Donald Trump has been involved in anywhere between 3,500 to over 4,000 lawsuits in his long career as a businessman, showman, and politician, according to a tally by USA Today. But here we focus on the plaintiff-in-chief — those suits levied at the man in the oval office, who, as Politico says, has a real relish for legal battles. He was sued at least 60 times in the first three weeks of his presidency, according to the Los Angeles Times — though many of those filings were frivolous and quite funny.
Litigation is quite a serious business for President Trump, however. Trump’s mentor was allegedly the “ruthless prosecutor,” Roy Cohn. As Trump rose to prominence in the absolutely cutthroat world of Manhattan real-estate, Cohh, then acting as Trump’s attorney, was the “hidden hand” there to help with “shady tax abatements, the zoning variances, the sweetheart deals, and the threats to those who might stand in the project’s way,” according to Vanity Fair.
The notoriously cantankerous Cohn and equally turbulent Trump eventually went separate ways, the future POTUS saying in 1980, “All I can tell you is he’s been vicious to others in his protection of me. He’s a genius. He’s a lousy lawyer, but he’s a genius.” Cohn was the archetypal attorney-pugilist, and Trump purportedly made that philosophy his own, using “lawsuits as cudgels and prods and publicity stunts,” claims Politico. And as president, the avalanche of often ludicrous litigation continues. Here are some of the most notable cases.
Donald Trump's niece alleges he stole the family jewels
Donald Trump’s estranged and surely least-favorite niece Mary Trump alleged in a 2020 lawsuit her famous uncle conspired to fleece her inheritance. Filed in Trump’s none-too-friendly home state of New York, the suit centers around funds Mary feels were owed to her from Trump’s father’s vast real-estate empire. She claims, “fraud was not just the family business — it was a way of life,” according to CNN.
Mary alleges a “complex scheme,” wherein she apparently voluntarily signed documents that ended up costing her tens of millions of dollars or more. This suit comes just months after publication of Mary’s tell-all book that sounds more like a biography of James Bond: Too Much and Never Enough: How My Family Created the World’s Most Dangerous Man. In the book, she alleges, among other lurid accusations, that Trump paid a friend to take the SAT for him, according to BBC News.
Trump quipped back on Twitter that he was now the “ultimate member of the Book of the Month Club,” and described Mary as a “a seldom seen niece who knows little about me, says untruthful things about my wonderful parents (who couldn’t stand her!) and me, and violated her NDA. She also broke the Law by giving out my tax returns. She’s a mess!” Mary had earlier leaked Trump’s taxes to the New York Times. Trump told Fox News, “she was not exactly a family favorite … It’s a lie.”
Donald Trump's rape accuser says he defamed her
Famed Elle columnist E. Jean Carroll alleges Donald Trump sexually assaulted her in either 1995 or 1996. She claims in her misandrist memoir What Do We Need Men For: A Modest Proposal that she ran into Trump at Bergdorf Goodman. They recognized each other. Initially attracted, Carroll describes Trump as “prettier than ever.” Trump was supposedly shopping for a lady friend and suggested Caroll try on some lingerie. She apparently agreed, and the pair headed for a dressing room. That’s when she says Trump raped her in a violent exchange beginning, “The moment the dressing-room door is closed, he lunges at me, pushes me against the wall, hitting my head quite badly, and puts his mouth against my lips.” Carroll further details the harrowing episode, excerpted for The Cut — where she lodges similar accusations at men throughout her life.
Trump flatly denied the allegations, quipping, “number one, she’s not my type. Number two, it never happened.” according to The Hill. Trump went on to say that Carroll was “totally lying,” and “I have no idea who she is.”
According to The New York Times, however, there is a photo of the two together from the 1980s. Carroll has now sued Trump for defamation, claiming by denying her rape allegation, he has damaged her reputation and career. Carroll says she is doing this for “every woman who has come forward and was dragged through the mud, ridiculed and called a liar.”
Donald Trump gets schooled over his University
If anyone has ever tried to make you feel bad about your degree from The University of Phoenix, well, you’re practically a Rhodes Scholar compared to unhappy students at Donald Trump’s now-defunct for-profit Trump University — at least according to former pupils.
Students allege in a series of class-action lawsuits spanning coast to coast they paid $35,000 in tuition — under duress from school reps using “high-pressure sales tactics” — for classes taught by “unqualified instructors,” according to The New York Times. Trump had initially disputed the class-action claims, and appeared interested in the legal fight ahead, “It’s something I could have settled many times. I could settle it right now for very little money, but I don’t want to do it out of principle,” per The New York Times.
