New twist in Donald Trump vs Eddy Grant case

See you in court...

As his mounting legal problems threaten to engulf him, Donald Trump is trying to narrow down a lawsuit that was filed against him in 2020. Read on to find out why – and discover which 80s music icon is at the center of the case. 

All dollar amounts in US dollars.

Eddy Grant vs Trump

During Trump’s second presidential campaign in August 2020, he shared a video on Twitter that mocked President Biden. The animation showed Biden driving an old-fashioned handcar, trailing behind a "Trump Train" that bears the phrase "KAG" ("keep America great"). It was retweeted almost 65,000 times – but one person was staunchly unimpressed.

Guyanese-British musician Eddy Grant sued Trump for copyright infringement because the video featured 40 seconds of Grant's 1983 hit Electric Avenue. Although Trump removed the video after Grant complained, Grant's attorneys filed a lawsuit on the basis that Trump "sought to encapsulate [his] intellectual property into derogatory political rhetoric, further encapsulated in a video production that can only be construed at best as being wicked, thereby causing considerable emotional distress."

Eddy Grant vs Trump

In response, Trump filed a motion to dismiss the claim. His lawyers argued that he had a right to use the music because it had been "transformed" for a "comedic, political purpose" and that Trump had "presidential absolute immunity" at the time. However, a New York federal judge dismissed both arguments and Trump was deposed in the case at some point in 2022.

Artists firing back at Trump for using their music without permission is nothing new – Village People, Adele, the Rolling Stones, Elton John, Rihanna, Neil Young, George Harrison's estate, and the son of David Bowie have all complained in the past – and Grant has been pressing ahead with his lawsuit. He's reportedly seeking $300,000 in damages.

Eddy Grant vs Trump

In the latest developments, it's just been revealed that Trump has asked presiding judge John Koeltl to narrow the scope of Grant's case. The former POTUS has argued that Grant doesn't own the rights to the recording of Electric Avenue, a claim that prompted Grant to ask the court to rule the defendants are liable for copyright infringement before the case goes before a jury. (A trial date hasn't been set yet.)

In the filing, Trump's lawyers wrote: "There can be no material dispute... that Plaintiffs only plead a copyright registration covering the composition (i.e., the written music and lyrics) of Electric Avenue, registered at around the time of its publication in 1983.

"Plaintiffs nevertheless claim that they own a valid copyright registration covering the sound recording (i.e., the fixation of a series of musical and spoken sounds to a “phonorecord”) of Electric Avenue by virtue a copyright registration for a “greatest hits” album (which they described to the Copyright Office as a “compilation”) that contains the song Electric Avenue."

Eddy Grant vs Trump

According to a new deposition transcript that was filed on Friday, Grant was asked by Trump's lawyers to explain what the song Electric Avenue is about – a question he seemed to resent, replying "Do I have to?"

"We can stay here all day," Grant went on. "And I can go round and round with this. But the bottom line of it is that... it is a protest against social conditions." The artist started reciting his lyrics before saying: "You know, I could go a long – you know, I mean, do we have to?"

We'll have to wait and see whether Trump's appeal is successful or whether he'll have to face the music in court. But one thing's clear: the 45th has no shortage of other major pending lawsuits, both as plaintiff and defendant...

McKoy vs The Trump Corporation

According to an anonymous source who spoke to Bloomberg, Trump was deposed in October 2022 in a fraud case originally filed in October 2018 by four investors who've been described in court documents as "working-class Americans."

They accused The Trump Corporation – including Trump himself and three of his adult children: Donald Jr, Eric, and Ivanka – of "defrauding economically marginalized people" by encouraging them to invest in businesses that paid the Trumps to promote them. These businesses included ACN Opportunity LLC, a company that sold a "tremendous" videophone touted as the next big thing. It flopped. 

McKoy vs The Trump Corporation

The plaintiffs haven't sued The Trump Corporation for a fixed sum. However, they claim that the Trumps "made millions" by conning "victims into giving hundreds or thousands of dollars – losses that many experienced as devastating or life-altering." 

One allegation in the lawsuit is that Trump and his children promoted ACN on The Celebrity Apprentice, which first aired in 2004. It's possible that clips from the show were used as evidence during the deposition.

McKoy vs The Trump Corporation

Although no specific details of the deposition have been revealed, the plaintiffs' lawyer Roberta Kaplan (pictured) reportedly told Insider: "We could not be more pleased with the substantial body of evidence we have developed that will prove our clients' claims. We are eager to move this case forward to trial as soon as possible."

After the deposition took place, Kaplan requested a trial date of October this year, saying: "Plaintiffs have no desire to interfere with the upcoming [presidential election] campaign, and are mindful that, should the schedule in this case extend into 2024, Defendants likely will, as they have in the past, use the campaign as a basis to seek further delay." However, a trial date of January 29 2024 has now been set.

In the most recent development, Trump's children have been dropped from the suit, according to Bloomberg.

E Jean Carroll vs Trump

Donald Trump suffered a legal blow recently after a judge ruled the forthcoming civil trial over defamatory comments he made about the writer E Jean Carroll will be limited to determining damages only as he is liable. The trial, set to begin in January, is the second in the case and comes after Trump's counterclaim against the American journalist and author was rejected.

