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Obama-appointed Florida judge to preside over Trump’s $10B suit against Murdoch and WSJ

Former prosecutor Darrin P. Gayles was unanimously confirmed to the bench by the Senate in 2014

Alex Woodward
in New York
Monday 21 July 2025 12:19 EDT
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The federal judge randomly assigned to oversee Donald Trump’s $10 billion lawsuit against The Wall Street Journal is a former federal prosecutor appointed to the bench by Barack Obama.

Judge Darrin P. Gayles with the Southern District of Florida is a former U.S. attorney who was appointed by the former president in 2014. He was unanimously confirmed in the Senate by a vote of 98-0.

The Howard University and George Washington University School of Law graduate became the first openly gay Black man to serve on the federal bench.

Trump’s lawsuit filed in federal court in Miami on July 18 accuses the newspaper, its parent companies, executives and journalists of falsely accusing the president of writing a 50th birthday card to convicted sex offender Jeffrey Epstein in 2003.

The lawsuit names right-wing media mogul Rupert Murdoch and his News Corp, WSJ publisher Dow Jones, executive Robert Thomson, and two WSJ journalists whose bylines appeared on the story.

Obama-appointed federal judge Darrin P. Gayles was randomly drawn to oversee the president’s lawsuit against The Wall Street Journal over its claims that he wrote a sexually suggestive birthday greeting to Jeffrey Epstein in 2003
Obama-appointed federal judge Darrin P. Gayles was randomly drawn to oversee the president’s lawsuit against The Wall Street Journal over its claims that he wrote a sexually suggestive birthday greeting to Jeffrey Epstein in 2003 (Getty Images/U.S. Senate Judiciary Committee)

The birthday greeting is described by the newspaper as including a sexually suggestive drawing and a birthday wish that says “may every day be another wonderful secret.”

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,” according to the lawsuit.

“The reason for those failures is because no authentic letter or drawing exists,” the complaint claims.

Trump’s 18-page complaint accuses the WSJ and its reporters of “concocting” a story in an effort to “malign President Trump’s character and integrity and deceptively portray him in a false light.”

Judge Gayles’s appointment to the case, which is by random drawing, followed the president’s Truth Social post of an AI-generated video showing Obama being arrested inside the Oval Office as Trump smiles and laughs next to him.

Trump and top administration officials have repeatedly accused Obama of conspiring against Trump’s 2016 campaign in an apparent effort to redirect coverage in the wake of the WSJ’s reporting and increased scrutiny of Trump’s relationship with Epstein.

The Trump administration is desperate to change the subject as he faces intense scrutiny over his relationship with Epstein
The Trump administration is desperate to change the subject as he faces intense scrutiny over his relationship with Epstein (AFP via Getty Images)

The president has posted about Obama roughly 20 times on Truth Social since filing the lawsuit, including the fake video of Obama’s arrest and another fake image of Obama and former administration officials in orange prison jumpsuits.

Trump’s national intelligence director Tulsi Gabbard has accused the Obama administration of committing “treasonous conspiracy” in her office’s attempt to undermine an eight-year-old assessment that Russia favored Trump’s election in 2016.

Multiple intelligence findings, including a Republican-led Senate report, have backed up claims that Russia sought to influence the election by damaging Trump’s then-opponent Hillary Clinton while boosting Trump.

In an apparent attempt to discredit those reports, Gabbard’s report states that “foreign adversaries did not use cyberattacks on election infrastructure” to alter election outcomes. But intelligence reports have long held that Russian hackers did not manipulate votes; Gabbard’s report instead falsely conflates cyber attacks with a broader influence campaign as she tries to argue that the Obama administration pressured the intelligence community to change its conclusions.

Top Democrats on congressional intelligence committees have blasted Gabbard’s report as baseless and an attempt to weaponize intelligence to bolster Trump’s bogus election conspiracy theories.

The district in which Trump filed the lawsuit is also the same as that of Judge Aileen Cannon, who Trump appointed to the bench and has since repeatedly praised.

Cannon presided over — and eventually dismissed — the blockbuster federal indictment accusing the president of hoarding government documents and classified materials at his Mar-a-Lago compound after leaving office in 2021, and then obstructing law enforcement’s attempts to get them back.

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