Lucky Loser: How Donald Trump Squandered His Father’s Fortune and Created the Illusion of Success by Russ Buettner and Susanne Craig (Book Review)

This book offers an in-depth look at Donald Trump—the businessman, real estate investor, entrepreneur, and brand. Much of the narrative focuses on his struggles to finance buildings, casinos, golf courses, and other projects. Despite his relentless self-promotion, Trump has repeatedly proven to be a poor businessman, often relying on his father, Fred Trump, to bail him out of financial trouble.

As you read, one question becomes unavoidable: Why would anyone choose to partner with Donald Trump? His track record as a business leader is riddled with failure, and those who have worked with him—contractors, lenders, and employees—frequently find themselves shortchanged. Why lend money to someone who appears to lack financial discipline in both his personal and professional life?

A Trump supporter might dismiss this book as misinformation, but the authors had access to extensive financial records, including Trump’s tax returns. Their research is bolstered by interviews with numerous individuals who have firsthand experience dealing with him.

The fact free bubble Fox News created around Donald Trump as president may have felt familiar. He had spent his entire life in a similar bubble, financed by his father. In this comfortable place, he could hide his failures, pay for them with his father’s money, and later a celebrity’s fortune. There would be no metrics measuring his success, just the impression of self created wealth that he willed into existence.From the moment he left his father’s careful planning practices behind, he protected his bubble by waging war on the fact based world that might pop it.

Trump’s failures in the casino industry in Atlantic City are well-documented. His attempt to buy an NFL franchise led instead to the downfall of the USFL. When journalists and analysts challenged his exaggerated business claims, he responded with lawsuits and intimidation tactics.

Perhaps his greatest success—if it can be called that—was The Apprentice, a reality show that portrayed him as a shrewd businessman with exceptional judgment. This carefully crafted image helped convince much of the public that he was a financial genius, a perception that played a crucial role in his 2016 presidential campaign.

The book is 456 pages long and thoroughly researched, with extensive footnotes to support its claims. In fact, published articles by the authors on Trump’s finances earned them a Pulitzer Prize.

I wish I could say this book might change the minds of his staunchest supporters, but realistically, many of them are unlikely to engage with a work of this length and depth.

Start of the Rout?

If America is a stock, is it time to dump it and sell?

Like the ouroboros, I believe Big Tech is eating itself alive with its component companies throwing more and more cash at investments in one another that are most likely to generate less and less of a return. Monday’s correction shows that our financial markets — and possibly your retirement portfolio — may be starting to reflect an understanding of this dynamic. New York Times 1/28/25 I Study Financial Markets. The Nvidia Rout Is Only the Start. Mihir A. Desai is a professor at Harvard Business School and Harvard Law School.

If Trump’s all-in-on-fossil-fuels, “drill, baby, drill” rallying cry — at the dawn of this era of artificial intelligence, electric vehicles, batteries and autonomous cars — really becomes our strategy, it will not make America great again. But it will definitely help make China great again. New York Times 1/28/25 Trump Is Going Woke Thomas Friedman

The bond market is telling us something about the dawn of the second Trump presidency, and it’s not pretty….Most of the policies proposed by President Trump, from tariffs to additional fiscal stimulus to deportations that tighten the labor market, are expected to add to inflation. And to the degree they are enacted, they will combine with an inflation rate that has declined rapidly, but which remains above the Federal Reserve’s target and is still higher than it was during most of the decade leading up to the pandemic. Rising long-term rates are bad for businesses and households that need to borrow, since the cost of loans such as mortgages and auto loans are directly linked to 10-year Treasury yields. New York Times 1/29/25 Trump’s Plans Are Already Making Your Life More Expensive Rebecca Patterson (is an economist and market strategist)

Snapshot

Pickleball: where tennis players go to die. (Seen on t-shirt)

“Kamala holds the hopes of a lot of people in this country who are praying that she doesn’t fall on her face in the next 72 days. She can take heart that she’s driving Trump crazy. He is jealous of her looks, her crowd sizes, her star power and her vivacious, bodacious vibes. That’s a good start.”

Daffy Donald, Turning Pea Green With Envy NYT Maureen Dowd

Planning a wedding has become so expensive that some couples are asking their guests to pay to attend their special day…Matthew Shaw, the founder of Sauveur, a wedding planning company in London, said that selling tickets “introduces a strange relationship between you and your guests, turning your guests into customers.”

