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

by Russ Buettner

“My father gave me a very small loan in 1975, and I built it into a company that’s worth many, many billions of dollars, with some of the greatest assets in the world,” Trump said.

The two of us—Susanne Craig and Russ Buettner of the investigative reporting team at The New York Times—had been exploring the moving parts of that claim

Then, days before the first debate, an anonymously addressed manila envelope arrived in Susanne’s mailbox at the Times. She opened it to find what appeared to be a few pages from Trump’s 1995 tax return. The line for total income showed a stunning figure, almost too jarring to seem plausible: negative $915,729,293.

The resulting story, published in October 2018, revealed for the first time that Donald Trump had received the equivalent of more than $400 million from his father, much of it through fraudulent tax evasion schemes.

The story disproved Donald Trump’s lifelong claim that his father gave him nothing more than a “small” $1 million loan.

The secret of his life, one that emerges in hundreds of moments big and small, is that the less he has been involved in decision-making, the better his chances of financial success.

Donald Trump came to be imbued with a host of attributes that speak to how we confer admiration and status in modern America. Our awe of celebrity. Our tendency to conflate the trappings of wealth with expertise and ability. Our eagerness to believe people of apparent status will not lie to us. Our inability to distinguish the fruits of hard work from those of sheer luck.

He would turn off any lights that had been unnecessarily left on and water down paint. The story told over and over to capture Fred Trump’s strict adherence to cost control is of him picking up unbent nails from the dust at construction sites and passing them on for one of his carpenters to use.

Fred Trump, son of a restaurant owner who dreamed of a career in real estate, would now live one block north of the famous estate built in his youth by Michael Degnon, the legendary builder of the city’s subways.

With his final child born, and only forty-three years old himself, Fred began the process of transferring his wealth to his children. He did so by creating a business artifice that served no business purpose whatsoever: making his children into his landlords at Shore Haven and Beach Haven.

He would pay the trusts rent every month. He did the same thing with Shore Haven, and split the rent he paid there between trusts for his children and his mother, providing her a secure income.

Donald and his siblings did nothing for the money. It was a gift with the potential to keep giving forever,

That roughly $20,000 a year paid to each of his children was the equivalent of about $265,000 in 2024. In postwar America, it was enough money to put each of the young Trump children in league with the wealthiest adults in the nation. At the time, only 3 percent of American families earned $10,000 or more a year.

The largest two-bedroom apartments at Shore Haven would soon rent for $1,260 a year; toddler Donald could easily have afforded four or five of them, and a new car.

Fred was still not satisfied. Federal income taxes could take as much as 70 percent of the total. In December 1950, Fred sent a politically connected Brooklyn lawyer named Richard P. Charles to meet with an official at the Internal Revenue Service.

The next day, Charles wrote a letter to the IRS commissioner repeating his position: “All of the work in connection with the construction was performed by subcontractors and none of the stockholders performed any work in connection with the erection of the said buildings. Due to favorable agreements with the subcontractors, the corporation was able to complete the work for less than the mortgage proceeds.”

It was a claim that was as audacious as it was absurd: after portraying himself as the hardest working man in construction for his entire life, Fred Trump asserted he had done no work on his signature accomplishment. It was, in this private telling, only an investment, and should be taxed as if he had simply bought and sold shares