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The New York case is far from the first time Donald Trump was caught in a crime

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Here are just some of the crimes of Donald Trump—those where we know that Trump essentially admitted his guilt by writing a check to cover his actions.

1975: Justice Department racial discrimination lawsuit

Practically the first time anyone ever heard the name Donald Trump was when he and Joseph McCarthy’s attorney, Roy Cohn, stepped in front of cameras in New York City to defend the Trump Organization against charges of racial discrimination. As The Washington Post reported in 2016, Black applicants who looked for a home at one of the apartment buildings owned by Trump and his father were routinely told that nothing was available. White applicants ran into no such issues. Employees who showed apartments at Trump properties even kept a log in which codes (such as the not-so-subtle C for “colored”) were placed next to the names of Black and Latino applicants. When Trump did rent to people of color, his company made an effort to segregate renters into specific buildings.

As NPR reported, those who worked for Trump were very clear when they were confronted about their actions: “Well, I’m only doing what my boss told me to do—I am not allowed to rent to black tenants,” said one building superintendent.

Trump, with Cohn leading the charge, fought the lawsuit until 1975, when he agreed to a settlement with the Justice Department. What did Trump have to pay? Nothing. He agreed to sign a document promising to stop “discriminating against any person in the terms, conditions, or privileges of sale or rental of a dwelling” and to “thoroughly acquaint themselves personally on a detailed basis” with the Fair Housing Act.

People who were turned away from Trump properties got nothing.

1998: Money laundering at Trump casino

In building the Trump Taj Mahal in Atlantic City—which was recently demolished after going bankrupt for a third time—Donald Trump indulged his tasteless gold-plated fantasies to the max, running up an astounding $1.2 billion bill in the process. In fact, the casino opened so far in debt that it was on its way to bankruptcy even before the first cards were played, with Trump facing lawsuits from contractors who had been shorted millions. As CNN reported in 2017, Trump did have one thing going for him. His casino became the go-to spot for Russian mobsters seeking a place to launder money.

Within a year, Trump’s casino ran up an incredible 106 charges of money laundering. These were federal charges, and each individual charge brought with it the possibility of a half-million-dollar fine and 20 years in jail.

But in January of 1998, a Trump employee signed a settlement agreeing to pay $477,000—less than the potential fine for just one count of money laundering. That settlement specifically states that it covers only the civil penalties of the case and that the DOJ reserved the right to apply criminal charges. They never did.

But even with his Russian mobster cash train, Trump managed to sink all three of his Atlantic City casinos. Not that it hurt him. Almost every dollar spent was from investors, not Trump. After the Taj Mahal’s first bankruptcy left in place a deal that kept Trump’s name on the door, he actually made money through an agreement that required them to buy Trump Water and other Trump-labeled products. At a time when other Atlantic City casinos were raking in money hand over fist, Trump lost more than $1.3 billion—of other people’s money. And then he walked away from 106 counts of money laundering without ever facing a day in court.

2018: Fraud at Trump University

Trump University was actually only open from 2005 to 2011, but in that time, it managed to defraud 15,286 “students” who were given a get-rich-quick real estate pep talk about a “real estate training program” that millions would recognize as the standard bait-and-switch of traveling scams everywhere. They started by offering free seminars in which prospective students were told that Trump had developed a secret program for making a fortune in real estate, and that hand-selected instructors would pass this knowledge on to a few select students who attended Trump’s courses. In truth, Trump didn’t develop the program, didn’t pick the instructors, and had little to do with it but picking up a paycheck and posing for a cardboard standee. Students who signed up for the actual courses faced one round after another of steeply rising course fees, but found they were never given anything of actual value—probably because neither Trump nor Sexton had any idea how to do what they were purporting to teach.

In 2013, New York Attorney General Eric Schneiderman opened a case against Trump, accusing him of defrauding students out of over $40 million. That case was still going on during the 2016 election, where it got far, far less attention than whatever Hillary Clinton might have been wearing in her latest speech. It took until 2017 for Trump to settle the case by writing a check for $25 million (actually, it was 2018 before Trump stopped fighting and the check was cashed).

A casual look at the numbers above says just about everything. Trump and Sexton defrauded people of $40 million, for which they were forced to pay $25 million. As in Atlantic City, Trump was guilty, but he still made money.

2019: Illegal use of charity funds

For more than two decades, Donald Trump made a pretense of running something called the Trump Foundation, which was supposedly a source of funds for community programs, schools, and other charitable causes. His charitable giving was even one of the subjects that “John Barron” spent time bragging about to the media. Not only did Trump show up at events acting as if he was a big contributor, even if his “foundation” hadn’t given a dime, very little of the money that actually did circulate through his eponymous charity ever came from Trump.

As The Washington Post reported:

Since the first day of his presidential campaign, Donald Trump has said that he gave more than $102 million to charity in the past five years.

To back up that claim, Trump’s campaign compiled a list of his contributions—4,844 of them, filling 93 pages.

But, in that massive list, one thing was missing.

Not a single one of those donations was actually a personal gift of Trump’s own money.

Instead, Trump used his foundation to draw in money from others, then sent it out again under his name. And that was when he wasn’t using the foundation for everything from buying sports memorabilia to paying off a golf bet. Trump got so used to dipping into the foundation to cover his everyday expenses that he even had to promise that he wouldn’t use his charity money to pay off his Trump University fine.

Finally, in 2019, Trump’s foundation was shut down and forced to pay a $2 million fine for misuse of charitable funds.

Additionally, as part of the settlement, Trump was required to agree to 19 admissions, acknowledging his personal misuse of funds at the Trump Foundation, and agreed to restrictions on future charitable service and ongoing reporting to the Office of the Attorney General, in the event he creates a new charity. The settlement also included mandatory training requirements for Donald Trump Jr., Ivanka Trump, and Eric Trump, which the three children have already undergone. Finally, the settlement required the Trump Foundation to shutter its doors last December and dissolve under court supervision.

Oddly enough, other charity scammers were going to jail for the same crimes within months of Trump signing his deal. Not only did Trump get off by writing a check, but Trump’s check wasn’t even an actual fine. It was just a required payment made to a set of charities—for which he got to take a tax deduction. Trump’s 2020 taxes showed that, deprived of his foundation, he gave not one cent to charity. The IRS could have acted against Trump, bringing charges related to tax avoidance and Trump’s use of the charity to bolster his political position. They did not.

People can, and do, get sentenced for criminal violations of the Fair Housing Act. People are regularly sentenced to long periods in prison for money laundering. College scams of all sorts net sizable terms. So does fraud. So does misuse of charitable funds. And all of them were much smaller than the dollars that went into Trump’s pockets for his various schemes.

So maybe the New York case is different. Maybe Trump will be forced to actually atone for his crimes by spending at least a small period in jail, rather than just writing another check attached to another settlement that says he admits nothing … but don’t bet on it.


On today’s episode, Markos and Kerry are joined by a friend of the podcast, Democratic political strategist Simon Rosenberg. Rosenberg was one of the few outsiders who, like Daily Kos, kept telling the world that nothing supported the idea of a red wave. Simon and the crew break down his strategy for Democratic candidates to achieve a 55% popular vote in all elections—a number that a few years ago would have seemed unattainable, but now feels within reach.


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