The former president brought the legal action after a jury in a civil case earlier this year found him guilty of having sexually abused Carroll in a New York department store changing room in the mid-1990s. Trump was ordered to pay Carroll $3 million for damaging her reputation and $2 million for the sexual abuse. 

Trump took to the airwaves the very next day and asserted live on CNN that the trial had been rigged, repeated his former claim that Carroll had "made up" her assault allegations, and called her a "whack job." In response, Carroll’s attorney formally asked to renew another defamation lawsuit to include these latest smears. 

E Jean Carroll vs Trump

Undeterred, Trump countersued Carroll for defamation, citing the jury's verdict that he sexually abused but didn't rape her as proof that she falsely accused him. Trump's lawyers, who were seeking unspecified punitive damages, said Carroll "made these false statements with actual malice and ill will with an intent to significantly and spitefully harm and attack" the ex-president.

That legal avenue has now been closed, with Judge Lewis Kaplan ruling that Carroll’s statements were "substantially true," asserting that the jury in the civil case found Trump had raped Carroll "as the term is understood more broadly." 

E Jean Carroll vs Trump

Carroll (pictured) first accused Trump of sexual assault in a 2019 New York Times article. She later described the assault – which she refers to as a "fight" – in her 2019 book What Do We Need Men For?: A Modest Proposal. 

Trump denied Carroll’s accusations in June 2019. In an interview with American digital media publication The Hill, he claimed Carroll was "totally lying" and "not [his] type." Five months later, Carroll filed a defamation lawsuit with the New York Supreme Court.

E Jean Carroll vs Trump

Carroll, who had an advice column in Elle magazine from 1993 to 2020, claimed Trump’s denial harmed her both personally and professionally. She allegedly received half as many Ask E. Jean letters and was fired from her position at Elle after The Hill published Trump’s interview, in which he accused Carroll of making up the story to publicize her new book. "It should be sold in the fiction section," he said. 

Trump was deposed in October 2022, which prompted him to describe the US legal system as a "broken disgrace." The deposition, a transcript of which was released by a federal judge in January, includes a string of insults leveled by Trump against Carroll. He called her a "wack job," "mentally sick," and a "nut job," stating that "there's something wrong with her in my opinion."

Mischaracterizing an interview Carroll conducted with CNN, Trump claimed that she'd talked about enjoying being sexually assaulted: "She actually indicated that she loved it. Okay? She loved it until [the] commercial break."

E Jean Carroll vs Trump

An upgraded lawsuit was filed on Carroll's behalf mere minutes after New York's new Adult Survivors Act was signed into law. The law enables survivors of sexual assault to file lawsuits against their attackers regardless of how long ago the assault occurred.

The filing, which explicitly accused Trump of rape too, sought "unspecified compensatory and punitive damages for pain and suffering, psychological harms, dignity loss and reputation damage." 

E Jean Carroll vs Trump

After months of legal wrangling, a civil trial finally began in New York on April 25, with the jury of six men and three women considering Carroll’s allegations of rape, sexual assault, battery, and defamation. After just two weeks, the jurors reached a verdict that shocked the world. Donald Trump was guilty of having sexually abused Carroll – the first president in American history to be convicted of such an offense. Carroll's claim that Trump raped her was rejected, but the writer's allegation that Trump later defamed her was upheld.

While many believed this would bring an end to the saga, the 45th made his already mentioned explosive claims about Carroll and the trial the next day during a town hall event hosted by CNN. Unsurprisingly, Carroll was not impressed.

E Jean Carroll vs Trump

Carroll’s attorney Roberta Kaplan, who is also representing the plaintiffs in the McKoy case, formally asked to renew another defamation lawsuit against Trump about comments he made in 2019 to include his smears in the CNN town hall event. Her request was granted on June 13, with a new trial date set for January 2024.

According to the amended lawsuit, Trump "doubled down on his prior defamatory statements, asserting to an audience all too ready to cheer him on that ‘I never met this woman. I never saw this woman,’ that he did not sexually assault Carroll, and that her account — which had just been validated by a jury of Trump’s peers one day before — was a ‘fake,’ ‘made up story’ invented by a ‘whack job.’"

Carroll is seeking damages, which Reuters reports could be up to $10 million. Trump's first response was to file a motion to request either a retrial in the original case or a reduction in the damages he's already been ordered to pay – a move that Kaplan has described as "magical thinking." Sure enough, the motion was rejected by the courts in June. Following the dismissal of his countersuit, Carroll's case will return to court on January 15 next year: the same day as the first Republican presidential selection contest.

NAACP LDF vs Trump

In November 2020, the Legal and Defense Fund (LDF) of the National Association for the Advancement of Colored People (NAACP) filed a lawsuit against Trump and his campaign. It claimed that Trump had violated Section 11(b) of the Voting Rights Act by pressuring officials not to certify the 2020 election result.

NAACP LDF vs Trump

The following month, LDF amended the lawsuit. The updated version alleged that Trump had also violated the Enforcement Act of 1871, known as the Ku Klux Klan Act, which protects everybody’s equal right to vote. By discarding votes in cities with large Black populations, LDF argued that Trump – who tried to dismiss the case in February 2021 – was discriminating against voters. LDF is asking for statutory damages, as well as a court order that will prevent people from intimidating voters and election officials in the future. 

