The case, filed in Florida, seeks to stop Letitia James’s lawsuit in New York and includes Mr. Trump’s signature rhetoric. His legal advisers are split on the wisdom of filing it.
A tirade of a lawsuit that Donald J. Trump filed on Wednesday against one of his chief antagonists, the New York attorney general, was hotly opposed by some members of his legal team, who attempted an intervention hours before it was submitted to a court.
The faction opposed to the suit told the Florida attorneys who drafted it on the former president’s behalf that it was frivolous and would fail, according to people with knowledge of the matter. The loudest objection came from the general counsel of Mr. Trump’s real estate business, who warned that the Floridians might be committing malpractice.
Nonetheless, the suit was filed. It accuses Attorney General Letitia James of trespassing on Mr. Trump’s right to privacy in Florida, where he lives, and seeks to halt her own civil case in New York against the former president and his company.
On Wednesday evening, Mr. Trump used his social network, Truth Social, to announce his suit and to criticize Ms. James in charged language, saying that “while James does nothing to protect New York against these violent crimes and criminals, she attacks great and upstanding businesses.”
In September, Ms. James filed her lawsuit against Mr. Trump after a three-year investigation into his business practices. Her suit accused Mr. Trump and his family business, the Trump Organization, of committing “staggering” fraud, overvaluing its assets by billions of dollars. It sought to bar Mr. Trump and three of his children from ever running a business in the state again and to essentially shut down some of his New York properties.
The former president has already tried unsuccessfully to stop Ms. James’s investigation, filing a complaint in federal court in New York that was dismissed in May. The new 41-page lawsuit against Ms. James was filed in Palm Beach by Timothy W. Weber, Jeremy D. Bailie and R. Quincy Bird, members of a St. Petersburg-based law firm — and was championed by Boris Epshteyn, an in-house counsel for the former president who has become one of his most trusted advisers.
While lawsuits filed on behalf of Mr. Trump often bear signs of the former president’s input, the Florida case at times sounds remarkably like him, replete with boasts and expressions of raw grievance.
“As a private company, nobody knew very much about the great business that then-businessman Donald Trump had built but now it is being revealed by James and much to her chagrin,” the lawsuit says. “The continuing witch hunt that has haunted and targeted Donald Trump since he came down the ‘golden escalator’ at Trump Tower in June of 2015 continues.”
But some legal experts questioned the merit of the suit.
“This, certainly on its face, appears to be objectively frivolous,” said Gerald Greenberg, a partner at Gelber, Schachter and Greenberg, a Florida law firm. “I’m aware of no authority that allows a state court in Florida to enjoin or otherwise interfere with a law enforcement investigation being conducted by New York state authorities.”
Unable to persuade the Florida lawyers to stand down Wednesday, the Trump Organization’s general counsel, Alan Garten, then took aim at Mr. Epshteyn, blaming him in an email to Mr. Epshteyn and other lawyers for the filing of the suit, said the people with knowledge of the discussion. Frustrations with Mr. Epshteyn among some of Mr. Trump’s other aides and representatives have been brewing for months and boiled over with the new legal action.
Another lawyer for Mr. Trump, Christopher M. Kise, a former Florida solicitor general, also objected to the filing of the lawsuit on Wednesday. And Mr. Trump’s legal team in New York expressed concern that the Florida lawsuit would undermine their defense in Ms. James’s case, costing them credibility with both the New York attorney general’s office and the judge overseeing the case, the people with knowledge of the matter said.
Indeed, on Thursday, Ms. James filed a letter with the New York judge, saying that Mr. Trump’s Florida lawsuit demonstrated that the former president was “attempting to shield the key documents governing the structure of his business conglomerate and ownership of his business assets from review.”
One person close to Mr. Trump who was briefed on the Florida suit insisted it was meritorious, because Ms. James had focused on Mr. Trump’s revocable trust, a legal entity that owns the Trump Organization, and Florida’s laws governing trusts and wills are relevant.
In a statement on Wednesday, Mr. Trump said that Ms. James is seeking to “go after my revocable trust and pry into my private estate plan, only to look for ways to recklessly injure me, my family, my businesses, and my tens of millions of supporters.”
A spokeswoman for Ms. James said in a statement that “multiple judges have dismissed Donald Trump’s baseless attempts to evade justice, and no number of lawsuits will deter us from pursuing this fraud.”
“We sued Donald Trump because he committed extensive financial fraud,” the statement said. “That fact hasn’t changed.”
Since Ms. James’s lawsuit was filed, Mr. Trump has been unsuccessful in several attempts to remove the judge presiding over the case, Arthur F. Engoron. The Florida lawsuit makes several references to Justice Engoron, saying that while he presided over the New York inquiry for months, “he made not a single ruling in favor of President Trump.”
Justice Engoron has ordered Mr. Trump to sit for a deposition and held him in contempt of court, fining him $110,000. On Thursday, he is expected to rule on a request by Ms. James that Mr. Trump’s company be prohibited from transferring its assets without court approval.
The Florida lawsuit is an expression of frustration from the former president about the pressure on his company. Despite all the investigations that Mr. Trump is personally facing, the cases against his company have a particular emotional resonance.
He has been livid about Ms. James’s suit for weeks and has mocked her appearance to his advisers, according to people familiar with what he has said.
He is equally angry that his company is being tried by the Manhattan district attorney’s office for 17 felony charges. The trial began this week.
Mr. Epshteyn, meanwhile, has emerged as one of the former president’s favorite defenders but has long vexed a large number of other aides in Mr. Trump’s world.
A key figure involved in the efforts to invalidate Joseph R. Biden Jr.’s victory in the 2020 election, he helped coordinate efforts to use what one of the campaign’s own lawyers called fake electors to keep Congress from certifying Mr. Biden’s electoral college victory on Jan. 6. He had his phone seized by federal agents executing a search warrant in September.
Recently, Mr. Epshteyn has been serving as an in-house counsel on issues related to the investigation of the former president’s handling of hundreds of classified documents held at his members-only club. Mr. Trump has repeatedly extolled to other advisers what he sees as Mr. Epshteyn’s gifts and has rejected their criticisms of him.
But several of Mr. Trump’s advisers consider Mr. Epshteyn to be a malign presence with dubious legal skills, enabling the former president’s pugilistic — and sometimes self-destructive — impulses.
Even before the current dispute, according to advisers, Mr. Epshteyn had friction over strategy with Mr. Kise, the former state solicitor general. Since then, Mr. Kise’s role has been minimized in the documents case and he has been asked to help with some of the New York cases, two people familiar with the situation said.
A spokesman for Mr. Trump did not respond to a request for comment about the criticisms of Mr. Epshteyn over the suit. Mr. Weber, the lead among the St. Petersburg lawyers who filed the case, did not respond to a request for comment.
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