Trump’s Well-Worn Legal Playbook Starts to Look Frayed

The expanding legal threats facing former President Donald J. Trump are testing as never before his decades-old playbook for fending off prosecutors, regulators and other accusers and foes, with his trademark mix of defiance, counterattacks, bluffs and delays encountering a series of setbacks.

In other legal maneuvering and in seeking to shape public opinion about cases involving him, Mr. Trump has experienced regular reversals in court in recent months even as he begins his campaign for another term in the White House.

“Mr. Trump is a prolific and sophisticated litigant who is repeatedly using the courts to seek revenge on political adversaries,” Judge Donald M. Middlebrooks of the U.S. District Court for the Southern District of Florida wrote this month in fining the former president and one of his lawyers nearly $1 million for filing a frivolous civil suit against Hillary Clinton and F.B.I. officials. “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.”

That fine appeared to lead Mr. Trump to quickly drop a similar suit he had filed against Letitia James, the attorney general of New York, who is pressing ahead with a $250 million suit claiming widespread financial fraud by the former president, his oldest children and his company.

The Manhattan district attorney’s office began presenting evidence on Monday to a grand jury about his role in paying hush money to a porn star during his 2016 presidential campaign — the latest in a series of investigations and legal proceedings that are grinding on despite Mr. Trump’s efforts to block or undercut them.

The Justice Department is investigating his handling of classified documents and his role in the efforts to reverse the outcome of the 2020 election, and he is facing a potential indictment from the prosecutor in Fulton County, Ga., in connection with his efforts to remain in power after his election loss.

Two suits against Mr. Trump brought by E. Jean Carroll, a New York-based writer who has accused him of raping her in the 1990s in a department store dressing room, are moving ahead despite his threats to sue her.

“Trump views the judicial system as he sees everything else: corrupt, ‘fixable’ and usable as a bullying tactic,” said Alan Marcus, a consultant who worked for the Trump Organization in the 1990s.

Mr. Marcus recalled Mr. Trump calling lawyers who had filed suit against him to try to convince them that “it was a waste of time and money,” then ultimately trying to get the case in front of a judge he perceived to be friendly.

A spokesman for Mr. Trump did not respond to an email seeking comment about his history of handling legal threats.

For all that he remains popular with many Republican voters, Mr. Trump, according to people who have spoken with him, is concerned about facing a criminal charge, something he has worked to avoid since the late 1970s. And he remains dedicated to the techniques for dealing with such threats — tactics he learned from his former lawyer Roy M. Cohn, who favored attacking the legal system while trying to work insider connections.

In the Georgia investigation, Mr. Trump has called Fani T. Willis, the district attorney leading the inquiry, as well as other Black prosecutors investigating him, “racist.”

He has relentlessly denounced the Justice Department as partisan and attacked Alvin L. Bragg, the Manhattan district attorney who recently brought a successful fraud prosecution against Mr. Trump’s company and is now pursuing potential criminal charges in the Stormy Daniels hush money case.

On Monday, Mr. Trump filed suit against the journalist Bob Woodward, saying that Mr. Woodward had released recordings of interviews with him as an audiobook without his permission. Mr. Woodward and his publisher, Simon & Schuster, called the suit, which seeks $49 million in damages, “without merit.”

But while it is not clear that Mr. Trump will ever be charged with a crime or found liable in the civil cases, that approach appears less effective for him than it has ever been in fending off investigations and potential legal peril.

“You can wear down a private party if they do not have the same resources as you, or you can settle a civil case and make it go away, but criminal cases are not about money,” said Chuck Rosenberg, a former U.S. attorney and F.B.I. official. “Criminal cases are about liberty and justice, and it is really rather difficult — if not impossible — to wear down federal prosecutors and the F.B.I. and make them go away.”

In purely political terms, Mr. Trump remains a force in the Republican Party, even as a diminished figure whose support has eroded from its highs of 2020. Several polls still show him with a plurality or a majority of support among Republican voters, for whom he is the only declared presidential candidate for 2024.