He added, “You’re no longer hosting — you’re offering them a paid experience, which introduces a very different narrative in terms of what guests are expecting.” (NYT)

NYT Hardcover Non-fiction Best Sellers

SHAMELESS by Brian Tyler Cohen

2. MEN HAVE CALLED HER CRAZY by Anna Marie Tendler

3. THE ART OF POWER by Nancy PelosI

“School board candidates backed by Moms for Liberty, a conservative vanguard whose members popularized restrictions on classroom library books, are losing elections in Florida and some swing states. Republican leaders who rallied against critical race theory and LGBTQ+ issues recently faced recalls in red pockets of California.”

Are Republicans losing the culture wars? Politico

Babe Ruth ‘called shot’ Yankees jersey fetches record $24M

Dow 41,175

S&P 5,634

Nasdaq 17,877

Review: Trust by Hernan Diaz

Taken from my review on Goodreads

My rating: 3 of 5 stars

I was anxious to read this book because of the excellent reviews and buzz surrounding it. I was not aware of the structure of the book where it was basically four novellas that presented different viewpoints and perspectives from different writers. I enjoyed the first novella and was somewhat disappointed and shocked that the story was about to change. Nonetheless I continued to read but found that my interest had lessened.

I am glad that I finished the book as I was able to find out the “secret” of how Benjamin became rich. And it struck me that this secret was somewhat plausible.

The book did provide one of the most interesting and provocative aphorisms that I have read.

“God is the most uninteresting answer to the most interesting questions.”

I did not find that the lifestyles of the characters were particularly interesting – – in fact they were a bit boring. Nonetheless, the book did provide some surprises and the ending justified my efforts in finishing it. I’m not sure how attractive this book would be for readers who have no interest in finance or in the period around the great depression.

A modest start to my new year of reading…

View all my reviews

The Psychology of Money: Timeless Lessons on Wealth, Greed and Happiness by Morgan Housel

Takeaways and notes from the book:

Voltaire’s observation: “history never repeats itself; man always does.“ The lowest income households in the United States on average spend $412 a year on lotto tickets, four times the amount of those in the highest income groups. 40% of Americans cannot come up with $400 in an emergency. Which is to say: Those buying $400 in lottery tickets are by and large the same people who say they can’t come up with $400 in an emergency.

Years ago I asked economist Robert Schiller, who won the Nobel prize in economics what do you want to know about investing that we can’t know? “The exact role of luck and successful outcomes,“ he answered.

The difficulty in identifying what is luck, what is skill, and what is risk is one of the biggest problems we face when trying to learn about the best way to manage money.

What Gupta and Madoff did is something different. They already had everything: unimaginable wealth, prestige, power, freedom. And they threw it all away because they wanted more. They had no sense of enough.

Reputation is invaluable. Freedom and independence are invaluable. Family and friends are invaluable. Being loved by those who you want to love you is invaluable. Happiness is invaluable.

Good investing is not necessarily about making good decisions. It’s about consistently not screwing up.

At the Berkshire Hathaway shareholder meeting in 2013 Warren Buffett said he’s owned 400 to 500 stocks during his life and made most of his money on 10 of them. Charlie Munger followed up: “If you remove just a few of Berkshire‘s top investments, its long-term track record is pretty average.“

The highest form of wealth is the ability to wake up every morning and say, “I can do whatever I want today.“

Controlling your time is the highest dividend money pays.

No one is impressed with your possessions as much as you are.

Savings in the bank that earn 0% interest might actually generate an extraordinary return if they give you the flexibility to take a job with a lower salary but more purpose, or wait for investment opportunities that come when those without flexibility turn desperate.

Having more control over your time and options is becoming one of the most valuable currencies in the world.

The most important driver of anything tied to money is the stories people tell themselves and the preferences they have for goods and services. Those things don’t tend to sit still. They change with culture and generation. They’re always changing and always will.

History can be a misleading guide to the future of the economy and stock market because it doesn’t account for structural changes that are relevant to today’s world.

The most important part of every plan is planning on your plan not going according to plan.

German tanks at Stalingrad – – field mice had nested inside the vehicles and eaten away installations covering the electrical systems. (No one had planned for this risk, hence German tanks were inoperative.)

The more you want something to be true, the more likely you are to believe a story that overestimates the odds of it being true.

Manage your money in a way that helps you sleep at night. Use money to gain control over your time.