A federal judge has dismissed Trump's claim that he had presidential immunity and said: "The Court concludes that Former President Trump is not immune from monetary damages in this suit." It's not clear how much he could stand to lose, but there have been further developments in the case...

NAACP LDF vs Trump

Last November, a district court agreed that the plaintiffs could amend their complaint to include "factual allegations regarding conduct by Defendant Republican National Committee (“RNC”) and Defendants Donald J. Trump and Donald J. Trump for President, Inc... especially conduct that occurred or evidence that became available after" the original lawsuit was filed. 

Deputy Director of Litigation at the NAACP, Deuel Ross (pictured far right), was part of a House Administration Subcommittee investigating election interference earlier this year. The ongoing Fulton County criminal investigation into Trump's alleged attempts to overturn the 2020 result doesn't seem to have affected the NAACP's lawsuit, so it's possible the former POTUS could face civil charges relating to the election in addition to his recent indictment.

Blassingame vs Trump

In March 2021, two Capitol police officers – James Blassingame and Sidney Hemby – sued Trump for the "physical and emotional injuries" they sustained during the Capitol riots on January 6, 2021. 

According to the lawsuit, Blassingame and Hemby were attacked with bear spray, hit with flagpoles and fists, and crushed against a door. Blassingame also claims that the pro-Trump intruders racially abused him while forcing their way into the Capitol building. 

Blassingame vs Trump

The case, which Trump filed an unsuccessful motion to dismiss in June 2021, alleges that the then-president incited his supporters to attack the police officers. Blassingame and Hemby believe Trump illegally conspired with the Proud Boys and Oath Keepers to storm the Capitol, and are asking for at least $75,000 in compensation, not counting interest and costs. 

Trump filed another appeal in July last year, fighting back against the court's claim that he lacked presidential immunity in the case. 

Smith vs Trump

Like James Blassingame and Sidney Hemby, police officer Conrad Smith and six of his colleagues also filed a lawsuit against Trump, the Proud Boys, and the Oath Keepers. Their case, which was filed in August 2021, alleges that the defendants conspired to start the riot and injure the Capitol officers on duty.

Smith vs Trump

Unlike Blassingame and Hemby, the second group of Capitol police officers claim that the defendants violated the DC Bias-Related Crimes Act. According to DC law, "bias-related crimes" include acts that are motivated by political affiliation. The officers allege that the Capitol rioters were motivated by their hatred of the Democratic Party and that Trump had praised the attack, saying: "We love you. You’re very special."

In January this year, Trump filed a motion to dismiss the lawsuit, arguing yet again that he was protected by presidential immunity. The court denied the motion that same month, and the case continues.

Trump vs Twitter

In July 2021, Donald Trump filed a class action lawsuit against Twitter, now rebranded to X, after it permanently suspended his account following the Capitol riots. The lawsuit, which he filed in a Southern Florida federal court, accused Twitter and its then-CEO Jack Dorsey of "impermissible censorship" and violating Trump's First Amendment right to free speech.

Trump's lawyers argued that Twitter and other big-name tech platforms such as Facebook and Google are effectively "state actors" rather than private companies, meaning it's unconstitutional for them to censor people.

Trump vs Twitter

The lawsuit also named Linda Cuadros and the American Conservative Union (Ivanka Trump is pictured here speaking at one of its conferences) as plaintiffs. Cuadros, who used to have around 10,000 followers on Twitter, claimed that her account was also permanently suspended after she shared a post about vaccines. Meanwhile, the American Conservative Union accused Twitter of removing a substantial number of its followers on the platform – allegedly as a form of partisan censorship.

According to the filing, "Dorsey and Twitter acted to censor" differing medical and political opinions, and were incentivized by the government to do so, as Democrat legislators "repeatedly requir[ed] their appearance at hearings" and "reinforc[ed] their potential to impose regulations."

Trump vs Twitter

Back in November 2020, Dorsey was ordered to testify remotely during a Senate Judiciary Committee hearing (pictured). Called "Breaking the News: Censorship, Suppression, and the 2020 Election," the hearing aimed to determine the extent to which social media platforms such as Twitter were to blame for spreading "fake news," and whether they should be held responsible for the content other people post. 

While being questioned, Dorsey said that Trump's social media account would be subjected to stronger moderation policies once he'd left office, claiming that political world leaders are given more freedom. "If an account is not a world leader anymore, that particular policy goes away," he said. Of course, Trump's Twitter account was removed just two months later. 

Trump vs Twitter

Trump has alleged that Twitter was unlawfully pressured into removing his account, which had 88 million followers at its peak, by Congress. He filed similar lawsuits against Facebook and Google, both of which were also questioned as part of the Congressional hearing (although neither of which banned him permanently from their platforms).

The three lawsuits were presided over by three different judges. Trump's Twitter suit was overseen by James Donato, a San Francisco federal judge who'd been appointed by Barack Obama. In May 2022, 10 months after Trump's attorneys filed the suit, Donato threw it out – but Trump wasn't prepared to let the matter lie. 

