Well before his oh-so-illustrious political career resulted in a truly breathtaking number of criminal charges, Donald Trump was no stranger to a courtroom. By the time he became the Republican nominee in 2016, Trump and his businesses had been involved in over 4,000 lawsuits. His litigious streak has continued, leading to a second term where Trump is actively litigating multiple cases. Here’s a rundown of some of the big lawsuits that Trump, the private citizen, is pursuing while also still being president.
So mad about the media
Trump has not yet sued CNN or The New York Times over their coverage of Iran. He did, however, have his personal lawyer send them letters threatening to sue, which is an absolutely unhinged thing to do, and a deliberate blurring of the lines between his role as president and his role as a private citizen.
Late Tuesday night, Paramount, the parent company of CBS, announced it would pay Trump $16 million to settle his whiny lawsuit where he alleged the network had deceptively edited an interview with former Vice President Kamala Harris.
That’s almost the same amount Disney paid in December 2024 to settle Trump’s baseless defamation lawsuit against ABC. To make things look slightly less like a straight-up bribe, these millions belong to Trump’s eventual presidential library rather than Trump personally. Nope, still looks like a bribe.
Trump also still has a lawsuit against Iowa pollster Ann Selzer and the Des Moines Register over her poll that predicted Harris would win Iowa. Well, he has two of them now, actually. Trump initially filed his suit in Iowa state court, but Gannett, the parent company of the Register, removed the case to federal court.
In June, Trump tried to get the case back in state court, but the federal judge denied the request. So Trump decided to voluntarily dismiss his federal case and refile in state court. That didn’t really work out either.
The judge in the federal case, U.S. District Judge Rebecca Goodgame Ebinger, struck Trump’s voluntary dismissal from the record, saying that because Trump had earlier filed a notice of appeal to the Eighth Circuit, that court now has jurisdiction over certain aspects of the case. Were Ebinger to grant the voluntary dismissal of the district court case, she would functionally be dismissing Trump’s appeal as well, which the district court doesn’t have the power to do. So, Trump needs to voluntarily dismiss his federal appeal first.
Yes, this is wonky procedural stuff, but that’s what lawyers are for. Unfortunately, in this instance, it appears that Trump’s personal attorneys aren’t super-sharp about basic court rules. But rest assured—their client seems to have all the time and money in the world to keep pursuing this in whatever court will take it.
So mad about the money he owes
During his time away from the presidency, Trump lost not one, but two cases to E. Jean Carroll. In May 2023, a jury found him liable for sexually abusing Carroll when he assaulted her in a department store dressing room in the 1990s and awarded Carroll $5 million. Then, in January 2024, a jury awarded Carroll $83.3 million in a separate case over Trump’s defamation of her, following the May 2023 verdict. He’s still battling to make both of those go away.
The full Second Circuit Court of Appeals just declined to reconsider the $5 million verdict, which likely means the next stop is the friendly confines of the United States Supreme Court. And if you’re wondering if Trump will try to argue that he is somehow immune from this civil lawsuit about a sexual assault he committed 20 years before becoming president? Absolutely. How can we be sure? Because that’s basically the argument he just made to the Second Circuit in his attempt to overturn the $83 million verdict.
During oral arguments last month, Trump’s personal attorney said that the verdict against Trump “severely damages the presidency” and that “President Trump was denied the protection of presidential immunity” when the trial judge let Carroll’s case proceed. It seems incredibly self-evident that Trump’s presidential immunity does not reach back in time to protect him from the consequences of his actions decades ago. Then again, no one could have expected the Supreme Court to make up that immunity doctrine out of whole cloth. Expect this one to go all the way up as well, and brace yourself for the possibility of a really, really stupid outcome.
So mad about his criminal conviction
Winning the 2024 election freed Trump from the dozens of federal criminal charges he faced, but it couldn’t undo his conviction in New York state on 34 felony counts over his falsification of business records to hide his payoff to Stormy Daniels during the 2016 election. He’s continuing to appeal that in the state courts, but he’s also begging the Second Circuit to let him move the criminal case to federal court.
It should be in federal court, per Trump, because, you guessed it, he believes his presidential immunity covers his criminal acts before becoming president. It should also be in federal court, Trump’s lawyers told the Second Circuit, because the scope of his immunity should be decided “by this court and the Supreme Court, not by New York State courts.”
In other words, the goal, as ever, is to get in front of a Supreme Court that has proven remarkably receptive to letting Trump off the hook.
So mad about Russia, still?
This case, where Trump sued the Pulitzer Prize Board for defaming him, has flown under the radar for a while, but it’s heating up now in ways that highlight exactly how bad it is that the sitting president is also a private litigant.
But first: How did the board defame him, exactly? By refusing to retract awards to the Washington Post and The New York Times for their coverage of Russian interference in the 2016 election. Trump demanded the awards be retracted, and the Pulitzer Board indulged him far more than they should have, conducting an independent review of all the stories. The board concluded that nothing in the award-winning stories had been discredited and declined to retract the awards, and Trump says that defames him.
This is a ridiculous case, and it should have been dismissed out of hand. But Trump drew an exceedingly friendly three-judge panel in Florida state court that ruled, in February 2025, that he could proceed. How friendly, exactly? Peep the concurrence by Judge Ed Artau, which kicks off by quoting some of Trump’s favorite phrases and glowingly recaps Trump’s complaint.
That concurrence served as a nice little sizzle reel for Artau, who Trump rewarded two months later with a nomination to the federal bench. And, as Jay Willis points out over at Balls and Strikes, Artau may have known he was under consideration when he wrote that suck-up concurrence.
This is a not-great collision between Trump’s role as president and his role as private litigant. He’s able to reward judges who rule in his favor in private matters with a reward that he can only extend because of his role as president.
It gets worse, actually. The Pulitzer Board has been attempting to put this case on hold until Trump is no longer president, given the complexities of litigating against the sitting president and the potential conflict between a state court’s exercise of judicial power and the president’s federal Article II powers. The board pointed out that Trump has argued in other civil cases that litigation would interfere with his duties as president, warranting a stay until the end of his term.
Nope, said that friendly appeals panel in May. Only Trump can invoke the privilege of saying he’s too busy being president to participate in litigation. That appellate panel went even farther, saying that if Trump sues someone, that’s cool because he is “uniquely equipped to determine how to use his time, to assess the attention a lawsuit will require, and to decide whether the lawsuit will divert him from his official business.”
But if someone sues Trump, he gets to decide if that’s too onerous. Needless to say, the Pulitzer Board is appealing this nonsense up to the state Supreme Court.
So mad at his former business partners
Because the president now runs private for-profit companies while also being president, said president now gets hauled into court over private business disputes. Also, because said president is a grifter with no loyalty, he gets hauled into court because his business associates allege that he screwed them over.
Two cofounders of Truth Social, Trump’s low-energy social media platform, sued Trump in 2024, alleging he tried to dilute their stake in the company and ice them out of the initial public offering. When the case was before the Delaware Chancery Court in May 2025, Trump argued the suit should be dismissed or stayed until the end of his term, as he is immune from civil suits while in office.
Yes, it’s exactly what the Pulitzer Board was referring to. When Trump is sued, he is the president, and you cannot take the president away from his important duties with lawsuits. When Trump sues people, he is a private individual who also happens to be president, and has assessed whether he has the time to drag parties into endless litigation.
It’s a double standard that exists only for Trump, another way that he is above the law. Heads, Trump wins. Tails, we all lose.
Campaign Action
