Trump's 'Extremely Bad Luck' Could Doom Lawsuit Against His Biggest Enemy

Former President Donald Trump has been dealt another tough hand that could mar his chances of winning a lawsuit against one of his biggest rivals, New York Attorney General Letitia James.

Two weeks ago, Trump's attorneys filed suit in Florida state court, seeking to block James' own civil case in New York against the former president and the Trump Organization. But this week, the case was moved to Florida's federal courts at James' request and the suit fell before Judge Donald Middlebrooks—a Clinton-appointed judge who just fined Trump's lawyers in a different suit days ago.

Politico's senior legal affairs reporter Kyle Cheney called the latest developments, "extremely bad luck for Trump."

Just last week, Middlebrooks sanctioned a group of the former president's lawyers for a "frivolous" lawsuit against Democrat Hillary Clinton and dozens of other political enemies.

The $55,000 fines were ordered several weeks after the same judge threw out the case as a "deliberate use of the judicial system to pursue a political agenda." Trump's lawyers have said they plan to appeal the sanctions.

In a scathing 19-page ruling last Thursday, Middlebrooks accused Trump of abusing the legal system, writing that, "Every claim was frivolous, most barred by settled, well-established existing law."

He sent a warning to Trump's team that the courts are "not intended for performative litigation for purposes of fundraising and political statements" and that such an abuse "is harmful to the rule of law, portrays judges as partisans, and diverts resources that should be directed to real harms and legitimate legal claims."

Middlebrooks' statement made clear the judge is unlikely to tolerate any lawsuits that could be perceived as politically motivated, which is how Trump's counter-lawsuit could be read.

Now, that same judge is set to preside over the Florida case, where Trump is suing James for "intimidation and harassment" over her $250 million lawsuit and accusing the attorney general of trespassing on his right to privacy in Florida.

Speaking to Newsweek, former federal prosecutor and former elected state attorney Michael McAuliffe called Middlebrooks a "very experienced" federal district judge with a history of rulings that require all litigants, even those who aren't a former president, to "properly plead causes of action."

"If the new case isn't properly pled and isn't grounded with a viable cause of action, the court will dismiss it," McAuliffe said. "Trump is having to confront that reality over and over."

Some of Trump's own legal advisers had questioned the merit of the suit even before it was filed.

Earlier this month, The New York Times reported that Alan Garten, general counsel for the Trump Organization, blamed attorney Boris Epshteyn for the filing in Florida after being unsuccessful in intervening before it was submitted. Trump's New York legal team also reportedly objected to the filing over concerns that the lawsuit in Florida could undermine their defense in the New York case. Nonetheless, the suit was filed.

Newsweek reached out to Trump for comment.

Update 11/17/22, 12:41 p.m. ET: This story was updated with comments from Michael McAuliffe.