Trump vs Twitter

Last November, Trump launched an appeal against the ruling and asked the 9th US Circuit Court of Appeals in San Francisco to revive his lawsuit, which seeks "an award of Compensatory and Punitive damages to the Plaintiff and the Class in an amount to be determined at trial," as well as an injunction ordering the immediate reinstatement of Trump's Twitter account.

Trump's lawyer has confirmed his client is pressing ahead with the case – despite his account having since been reinstated.

Trump vs Trump

In September 2021, Donald Trump sued The New York Times and his own niece Mary L Trump for at least $100 million, claiming they'd hatched an "insidious plot" to "smuggle" his tax records.

A vocal critic of her uncle Donald, writer and psychologist Mary wrote a best-selling book about him titled Too Much and Never Enough: How My Family Created the World’s Most Dangerous Man. The memoir was published by Simon & Schuster in July 2020, after a previous lawsuit from the Trump family – which resulted in a temporary restraining order against the book's publication – was lifted by a New York appellate judge. 

Trump vs Trump

In Too Much and Never Enough, Mary revealed that she'd provided copies of her uncle's tax records to New York Times journalists for a 2018 article about his finances. Co-writers Susanne Craig, David Barstow, and Russell Buettner won the 2019 Pulitzer Prize for their exposé, which Trump's lawsuit claimed was motivated by "their desire to gain fame, notoriety, acclaim, and a financial windfall [to] advance their political agenda."

The article, Trump Engaged in Suspect Tax Schemes as He Reaped Riches From His Father, alleged that Trump took part in numerous "tax dodges in the 1990s" to inflate his fortune, including through "instances of outright fraud." The report was the result of an 18-month investigation into Trump's tax dealings, challenging his supposed status as a self-made billionaire.

Trump vs Trump

Mary filed her own lawsuit against her uncle as a result of the findings of the New York Times investigation. The daughter of Trump's older brother Fred, who died from complications associated with alcoholism when Mary was just 14, she claimed that Donald and his other siblings siphoned money away from her share of inheritance while they were managing it on her behalf. 

Beginning to suspect she was being defrauded in 1999 after the death of her grandfather Fred Sr, Mary took issue with the terms of his will, which she believed didn't enable her to inherit her late father's fair share, and launched a lengthy legal battle. Eventually, as legal costs continued to climb, the older Trumps offered her an ultimatum in 2001: if she relinquished her interests in the family fortune, they would agree to settle the probate case. Reluctantly, Mary agreed to the settlement. 

After reading the New York Times' article, however, Mary says she realized the settlement figure of over $2.7 million (around $5 million today) was just a fraction of what she was owed...

Trump vs Trump

Donald Trump fought back against the lawsuit, arguing the terms of their 2001 settlement case meant that Mary had no stake in her grandfather's fortune. In November 2022 – over a year after the former POTUS filed a motion to dismiss his niece's lawsuit – a judge finally granted his request, a move that Mary's lawyer Roberta Kaplan described as "both incorrect and disappointing." 

The ruling might have halted Mary's lawsuit against her uncle, but the relatives' legal battle has rumbled on. In May this year, New York state court Justice Robert Reed finally ruled against the writer's attempts to dismiss Donald's September 2021 suit, allowing him to continue pursuing his allegations that Mary broke the terms of their 2001 settlement.

Trump vs Trump

Earlier this year, an appeals court denied Mary's bid to overturn the November ruling, saying "We have considered the plaintiff's remaining contentions and find them unavailing." Kaplan has again hit back at the judgment and said: "We respectfully disagree with [the] decision and are reviewing it closely."

However, it's not a total victory for the former president. Reed has previously dismissed all of his claims against the New York Times, and has also dismissed his allegations of unjust enrichment and bad-faith conduct against Mary.

Sicknick vs Trump

The estate of a police officer who died after defending the Capitol during the January 6 riots has filed a wrongful death lawsuit against Donald Trump. Brian Sicknick passed away on January 7, 2021 after suffering a series of strokes, a condition that a medical examiner has ruled as "natural causes." However, the examiner added that the stress of the insurrection likely "played a role in" Sicknick's death.

Sicknick's family is reportedly seeking $10 million in damages. In court papers, the plaintiffs have claimed that "Defendant Trump intentionally riled up the crowd and directed and encouraged a mob to attack the US Capitol and attack those who opposed them... The violence that followed, and the injuries that violence caused, including the injuries sustained by Officer Sicknick and his eventual death, were reasonable and foreseeable consequences of Defendant Trump's words and conduct."

Sicknick vs Trump

As well as "Donald J Trump (in his personal capacity)," the lawsuit also names the January 6 protestors Julian Elie Khater and George Pierre Tanios as defendants. The case accuses the trio of wrongful death, assault, negligence, and of assaulting Sicknick's civil rights. 

Additionally, Sicknick's girlfriend has filed her own lawsuit against the trio. Sandra Garza has reportedly sued Trump, Khater, and Tanios for $30 million, claiming they were "directly and vicariously" responsible for her long-term partner's death. 