Trump had a change of heart, however, shortly after his election in 2016 — perhaps at the prospect of testifying — and settled the suit out of court for a whopping $25 million. The case, fought partially in Trump’s home state of New York, included a $1 million penalty “for violating state education laws.” Trump’s attorney claims he settled, “without an acknowledgment of fault or liability,” but New York attorney general Eric T. Schneiderman insists this was long overdue justice, “The victims of Trump University have waited years for today’s result, and I am pleased that their patience — and persistence — will be rewarded by this $25 million settlement.”
Trumps sued for stealing 'Make America Great Again'
Many of the lawsuits pursued against the rich and famous are obviously frivolous but none-the-less funny. A hallmark of the great yet labyrinthine American legal system is you really can sue anybody for anything. That doesn’t mean you’re going to win, or not go broke in the process, but it is a blunt way to get on the radar of your least favorite celebrity.
An Oregon inmate in a case dubbed McNair vs. Trump et al sued Trump and basically his entire cabinet in 2017 for being “illegally elected” and supposedly violating the Constitution’s emoluments clause, according to the Los Angeles Times. This is part of a spate of suits from inmates and various eccentrics across the country and beyond.
Another man sued Trump in a “rambling, handwritten” filing accusing the president of a highly legalistic distinction this plaintiff no doubt developed himself: “rampant corruption.” Another self-filed — and yet apparently pro-Trump suit — simply asks the president to employ “extreme vetting” on foreign travelers, and to punish “sanctuary” cities. Two other suits, from Illinois area prisoners, are described, perhaps generously, as “unintelligible,” and “incomprehensible.” A more peeved plaintiff sued Trump alleging the president used “Make America Great Again … without permission.” The same suit, Nanney vs. Bank of America, also claims the mega-bank failed to just straight-up give him $4 billion — many Americans have experienced this second crime first hand, so it may be worth investigating further. Much injustice.
Trump sued for sharing fake 'racist baby' video
Many of the countless lawsuits levied at the often-orange executive are based on this conservative politician’s infamously liberal policy regarding retweets. Donald Trump shared a video in 2020 with his 86 million Twitter acolytes that purported to be a clip from the president’s cable news nemesis CNN featuring a black baby running from a white baby above a diabolical chyron that read, “Terrified Toddler Runs From Racist Baby.” The clip, which can still be seen on Youtube, went viral. Some saw the joke, some were outraged CNN would (they thought) impute such motive to small children.
In actuality, babies aren’t savage racists — even CNN knows this — and the video was, of course, doctored, by a conservative meme creator, “Carpe Donktum,” real name Logan Cook. The original video, which was indeed featured on CNN is simply a wholesome clip of the same two toddlers embracing in what appears to be an ecstatic reunion of long-lost friends — which in toddler time might be half a day.
The parents of the toddlers didn’t see the humor and sued both Trump and Cook in New York Supreme Court for copyright infringement, according to The Wrap – and are seeking unspecified damages. They suit dubs the video “extreme, shocking and outrageous” and “beyond the bounds of decency.” Both Facebook and Twitter have censored it. Twitter branded the video “manipulated media” and subsequently banned its creator Cook for “repeated copyright violations,” according to Variety.
The People of California vs. Donald Trump
In more professional and far less fun legal wrangling, the great state of California has basically been suing Donald Trump and his administration since day one. At issue are a variety of federal policies for which the Golden State has spent $43 million in litigation costs in the first four years of Trump’s administration, according to The Sacramento Bee.
California Attorney General Xavier Becerra claims, however, the suits have saved his state billions. They cover three main areas of dispute. According to the Los Angeles Times, the Trump administration wants to weaken California laws on higher fuel efficiency standards and take away the state’s ability to set its own emission standards. That second part of the overall environmental case is set to hit the Supreme Court. California has further moved to block Trump’s border wall and an attempt to undo DACA, the Obama-era carve-out that was created to allow children of immigrants who arrived illegally to stay in the US. Thirdly, California is suing to prevent Republicans from rescinding another Obama-era law, the Affordable Care Act, which allows in part, patients with pre-existing medical conditions to buy healthcare at reduced prices.
“Every single case is based on Donald Trump and his administration doing something against the law,” claims the California Attorney General. “We didn’t wake up in the morning and say, ‘Wouldn’t it be fun to sue Donald Trump again?” California has now filed over 90 lawsuits against the Trump administration.
