Home Politics A Brief History of Donald Trump’s Legal Battles

A Brief History of Donald Trump’s Legal Battles

by Scott Kacsmar
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Donald Trump Hush Money Trial

Donald Trump has been a businessman, television show host, and the 45th President of the United States. You can add convicted felon to that list after a Manhattan jury returned a guilty verdict for all 34 counts of falsifying business records in regards to the Stormy Daniels hush money case

It is the first time in U.S. history that a former president has been convicted of a felony, or in Trump’s case, 34 of them. He could even face prison time when he is sentenced in July by the judge, though that part is unlikely to come to fruition. Trump will also appeal the verdict.

Some might say this is Trump, who was twice impeached as president, finally facing accountability for his actions. No man is above the law.

However, while this is the 1st time Trump has been convicted of a felony, it is far from his 1st defeat in court. In fact, few human beings in recorded history have been tied up in as many lawsuits as Donald J. Trump.

Between Trump and his businesses, he has been involved in over 4,000 legal cases in federal and state courts.

While these cases have been civil cases rather than criminal like the hush money trial, there is still a ridiculously long list of litigation involving Trump. We thought now would be a good time to briefly go over some of his “greatest hits” from his many legal battles.

Federal Housing Discrimination Lawsuit (1973)

In 1973, Trump, in his real estate tycoon phase, was accused of violating the Fair Housing Act as the operator of 39 buildings for refusing to rent to African Americans. The black candidates were turned away from renting while white “testers” had no problem getting an apartment in the same building.

Trump’s lawyer was the infamous Roy Cohn, who filed a countersuit against the government for $100 million. It was laughed out of court and called a “waste of time and paper.”

In 1975, Trump settled the case but denied any wrongdoing. However, the Trump corporation was required to send bi-weekly updates on their operations and to make sure they were following anti-discrimination laws.

The Trump University Lawsuits (2010s)

Trump University was a real estate training program that existed from 2005 to 2011 despite numerous claims of fraud and misleading information. In 2010, Trump was ordered by New York regulators to drop the word “University” from the name of the school, which many said offered subpar educational services. Even as early as 2005, the state was warning Trump not to call it a university or to offer seminars.

Trump was accused of defrauding more than 5,000 people of $40 million who came to learn his real estate investment techniques at a for-profit training program.

Ultimately, Trump settled 3 lawsuits related to Trump University in 2016 for $25 million. He admitted to no wrongdoing.

The Bill Maher Orangutan Lawsuit (2013)

In 2013, HBO’s political comedian Bill Maher appeared on The Tonight Show with Jay Leno and offered $5 million to a charity if Trump could produce his birth certificate to prove that his mother did not mate with an orangutan.

This was a play on Trump going after President Barack Obama to produce his birth certificate. Trump ended up suing Maher after he produced his birth certificate and Maher did not pay the money.

After 8 weeks, Trump withdrew his lawsuit against Maher.

The Trump Foundation Lawsuit (2018)

In 2018, the Donald J. Trump Foundation faced a civil suit after years of illegal practices involving money were ongoing in the organization, including self-dealing and illegal coordination with Trump’s 2016 presidential campaign.

The Trump Foundation was ordered to be dissolved, and in 2019, Trump was ordered to pay $2 million in restitution. Trump’s adult children had to undergo training in the duties and ethics of running a charitable organization.

The First Impeachment Trial (2019)

In 2019, Trump became the 3rd president to be impeached by the House of Representatives for abuse of power and obstruction of Congress. The charges stemmed from Trump withholding military aid to Ukraine unless its president (Volodymyr Zelenskyy) announced an investigation into Trump’s political opponent (Joe Biden).

In February 2020, Trump was acquitted on both counts by the Senate.

The Second Impeachment Trial (2021)

Shortly after the insurrection on January 6, 2021, Trump became the 1st U.S. president to ever be impeached twice by the House of Representatives. This was for his role in inciting the insurrection that led to the storming of the Capitol on that day.

The Senate trial started in February after Trump was already out of office. He was again acquitted by the Senate.

The E. Jean Carroll Sexual Assault and Defamation Case (2023)

Trump has been accused of sexual harassment and sexual assault by numerous women over the years. He denies all wrongdoing.

One of those women is author E. Jean Carroll, who accused Trump of sexually assaulting her in the 1990s. Trump denies ever meeting Carroll despite the existence of a photograph of them mingling from 1987.

Carroll sued Trump for defamation and battery in 2023. Trump was found liable for both and awarded $5 million in damages. After the ruling, Trump publicly referred to Carroll as a “fake” with a “made-up story” invented by a “whack job.”

Carroll sued Trump again for defamation, and in 2024, she won and was awarded $83.3 million in damages.

The Trump Organization in New York (2024)

In New York in 2021, an investigation was launched into the Trump Organization for claims of loan fraud and tax fraud. In December 2022, the Trump Organization was convicted of 17 criminal charges. This was the case where Trump inflated his wealth to get more favorable loans, which is illegal.

In February 2024, Trump was ordered to pay $355 million in the civil case. For the next 3 years, Trump is not allowed to hold any major title at a New York company, and his sons Don Jr. and Eric are not allowed to do so in New York for the next 2 years.

The Stormy Daniels Hush Money Trial in New York (2024)

It took almost 18 full years to bite him, but Donald Trump’s alleged affair with porn star Stormy Daniels in 2006 finally led to him becoming a convicted felon in New York in 2024.

When Trump was running for president in 2016, he learned that Daniels was planning to sell her story of the affair, which would hurt his candidacy among voters. With the help of his lawyer Michael Cohen and National Enquirer CEO David Pecker, Trump schemed to “catch and kill” the story from Daniels by sending her a hush money payment that Cohen put together under Trump’s discretion. They also did this for Karen McDougal, the former Playboy playmate who had an affair with Trump in the 2000s.

By falsifying business records for the hush money payment, Cohen went to prison over this case. After years to build the case against Trump, the trial for it finally began in April 2024, and he was found guilty on all 34 counts of falsifying business records last week. It is the 1st time ever a former U.S. president has been convicted of a felony. It was the 1st time a U.S. president was involved in a criminal trial period.

Paying off an affair is not a felony by itself nor is falsifying business records. But where they got Trump on a felony was by linking the payments and falsified records to illegally influencing the 2016 election.

Trump’s Future Trials (2024 – ??)

Trump’s hush money trial may be over, but let’s not forget he had a record 91 charges over 4 indictments. We should still see 3 more trials involving Trump in the near future (some of which you may be able to bet on at the top politics betting sites):

  • Mishandling of classified documents in Florida (40 charges)
  • Attempting to overturn the 2020 election in the District of Columbia (4 charges)
  • Attempting to change the outcome of the 2020 election in Georgia (10 charges)

Trump has already been found guilty of 34 felonies on what was believed to be the weakest case of the 4. His troubles may only be starting should he end up facing consequences for his actions on January 6, 2021 (the insurrection) and what he did in Georgia with his phone call begging to find the 11,000 votes he needed.

Even if Trump never spends a day in prison, he has spent an inordinate amount of time in courtrooms over the decades. But between the hush money verdict and recent judgments in lawsuits against his organization and E. Jean Carroll, the legal losses (and their consequences) are finally starting to pile up for Trump.

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Scott Kacsmar
NFL football picks are Scott Kacsmar's expertise, serving as his main focus. He has contributed to various sports websites and blogs, such as NBC Sports, ESPN Insider, FiveThirtyEight, and, JoeWager. Originating from Pittsburgh, Scott maintains a love-hate connection with the Pirates.

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