Trump has since sought absolute immunity from Garza's suit, with his lawyers filing a motion that says: "Plaintiff's Complaint relies upon cherry-picked statements intended to mischaracterize political speech as unlawful conspiracy, fails to take into account President Trump's repeated and unequivocal urging for peace, and simply ignores the absolute immunity provided by the Constitution to President Trump." This is despite the fact that lawmakers have previously ruled against Trump's claims of presidential immunity in cases concerning the January 6 riots. 

Sicknick vs Trump

And Trump's efforts to avoid the lawsuit didn't end there. He's since asked a judge to delay Garza's lawsuit until the investigation into the 2020 election and subsequent Capitol riots has concluded.

Trump's lawyers Jesse Binnall and David Warrington made the case that Garza had already waited two years to file her wrongful death lawsuit, so an additional wait wouldn't be harmful. They have claimed: "Absent a stay, President Trump will be placed in the untenable position of fully litigating this case and risking his criminal defense, or pleading the Fifth Amendment and hampering his chance of success in this case."

"Such a dilemma should especially be avoided when it involves a former President of the United States and current frontrunner presidential candidate for the Republican party in 2024."

Letitia James vs the Trumps

In September last year, New York Attorney General Letitia James formally accused Donald Trump, three of his adult children, and the Trump Organization of massive fraud. 

Following a three-year inquiry, James filed a civil lawsuit alleging that Trump "falsely inflated his wealth by billions of dollars," hugely overvaluing his assets when asking for loans but undervaluing them when filing taxes. Although Trump can't go to jail for losing a civil lawsuit, James has referred her findings to federal prosecutors in Manhattan. These prosecutors could open a criminal investigation, which could end in a possible jail sentence if Trump is found guilty of bank fraud. 

Letitia James vs the Trumps

The former president's oldest children Donald Jr, Ivanka, and Eric – each of whom has worked for the Trump Organization – were also named in the lawsuit. According to James (pictured), it was "with the help of Donald Jr, Eric, Ivanka, and other defendants" that Trump perpetrated his crimes. (Ivanka, who left the Trump Organization in 2017, has since been successful in having herself formally removed as a defendant in the case.)

James announced that "significant evidence" had been found that Trump, Donald Trump Jr, and Ivanka were guilty of falsifying records, after her team submitted a 160-page court filing in January 2022. More potential evidence surfaced when it was revealed that Trump registered a new company called Trump Organization II LLC on the same day that James filed her lawsuit, a discovery that prompted her to urge an independent monitor to be appointed to investigate whether the company was established as part of an attempt to offload assets from the original Trump Organization.

The new business, which is listed in New York, was registered by a Delaware entity that was itself established less than a week before.

Letitia James vs the Trumps

The New York Times received word from three sources "with knowledge of the matter" that James, who launched her investigation back in 2019, rejected an offer to settle the case. Announcing her lawsuit against Trump, James declared: "Mr Trump thought he could get away with the art of the steal, but today, that conduct ends.

"There aren't two sets of laws for people in this nation: former presidents must be held to the same standards as everyday Americans." 

James' lawsuit seeks a colossal $250 million in penalties but also a permanent ban on the Trumps operating businesses in New York, as well as a ban on Donald or the Trump Organization buying commercial real estate in New York for five years. 

Letitia James vs the Trumps

James subsequently asked for the investigation to be sped up, claiming the Trumps were still breaking the law. "Since we filed this sweeping lawsuit," James said in a statement, "Donald Trump and the Trump Organization have continued those same fraudulent practices and taken measures to evade responsibility." A New York judge granted her request and the October 2 trial date was scheduled.

James also urged a judge to prevent Trump from moving any assets to the new company. That's because the plaintiffs could find it difficult to uphold a fine if the Trump assets are held by an entity that hasn't been named as a defendant. Judge Engoron granted James' request for a monitor – which must be paid for by the Trump Organization – to oversee the business' accounts and financial disclosures. He also prohibited the company from "selling, transferring or otherwise disposing of any non-cash asset" that was listed in Trump's most recent financial statement without the court's knowledge and permission. 

Letitia James vs the Trumps

Trump filed his own lawsuit against James in November 2022. The former POTUS accused James of "extraordinary wrongdoing" and waging "a war of intimidation and harassment" against him. He'd previously claimed that the Attorney General, a Democrat, was hounding him for political reasons, adding that James wanted to destroy him "personally, financially, and politically." 

The civil suit sought an unspecified amount in damages, according to reports. The 41-page lawsuit, which was filed at Florida State Circuit Court in Palm Beach, also aimed to block James from accessing documents from a Florida trust that partially owns the Trump Organization. 

Letitia James vs the Trumps

Trump announced the lawsuit in a post on Truth Social in November last year, accusing "Peekaboo" James of attacking his "great and upstanding" business while letting crime rates in her jurisdiction of New York skyrocket. His lawyers claimed that James' ongoing investigation was "contrary to both the laws of New York and Florida," with the lawsuit naming her "individually and in her official capacity as Attorney General of the State of New York." 

The suit also suggested that James began "amping up her attacks on President Trump to rev up her political base" ahead of the midterm elections. According to James' office, Trump's lawsuit was an attempt "to shield the key documents governing the structure of his business conglomerate and ownership of his business assets from review." 

