A lawsuit filed by former President Donald Trump against New York Attorney General Letitia James is off to a rough start after the case landed in front of the same judge who sanctioned his attorneys for “frivolous claims” last week.
Two weeks ago, Trump countersued James for “intimidation and harassment” after her office brought a $250 million civil lawsuit against the Trump Organization in September, accusing it of manipulating its asset valuations.
Trump’s attorneys filed the lawsuit in Florida state court, though James moved the case to federal court on Wednesday and landed in front of Judge Donald Middlebrooks, the same judge who hit several of his lawyers with $66,000 in fees for “reckless and factually untrue statements.”
TRUMP LAWYERS FACE $66,000 IN FINES OVER TOSSED RUSSIAGATE SUIT
Extremely bad luck for Trump. He filed a lawsuit against NYAG Letitia James in Florida state court. James yesterday removed the case to federal court and it landed before … Judge Donald Middlebrooks, who just days ago sanctioned Trump attorneys for a frivolous lawsuit. pic.twitter.com/5mAOesdgjk
— Kyle Cheney (@kyledcheney) November 17, 2022
The case that drew sanctions from Middlebrooks, an appointee of then-President Bill Clinton, alleged that Hillary Clinton and a slew of Democrats peddled false Russia collusion allegations against Trump. The judge said Trump’s attorney, Alina Habba, and several associates participated in clogging the courts and undermined the rule of law “by the toxic combination of political fundraising with legal fees paid by political action committees.”
In his fiery 19-page ruling, Middlebrooks warned Trump’s legal team the courts are “not intended for performative litigation for purposes of fundraising and political statements” and that such abuses are “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’ ruling sent a message to the Trump legal orbit to tread with caution on future cases.
Prior to Trump’s countersuit filing against James, several of his long-standing legal advisers opposed the filing in Florida state court and even attempted to intervene just hours before it was submitted, according to the New York Times.
The outlet reported earlier this month that Alan Garten, general counsel for the Trump Organization, blamed lawyer Boris Epshteyn for the filing in Florida after being unsuccessful at intervening before the filing was submitted.
Trump’s New York-based legal team was also reportedly fraught over the decision to file the countersuit in Florida, expressing concerns it could undermine their defense in the Empire State civil case.
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The former president has tirelessly gone after James at various rallies and public speaking events and has even dubbed her “Peekaboo James,” adding her to his list of nicknames for his political enemies similar to “Sleepy” Joe Biden or “Crazy” Nancy Pelosi. Like many of Trump’s concocted nicknames such as “Old Crow” Mitch McConnell, it’s not clear the genesis for James as “Peekaboo.”
Trump railed against the New York State Court System and James in a post on his Truth Social platform earlier this month, calling her a “Corrupt, Racist, Weak on Crime Attorney General.”

