President Donald Trump’s bid to take down the Wall Street Journal over its coverage of his connection to Jeffrey Epstein has landed in the courtroom of Darrin Gayles, who is likely experiencing deja vu.
That’s because Gayles, a 2014 appointee of Barack Obama, had another brush with a litigious Trump in 2023, when the then-former president sought to punish his onetime lawyer and fixer Michael Cohen.
Trump sued Cohen in April 2023 seeking a $500 million payout for claims that Cohen violated his attorney-client relationship with Trump and enriched himself off their relationship. Six months later, Trumpabandoned the lawsuit, just before Cohen’s lawyers were set to question him under oath.
Trump’s new lawsuit against The Wall Street Journal and owner Rupert Murdoch seeks an even more audacious sum: $20 billion. Trump says the newspaper defamed him by reporting last week that Trump may have sent Epstein a suggestive birthday card more than two decades ago. Trump filed the lawsuit on Friday, and Gayles was assigned to preside over the case on Monday.
But as with the Cohen case, there’s an open question of whether Trump’s new lawsuit is more of a political stunt than a serious attempt to litigate the issue. If Trump pursues the case, he would open himself up to answering questions under oath about his connection to the disgraced financier who killed himself in 2019 while awaiting trial on sex trafficking charges.
Trump’s decision to file the case in southern Florida led to suspicions he was hoping to draw U.S. District Judge Aileen Cannon, his own appointee who helped him escape criminal charges brought by special counsel Jack Smith. But Trump’s attorney Alejandro Brito — the same lawyer who led the ill-fated Cohen suit — filed the case in the Miami division of the federal judicial district of south Florida. Cannon sits in the Fort Pierce district, making it unlikely she would have been selected under the court’s assignment process.
Gayles, a George Washington University law graduate who made history as the first openly gay Black man appointed to the federal bench, was confirmed unanimously by the Senate. One reason: His judicial background tilts bipartisan. He was appointed to state-court judgeships in Florida by two Republican governors, Jeb Bush and Charlie Crist, before Obama nominated him to his current role.
His prominent cases include a $73 million judgment against the Venezuelan government in 2022 over a purported murder-for-hire scheme. Gayles ordered a new trialin a $25 million fraud scheme in Florida after finding that the Justice Department had committed misconduct and then lied to him about it. And Gayles notably sat with the 11th Circuit Court of Appeals on a voting rights case, writing a dissent that found evidence of discrimination behind an Alabama voter ID law.
Speaking at an American Bar Association conference in March, Gayles lamented the decline in public confidence in the judiciary. He gave a few reasons for that decline, including the Supreme Court’s frequent reliance on its “shadow docket” to issue short-form emergency rulings. He also blamed the practice of litigants strategically filing lawsuits in certain districts in hopes of drawing favorable judges willing to issue nationwide injunctions. And he lamented expectations that judges will rule based on the president who appointed them.
“We all have to do better and push back. We are independent, we make decisions on the facts and the law,” he said.
Gayles also denounced attacks on the judiciary that go beyond mere criticism and put people in danger. “We’re not infallible. Sometimes we get it wrong because we deal with a lot of very difficult, complicated issues,” he said. “It’s the nature of the criticism. If it’s done in a way that subjects us to harm, that’s problematic.”
After Obama nominated him in 2014, Gayles explained his judicial philosophy and experience in a 48-page Senate Judiciary Committee questionnaire. He described presiding over hundreds of criminal trials as a state judge in Florida.
Responding to a question about his philosophy on recusal, he said he closely follows long-established ethical procedures but pointed out one memorable example: when a lawyer asked him to recuse from a case because he was Facebook friends with one of the other attorneys.
“After verifying that the attorney and I were Facebook ‘friends,’ I granted the motion,” Gayles noted. “I also ‘defriended.’”
Gayles does not appear to have handled any substantial media-related cases, though he did note in his questionnaire that an article about him in 2008 “contains several misstatements, inaccuracies, and grammatical errors” and that his “immediate written request for corrections” went ignored.
Erica Orden contributed to this report.