Letitia James vs the Trumps

In January, US District Judge Donald Middlebrooks ordered Trump and his former lawyer Alina Habba (pictured) to pay a joint $938,000 to defendants including Hillary Clinton in a separate case that he dismissed as "frivolous." (It's since been reported that the pair have appealed the fine, offering instead to post a $1.03 million bond.)

Trump's lawsuit against James also landed before Middlebrooks, so the former president chose to "voluntarily" dismiss it shortly after he was hit with the Clinton fine. 

Letitia James vs the Trumps

On January 24, Trump and James' office came to an additional agreement that would end his appeal to reverse the court's dismissal of his original lawsuit, leaving the coast clear for James' own suit. According to Habba (pictured here with Trump), the litigation was "voluntarily withdrawn for strategic purposes."

Trump and his lawyers also abandoned an appeal to get a check for $110,000 for contempt of court back, after filing a staggering 977 pages of appellate paperwork to request the return of the funds, as well as the expungement of the original court order. Trump is currently worth $2.5 billion, according to Forbes.

The court upheld the original order, including the "correctly determined" $110,000 fine, due to the former president's failure to comply with a subpoena asking for financial documentation.

Letitia James vs the Trumps

Trump may have lost his appeal, but he's still battling James' lawsuit, and it's emerged that he and his fellow defendants have filed a total of 5,000 pages in response. One of their key arguments claims that the Trump Organization can't be sued because 'Trump Organization' is branding shorthand, not a legal entity. The lawsuit references the Trump Organization on more than 300 occasions, using the term as a "collective" name for Trump's various businesses, but doesn't specifically name the company as a defendant. It does name The Trump Organization, Inc, a company that was registered in New York in 1981.

"To the extent a response is required, Defendant specifically denies the definitions of 'Trump Organization' and 'Defendants,'" reads Trump's response to the suit. 

"While the shorthand 'Trump Organization' is utilized by Defendants for branding and business purposes, no entity as such exists for legal purposes." 

Letitia James vs the Trumps

CBS News released footage of Trump's initial deposition in the case, which took place last year. The video revealed that Trump pleaded the Fifth Amendment, designed to protect people from self-incrimination, more than 400 times in response to questions from James. 

Trump returned to New York in April for a second deposition in the fraud case and answered questions for seven hours – a stark contrast to his previous deposition, during which he refused to answer the majority of James' questions. In sworn testimony, Trump said he didn’t think his financial statements would be taken seriously because they have a disclaimer that says they shouldn’t be trusted. He told James: “You don’t have a case and you should drop this case.”

Letitia James vs the Trumps

It's since been revealed that Trump's legal team issued as many as 10 subpoenas to individuals including his former accountant Donald Bender and former lawyer Michael Cohen. The last-minute legal orders were issued "right up against what's known as the 'timely notice' deadline," according to Business Insider.

The subpoenas were issued in February this year, despite the deadline being agreed back in November.

Letitia James vs the Trumps

The Attorney General claimed that "approximately 85 percent of all documents held by OAG [office of the Attorney General] in this action were already available to the Trump Organization from the time they were created" and that the defendants' "claimed hardship is self-inflicted." 

Yet the OAG could be considering more depositions of its own. Prior to filing the lawsuit, James' side spent over a year deposing witnesses, and has now suggested it could re-depose both Donald Trump and his son Eric, as well as disgraced former Trump Organization CFO Allen Weisselberg.

James isn't the only person who's unhappy with Trump's legal tactics. Michael Cohen (pictured) has said: "After advisement by counsel, I have decided to challenge the subpoena and intend on making a motion to quash. The subpoena was improperly served, I am not a party to this action and the subpoena lacks any specificity as to why I am being called as a non-party witness.

"It's just bad lawyering by Team Trump."

Letitia James vs the Trumps

But Donald Trump won a rare court victory, and some breathing pace amid his many legal woes, after a judge temporarily halted the upcoming trial.

The trial, due to begin on October 2, is now in limbo after Trump directly sued Justice Arthur Engoron, the trial judge overseeing the case. The former president’s lawyers have accused Engoron of defying a June court order that could narrow the case against their client. The legal action also references Engoron’s refusal earlier in September to grant the Trump camp’s request for a three-week delay to the trial.

Letitia James vs the Trumps

This latest twist in the long-running fraud trial saga has surprised many Trump observers, not least given the speed at which events unfolded. Lawyers for Trump made an emergency court filing last week, asking New York’s higher courts to commence an 'Article 78 special proceeding' against Engoron, a lawsuit mainly used to challenge an action (or inaction) by agencies of New York State and local governments. 

A virtual hearing took place in the afternoon of September 14, with Appellate Justice David Friedman granting the request, effectively putting the start of the trial on hold, for now at least. The matter has been referred to a five-judge panel, which is expected to rule in the last week of September. While the fraud trial could still begin on October 2, any delay in the panel’s decision could lead to a lengthy stay. Meanwhile, the office of Attorney General Letitia James has released a statement saying: “We are confident in our case and will be ready for trial.”

Letitia James vs the Trumps

This strategy of last-minute appeals and interventions is one Trump is increasingly deploying as he seeks to delay and postpone the various legal proceedings against him. It's clearly something that's annoying Attorney General Letitia James too. Earlier this month, she requested that Trump and other defendants in the case be sanctioned, accusing them of “frivolous conduct” for repeatedly asserting "previously-rejected arguments."

