“Readers love lists.  Whenever you can, build your column around a list.” 

Tina Brown, the brilliant editor of The Daily Beast and, before that, The New Yorker, gave me that advice while we were sitting in her Daily Beast office overlooking the Hudson River.  That was 20 years ago, and I was too immature–only 63!–to embrace the wisdom, but I realize now that she was correct.  

And so here’s a column with not one but THREE lists, and an opportunity for readers to rank the current occupant of The  White House on three aspects of his character and behavior: Greed, Narcissism, and Business Acumen.

(Scoring: Give Trump the points that correspond with your ranking.  IE, if you rank Trump the second-greediest person in history, he gets TWO points. Third most narcissistic, he gets THREE points. Worst businessman ever, ONE point.  Lowest total score wins!) 

Let’s start with greed or avarice.  Below are short descriptions (in alphabetical order) of 10 greedy people from human history. Where would you rank Donald Trump?

1. Caligula, the Roman Emperor, is infamous for his tyrannical and extravagant reign, driven by greed and madness. His rule was marked by excessive spending and cruel demands.  Caligula’s desire for wealth led to heavy taxation and confiscation of property, causing public unrest. His erratic behavior and lavish projects drained the empire’s resources.
2. Marcus Licinius Crassus was a Roman general and politician known for his immense wealth and insatiable greed. He became obsessed with wealth as a young man. He rented land and bought slaves to sell later on for profit. Rome’s failure to provide housing fueled his business. He organized teams of firefighters who would save the burning houses (fires were quite common) and then buy them cheap so he could rebuild them and rent them. He had a net worth of $2 Trillion in today’s money. 
3. Hetty Green, known as the “Witch of Wall Street,” was one of the wealthiest women of her time. Her frugality and aggressive investment strategies earned her a reputation for greed and shrewdness. Green amassed a vast fortune through real estate and railroads, often lending money at high interest rates. Her financial decisions were marked by extreme thrift and an unyielding focus on profit.
4. Leona Helmsley, dubbed the “Queen of Mean,” was an American businesswoman known for her opulent lifestyle and notorious greed. Her harsh management style and tax evasion convictions marked her career…Her downfall came with her conviction for tax evasion, exposing her lavish spending and disdain for the law. Helmsley’s story is a testament to the consequences of greed and the importance of integrity in business leadership.
5. Leopold II of Belgium amassed a $500,000,000 fortune from his rubber plantations in Congo. In the process he killed some 8 million people and maimed uncountable men, women and children. He did not kill for pleasure or political/military gains. He did not kill with guns and swords. He killed for profit, and killed with overwork, hunger and punishment (his favourite was chopping off the hands of child-workers when they failed to meet inhuman work production requirements).
6. Bernie Madoff was an American financier who orchestrated the largest Ponzi scheme in history, defrauding thousands of investors of billions of dollars. His greed and deception shattered lives and financial institutions.  Madoff’s reputation as a trusted financier concealed his fraudulent operations for decades. 
7. Imelda Marcos, the former First Lady of the Philippines, became infamous for her extravagant lifestyle and accumulation of wealth. Her collection of shoes and lavish spending symbolized her greed. Marcos wielded significant influence during her husband’s regime, using her position to amass personal fortune and power. Her opulent lifestyle was funded by embezzled public funds and corruption.
8. Queen Ranavalona I of Madagascar ruled Madagascar with an iron fist from 1828 to 1861. Her greed for power and wealth was evident in her harsh policies and isolationist stance. Ranavalona’s regime was marked by forced labor and heavy taxation, which enriched her court but impoverished her subjects. Her ruthless approach to governance ensured her control over Madagascar, but at a significant cost to her people. Despite her reputation for cruelty, she maintained power for over three decades, leaving a legacy of greed and tyranny that still resonates in Madagascar’s history.
9. Cecil Rhodes was a British imperialist known for his exploitation of African resources and people. His insatiable greed fueled colonial expansion in southern Africa, leading to the establishment of Rhodesia. Rhodes’ pursuit of wealth was driven by diamond mining, which he monopolized through De Beers.
10. John D. Rockefeller, an American industrialist, became the richest man in modern history through the establishment of Standard Oil. His relentless pursuit of wealth led to monopolistic practices that crushed competitors and controlled the oil industry.

(Contemporary nominees include Elon Musk, Jeff Bezos, Larry Ellison, Mark Zuckerberg, Vladimir Putin, Xi Jinping, and Charles Koch.)

