In a scathing ruling, a federal judge in Florida on Thursday ordered Donald J. Trump and one of his lawyers together to pay nearly a million dollars in sanctions for filing a frivolous lawsuit against nearly three dozen of Mr. Trump’s perceived political enemies, including Hillary Clinton and the former F.B.I. director James B. Comey.
The ruling was a significant rebuke of Mr. Trump, who has rarely faced such consequences in his long history of using the courts as a weapon against business rivals and partners, as well as former employees and reporters.
And it was the latest setback for Mr. Trump as he faces a broad range of legal problems and criminal investigations. His lawyers are increasingly under scrutiny themselves for their actions in those cases, as well as divided in the advice they are offering him.
“This case should never have been brought,” U.S. District Judge Donald M. Middlebrooks wrote in a 46-page ruling. “Its inadequacy as a legal claim was evident from the start. No reasonable lawyer would have filed it. Intended for a political purpose, none of the counts of the amended complaint stated a cognizable legal claim.”
While Mr. Trump has often blamed his lawyers for his problems, the judge, in his ruling on Thursday, addressed Mr. Trump’s history of using the courts as a cudgel, going back decades in his business career.
What to Know About the Trump Investigations
Numerous inquiries. Since leaving office, former President Donald J. Trump has been facing several investigations into his business dealings and political activities. Here is a look at some notable cases:
Classified documents inquiry. The F.B.I. searched Mr. Trump’s Florida home as part of the Justice Department’s investigation into his handling of classified materials. The inquiry is focused on documents that Mr. Trump had brought with him to Mar-a-Lago, his private club and residence, when he left the White House.
Jan. 6 investigations. In a series of public hearings, the House committee investigating the Jan. 6 attack laid out a comprehensive narrative of Mr. Trump’s efforts to overturn the 2020 election. This evidence could allow federal prosecutors, who are conducting a parallel criminal investigation, to indict Mr. Trump.
Georgia election interference case. Fani T. Willis, the Atlanta-area district attorney, has been leading a wide-ranging criminal investigation into the efforts of Mr. Trump and his allies to overturn his 2020 election loss in Georgia. This case could pose the most immediate legal peril for the former president and his associates.
New York State’s civil case. Letitia James, the New York attorney general, has accused Mr. Trump, his family business and his three adult children of lying to lenders and insurers, fraudulently inflating the value of his assets. The allegations, included in a sweeping lawsuit, are the culmination of a yearslong civil investigation.
Manhattan criminal case. Alvin L. Bragg, the Manhattan district attorney, has been investigating whether, among other things, Mr. Trump or his family business intentionally submitted false property values to potential lenders. As a result of the inquiry, the Trump Organization was convicted on Dec. 6 of tax fraud and other crimes.
“Mr. Trump is a prolific and sophisticated litigant who is repeatedly using the courts to seek revenge on political adversaries,” Judge Middlebrooks wrote. “He is the mastermind of strategic abuse of the judicial process, and he cannot be seen as a litigant blindly following the advice of a lawyer. He knew full well the impact of his actions.”
Judge Middlebrooks said Mr. Trump’s suit had been “brought in bad faith for an improper purpose” and had “needlessly harmed” the 31 individuals and organizations, including the Democratic National Committee, he had sued “in order to dishonestly advance a political narrative.” The judge added that Mr. Trump’s use of the courts had helped to undermine the public’s confidence in them.
“A continuing pattern of misuse of the courts by Mr. Trump and his lawyers undermines the rule of law, portrays judges as partisans and diverts resources from those who have suffered actual legal harm,” he wrote.
The judge said Mr. Trump and the lawyer who filed the case for him, Alina Habba, and her firm, Habba Madaio & Associates, were to pay $937,989.39.
Neither a spokesman for Mr. Trump nor Ms. Habba immediately responded to requests for comment.
Ms. Habba was the lead lawyer among a group who filed the suit on Mr. Trump’s behalf in March. She is also representing Mr. Trump in a sweeping fraud case brought by the New York State attorney general and a case filed by E. Jean Carroll, a woman who alleges that Mr. Trump raped her in the 1990s. Ms. Habba has offered advice in the federal investigation into Mr. Trump’s handling of classified documents as well, according to people close to Mr. Trump, including arguing he should hire someone to search his properties for any additional documents.
The suit names Mrs. Clinton, the Democratic National Committee and other people and entities that he claimed conspired to damage him in the 2016 election with what he called false claims about his ties to Russia. Among the defendants were Mr. Comey; the former deputy F.B.I. director Andrew G. McCabe, who opened the counterintelligence investigation into Mr. Trump’s ties to Russia; and the former British intelligence agent Christopher Steele, who helped circulate a dossier of lurid claims about Mr. Trump and Russia, many of which were unsubstantiated.
The conspiracy-minded racketeering suit was filed with hyperbole and exaggerations, and made claims easily shown to be false. In the ruling on Thursday, Judge Middlebrooks broke down how the suit’s claims — including that Mrs. Clinton and Mr. Comey had conspired to take down Mr. Trump — were “implausible” and “categorically absurd.”
Mr. Trump’s claims were “a hodgepodge of disconnected, often immaterial events, followed by an implausible conclusion,” the judge wrote, adding, “This is a deliberate attempt to harass; to tell a story without regard to facts.”
Judge Middlebrooks, who was nominated by President Bill Clinton in 1997, threw out the suit in September, saying that “most of plaintiff’s claims are not only unsupported by any legal authority but plainly foreclosed by binding precedent.” The judge said that what the suit “lacks in substance and legal support, it seeks to substitute with length, hyperbole, and the settling of scores and grievances.”
He said Mr. Trump was trying to brandish a “political manifesto” against political rivals, masquerading as a lawsuit.
In November, Judge Middlebrooks fined Mr. Trump’s lawyers $50,000 and ordered them to pay the legal fees of one of the defendants. But a number of defendants, including Mrs. Clinton, filed jointly seeking additional sanctions, which the judge wrote at the time “may be appropriate.” The actions of Mr. Trump’s lawyers, he warned then, could also merit attention from “the bar and disciplinary authorities.”
The additional fine was sure to add stress to Mr. Trump’s legal team, which has already been displaying tensions. That has been especially true on his handling of classified documents, more than 300 of which made their way from the White House to Mar-a-Lago, his Florida club and residence, and remained there long after he left office.
In that case, Mr. Trump’s lawyers have divided into camps, with Boris Epshteyn, who is also an adviser to the former president, among those seen as enabling some of his pugilistic instincts.