By Don Terry | Wednesday, September 10, 2025 | 6 min read
It looks like Donald Trump’s latest legal gamble has backfired in spectacular fashion. What was supposed to be a carefully calculated move to stack the deck in his favor has instead landed him in front of a judge who is perhaps the last person he wanted overseeing his case. For someone who has made a career out of bending the legal system to his advantage, this feels like instant karma.
Late last Friday, Trump filed a massive lawsuit against the Wall Street Journal, Rupert Murdoch, and News Corporation. Reports vary on the amount he’s seeking—some place the damages at $10 billion, while others suggest as high as $20 billion—but regardless of the number, this is one of the most ambitious legal moves he has made in recent years. The lawsuit stems from claims of defamation, something Trump has long used as both a shield and a sword when facing unflattering coverage.
But the details of where and how he filed are telling. Trump didn’t choose Montana, where Murdoch has a residence. He didn’t go to New York, where both the Wall Street Journal and News Corp are headquartered. He didn’t even file in Washington, D.C., the city he officially calls home. Instead, he went to the Southern District of Florida, the same jurisdiction that has become his go-to legal playground.
This wasn’t a random decision. Trump has long been accused of “forum shopping”—essentially picking courts he believes will give him a friendly judge or favorable conditions. In this case, he appeared to be angling to land Judge Aileen Cannon, a Trump-appointed judge who has previously handed him controversial wins, including rulings related to the classified documents investigation. For Trump, Cannon represented something of a legal safety net.
But this time, the net didn’t catch him. Instead of Cannon, the case was assigned to Judge Darren Gayles, an Obama appointee who has been on the federal bench for more than a decade. And for Trump, that assignment may be the worst-case scenario.
Judge Gayles has already dealt with Trump once before. He presided over Trump’s failed $500 million lawsuit against Michael Cohen, Trump’s former attorney turned outspoken critic. In that case, Gayles ordered Trump to sit for a deposition. Within days, Trump abruptly dropped the lawsuit rather than risk being questioned under oath. That episode alone highlights how dangerous Gayles could be for Trump—he’s not a judge who entertains frivolous filings or allows litigants to use the courts as a stage for political theater.
Legal analyst and former prosecutor Glenn Kirschner didn’t mince words when discussing the situation. He pointed out that Gayles has already seen “the Trump show” play out in his courtroom: file a lawsuit, puff up the claims, and then abandon ship the moment real accountability looms. According to Kirschner, Trump may have finally run headfirst into a wall he can’t dodge.
To make matters worse, Trump’s filing may already be fatally flawed under Florida law. State rules require that anyone pursuing a defamation case provide the defendant with at least five days’ notice before filing. Trump didn’t bother. Instead, he rushed to file the lawsuit just 24 hours after the article in question was published. By the letter of the law, that mistake could result in an automatic dismissal. And Judge Gayles is exactly the type of judge who would enforce that rule to the letter.
If Gayles does dismiss the case, Trump walks away empty-handed and publicly embarrassed. If, for some reason, the case moves forward, Trump could find himself in an even worse position—being forced into a deposition where he would have to answer uncomfortable questions under oath. Observers have already noted that such questioning could open the door to sensitive topics, including Trump’s long-rumored ties to Jeffrey Epstein. In other words, every possible path forward is fraught with danger.
Adding to Trump’s woes, Rupert Murdoch himself seems ready for a fight. While many media outlets have chosen to settle or back down in the face of Trump’s legal threats, Murdoch reportedly has no intention of caving. On the contrary, insiders suggest he’s itching for the chance to take Trump on in court and, if given the opportunity, humiliate him publicly.
That sets up a potentially explosive showdown: a former president known for his relentless litigation tactics squaring off against one of the most powerful media moguls in the world, all under the watchful eye of a judge who has no patience for games.
Trump had hoped to find a sympathetic ear in Judge Cannon. Instead, he ended up with Darren Gayles, a judge who has already forced him to retreat once before. And because of that twist of fate, Trump’s odds of coming out of this case unscathed have dropped to nearly zero. For a man who prides himself on always winning, this time it looks like karma may have finally caught up.