Effectively all of our net worth is a house, a checking account and some Vanguard index funds. One of my deeply held investing beliefs is that there is little correlation between investment effort and investment results. The reason is because the world is driven by tales – – a few variables account for the majority of returns. (Author describing his financial management.)

The Price is Right (1970s edition)

I have maintained a personal journey since I was 16 years old. Here are some golden oldies on my entries on what prices used to be fifty years ago…Note gas prices…

March 17, 1973

A haircut cost me $4.25 today. I can remember when they were only two dollars. People are rightfully angry at rising prices and costs. Where does one begin to hold the line?

August 9, 1973

Pair of glasses cost me $44.

Friday, March 22, 1974

Bought an $85 suit on Monday. Pretty snazzy!

Saturday, December 7, 1974

Bought a 1973 Maverick. Price $2118.

Wednesday, January 29, 1975

Gas prices for regular run about $.47 a gallon right now on the average.

Tuesday, July 31, 1979

Prices:
Flounder $2.29 a pound
Eggs one dollar a dozen
Bread $.53 a load
Steak $2.49 a pound
Pepsi 64 oz. $.99
Lettuce $.59 a head
Milk $.86 for a half-gallon
Hamburger $1.99 lb.
Movies $3.50

Saturday, April 12, 1980

Price trivia:
Gas $1.27 per gallon unleaded
Egg McMuffin, hash browns, OJ $1.94
Sunday Inquirer $.60
Sunday Courier $.35
Gatorade $.69 a bottle

Political Potpourri

Why should I worry about the future? Political, religious and cultural groups are pushing an agenda to return to the way things were in the mid-1960s when I was in my teens. Intolerance, racism, sexual repression, discrimination, and religious fanaticism are making a return thanks to Republicans and the Supreme Court, though I’m sure they have never left.

In my almost eight decades of life in the United States, I have seen so much improvement in our technology, medicine and science. Sadly I have not seen the same level of improvement in our national character.

Studying American history after November 21, 1963 is like reading a tragedy. The previous four Presidents before that date were successful ones: FDR, Truman, Eisenhower and JFK. The next four Presidents were LBJ, Nixon, Ford and Carter. They were responsible for the Vietnam War, Watergate, Nixon’s pardon and Iran hostage crisis. Since 1963, we have been involved in unnecessary wars in Vietnam, Iraq and Afghanistan. Starting with the Reagan years, we have hollowed out the middle class in this country and made it much harder for young citizens to achieve the “American dream.” The United States has largely lost the immense respect it had in the world after World War II.

Was the last great national achievement of this country the moon landing in July 1969?

So many Americans are content to being entertained as opposed to being informed and educated. Those Americans are like professional wrestling “marks”. They are gullible to the most ludicrous story lines and pontifications…

Today’s Supreme Court has the same credibility as a moral, ethical, judicial and intellectual authority and arbiter as the Vatican.

While many in this country seem to celebrate individual success stories, one senses that many in the public secretly revel more in the failures, scandals and downfalls of those individuals. The media like to highlight the successes but love to cover and commentate on the downfall.

“Next time the National Anthem is played, every woman and girl should take a knee.” Cheri Jacobus, writing on Twitter

I think that you may receive a more accurate projection of your money and finances from a carnival fortuneteller then a certified financial advisor.

Eloquence

“My money was losing 7% every year due to inflation so I decided to invest it in the stock market. Now I’m losing 7% every day.” Not Jerome Powell, Twitter

***

“Here we are with a vaccine that can save you from dying or going to the hospital with Covid, and tens of millions of people refuse to help themselves by taking it. Which goes to prove that no pandemic is deadlier than stupidity.” Bret Stephens NYT

***

“Humorlessness has crept in its petty pace to the right, where it is conducted with North Korean-level solemnity by the bellowing myrmidons of MAGAdom. A sense of humor, much less self-awareness, is not a trait found in cults of personality. If Tucker Carlson has said anything advertently funny, witty or self-knowing from his bully pulpit, I missed it. Maybe you had to be there.”Christopher Buckley PJ. O’Rourke and the Death of Conservative Humor

***

There is no official count of the number of pregnant women who have turned to hospitals and clinics when something goes wrong, only to be denied the medical treatment they need on religious grounds. And it’s not easy to publicize the most intimate details of traumatic experiences in order to prove what should not have to be proved: that pregnancy carries significant risk of complications, and hospitals and medical professionals in a modern society ought to allow best practices, rather than religious dogma, to guide their protocols of care.