Trump’s lawyers have also been aggressively pursuing Engoron for months. In the summer, an appellate court ordered the judge to establish which real estate deals by the Trump Organization were too old to be considered in the fraud case. Judge Engoron has yet to do so, prompting the latest legal salvo that’s now resulted in a potential delay to the fraud trial.

While Donald Trump faces potential jail time due to the other federal cases against him, Letitia James' civil lawsuit threatens to hit the former POTUS where it really hurts, jeopardizing his entire business empire. 

Castro vs Trump

On January 6 this year, Texas attorney John Anthony Castro (pictured left) filed a lawsuit in Florida against Donald Trump, Bloomberg reports. His case argues that Trump's alleged involvement with the Capitol riots should disqualify him from the presidential race under Section 3 of the 14th Amendment, which states that people who engage in an insurrection cannot hold public office. 

Castro filed the lawsuit just a few weeks after the committee investigating the riots recommended that criminal charges be brought against Trump. The panel has formally asked the US Justice Department to prosecute the former POTUS for inciting an insurrection, conspiracy to defraud the US, conspiracy to make a false statement, and the obstruction of an official proceeding.

Castro vs Trump

At the time Castro filed his lawsuit, it wasn't clear whether the Justice Department was going to prosecute Trump – and although several state-specific groups had announced their intention to protest Trump's spot on their ballots, Castro stated: "I don't feel comfortable waiting that long."

Instead of challenging Trump after he launched his campaign, the attorney wanted to prevent him from being able to stand in the first place. It's not the first time he's attempted to do so: Castro filed a similar lawsuit at the end of 2022, but a judge dismissed the case and Castro is still appealing the decision. 

Castro vs Trump

But who is Castro? A few years after graduating from Georgetown University Law Center in Washington DC, Castro launched his own tax law firm, Castro & Co. According to his website: "In a span of only a few years, John Anthony goes from struggling under the pressure of mounting student loan debt to having a net worth in excess of $20 million." But he always had political as well as professional aspirations, announcing his own intention to run for the Republican nomination in December last year.

He's said: "I could spend the rest of my life building a business empire and even becoming a billionaire if I really set my mind to it, but that's not who I am. I've proven I can do it. But that's just not who I am. This is who I am. I was born to help people. I was born to serve my country. I was born to lead my country that I love so dearly." 

It's not clear what the status of Castro's lawsuit is, but he did unsuccessfully sue the Federal Election Commission after it rejected his request to have Trump's presidential candidacy denied. He's now fighting the former president on the campaign trail rather than the courtroom, according to Rawstory.

Trump vs Michael Cohen

On April 12, Donald Trump filed a lawsuit against his former attorney and fixer Michael Cohen (pictured), accusing him of making "improper, self-serving, and malicious statements about his former client, his family members, and his business." 

He also claimed that Cohen had violated a non-disclosure agreement (NDA) made as part of their attorney-client relationship: "This is an action arising from [Cohen’s] multiple breaches of fiduciary duty, unjust enrichment, conversion and breaches of contract by virtue of [Cohen's] past service as [Trump's] employee and attorney," the lawsuit alleges.

Trump vs Michael Cohen

Trump is seeking $500 million in damages, a figure that Cohen has publicly derided. In an interview with CNN, he said he was "not shocked, but [he] was surprised. It's part of the Trump playbook."

Referencing a character from the Austin Powers movie series, he went on: "I was wondering whether Donald at the time that he was coming up with $500 million thought he was like Dr. Evil, putting his finger up to his mouth, you know, trying to think about having fun at somebody else's expense."

Trump vs Michael Cohen

The ex-attorney also revealed that he's considering filing a countersuit against Trump, as he allegedly believes he never signed a Non-Disclosure Agreement (NDA). A GoFundMe page has been launched to collect donations to help Cohen fight his former boss in court. The fund recently passed the $260,000 mark, meaning it's surpassed its $250,000 goal.

Cohen's lawyers have asked for the lawsuit to be dismissed, filing a motion saying it is "yet another brazen and indeed unlawful attempt to intimidate and silence a key witness against Mr Trump." It's not clear whether Judge Darrin Gayles has responded to the motion yet, but in June he set a trial date of August 26, 2024, encouraging the former colleagues to reach an agreement before then.

Trump vs Michael Cohen

And now there are new developments in the case. It was recently revealed that Trump had been called to sit for his deposition on September 6, with Cohen's lawyers saying in a statement: "Mr Trump has put at issue significant matters relating to at least one of his pending criminal indictments. He will have to answer under oath, among other things, exactly what happened with the payments to Stephanie Clifford. Or he can assert his Fifth Amendment privilege against self-incrimination. Either way, his testimony will strip the lie as to his claims against Mr Cohen."

Stephanie Clifford is the real name of Stormy Daniels, the adult film star that Cohen allegedly paid $130,000 at the bidding of Donald Trump before the 2016 election.

