Trumps on the Couch

Mary L. Trump and Donald Trump; Illustration by Tom Bachtell
Illustration by Tom Bachtell

In 1996, at a boozy lunch in Manhattan, a Connecticut lawyer was told about the Trump Organization’s “punishment room” by an Atlantic City lawyer who said that he had represented Donald Trump’s casino interests. According to the story, the truth of which is unconfirmed, employees there devised ways to punish Trump’s enemies, including the journalists who wrote critically of him. One supposed method was to send the IRS a fake Form 1099, showing that the target had been paid a considerable sum for contract work. The aim was to trigger a bill or an audit when the IRS discovered the putative payee had not reported the income. The victim might eventually straighten things out with the government, showing no such money was received: the point was the hassle.

Such stories about Trump are unavoidable if you’ve lived in New York City for a while. Some have become public. Many—like the one above, told by the Connecticut lawyer to my partner in the summer of 2016—have not. But no tale of dishonesty, vindictiveness, bullying, and advantage-seeking is surprising. To Trump, everyone is either a crony to be exploited or an adversary to be defeated and humiliated. He demands loyalty but refuses to give it, except, it’s generally assumed, to certain members of his family.

In 1990 Donald secretly enlisted a lawyer to draft a codicil to the will of his father, Fred Sr. The addendum put Donald in complete control of Fred’s vast estate; his siblings would need his approval for the smallest transaction. According to Too Much and Never Enough by Mary L. Trump, the daughter of the late Fred Trump Jr. (Trump’s older brother, known as Freddy, who died in 1981), the document was presented to Fred Sr. at his home in Queens as if it had been his idea. Fred, who was eighty-five and in the early stages of Alzheimer’s, was lucid that day and refused to sign. He talked to his wife, Mary, who called the eldest of their five children, Maryanne, by then a federal judge. She agreed that the whole thing “didn’t pass the smell test.” Fred swiftly had a new will drawn up, one that ensured equality among his four living children.

A slightly different version of this story, like several in Mary Trump’s book, appeared in a New York Times exposé of the Trump family’s finances in October 2018. There is a certain justice in the granddaughter’s getting to tell the story herself: when Fred Sr. died, in 1999, Mary and her brother, Fred III (whom she calls Fritz), discovered that their father had been cut out of their grandfather’s will, and that they were to receive the same modest individual bequests as all the other grandchildren. When negotiations with their uncle Robert stalled, Mary and Fritz sued…


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