Where would you put Trump on that list?  Here’s his own assessment: 

My whole life I’ve been greedy, greedy, greedy. I’ve grabbed all the money I could get. I’m so greedy. But now I want to be greedy for the United States. I want to grab all that money. I’m going to be greedy for the United States.

You have to admire how Trump takes a very negative quality and turns it to his political advantage. He always makes it about himself….which is a perfect segue to Narcissism, and another list: The World’s Worst Narcissists. First, a definition:  Narcissists, who have an inflated sense of self-importance, rarely think about others but instead prioritize their own needs and desires. 

Here’s a list of ten candidates (in alphabetical order) for “History’s Worst Narcissist.”

1. Ted Bundy was an American serial killer and a psychopath who was convicted of killing more than thirty people, most of them young women. He was a manipulative, extremely self-centered, and charismatic man who loved attention and limelight.
2. Cleopatra, the last active ruler of the Ptolemaic Kingdom of Egypt, is often characterized as a narcissist, particularly in her pursuit of power and dramatic life choices.
3. Adolf Hitler, the Nazi politician who started World War II, slaughtered 6 million Jews and many other innocent people in his goal of establishing white Germans as the superior race.
4. Jim Jones was an American cult leader and a preacher who persuaded more than nine hundred followers to accompany him to Guyana. There he forced his followers to drink poison in the name of spirituality. Those who declined to commit suicide were murdered.
5. Kim Jong Un, the North Korean dictator, is known as a brutal and self-obsessed leader.  North Korean citizens are required to worship him as their leader, and do so out of terror and fright. 
6. Kim Kardashian is a businesswoman, media personality, and model who relentlessly promotes herself, her wealth, and her pompousness publically. 
7. Madonna, the American singer, actress, and songwriter, is known for her exploitative behavior towards her employees and staff members by making unreasonable and unfair demands. She is known for abusing her employees by making them work unreasonably long hours.
8. King Louis XIV of France, known as The “Sun King,” was infamous for his extravagant lifestyle and his firm belief in his divine right to rule, emphasizing his grandeur and importance. “L’etat c’est moi,” he is said to have pronounced.
9. Elon Musk: The CEO of X, Tesla and, SpaceX is often considered a modern-day narcissist due to his self-promoting behavior and controversial public statements.
10. Joseph Stalin, the Soviet dictator, exhibited many traits associated with narcissism, including a cult of personality, paranoia, and a ruthless pursuit of power.

Is Donald Trump a textbook narcissist?  He is said to have almost all the traits that a narcissist might possess. He only cares about his personal needs, dismissing the needs of his family members; he is thin-skinned when it comes to criticism. He promotes himself above the needs of the nation, while sidetracking or ignoring his Constitutional responsibilities as President.

And, finally, the worst business leaders of all time.  Here are 10 candidates, again in alphabetical order

