A Florida-based federal judge called Donald Trump’s latest 85-page lawsuit against the New York Times a confusing “rage against an adversary” and returned it to Trump’s legal team. The judge demanded Trump’s attorneys rework his complaint into something clearer and more concise, cutting more than half the length down to no more than 40 pages. Just recently, Trump has been targeting media companies that have been giving him unfavorable coverage. Reportedly, when Paramount was trying to secure a sale to David Ellison — one of the things they had to do was secure a greenlight from the Trump administration. A considerable number of media experts believe Trump used that situation to secure a settlement for his CBS lawsuit. And when Stephen Colbert called it a bribe — his CBS show was conveniently canceled a few days later. A situation that echoes that very theme of Trump targeting the media and going after people who criticize him directly played out with Jimmy Kimmel recently. Trump was asked about how he was holding up after Charlie Kirk’s murder — Trump said he was fine because he was actually focused on building a ballroom. Kimmel made fun of that, and his show was flagged by the FCC and he was placed on indefinite leave until he donates money to Kirk’s family, among other demands. All of this was followed by a renewed and reinvigorated Trump going after his adversaries in the media — so his attorneys submitted an 85-page lawsuit against the New York Times asking for $15 billion. Before the case even hit the court, the POTUS was busy flexing his prowess and bragging that NYT was headed for the same fate that had befallen his other adversaries. You’d think that for a lawsuit that extensive, and an amount that astronomical, Trump must have such a strong case — but according to U.S. District Judge Steven Merryday, the filing was rather weak. Per Politico, the judge said, “A complaint is not a megaphone for public relations or a podium for a passionate oration at a political rally, or the functional equivalent of the Hyde Park Speakers’ Corner.” Trump’s legal team released a statement saying they plan on refiling in accordance with the judge’s logistics. The original lawsuit, however, did not inspire most people online to see where Trump was coming from. When he first announced the lawsuit, it was simply understood online as the president going after the New York Times because he believes they endorsed Kamala Harris instead of him in the 2024 elections. Grandpa Don is now suing the New York Times for $15B simply because they endorsed Kamala Harris and they have always told the truth about him.This is what dictatorship looks like. pic.twitter.com/n5w2uS4tkH— Ron Smith (@Ronxyz00) September 16, 2025 On X, people didn’t miss the chance to ridicule Trump on this decision by the judge. One user said that the judge was calling Trump’s filing “essentially, garbage.” Another user said with authority that this was a warning shot by the judge, but he also added, “The bigger story here is the pattern, as Trump continues using lawsuits not to win, but to intimidate dissent.” Which, hopefully, is the lesson carried by those in the media. He’s hardly winning. When a judge calls your complaint garbage and gives you 28 days to fix it, that’s not a victory, but a warning shot. But the bigger story here is the pattern, as Trump continues using lawsuits not to win, but to intimidate dissent. It’s legally flimsy,…— Evaristus Odinikaeze (@odinikaeze) September 19, 2025 Trump has shown all the centrists who convinced themselves he was a moderate option that he’s not afraid to dip his toes into authoritarian waters. Media and entertainment once brimmed with people who wore their principles on their sleeves. Perhaps Trump — while often out of control — presents them with a challenge to finally stand up for what they believe in. Because if they choose to placate themselves, Trump will certainly take full advantage.