
President Donald Trump's luck in the courtroom may be starting to run out, according to a former federal prosecutor.
Glenn Kirschner, MSNBC legal analyst and the host of the "Justice Matters" podcast, created a short podcast episode about Trump's attempts to find a friendly judge for his lawsuit against the Wall Street Journal. He sued the outlet last week for $20 billion for defamation over the recent report about a "bawdy" letter that Trump sent to Epstein for his 50th birthday.
Trump filed the lawsuit against the Wall Street Journal in southern Florida, where one of his favorite judges happens to sit on the bench. Trump previously won a lawsuit over his handling of classified documents in southern Florida, a case that was argued before Judge Aileen Cannon.
Instead of having Cannon assigned to the case, Trump's lawsuit was handed to Judge Darrin Gayles.
Gayles was appointed to the bench in southern Florida in 2013 by former President Barack Obama. He previously presided over a lawsuit Trump filed against his former lawyer, Michael Cohen. Trump sought to collect $500 million from Cohen over claims that Cohen violated his attorney-client privilege. After six months, Trump abandoned the lawsuit.
"Who that judge is tends to suggest that karma is alive and well," Kirschner said.
This isn't the first time that Trump has sought to influence legal proceedings against him. For instance, he signed executive orders targeting multiple big-name law firms, some of whom hired lawyers who worked on Robert Mueller's investigation into the 2016 election.
"Judge Gayles has seen the Trump show before, in court, up close and personal," Kirschner added. "Bring a frivolous lawsuit, and then right before you are going to be deposed, right when you are going to have to answer questions under oath, when you are going to have to put up or shut up, you give up."