Some Potential Trump Witnesses Get Carrots. Michael Cohen Got the Stick.

Donald J. Trump watched anxiously from the White House in April 2018 as news broke about federal agents searching the home of Michael D. Cohen, the man entrusted to conceal some of the president’s deepest secrets. After initially coming to Mr. Cohen’s defense, Mr. Trump washed his hands of his fixer within weeks, brushing aside Mr. Cohen’s feelers about a pardon and disavowing his legal bills.

Mr. Trump took a different tack when prosecutors shifted their scrutiny to Allen H. Weisselberg, the Trump family’s longtime financial gatekeeper. Mr. Trump’s company paid Mr. Weisselberg’s legal bills and awarded him a $2 million severance, with a condition: He could not voluntarily cooperate with any law enforcement agency.

After Mr. Weisselberg signed the deal last year, Mr. Trump’s lawyers privately pressed him to testify in a civil fraud case filed against the former president, hoping the finance chief’s testimony would aid their defense, according to people with knowledge of the discussions, which have not previously been reported. But prosecutors say Mr. Weisselberg lied during his testimony, and this month he pleaded guilty to perjury.

The fixer and the moneyman both landed behind bars. But while Mr. Weisselberg remained loyal, refusing to implicate his boss, Mr. Cohen is poised to become a central witness for the Manhattan district attorney at Mr. Trump’s criminal trial next month, the first prosecution of a former U.S. president.

The contrasting cases of Mr. Cohen and Mr. Weisselberg — detailed in court records and interviews with 18 people directly involved in the cases, some of whom requested anonymity to discuss confidential conversations — demonstrate the power and peril of Mr. Trump’s tactics for avoiding a crisis like the one he now faces. The trial, in which Mr. Trump is accused of covering up a sex scandal surrounding the 2016 presidential campaign, is the realization of his long-held fear that prosecutors would flip trusted aides into dangerous witnesses.

The former president, facing four indictments and several lawsuits while seeking to reclaim the White House, careens from one case to the next, seeking to exert control over witnesses. In screeds posted on his social media site, he mixes enticements with threats, praise with scorn, and when all else fails, he makes life miserable for anyone audacious enough to cross him.

Mr. Trump’s company praised Mr. Weisselberg as a “fine and honorable man,” but Mr. Cohen felt the brunt of the former president’s attacks. Mr. Trump has sued him, called him a “rat” and referred to him as “death.”

That aggressive approach — stick, rather than carrot — will be tested at the Manhattan criminal trial, and at others that may follow in Florida, Georgia and Washington, D.C. Despite Mr. Trump’s public lashing of Mr. Cohen and others, they are still set to testify against him.

The former president’s attacks now might put him in even greater legal jeopardy. On Tuesday, the judge in the Manhattan case issued a gag order that bars Mr. Trump from assailing potential witnesses and labeled his invective “threatening, inflammatory, denigrating.”

Steven Cheung, a spokesman for Mr. Trump’s campaign, did not respond to requests for comment, but he criticized the gag order previously as unconstitutional because, he said, it prevented Mr. Trump “from engaging in core political speech, which is entitled to the highest level of protection under the First Amendment.”

The prosecution’s potential witness list for the Manhattan trial is expected to resemble a 2016-era roster of Mr. Trump’s employees, campaign aides and friends.

Mr. Cohen will testify that Mr. Trump helped orchestrate the hush-money deal with Stormy Daniels, the porn star at the center of the case. Ms. Daniels may testify as well. David Pecker, the former National Enquirer publisher who was once friends with Mr. Trump, is expected to tell the jury that he helped initiate that deal and buried other damaging stories for Mr. Trump. And Hope Hicks, a former campaign and White House aide to Mr. Trump, may be called to shed light on the tumultuous period.

Mr. Weisselberg is not expected to testify for either side. Although prosecutors have sought his help for years, he has repeatedly rebuffed them, disputing Mr. Cohen’s account of the hush-money deal and contending that he has no decisive information to offer. Given his guilty plea to perjury, and his financial dependence on the Trumps, he would not make a particularly credible defense witness either.

Mr. Trump’s lawyers have portrayed Mr. Weisselberg as a victim of prosecutorial overreach, and Mr. Cohen as an opportunistic liar who has admitted to perjury. They note that Mr. Cohen, whose memoir is titled “Disloyal,” pleaded guilty to federal charges involving the hush-money deal as well as personal financial crimes unrelated to Mr. Trump.

Mr. Trump has never said that refusing to pay more than $1 million of Mr. Cohen’s legal bills was shortsighted, but Mr. Cohen has told people it was “the biggest mistake” the former president ever made. Mr. Trump has, however, wondered aloud whether it might have been possible to handle Mr. Cohen differently to keep him loyal.

And Mr. Cohen’s break from Mr. Trump helped inform how Mr. Trump has handled other witnesses, a person with knowledge of the former president’s thinking said. His political action committee has paid more than $50 million in legal fees, mostly for aides and employees who are now witnesses in the cases against Mr. Trump.