Trump sued for blocking haters on Twitter
Back to the fun stuff. Donald Trump is being sued for blocking critics on his personal Twitter account. The initial suit, filed in 2017 by a free speech organization out of Columbia University, auspiciously dubbed the Knight First Amendment Institute, who claims that Trump’s Twitter amounts to a “public forum” and is therefore protected by the First Amendment to the United States Constitution, according to said Knights.
In 2018, Trump was felled in the case when a federal court judge ruled in favor of the valiant Knights. Trump, obstinate as always, appealed, but lost in 2019, according to Forbes. Republicans aren’t the only target of these open forum jousts, though. Democratic Rep. Alexandria Ocasio-Cortez was also sued on this same basis. She initially disputed the case, arguing her personal Twitter is just that, personal. She eventually backtracked, however, and issued a public apology, per The Wall Street Journal.
Trump has been less pliable, however, and was sued again by these same Knights, who also claim it’s just as unconstitutional for him to fail to unblock Twitter users as it is to block them in the first place. Trump’s legal team argues they don’t need to unblock users who can’t specify the Tweet that got them blocked in the first place — or those who were blocked before reality-show Trump became President Trump. At the time of this writing, that part of the case is ongoing.
Donald Trump vs the internet
Twitter announced in 2020 that it would begin fact-checking tweets about COVID-19 — including dubious links between 5G technology and the coronavirus pandemic, according to Business Insider. Donald Trump soon ran afoul of Twitter’s more aggressive editorial attitude in a tweet about mail-in ballots, which he contends are a potential source of election fraud. Twitter marked his tweets with a label reading, “get the facts about mail-in ballots,” which links to a blurb sourced to CNN disputing his claim.
The president found all this quite partisan on Twitter’s part and signed an executive action that could “open the door for the U.S. government to assume oversight of political speech on the Internet,” according to The Washington Post. Trump, however, contends censorship is already afoot, “Republicans feel that Social Media Platforms totally silence conservatives voices. We will strongly regulate, or close them down, before we can ever allow this to happen,” he tweeted.
That’s when Silicon Valley rallied. A group representing Google, Facebook, and Twitter called the Center for Democracy and Technology brought suit against the executive action. But it’s a tricky case. Social media companies have avoided being regulated as publishers and thus liable for much of their content. The move to add editorializing on political tweets seems to run counter to their strategy of avoiding governmental oversight. Thus this legal clash with Trump is more like an initial volley in the deep quandary of what role powerful tech companies play in American democracy.
Donald Trump faces the music
This case is a classic, as in classic rock. Musicians don’t usually have a conservative bent, and thus don’t like their songs blaring at Republican rallies — particularly without their permission. John Mellencamp came after Ronald Reagan, George W. Bush, and John McCain for the use of his songs, according to Entertainment Weekly. Tom Petty similarly wouldn’t back down when George W. Bush and Michele Bachmann used his songs for campaign purposes.
Neil Young had exactly the same feeling when Donald Trump used “Rockin’ in the Free World” and “Devil’s Sidewalk” at a campaign rally in Tulsa, according to The Hollywood Reporter. “This complaint is not intended to disrespect the rights and opinions of American citizens, who are free to support the candidate of their choosing,” said the suit. Cue a tone shift in this filing, “However, Plaintiff in good conscience cannot allow his music to be used as a ‘theme song’ for a divisive, un-American campaign of ignorance and hate.”
Adele, Steven Tyler, the Rolling Stones, R.E.M., Pharrell, Rihanna, Queen, and even Nickelback have all objected to Trump using their songs.
George Floyd protestors sue Donald Trump
In the aftermath of the death of George Floyd, protestors, then arguably rioters, stormed Washington DC’s iconic St. John’s Church in Lafayette Park where every president since Franklin D. Roosevelt, besides Richard Nixon, has attended services on inauguration day. Roosevelt, of the legendary, “The only thing we have to fear is fear itself,” speech, at the time, tried to buck up a frightened nation facing The Great Depression.
Never have similar words of national encouragement felt more needed than in 2020 when Donald Trump, with an escort of the federal police, appeared to tear gas protestors to make way for a photo op at the iconic church, according to The Washington Post. Three protestors then sued the POTUS, claiming they were peaceful, and that officers used rubber bullets and pepper spray, according to TMZ. They are further suing Attorney General Bill Barr, who was present, for violating their rights, and are seeking damages.
