President Trump’s $20 billion defamation lawsuit against the Wall Street Journal and its owner, Rupert Murdoch, has been assigned to a federal judge, Darrin Gayles, who made history as the first openly gay Black man appointed to the federal judiciary.

It won’t be the judge’s first interaction with Mr. Trump’s legal endeavors. Judge Gayles, a 2014 appointee of President Obama, presided over another lawsuit filed by Mr. Trump in 2023. At the time, Mr. Trump sought $500 million in damages from his former lawyer, Michael Cohen, accusing Cohen of violating attorney-client confidentiality and allegedly profiting off their relationship. 

Mr. Trump ultimately dropped that lawsuit shortly before Cohen’s lawyers were scheduled to question the president under oath.

Now, Judge Gayles is set to oversee Mr. Trump’s latest lawsuit, which alleges that the Journal defamed him by claiming he sent a convicted sex offender, Jeffrey Epstein, a provocative birthday card 22 years ago.

Mr. Trump filed the lawsuit in southern Florida, with some observers suggesting the president hoped to be assigned to U.S. District Judge Aileen Cannon, one of his own judicial appointees. However, due to geographic jurisdictional rules, the case was assigned to Judge Gayles, who sits at Miami. 

The lawsuit brings high stakes as Mr. Trump would face scrutiny of his alleged ties to Epstein. Should the case proceed, Mr. Trump may be required to testify under oath about details of his connections to the convicted pedophile, who died by suicide in 2019 while facing sex-trafficking charges. 

Before the Journal published the story, Vice President Vance flew to Montana, where he spoke to Mr. Murdoch, according to the Associated Press. Others in the meeting included his son, Lachlan Murdoch, the head of Fox News and News Corporation, and other Fox News executives.

After the Journal ran the story, Mr. Trump said he warned the newspaper and Mr. Murdoch that the Epstein birthday letter “was a FAKE and, if they print it, they will be sued,” calling the report “defamatory lies.”

The Journal shot back. “We have full confidence in the rigor and accuracy of our reporting, and will vigorously defend against any lawsuit,” a representative of Dow Jones, publisher of the paper, said.