump wants to mask his identity or to shift blame, he occasionally uses an alter ego – a fictitious employee named "John Baron" who gums up the works. Donald John Trump is a good man, a man of honor devoted to helping humanity through his political skills and economic savvy; John Baron is a devious liar bent on amassing personal wealth and power. Buettner and Craig report that on occasion, when Trump has been accused of doing something inappropriate, he's responded "I didn't do that. That was John Baron."
‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎‎ The unsettling question is whether "John Baron" is just Trump's conscious convenient foil – a fictitious character to divert blame onto another – is an alternative Trump personality, a subconscious character capable of coming out to do harm, then sliding back into Trump's neural network. In the latter case, we should be very afraid of Trump – rather than the adoration he so obviously needs, he should be receiving psychiatric treatment.
‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎‎ ‎‎Donald John Trump's behavior has clearly been despicable by any moral standards outside of Russia. He is a confidence man and a manipulator, who once drove prospective investors around a completed housing development to show them the quality of his work. They were so impressed that they became investors, never knowing that The Donald had nothing to do with that development.
‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎‎ Trump is also a convicted felon many times over, a probable rapist found liable for sexual abuse and defamation, a financial engineer who manufactured his success by downplaying his father's role in seeding The Donald's wealth, and a "great businessman" who never pays income taxes because the losses in value of his enterprises more than offsets his income –for decades Trump has been eating his buildings to finance his image as a successful businessman.
‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎‎ He is a man who proudly announces his degree from Wharton and his expertise in economic matters, but fails to mention that it was a bachelor's degree and that he was admitted because of his father's wealth and because the then new Wharton School needed student (his entering class was just 21 students). His frequent claim that he was at the top of his Wharton class is not consistent with the record: he was never on the Dean's List, much less the Honors list.
‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎‎ ‎What appears to me to be the value-added portion of Lucky Loser – in addition to its hint about Trump's split personality – is its early chapters about growing up as the son of Fred C. Trump Sr. There we see how Donald J. Trump/John Baron came to be today's über-confidence man. There we rediscover that the apple never falls far from the tree.
‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎‎ ‎Fred Crist Trump Sr. was a New York home builder of single-family homes and, later, of apartment buildings. Born in 1905, he began his career in the 1922 as an apprentice and became a reputable builder of affordable housing units, both single-family and apartment buildings. His success derived largely from an astute eye for New York property and creative application of new and efficient assembly-line construction methods. An honorable beginning, indeed.
‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎‎ ‎That success was threatened by the arrival in 1930 of the Great Depression, when median real estate transaction prices per square-foot in the Trump territory of Manhattan fell sharply, by 58 percent from the late 1929 peak to late 1932 (Tom Nicholas, Harvard Business Review, 2013). Because mortgage instruments are fixed-price obligations, a median property purchased in late 1929 for $10,000 and financed with an $8,000 mortgage was valued at $4,200 in late 1932, with a mortgage not much less than $8,000. A property owner would be far better off by defaulting on the loan and turning the house over to the bank ,than by selling it in the market. The natural result was massive defaults on home mortgage loans, followed by bank foreclosures and resale of the homes by the banks.
‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎‎ This drove home prices down farther and created even more defaults. Commercial banks and savings institutions – the primary mortgage lenders –failed en masse, and the disease spread to other sectors of the U.S. economy. ‎Among the many responses to the Great Depression was the 1934 creation of the Federal Housing Administration (FHA). The FHA made no loans to either home builders or buyers; its role was to provide insurance for the mortgage loans made to home buyers: a bank would make a mortgage loan and buy an FHA insurance policy protecting itself against default.
This was a promising approach to the housing finance crisis – it shifted the burden of declining home prices from the overstressed financial institutions and credit markets to the federal government, and it inhibited the snowball effect of deflation on the broader economy.
‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎‎ ‎But Fred C. Trump Sr. gamed the system. Among Trump Sr.'s tricks was the systematic overvaluation of the budgeted costs of homes constructed. Because the amount of FHA mortgage insurance was based on the construction budget, not on actual construction costs, this practice allowed Trump Sr. to borrow more money from private lenders than would be needed to complete the project, pocketing the difference between the budgeted and actual construction costs. The results were an immediate fattening of the Trump wallet, excessive lending by banks, and ultimately an increase on bank failures. In short, Fred Trump's construction budget practices reduced the value of the FHA as a bulwark against defaults, and it increased the economy-wide tailspin in the first two years of the Depression.
‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎‎ ‎To compound the felony, Fred C. Trump Sr. then reported the fictitious "saving" in construction costs (the difference between budgeted construction costs and actual sale value) as capital gains rather than as ordinary income, allowing the fictitious income to be taxed at the favorable tax rate for capital gains. This odd practice was endorsed by corrupted officials at the FHA, and it became the core of a major corruption scandal at the FHA during the 1930s.
‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎‎ ‎This was what Donald J. Trump/John Baron learned at his adoring father's knee. This was the cauldron that skewed The Donald's moral compass and gave birth to John Baron. It's no surprise that the young Donald was a boy who took delight in cannonballing guests at the family's country club, or that the young Donald grew into a towering narcissist unable to behave with the minimal empathy expected by society, a man who delighted in harming those he saw as opponents.
‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎‎ ‎Donald's frequent misbehavior in his teens resulted in his relocation to the New York Military Academy, a military school from which he graduated with no academic accolades but with the high rank of Captain, a triumph spurred by his father's generosity to the school. The Donald was then admitted to an easy-to-enter undergraduate program at Fordham University, and after two years he transferred to UPenn's new undergraduate business school (Wharton), from which he received a B.S. in Economics. Those two initials described his style well.
‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎‎ ‎And so, Donald Trump grew to become the man we see today: a man whose sole concern is himself, a man who automatically reverses the finger of blame (John Baron did it!) and blindly meets criticism by viciously blaming his critics for the same faults they attribute to him; a man for whom not getting re-elected in 2020 was a clear sign of electoral fraud because, well, in a truly just world he simply couldn't lose; a transactional leader who never gives unless he receives a personal favor in return, a man whose sole response to a request is, "What can you do for me?"
‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎‎ ‎Trump's transactional behavior is the source of his well-known opposition to assisting Ukraine in its conflict with Russia. In 2019 then-President Trump had a phone conversation with Volodymyr Zelensky, President of Ukraine. Russia had annexed Crimea in 2014, an act of war that violated a number of past Soviet and post-Soviet assurances of Ukraine's autonomy. The West turned a blind eye, thus encouraging continued aggression. In 2019 the common bet was that Russia would grasp for more of Ukraine – which it did in 2022.
‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎‎ ‎On that phone call, Zelensky asked President Trump to provide military assistance to Ukraine to help it prepare for further Russian aggression. Trump's response was to ask Zelensky to ask for a quid pro quo – an investigation by Ukraine of the business activities in Ukraine of Hunter Biden, son of Joseph Biden who was Trump's likely opponent in his 2020 campaign for reelection. Zelensky properly demurred, noting that it would violate international understandings about interfering in another country's elections.
‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎‎ ‎Trump demurred on the military assistance, and since then he has consistently resisted U.S. assistance to Ukraine. When Trump and Zelensky later had another phone conversation, Zelensky remarked that he hoped the U.S. and Ukraine would have a good relationship going forward. Trump's reported response was "It takes two to tango." In other words, if you want me to help you maintain our autonomy, you have to help me win an election. Apparently, Trump believes that the importance of his personal stature as President trumps the importance of world peace.
‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎‎ ‎It should be no surprise that one of DJT's most vocal supporters is Elon Musk, a business figure whose aura of success is earned by his wide range of winning innovations, from electric cars to electrical grid management to space exploration. In his biography of Elon Musk, titled simply Elon Musk, Walter Isaacson notes that Musk is a man without empathy, a man who cares only about results and the impact on him. Musk and Trump appear to compete for last place on the global empathy thermometer; this is a hallmark of narcissism. The only difference between Musk and Trump is that Musk has actually created something real, while Trump's sole creation appears to be himself.

