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The legal strategy being deployed by Trump attorney Alina Habba in hopes of overturning the $83.3 million verdict could backfire and end up costing her and her client more money than already owed, an attorney has claimed.
Habba made a last-ditch attempt to overturn the verdict in the defamation trial brought by columnist E. Jean Carroll on Monday, asking the judge in the case to respond to allegations of a possible conflict of interest between him and Carroll's lead counsel. In a letter to Judge Lewis Kaplan, Habba argued that the alleged mentor-mentee relationship between the judge and attorney Roberta Kaplan, no relation, may justify a new trial on liability and damages in the case.

But while Habba sought to toss the case entirely or at least reduce the amount that former president Donald Trump owes the columnist for defaming her, Carroll's attorney cautioned that such a tactic could drive up the multi-million-dollar number that Trump's defense team is already up against.
In a Tuesday letter addressing Habba's accusations, Roberta Kaplan threatened to pursue sanctions against Trump and his legal team, arguing that the defense had pushed a "false narrative of judicial bias" since the beginning of the trial to undermine the jury's verdict.
"While Ms. Habba ends her letter by characterizing this as a 'troubling matter,'" Kaplan wrote, "what is actually troubling is both the substance and timing of her false accusations of impropriety by on the part of E. Jean Carroll's counsel or the Court. Accordingly, while we wanted to submit our response to Ms. Habba's letter as soon as possible, we reserve all rights, including but not limited to the right to seek sanctions."
Newsweek reached out to Habba via email for comment.
On Friday, a jury ordered Trump to pay $83.3 million in damages to Carroll on Friday for defaming her by denying that he sexually assaulted the columnist in a Bergdorf Goodman department store dressing room in the mid-1990s. A separate jury in May found Trump liable for sexually abusing Carroll and had already awarded her $5 million.
Former federal prosecutor and elected state attorney Michael McAuliffe told Newsweek that while a lawyer shouldn't necessarily be condemned for vigorously defending their clients, Habba's claims is "a self-evident exercise of repeating anonymous information and hoping the repackaging gives it a longer life."
"The speculative accusation of an undisclosed, improper relationship between the presiding judge and an opposing lawyer is a transparent attempt to introduce inaccurate fodder for political purposes, not legal ones," McAuliffe said.
He said that Carroll could consider seeking sanctions against Habba if her claims about Kaplan are "frivolous and lacks a good faith foundation" because that would make the submission of those claims punishable by a court.
"However, the smarter move might be to relegate the issue to the dustbin of forgotten nonsense," McAuliffe added.
Habba was already been sanctioned last year for Trump's sprawling lawsuit against Hillary Clinton and his other political rivals in a "completely frivolous" lawsuit that "should have never been filed." In January 2023, a Florida judge fined Habba and Trump nearly $1 million for filing the suit, accusing them of a "pattern of abuse of the courts" by filing lawsuits that undermine the rule of law and amount to "obstruction of justice."
On Tuesday, Kaplan denied that she saw the judge as a mentor during their shared time at Paul, Weiss, Rifkind, Wharton & Garrison, a large Manhattan law firm. She acknowledged that while the two overlapped at the firm between October 1992 and August 1994, she had "no recollection" of ever directly interacting with the judge during that time period.
"Needless to say, at no point have we ever had a '"mentor" type relationship,' as alleged by Ms. Habba," Kaplan wrote, before going so far as to suggest that the Trump attorney made up the Paul, Weiss, Rifkind, Wharton & Garrison source who allegedly informed her of the judge and counsel's shared past at the firm.

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About the writer
Katherine Fung is a Newsweek senior reporter based in New York City. She has covered U.S. politics and culture extensively. ... Read more