On a quiet suburban street in 1950s Queens, a Cadillac Eldorado Brougham glides up in front of the Trump family’s 23-room mansion.
Behind the wheel sits real estate tycoon Fred Trump Sr.
A small boy rides by on his bicycle. When a quarter falls out of his pocket and rolls across the sidewalk, Donald Trump’s father jumps out of the car, picks up the coin, and says:
»It’s mine now.«
A miserly gesture to most, but a norm in the Trump family.
It was precisely such actions that came to shape the siblings Donald Trump grew up with. He was actually fourth out of five, while his elder brother Fred Jr. was initially designated to take over the family empire.
But that didn’t happen.
»When Donald saw that his brother couldn’t bring himself to be the ruthless, greedy little devil their father wanted, he stepped in. Because there he saw an opportunity,« says Pulitzer Prize-winning journalist David Cay Johnston, who has just recounted the coin story.
He is the author of the book ’The Making of Donald Trump’ from 2016 and has covered the U.S. president since the 1980s—a job that has led to »hundreds of hours with Donald Trump.«
Throughout his career, David Cay Johnston has written for some of America’s largest newspapers, including The New York Times, and today he teaches journalism at the Rochester Institute of Technology in New York State.
According to Johnston, the relationship between Donald Trump and his elder brother Fred Jr. was deeply influenced by their domineering father, who constantly pitted them against each other. The father mocked Fred Jr. for not living up to the family’s ideals, and Donald took note—and began to mock his brother as well.
While the elder brother broke under the weight of the humiliations, Donald learned to play the game—and transformed the family’s coldness and competition into fuel for his own life’s project.
Killer Instinct
Fred Sr. believed that his eldest son and namesake, Fred Jr.—or Freddy, as he was called—lacked the most important thing of all: killer instinct. To be invulnerable, uncompromising, ruthless.
»He wasn’t a killer. Their father told the boys they had to be killers, but Freddy never was. He wasn’t hyper-aggressive. He wasn’t extremely competitive,« said Gwenda Blair, author of the book ’The Trumps,’ in the PBS documentary ’Trump’s Comeback’ from 2025.
The same picture is painted by Mary Trump, Fred Jr.’s daughter and Donald Trump’s niece, in the book ’Too Much and Never Enough.’ She is also a psychologist.
»Freddy simply wasn’t who his father wanted him to be,« she writes.
»Fred simultaneously told his son that he had to be an unconditional success—and that he could never be one. Freddy thus existed in a system where there was only punishment and no reward. The other children, especially Donald, couldn’t help but notice it,« writes Mary Trump.
After college, Donald Trump’s elder brother began working in the family business. He tried to take responsibility and suggested improvements. But he was rejected time and again.
One day, Fred Jr. made a decision on his own and ordered new windows for a rundown building. When Fred Sr. found out, he exploded. According to Mary Trump’s book, he shouted in front of all the office employees:
»You should have slapped some damn paint on them instead of wasting my money! Donald is worth ten times more than you. He would never do something so stupid.«
Clouds instead of skyscrapers
Instead of following in his father’s footsteps, Fred Jr. chose his own path. His younger brother Donald, however, followed the father.
Donald Trump has recounted how, in the mid-1960s, he sat at home reading reports on paint and mops—preparing for a life in his father’s footsteps. To his amazement, he discovered that his elder brother was reading books about aviation, hoping to fulfill his dream of becoming a pilot for the airline TWA.
»Come on, Freddy, what are you doing? You’re wasting your time,« Trump recalled to The Washington Post in 2019.
For the father, the eldest son’s career choice was not just incomprehensible—it was betrayal.
In 1964, the father sent Donald and his younger brother Robert to Marblehead, Massachusetts, where Fred Jr. lived while working as a pilot.
In Mary Trump’s book, she describes how Donald—only 18 years old—took the father’s criticism to heart and used it against his brother:
»Dad’s right. You’re nothing but an elevated bus driver,« Donald said to his elder brother.
The career as a pilot lasted less than a year. Fred Jr. had to leave the job—mainly due to alcoholism—and the defeat forced him back into the family business he had tried to escape.
In his father’s eyes, he had failed, and attention now turned to Donald, who took on the role of the father’s successor.
At any cost
When Donald finished his education, he was ushered directly into the family empire’s engine room—with higher pay, greater responsibility, and a respect his elder brother never received.
»The sons were set up against each other in competition. The father deliberately placed them in rival positions,« says David Cay Johnston.
Donald wanted to win his father’s favor at any cost.
According to David Cay Johnston, Donald Trump once went so far as to jab a finger hard into the chest of New York’s mayor at the time, Abraham Beame, and snarled: »You’d better do what my father wants.« The mayor had refused to give the Trump family special treatment in a real estate deal. An employee present at the meeting pressed an alarm button under the desk—and shortly afterward, Donald Trump was escorted out by the police.
»That’s how eager Donald was to do everything his father wanted to win his favor,« says David Cay Johnston.
By the late 1970s, Donald Trump emerged as a young business comet with star status. He partied at the iconic nightclub Studio 54, married his first wife, Ivana, and embarked on his first real estate ventures in Manhattan—propelled by his father’s money.
In 1980, he was asked by the famous gossip columnist Rona Barrett whether one needs to have a killer instinct to succeed.
»I believe you need to have a bit. To a large extent, I think you need to have at least a winning mentality. I believe the world consists of people with killer instinct and people without.«
Words that could have come directly from his father’s mouth.
Regret
Meanwhile, things went downhill for Fred Jr., who had to move back in with his mother and father. He died in 1981, just 42 years old. Decades of humiliations and defeats had destroyed him. The alcohol abuse spiraled, and his body gave out.
Donald Trump has since explained that it was his elder brother’s alcoholism that led him to avoid alcohol entirely. But the motive is not necessarily so honorable, David Cay Johnston believes:
»My guess is that it’s more likely because his father didn’t like alcohol—not that Donald was driven by concern for his brother.«
In 1990, in an interview with Playboy, Donald Trump described a home where his elder brother came up short:
»Our family environment—competitive as it was—had a negative effect on Fred. It wasn’t easy for him to be thrown into such a tough atmosphere, and I think it did great damage to him,« said Donald Trump.
In 2019, he went a step further in an interview with The Washington Post and admitted that he was partly responsible:
»I regret that I put pressure on him.«
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