[Bruce Kellison · Rating 5 out of 5]

This is a great book to read right before Halloween: horrifying and compelling at the same time. Trump's business history is now largely a matter of public record thanks to these great reporters, the same ones who uncovered Trump's tax returns during his presidency. Trump pulls off con after con on his business associates, relatives not by cunning, treachery, or some master plan. He wins because he's a lucky loser. Just a great read from start to finish.

[Natalia · Rating 3 out of 5]

TLDR: Trump “made” his money by being born to an obscenely wealthy dad and proceeded to squander so much of that money with absolutely stupid “business” ventures.

This book way just way too long. I’d have rewritten this as a handful of vignettes of a few of his career mishaps over the decades.

The authors spend way too much time on things like his dad’s career and provided too much detail on other things (for example: the contours of Mark Burnett’s career before he created the apprentice).

[Steve Peifer · Rating 5 out of 5]

This is the book you give to people who say ‘But he’s a successful businessman!’ He never ever was. He was a failure bailed out by a rich father and so much luck. The book does credit him with charisma and the ability to absorb lots of detailed information through oral presentations.

But he lies and fails. Buckle up; it is going to be a challenging four years.

Besides the extraordinary research, it’s an absorbing read. It is worth your time.

[Bailey · Rating 5 out of 5]

This is a book I think everyone who voted for Trump should have to read. Unfortunately, those are the exact people who either won't read it, or say it's bias even though it is all factual information that can be checked.