Why was a Catholic Hospital Willing to Gamble with my Life by Katherine Stewart NYT

***

Ukrainian President Volodymyr Zelenskyy was asked to evacuate Kyiv at the behest of the U.S. government but turned down the offer. An American official tells me Zelenskyy said, “The fight is here; I need ammunition, not a ride.”

Blog Buffet

Ruminations on various topics…

Instead of raising and lowering our U.S. flags, keep them at permanent half staff. We are having daily shootings, acts of terrorism and other violence. The half staffed flags are a symbol and a constant reminder of how this country has fallen into shame and disrepute.

Choose your martyrs and outrage carefully! Not every police shooting is an unjustified act or murder.

A five second slip of the tongue can undermine 20, 30, 50 years of exemplary behavior and reputation OR can propel you to a career at Fox or Newsmax.

The line between flirtation and harassment often falls on the perceived interest level of the person receiving the attention.

I think it’s very possible that what we don’t know about what we don’t know is greater than what we know about what we don’t know.

Anyone else notice that any UFOs captured on photos and films are not the same? They differ in size, speed, shape. It’s as if the aliens have compact, economy and luxury space crafts.

Maybe the reason that aliens don’t make landings on earth is the same reason championship sports teams did not stop at the White House between 2017-2020—-they did not like the company.

To the best of my knowledge, there has been only one sore Presidential election loser. Not even Richard Nixon in 1960, who could have easily contested disputed votes in Illinois, raised an objection. Nixon also certified John F. Kennedy’s election.

Those who try to persuade by faith alone are poorly armed against those who persuade or argue with knowledge and facts. An argument made without knowledge or facts is like firing a gun without bullets.

2021: Athletes and celebrities acting or wanting to be political leaders. Politicians content to be celebrities.

Everything we were taught about money, not that long ago, including the conventional financial advice to avoid debt, keep your money in a bank savings account, and invest long term in blue chip stocks has been swept away by bitcoin, NFG and cryptocurrency. There are now two types of financial investors: those deceived by the magic and those that understand the sleight of hand.

“Generalissimo Francisco Franco is still dead.”

Common Cents (12 Observations on Money)

I believe that every state should mandate a high school course teaching students personal financial management. Normally parents are expected to pass down their knowledge on this subject but just like sex education, the message does not always get passed or understood. Students would be taught the following lessons:

How and where to save money
Building an emergency cash fund
How to create a budget
How, when and where to apply for debt
How to maintain an excellent credit rating (FICO)
Principles of smart shopping (car, clothes, etc.)
Student loan programs for college (qualifications, terms, costs)
Paying personal Income and other taxes
Mortgages and Home Equity lending
Purchasing Insurances (car, renters, health, home)
Principles Of Investing (Stocks, Bonds, Gold)
Retirement Planning

In lieu of the course, this is the type of financial guidance I would offer young people about to graduate high school or college. These observations also apply to those who are a bit older:

For many young people, a university education may not be worth the costly tuition in terms of return of your investment, and like a new car leaving the dealership, may become a depreciating asset.
Often the person most responsible for your financial success or failure is not your banker, your financial advisor, Jim Cramer or your accountant. It’s your spouse or life partner, so choose wisely!
The same foolproof strategy applies to both successfully investing in the stock market and gambling in a casino: Luck
In investing, the only “sure thing” is that there is no sure thing.
The best skills for financial management in business or personally are the abilities to first, create a workable budget and second, keep to the budget.
Before retirement, your focus should be on stoking your retirement funds with contributions and a smart investment strategy. After retirement, you should be focused on your burn rate (how quickly and smartly you spend your retirement dollars). A controlled burn rate can mitigate shortfalls in your retirement strategy.
The smartest career strategy in terms of financial independence is to transition from getting a paycheck (employee) to either issuing paychecks to your employees (as a business owner) or collecting receivables (as an entrepreneur)
The most satisfying experiences are gained from, as a businessman, turning around a failing company and from as a caring person, turning around an individual who needed help and guidance.
Buy lifelong experiences as opposed to buying things whose pleasure is transitory.
The greatest investment of your time and energy should be in your health not your wealth.
Despite their advertising, banks are not your friend or your “neighbor”. They are in business to make money off of you. They collect your deposits and pay you .01% interest while charging you 100+x more for interest if you borrow for a mortgage or car loan.
You should be as dubious about the accuracy of the numbers on a corporate balance sheet as you would the age of an actress or the net worth of President Trump.