And part of his approach to his own difficulties over many years has been capitalizing on the misfortunes of his critics and his opposition. That has once again become a toll, as a special counsel is investigating how documents with classified markings came to be stored at President Biden’s home and an office he used after his vice presidency, a fact that Mr. Trump has used to try to obscure how hundreds of classified documents came to be held at his club, Mar-a-Lago.

Victor A. Kovner, a prominent First Amendment lawyer and Democratic activist in New York, attributed Mr. Trump’s approach to legal matters to what he learned from Mr. Cohn, who died of AIDS in 1986 and whom Mr. Kovner despised for his tactics.

“Always distraction, and apparent scorched earth and counterattacks at the start, and after much passage of time, settlement as quietly as possible,” Mr. Kovner said of Mr. Trump’s behaviors in what were primarily civil suits. “And the counterattacks as scurrilous as possible. Mostly from the Roy Cohn playbook.”

Since the 1970s, Mr. Trump has alternately denounced prosecutors or investigators or cajoled, schmoozed and tried to work an inside track to head off an investigation or inquiry. And he established relationships with the power elite in New York, many of whom also happened to be in positions that could be threatening to a businessman.

In the 1980s, Mr. Trump began cultivating what would become a decades-long connection to Robert M. Morgenthau, the powerful Manhattan district attorney in whose jurisdiction Mr. Trump’s company was located, by getting involved in the charity Mr. Morgenthau cherished, the Police Athletic League. Mr. Trump announced in 1988 that he would raise money for Rudolph W. Giuliani, then seen as a prospective mayoral candidate as he served as the U.S. attorney in the Southern District of New York (Mr. Giuliani was the Republican nominee the following year).

In 1979, as Mr. Trump was endeavoring to become a more significant player in Manhattan real estate after an initial foray — refurbishing a decrepit East Side hotel into the Grand Hyatt — his acquisition of a different parcel of land was under investigation by the Brooklyn federal prosecutor, Edward R. Korman.

Mr. Korman, following the road map laid out in reporting by Wayne Barrett, The Village Voice muckraking journalist, investigated whether Mr. Trump had agreed to sign onto a landlord suit against an oil company being filed by a lawyer whose help he needed to acquire a large for-lease parcel of undeveloped land in Manhattan. Mr. Trump met with federal investigators, with no lawyer present, according to Mr. Barrett.

It was a roughly six-month investigation with a weak witness, according to people familiar with the work, with a statute of limitations approaching, making charges less likely to be brought. Still, the lesson that Mr. Trump appeared to take from it was that he had the ability to get himself out of difficult situations by persuading his antagonists.

When Eric T. Schneiderman, the New York attorney general at the time, began an investigation in 2011 into Trump University, looking into whether Mr. Trump’s for-profit classes claiming to instruct people on how to succeed in business were a scam, Mr. Trump first tried flattery and relationship building.

He hired Avi Schick, who had been the director of Mr. Schneiderman’s inauguration. But no deal with Mr. Schneiderman was negotiated, and eventually Mr. Trump accused Mr. Schick of being part of a ploy by Mr. Schneiderman to pressure Mr. Trump into donating money to his campaign in exchange for dropping the investigation. Mr. Trump bitterly complained that one of his company’s lawyers complied with Mr. Schneiderman’s demand for documents, Michael D. Cohen, Mr. Trump’s former fixer, recalled in a 2021 interview.

Mr. Trump fought the case until he abruptly settled it just after he was elected in 2016.

Since becoming president, Mr. Trump has been in search of his next Roy Cohn. When he was in the White House and a special counsel was appointed to investigate whether his campaign conspired with Russians in the 2016 election and whether he had obstructed justice, one of Mr. Trump’s first impulses was to meet with the people investigating him. He told his lawyers he wanted to sit with the special counsel, Robert S. Mueller III, at the outset.

Those lawyers declined to follow the president’s impulses. But some of his recent lawyers have given in to his desires, most often to attack aggressively.

“I think he thinks that everything can be bought or fought,” Mr. Rosenberg said, “and that is just not true.”