President Donald Trump filed a $10 billion lawsuit against The Wall Street Journal last week —hoping, it seems, for a favorable draw in a familiar courtroom. He filed the suit in the same district where Judge Aileen Cannon — whom he appointed — had previously dismissed a separate case accusing him of hoarding classified documents at Mar-a-Lago and obstructing efforts to recover them. He’s openly praised Cannon for her rulings.
But this time, he didn’t get Cannon. Instead, the case landed with Judge Darrin P. Gayles, a federal judge appointed by Barack Obama in 2014. Gayles, a former U.S. prosecutor, was confirmed unanimously by the Senate and made history as the first openly gay Black man to serve on the federal bench.
Trump’s lawsuit, filed in Miami on July 18, targets The Wall Street Journal, its parent companies, executives, and journalists over a report claiming he once sent a 50th birthday letter to convicted sex offender Jeffrey Epstein.
The suit names media mogul Rupert Murdoch, News Corp, WSJ publisher Dow Jones, executive Robert Thomson, and two reporters. According to Trump’s legal team, the article falsely accused him of having written the letter, but failed to include any evidence.
“The defendants failed to attach the letter, failed to attach the alleged drawing, failed to show proof that President Trump authored or signed any such letter, and failed to explain how this purported letter was obtained,” the complaint says.
“The reason for those failures is because no authentic letter or drawing exists,” it continues.
The lawsuit calls the story “concocted” and claims it was designed to “malign President Trump’s character and integrity and deceptively portray him in a false light.”
The judge’s assignment came just days after Trump posted a bizarre AI-generated video to Truth Social depicting Obama being arrested in the Oval Office, with Trump watching and laughing in the background. Since filing the lawsuit, Trump has posted about Obama around 20 times, including fake images of the former president and his ex-officials in prison jumpsuits.
Trump and his allies have long accused Obama of working behind the scenes to sabotage his 2016 campaign. Trump’s Director of National Intelligence, Tulsi Gabbard, recently released a report accusing the Obama administration of a “treasonous conspiracy” to pressure the intelligence community into blaming Russia for election interference.
But multiple bipartisan findings—including a Senate report led by Republicans—concluded that Russia did interfere in the 2016 election to hurt Hillary Clinton and help Trump. Intelligence reports have consistently said no votes were changed, but Gabbard’s report misrepresents those findings, falsely claiming there were no cyberattacks and attempting to downplay the broader influence campaign.
Top Democrats on congressional intelligence panels have slammed Gabbard’s claims as “baseless” and say she’s twisting classified findings to support Trump’s discredited election conspiracies.
Now, it’s up to Judge Gayles—an Obama appointee, not a Trump loyalist—to decide whether Trump’s $10 billion lawsuit over the alleged Epstein letter will move forward.
Trump filed the lawsuit in the same district where Judge Aileen Cannon — whom he appointed — had previously dismissed a separate case accusing him of hoarding classified documents at Mar-a-Lago and obstructing efforts to recover them. He’s openly praised Cannon for her rulings.
But this time, he didn’t draw Cannon. Instead, it’s Judge Darrin Gayles — appointed by Obama — who will decide whether Trump’s $10 billion battle with The Wall Street Journal moves forward.