1. John Akers – IBM  Under John Akers’ leadership in the late 1980s and early 1990s, IBM encountered significant challenges adapting to the rapidly evolving technology landscape. Akers’ inability to foresee the shift from mainframe to personal computing led to a loss of market share and financial stability for IBM. By 1992, the company reported an unprecedented annual loss of $8 billion, marking a significant downturn from its previous market dominance. 
2. Leo Apotheker – Hewlett-Packard (HP): Leo Apotheker’s brief tenure as CEO of HP in 2011 was characterized by a series of strategic missteps that significantly impacted the company’s market position and shareholder value. His decisions to discontinue HP’s smartphone and tablet lines and the announcement of plans to spin off its lucrative PC business potentially caused confusion and uncertainty among investors, customers, and employees alike. These moves, along with the costly acquisition of Autonomy for $11 billion—a decision later mired in controversy over allegations of financial misrepresentation—resulted in a sharp decline in HP’s stock price and a loss of confidence in the company’s strategic direction. 
3. Steven Ballmer – Microsoft: Steven Ballmer’s tenure as CEO of Microsoft from 2000 to 2014 was marked by financial success but also significant strategic oversights, particularly in mobile computing and internet services. Despite maintaining profitability and growing revenues, Microsoft, under Ballmer’s leadership, failed to capitalize on the early stages of the mobile revolution and the rise of search engines like Google, allowing competitors to dominate these critical market segments.
4. Carly Fiorina – Hewlett-Packard (HP): Carly Fiorina’s leadership at HP was marked by bold decisions, most notably the contentious acquisition of Compaq in 2002 for $25 billion. This move was intended to solidify HP’s position in the personal computing market but instead led to significant internal and external turmoil. 
5. Fred Goodwin – Royal Bank of Scotland (RBS): Fred Goodwin’s leadership of RBS is often cited as a prime example of the dangers of overexpansion and the risks associated with high-stakes acquisitions. His aggressive pursuit of growth led RBS to acquire ABN Amro in 2007 for approximately £49 billion, just before the global financial crisis. This acquisition stretched RBS’s financial resources thin and exposed the bank to significant risks, contributing to its near-collapse and the largest bailout in British history, costing taxpayers around £45 billion. 
6. Elizabeth Holmes – Theranos: Elizabeth Holmes promised to revolutionize the healthcare industry with Theranos’ technology, which claimed to perform comprehensive blood tests with just a few drops of blood. However, investigative journalism and regulatory scrutiny revealed that the technology was fundamentally flawed and incapable of producing accurate results. Holmes’ ambition led to over $700 million in investor losses and a criminal conviction for her.
7. Ron Johnson – J.C. Penney: Ron Johnson’s attempt to transform J.C. Penney’s retail strategy was bold and forward-thinking but ultimately disconnected from the reality of the company’s customer base and market position. By eliminating coupons and sales in favor of everyday low prices and rebranding stores with an upscale flair, Johnson alienated long-time customers without attracting a new clientele. This misalignment led to a 25% drop in sales in his first year alone, a loss from which the company never recovered.
8. Kenneth Lay and Jeffrey Skilling – Enron: The Enron scandal, masterminded by CEO Kenneth Lay and COO turned CEO Jeffrey Skilling, represents one of the most dramatic collapses in corporate America. Their use of off-the-books special purpose vehicles (SPVs) to conceal debts and artificially inflate the company’s stock price not only misled investors but also compromised the integrity of the financial reporting system. The fallout from Enron’s bankruptcy in 2001 was profound, leading to the loss of thousands of jobs, the erasure of $74 billion for shareholders, and the dissolution of the Arthur Andersen accounting firm.
9. Bob Nardelli – Home Depot: Bob Nardelli’s tenure at Home Depot is often criticized for prioritizing cost-cutting and operational efficiency at the expense of customer service and employee satisfaction. His focus on centralizing operations and reducing staff levels deteriorated the company’s core competency of knowledgeable and friendly customer service. This approach, coupled with his autocratic leadership style, decreased employee morale and customer loyalty. 
10. Martin Winterkorn – Volkswagen: Under Martin Winterkorn’s leadership, Volkswagen became embroiled in one of the largest scandals in automotive history. The “Dieselgate” scandal, involving the manipulation of emissions tests through software installed in diesel engines, highlighted a failure in ethical leadership and a systemic issue within the company’s pursuit of market dominance. The scandal resulted in over $30 billion in fines and settlements and a significant tarnish on Volkswagen’s reputation for reliability and trustworthiness.

Where does Donald Trump, with five bankruptcies, a failed airline, a failed professional football team, a failed on-line university and so on, rank?  His less-than-admirable track record of 15 or more failures, include these four: 

1. Trump Airlines — Trump borrowed $245 million to purchase Eastern Air Shuttle. He branded it Trump Airlines. He added gold bathroom fixtures. Two years later Trump could not cover the interest payment on his loan and defaulted. 
2. Trump Beverages — Although Trump touted his water as “one of the purest natural spring waters bottled in the world,” it was simply bottled by a third party. Other beverages, including Trump Fire and Trump Power, seem not to have made it to market. And Trump’s American Pale Ale died with a trademark withdrawal. 
3. Trump Game — Milton Bradley tried to sell it. As did Hasbro. After investment, the game died and went out of circulation. 
4. Trump Casinos — Trump filed for bankruptcy three times on his casinos, namely the Trump Taj Mahal, the Trump Marina and the Trump Plaza in New Jersey and the Trump Casino in Indiana. Trump avoided debt obligations of $3 billion the first time. Then $1.8 billion the second time. And then after reorganizing, shuffling money and assets, and waiting four years, Trump again declared bankruptcy after missing ongoing interest payments on multi-million dollar bonds. He was finally forced to step down as chairman. .

So where does Donald Trump rank among the worst business leaders of all time?  Please  tally up your results, and, if you want to share, post your scores here.