Barr bit back, however, telling Face The Nation the gatherings were anything but peaceful. He points out protestors had injured over 150 police officers in DC — some pummeled with bricks and incendiaries. St. John’s Church itself was set ablaze the night before Trump’s photo op. Barr says given the brazen attempts to destroy a national landmark, the action against protestors was merely an operation to establish a perimeter around the church to protect a historic site from further desecration. The protestors suing Trump, however, are also citing this very perimeter as unconstitutional.
Trump sued for allegedly cashing in as president
It’s not only various federal inmates worried Donald Trump has been profiteering in as executive in chief. Congressional Democrats filed a trinity of lawsuits against the POTUS for violating the Constitution’s emoluments clause — which bars a sitting president and his or her business interests from receiving money from foreign governments without prior approval of Congress.
Recall, after Trump’s inauguration, he declined to divest from his business interests, according to Forbes, which include many foreign ventures. Trump instead passed control to his sons, saying, “They’re going to be running it in a very professional manner. They’re not going to discuss it with me.”
That wasn’t good enough for Democrats who claimed foreign officials patronizing his hotels and other properties was illegal. The suit was, however, thrown out by a Washington DC federal court appeals judge ruling that “Individual members of Congress lack legal standing to sue the president for alleged violations of law,” per CNBC. The three-judge panel, however, did not rule on the actual issue of the emoluments clause. This is the first-ever emoluments clause case against a sitting president, also according to CNBC, but the legal defeat bars Democrats from further pursuit of this claim. Trump crowed over the news via Twitter, “Another win just in. Nervous Nancy Pelosi and the Democrats in Congress sued me, thrown out. This one unanimous, in the D.C. Circuit. Witch Hunt!”
Porn star sues Donald Trump for defamation
Porn star Stormy Daniels claims she met Donald Trump at a celebrity golf tournament in 2006. She says they hit it off and had sex, kiss and telling In Touch in 2011, “I can definitely describe his junk perfectly.” The interview, though, didn’t drop until 2018 because Trump allegedly had his former attorney Micheal Cohen give Daniels $130,000 before the 2016 election to keep quiet, according to The Wall Street Journal.
Daniels, however, told 60 Minutes that just after she’d done the tell-all with In Touch, a strange man approached her and her infant daughter in a parking lot. The man allegedly threatened, “leave Trump alone, forget the story,” and then added ominously, “that’s a beautiful little girl, it’d be a shame if something happened to her mom.”
Daniels claimed she’d never forget the face and turned to her infamous attorney, Michael Avenatti, for help. Avenatti was sentenced to prison in 2020 for attempting to extort $25 million from Nike — and faces charges he defrauded Daniels too, according to The Washington Post. But in 2018, the brazenly criminal, comma, lawyer dropped a sketchy sketch of the supposed suspect, which Trump retweeted next to a photo of Daniel’s also-estranged husband, adding, “A sketch years later about a nonexistent man!” The resemblance between the sketch and her ex is hilariously uncanny, but Daniels sued for defamation. The judge even ordered Daniels to pay Trump’s legal fees, according to The New York Times.
Donald Trump makes charitable donations to himself
Donald Trump was ordered by the New York Supreme Court in 2019 to pay $2 million in damages for using his charitable organization to benefit his run through the Republican primary in 2016, according to a ruling announced by Attorney General Letitia. Trump also had to admit to “personally misusing funds at the Trump Foundation.”
The suit levied against Trump Foundation directors, Trump, Donald Trump Jr., Ivanka Trump, and Eric Trump, claims, “Trump repeatedly used Foundation money for his own personal, business, and political interests, including the unlawful coordination with his 2016 presidential campaign.” The settlement dissolved the foundation entirely, and, perhaps, most embarrassingly, the organization’s remaining assets were donated to charities of Attorney General James’ choosing. Libertarians everywhere fainted.
As part of the settlement, Trump’s team was forced to admit abusing the ostensibly charitable organization for personal ends including the starkest detail, “the Foundation paid for a portrait of Mr. Trump that cost $10,000.” Trump was then forced to reimburse the defunct foundation (because paying back a fraudulent charity that doesn’t exist makes sense, but okay) for the cost of the painting as well as “$11,525 for sports paraphernalia and champagne purchased at a charity gala.” The object of charity at this gala, if it’s not clear, was just Trump.
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