Trump vs Michael Cohen

Donald Trump has responded to the call, with court filings showing he's seeking legal protection from having to make evidential documents public. Trump's lawyers have claimed that the evidence sought by Cohen's lawyers, including financial records from the Trump Organization, could "interfere with and/or relate to [other] pending criminal proceedings and the underlying facts that form the basis of such criminal proceedings." Attorney Alejandro Brito added: "The existence of the criminal proceedings currently ongoing against the Plaintiff establishes 'good cause' for the entry of the confidentiality order due to the risk of self-incrimination."

Unsurprisingly, Cohen is less than impressed. "If Donald was concerned that release of this information could or will cause him damage in the ongoing criminal investigations, he should have thought twice about bringing the lawsuit in the first place. You can't have it both ways."

Trump vs The Washington Post

The Washington Post has been slapped with a lawsuit from the company behind Donald Trump's social media platform Truth Social. The lawsuit, filed by Trump Media & Technology Group Corp (TMTG), alleges that the company was defamed by a Post article published in May.

According to the May 13 article, TMTG concealed information about a proposed merger from shareholders and the Securities and Exchange Commission. TMTG denies that this is the case and accuses the Post of “falsely insinuating that TMTG was involved in shady business dealings.”

Trump’s lawsuit seeks a staggering sum in damages: $3.78 billion. This figure is particularly surprising given how it dwarfs the value of Truth Social, which Forbes estimated to be about $1.2 billion in April.

Trump vs The Washington Post

This isn’t the first time that Trump has taken on The Washington Post. In March 2020, his 2020 presidential campaign sued the Post for "millions of dollars." The lawsuit focused on two articles that the American newspaper published in June 2019, both of which linked Trump’s 2016 election to foreign interference from Russia and North Korea. 

The opinion pieces were written by Washington Post writers Greg Sargent and Paul Waldman. Trump’s campaign described the articles as "false and defamatory," focusing on the following statements: Sargent's claim that Trump's 2016 campaign "tried to conspire" with Russia; and a line in Waldman's piece that reads "Who knows what sort of aid Russia and North Korea will give to the Trump campaign, now that he has invited them to offer their assistance?"

Trump vs The Washington Post

This year, Judge Rudolph Contreras (pictured) ruled that Trump's campaign had failed to meet legal standards for defamation.

According to Contreras, Trump's team weren't able to show that Sargent acted with "actual malice" when writing his article, which concerned the report of Special Counsel Robert Mueller’s investigation into Russian interference in the 2016 US election. Meanwhile, Contreras ruled that Waldman's op-ed article was protected by the First Amendment of the US Constitution. 

So will the judge think Donald Trump's new defamation case has more merit than the last? Watch this space. 

Trump vs Woodward

Earlier this year Trump launched a lawsuit against journalist Bob Woodward (pictured).

Famed for breaking the Watergate scandal in the 1970s, Woodward has since become a vocal critic of the 45th president, writing a trio of books based on 20 interviews he conducted with Trump from 2016 to 2020. The lawsuit concerns the publication of these interviews in the form of an audiobook, The Trump Tapes, which was released by Simon & Schuster last year. 

Trump vs Woodward

Trump and his legal team are seeking almost $50 million in damages, claiming they calculated the sum based on the retail price of the audiobook ($24.99) and sales figures from Woodward's previous Trump-related releases: Fear, published in 2018; Rage, published in 2020; and Peril, published in 2021. The lawsuit claims that Woodward sold around two million copies of Fear and they expect The Trump Tapes to sell a similar number of copies.

The lawsuit also suggests that Rage wasn't as commercially successful as Woodward hoped, prompting him to release the tapes. "Faced with the reality that Rage was a complete and total failure, Woodward decided to exploit, usurp and capitalize upon President Trump's voice."

Trump vs Woodward

Trump's lawsuit, which was filed on January 30 in Florida, claims he never gave his consent for the recordings to be released. Accusing Woodward of "systematic usurpation, manipulation and exploitation of audio of President Trump," the suit names Woodward, Simon & Schuster, and the publisher's parent company Paramount Global as defendants.

Woodward responded to the claims on CNN, saying: "Well, they were done voluntarily, it was all on the record. I had used some of it before. So he's president and... so he's out there. And this is out there to the tenth power." Meanwhile, various lawyers told CNN the suit "has no legal merit whatsoever." 

Trump vs Woodward

Fighting back against Woodward's claim that Trump was speaking in his capacity as POTUS, which means he can't copyright the interviews, lawyers for Trump have said he was actually acting in a "personal" capacity. "The government works preclusion cannot be dispositive of President Trump's rights with respect to [the interviews] because these works are personal records, not presidential records."

Meanwhile, Woodward hasn't shied away from commenting on Trump's other legal issues, saying he's "never seen anything like" the 45th's handling of classified documents. "It really shows that Donald Trump is an alarming, dangerous threat to national security... If there's something to not joke about, this is it. Look, I've spent 50 years reporting on national security and I've never seen anything like this from anyone."

Publishers Weekly previously reported that Woodward's team filed two motions to have the lawsuit dismissed. Now, Woodward, his publisher Simon & Schuster, and the publisher's parent Paramount Global have reportedly filed a motion to dismiss Trump's lawsuit in a Manhattan federal court.

Now take a look at Donald Trump's worst business decisions