New York Attorney General Letitia James released a court filing Tuesday outlining what she believes to be a pattern of fraud perpetrated by the Trump Organization and specifically Donald Trump, Donald Trump Jr. and Ivanka Trump. James’ civil investigation is running parallel to a criminal investigation the Manhattan district attorney’s office is conducting into the Trump Organization’s activities; between the two, it seems that the Trump family may finally face some type of accountability for what prosecutors allege amounts to years of malfeasance and corruption. (A spokesperson for the Trump Organization said “the allegations are baseless and will be vigorously defended”; lawyers for Ivanka and Donald Jr. say they will continue to fight James’ investigation.)
Between the two, it seems that the Trump family may finally face some type of accountability for what prosecutors allege amounts to years of malfeasance and corruption.
That the Trumps are in hot water again isn’t surprising. What’s more surprising is that they haven’t faced any consequences before now. The former president’s business empire has a history of misrepresentation to lenders, government agencies and the public, and this isn’t his first experience with law enforcement. (The Trump Organization settled with the Treasury Department’s Financial Crimes Enforcement Unit in 1998 after it determined that the company had broken anti-money laundering laws.) This history of dealing with law enforcement actually goes back even further. The federal government accused Trump; his father, Fred; and Trump Management of racial discrimination in housing because they refused to rent apartments to Black people. (The Trumps settled.)
This is also not the first time Trump has been investigated for allegations of fraud. It’s not even the first time Ivanka and Don Jr. have been investigated for allegations of fraud.
Let’s start with Donald Sr., though. SPY magazine, a New York-centric satirical monthly publication that folded in 1998, often covered Trump as a kind of recurring New York City character. It portrayed him the way much of the media did at the time — as a “venal puppet” and a “buffoon” — but it also noted that his image as a kind of developer clown protected him from real scrutiny, a pattern that was repeated when he ran for president.
One particular story from that era stands out. In a 1991 feature titled “All of the People All of the Time: How Donald Trump Fooled the Media, Used the Media to Fool the Banks, Used the Banks to Fool the Bondholders and Used to Bondholders to Pay for the Yachts and Mansions and Mistresses,” reporter John Connolly highlighted certain financial representations he found suspicious. He claimed that Trump’s sale of Resorts International to Merv Griffin was the subject of two criminal investigations, one related to organized crime. Obviously, nothing came of this or we wouldn’t be here right now, but it’s worth looking at Trump’s alleged financial shenanigans in the late ’80s and ’early 90s to get a sense of what the ongoing investigations might uncover now.
If Trump actually testifies, his history of dissembling and making misrepresentations is relevant, too. (From the same article: “A mobster who knew Trump socially said of him once, ‘he’d lie to you about what time of day it is — just for the practice.’”) Will Trump perjure himself if he testifies?
Connolly’s thesis was that Trump was able to get bank loans he wasn’t qualified for by using the media to advance the notion that he was worth far more than he was. No one bothered to do a full financial audit of him, not even his accountants at Arthur Andersen. Connolly attributes a lot of this to gullibility on the part of the media and Trump’s lenders, who made assumptions about his net worth and used Trump’s own questionable estimates of his asset values and never bothered to check whether he was telling the truth. Or maybe it was a kind of willful financial delusion that everyone assumed would ultimately be profitable.
Anyone who doesn’t believe “The Apprentice” was a documentary already knows Trump has a history of terrible business decisions.
Anyone who doesn’t believe “The Apprentice” was a documentary already knows Trump has a history of terrible business decisions, which resulted in six bankruptcies. (Since the ’90s, he has mostly done business with Deutsche Bank, which has slowly been backing away from him as of late and is cooperating with investigations into his activities.)
Unfortunately for his creditors, incompetence isn’t illegal. Misrepresenting your assets to the IRS and lenders is. This is the crux of the New York attorney general’s investigation. But in part because of the interconnected nature of Trump’s family and businesses, Trump Sr. isn’t the only one on her list.
According to James, the Trump children are alleged to be involved, too. Ivanka, who is named in James’ filing, was the point person for all of the Trump Organization’s dealings with Deutsche Bank, and according to the attorney general’s office, she caused misleading statements to be submitted to the bank. Donald Jr., a manager of the Trump Organization and a trustee of the Donald Trump Revocable Trust, is also alleged to have been responsible for statements with misleading asset valuations.
They are their father’s children, after all. In 2012, the Manhattan district attorney’s office considered bringing charges against Donald Jr. and Ivanka over allegations that they misled potential buyers of condo properties at Trump SoHo. According to a 2017 investigation by ProPublica, WNYC and The New Yorker, the pair even discussed over email how they would coordinate their lies. (A lawyer for the Trump Organization told ProPublica that it was all just a case of “buyers’ remorse.”) Nevertheless, the district attorney at the time, Cy Vance, decided to drop the charges — overruling the recommendations of his own prosecutors. Trump’s then-lawyer Marc Kasowitz later donated $50,000 to Vance’s re-election campaign, a development Kasowitz and Vance insisted had no bearing on his decision. (Vance also opened the more recent criminal investigation that is ongoing but is now overseen by his successor, Alvin Bragg.) History may have the Trumps feeling confident that they will once again best the authorities. But the past can also highlight patterns. And the New York attorney general’s filings include one detail that feels particularly, well, Trump-y. The attorney general alleges that the Trumps inflated their asset values to lenders, in part by adding a nebulous “brand value” to the overall estimate, while stating explicitly in documents that the ultimate valuations didn’t include this totally made-up premium. We can assume these premiums were fairly large. The Trump brand isn’t doing so well right now, of course. It’s increasingly associated with the family’s liabilities: accusations of mismanagement and misrepresenting assets, on top of a familywide predisposition to lie extensively and often. But to anyone who looks closely, fraud has always been the Trump brand.
Elizabeth Spiers
Elizabeth Spiers is a writer and digital strategist who has advised progressive candidates and organizations and various media companies and brands. She was previously the editor-in-chief of The New York Observer, and the founding editor of Gawker. 