[Jenny · Rating 5 out of 5]

While I give the book 5 stars, the subject matter gets 0. Kudos to Buettner and Craig for going in depth into Trump's history to write this easy-to-follow and coherent book about Trump's fortune and his work as a "businessman." The people who should read this book won't, but here's the gist: Donald Trump has lied all of his life. Small things, large things, it doesn't matter. Donald's ability to join the real estate development world strictly came from his father and his father's fortune, although Donald will tell you he is self-made and his father gave him barely anything (the hundreds of millions he did indeed get as a result of his father are apparently peanuts.) Although Fred Trump did many fishy things to save money and become successful, he did become successful on his own and through much hard work, with some political connections thrown in. This allowed Donald Trump to start with a leg up in the business world. As the book says, Donald Trump was lucky because he was born to Fred Trump. Fred, much to my chagrin, believed Donald was a wunderkind who could do no wrong, which I believe gave Donald his grandiose sense of self that has never abated.

Just about everything Donald Trump has touched has lost money. Donald believes that his "instinct" is all he needs to be successful, and because of that he does not do due diligence before making a real estate deal. In addition, he wildly overpays and leverages himself to a level he cannot pay back. This has resulted in bankruptcy after bankruptcy after bankruptcy. The only way he's made money is by appearing on the Apprentice, raking in money on sponsorship deals incorporated into the show, and by accepting endorsement deals that paid him upfront, because many of those deals turned out to be for companies and products that went bust. He's also engaged in questionable practices to take as much money out of projects as he can while leaving others to deal with the debts.

Donald really did become successful, whatever you believe that success is, based on luck, and we're all reaping the consequences today. I truly believe both the publicity Donald brought for himself, not all of it good, that the press so readily bought into and promoted in the 80s and 90s, and Donald appearing on the Apprentice as a successful businessman, which he was not, led to 2016 and beyond. Donald has always believed that anything bad that has happened to him is someone else's fault, never his, and Donald's appeal is telling others that anything bad that happens to them is not their fault, either, which they believe.

[Mindaugas Mozūras · Rating 5 out of 5]

Perception is reality.

The quote above is not from this book. It's the long-standing name of the poker group I'm a part of (which slowly morphed into a poker/board games group). It feels like a pretty good name when the context is an imperfect information game.

For me, it feels equally apt to describe what Donald J. Trump is great at. There are many things he's not good at, as this book shows in detail. There are also quite a few negative qualities this book portrays, like being a lazy, impetuous, and shameless liar. But he seems to understand at least one thing - that reality might not be as important when you can manage perception.

I found the book to be well-written and well-researched. It takes the history of Fred Trump and his son, the 45th and 47th President of the USA, and weaves it into a narrative that I found enthralling.

[Jeb Myers · Rating 4 out of 5]

Informative, fascinating, and well written. I appreciated that it stayed focused on Donald Trumps business record-a lifetime of killing the golden geese he keeps falling into.

While not a fan of Donald Trump, I recognize he is more transparent than most of humanity. His impulsive and self-serving behavior is true to his desires. Most of us filter our desires.

The business losses he has incurred are astonishing. While the story is unfinished -he is our 47th president- Donald Trump is the “luckiest loser” in history.

[Fred Forbes · Rating 5 out of 5]

Great to finish the year with 3 five star books in a row! Ironic that I would not have noticed this book if the subject had not decided to sue the authors. Probably not a suit he will win since this work is meticulously researched and documented.

It is surprisingly well written for something analyzing fairly complex topics like commercial real estate, the gambling and entertainment industries, tax forms and regulations and estate planning and trust issues. As a finance guy, I enjoyed it but I'm not sure if readers on average will like plowing through it despite the excellent job the authors do in explaining some fairly complicated topics.

Still, a worthy read for those attempting the understand the attitudes and modus operandi of the subject.

[Csparrenberger · Rating 4 out of 5]

What have we got here? We have one of the most thoroughly researched books on every business transaction that Donald Trump has ever undertaken. I have no doubt that everything in this book is 100% true. That said, to me, this book reads like one of the most boring College textbooks I ever had to read. I would suggest getting this book at the library, and reading the chapter on the apprentice and the epilogue. Then, if the reader is so inclined, selectively read other chapters. I am giving the book 4 stars for the extensive research that went into it. Let the readers decide!

[Coral · Rating 5 out of 5]

Fear keeps people watching

[Steve · Rating 5 out of 5]

I’ve read a number of books about Trump, but this one is the most enlightening. The final section of the book, regarding the Apprentice years to the present, should be required reading for anyone who voted for him in the last election. I’m not sure how we avoid another con man in our political future, but this book gives us a road map of what to beware of.