Donald Trump: Spoilt Rich Kid or Savvy Entrepreneur?

Donald Trump 1946 –

Donald John Trump was born on June 14, 1946 in Queens, New York, the second child of Fred and Mary Trump. His father was a very successful builder and real estate developer. Most of Fred Trump’s property was located in Queens. Donald was brought up to fend for himself and learned the real estate business at his father’s knee. While growing up, Donald was expected to work and was given jobs in his father’s firm sweeping floors, running bulldozers, and just hanging around. His father made sure he understood the value of money and if he was going to get money he had to earn it. Fred once refused to buy Donald a baseball mitt because it cost $45. Donald never forgot that lesson.

Donald’s older brother Fred, who didn’t like the real estate business, eventually moved to Florida where he became a professional pilot and flew for TWA (Transworld Airlines). Subsequently, Fred developed a drinking problem and died prematurely at the age of 43. Witnessing his brother’s tragic decline prompted Donald to abstain from alcohol and cigarettes throughout his life.

In his first book, Donald describes his relationship with his father (Trump, 1987, p. 71):

…I was never intimidated by my father the way most people were. I stood up to him, and he respected that. We had a relationship that was almost businesslike. I sometimes wonder if we’d have gotten along so well if I hadn’t been so business-oriented as I am. 

Donald’s father had encouraged him to learn survival in the street. Trump told A&E Biography (1994), “By my teens I knew everything about constructing buildings.” Fred had Donald accompany his rental collection agents in Queens. The experience persuaded him that this was not how he wanted to spend his life, for it showed him the seamy side of the human struggle. In the process, he learned some lessons in “street smarts,” such as “Don’t stand in front of a door when knocking to collect the rent,” because some tenants answer a knock with bullets.

By the time he reached his teens, Donald’s behavior had become aggressive and belligerent. His father, fearing Donald would end up in reform school, enrolled him in the New York Military Academy in upstate New York. In this structured environment, aberrant behavior was not tolerated. The imposed structure worked, Donald learned to live within rules, and he excelled. He was voted the neatest student and Captain of the baseball team. Trump told the media, “That is where I learned discipline and channeled my aggression into achievement.” After graduation in 1964, Trump attended Fordham University in the Bronx. After two years he entered the prestigious Wharton School of Finance at the University of Pennsylvania where he learned the nuances of business. He graduated in 1968 with a major in business finance. 

On July 29, 1974, when Donald Trump was just 28 years of age, he obtained an option to purchase several key waterfront sites owned by Penn Central  for $62 million with no money down. There followed four years of public debate, controversy, and politicking about whether or not one of these sites should be used as the location of a new Convention Center for the city. New York City ultimately paid Penn Central $12 million for one site as the location for their new Convention Center and Donald received $833,000 for releasing his option. 

While the debate was raging about the appropriate use of the Penn Central waterfront sites, Donald entered another bold venture with another Penn Central property. He acquired the defunct Commodore Hotel for $10 million and then sold it within a week to the city of New York for $1. On the face of it, this was a financially disastrous transaction.

The sale of the Commodore Hotel to New York City was contingent on receipt of a 99-year lease on the property and tax abatements worth $120 million over the next forty years. Armed with this contract, Donald Trump set out to find a classy hotelier to build a hotel on his property. After 5 years of negotiation, Trump was able to secure a contract with Hyatt Hotels for the Trump Organization to build and operate it. He then used his contract for the hotel construction as collateral for an $8-million mortgage to renovate the building and make it into the Grand Hyatt. At the time, Trump had built nothing in his young life and didn’t know if he was equal to the challenge. When the Grand Hyatt was finally opened in September 1980, Donald was a 50% owner of the Hyatt flagship hotel.

In August, 1976, when Donald had just reached thirty years of age, he went to the Summer Olympics in Montreal, Canada. There he met a beautiful model, Ivana Winklmayr, who had been an alternate on the Czechoslovakian ski team at the Sapporo Winter Olympics. She was a dignified and intelligent woman who displayed the poise and elegance worthy of a wealthy tycoon’s attentions. They courted, and were married in the following year. Ivana would eventually become his business partner and the mother of their three children, Donald Jr., Ivanka, and Eric.

The drama describing how Donald Trump built a real estate empire and became one of the wealthiest billionaires in the world is a fascinating story, described in more detail in Dr. Gene Landrum’s book, Entrepreneurial Genius: The Power of Passion. During these decades Trump brought gambling to Atlantic City, built Trump Tower, Trump Castle, and The Taj Mahal Casino.

As 1990 came to a close, the recession in real estate was deepening and declining property values were reducing Trump’s equity in the casino-hotels. The whiplash effect of reverse leverage was escalating exponentially the debts of the Trump empire. Furthermore, Ivana’s uncontested divorce from Donald was granted on December 11, 1990, and the settlement agreement, which would require a huge cash payout, was scheduled for the following April. Donald Trump seemed to be approaching the nadir of his personal and business lives.

Through the 1990’s, Donald J. Trump struggled to regain his fortune and by the year 2001, he had recovered from bankruptcy to become a billionaire with a net worth of $1.7 billion. In the years that followed, he built golf courses and hotels throughout the world and in 2016, at the age of 70, he became the 45th President of the United States.

During and after his term as President, America became strongly polarized in their attitudes toward Donald J. Trump. His legion of devoted supporters praised his leadership and his policies; those on the other side disliked, or at worst hated both him and his policies. While the rest of Trump’s biography is currently unfolding in the courts, and perhaps at the ballot box in 2024, even his most vitriolic opponents must acknowledge his remarkable tenacity and entrepreneurial skills.

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