While Mr. Trump’s legal fate is still undecided, Mr. Cohen and Mr. Weisselberg had their lives upended and their freedom revoked.

“I was the first lamb led to the slaughterhouse,” Mr. Cohen said in an interview.

The Fixer

It was Mr. Cohen’s loyalty that first caught Mr. Trump’s eye nearly two decades ago.

Mr. Trump was embroiled in a dispute over control of the condo board at his tower across from the United Nations when Mr. Cohen, a former personal injury lawyer who had bought several Trump apartments, helped him win.

The feat earned him a job at the Trump Organization, and the next decade of Mr. Cohen’s professional life was an act of devotion to the real estate mogul turned reality television star turned presidential candidate.

But Mr. Cohen ultimately concluded that his loyalty was not being reciprocated, setting in motion the events that led to the Manhattan criminal trial, which is scheduled to begin on April 15.

The case stems from the 2016 presidential campaign, when, behind the scenes, Mr. Cohen was cleaning up his candidate’s messes.

Mr. Pecker, the National Enquirer publisher, alerted Mr. Cohen to one such mess that October: Ms. Daniels was interested in selling her story of a sexual encounter with Mr. Trump. The threat came as the campaign reeled from the release of the infamous “Access Hollywood” recording that captured Mr. Trump boasting about groping women.

Soon after, Mr. Cohen negotiated a $130,000 hush-money deal.

Mr. Cohen put up the money, and Mr. Trump reimbursed him. But Mr. Trump’s company falsely recorded the reimbursements in its books as “legal expenses.”

The hush money caught the attention of the federal authorities, leading them in April 2018 to search Mr. Cohen’s home and office; a hotel room where he was staying; and a safe deposit box.

Initially sympathetic, Mr. Trump called Mr. Cohen a “good man” and the search “a disgraceful situation.” He also called Mr. Cohen with a message — stay strong — and the Trump Organization paid for Mr. Cohen’s main lawyer.

But Mr. Trump’s advisers were concerned about witness tampering accusations and he stopped reaching out. Their relationship soon soured.

When Mr. Trump called into one of his favorite television shows, “Fox & Friends,” a few weeks after the search, he distanced himself from Mr. Cohen, who he said had handled just “a tiny, tiny little fraction” of his legal work, adding: “From what I understand, they’re looking at his businesses.”

“I’m not involved,” Mr. Trump added three times.

At the time, people close to Mr. Trump were dangling possible presidential pardons to advisers who had been caught up in criminal investigations. Mr. Cohen dispatched lawyers to ask whether Mr. Trump was open to giving him one, but the response from Mr. Trump’s then-personal lawyer, Rudolph W. Giuliani, was that discussion of a pardon was premature.

The final straw, Mr. Cohen said, came when the Trump Organization stopped paying his main lawyer in June 2018. The company reasoned that it already had spent more than $1 million on the lawyer, and that Mr. Cohen was facing prosecution for his own business dealings in addition to the hush-money deal.

Mr. Cohen soon hired Lanny J. Davis, a veteran Washington lawyer and public relations strategist with close ties to Democratic politicians, and was telling friends that he was willing to cooperate with prosecutors.

When he pleaded guilty to federal charges that August, Mr. Cohen pointed the finger at Mr. Trump, saying he had paid the hush money “at the direction of” his former boss — an accusation he is expected to repeat on the witness stand in the Manhattan trial. A spokeswoman for Alvin L. Bragg, the Manhattan district attorney, declined to comment.

Before going to prison, Mr. Cohen also appeared before Congress, where he was asked who else had worked on the hush-money deal. His answer: Mr. Weisselberg.

After spending decades in relative anonymity as Mr. Trump’s finance chief, Mr. Weisselberg now had a target on his back.

The Manhattan district attorney’s office had come to view Mr. Weisselberg, whose relationship with the Trump family had begun under Mr. Trump’s father nearly a half-century before, as a linchpin in its investigation of the former president. When he rebuffed the prosecutors, he was indicted on tax fraud charges. He pleaded guilty in 2022.

While Mr. Weisselberg was serving time at the Rikers Island jail complex early last year, prosecutors offered him a path to freedom: Turn on Mr. Trump.

But that path was closed. The day before he arrived at Rikers, Mr. Weisselberg had signed the $2 million severance deal with its provision against cooperation.

The money is paid in installments. And while the Trump Organization agreed to pay Mr. Weisselberg’s lawyers, there was a caveat: “The company must approve the selection of employee’s counsel.”

If that were not incentive enough to remain loyal, one of Mr. Weisselberg’s sons works for the company.

Still, when Mr. Weisselberg returned home from Rikers last April, prosecutors tried a final squeeze. Unless he talked, they warned, he would face a new round of charges for misleading investigators over the years.

The threat could not have come at a worse moment for Mr. Weisselberg. The New York attorney general’s office, which had sued Mr. Trump and Mr. Weisselberg for fraudulently inflating the former president’s net worth, was set to question the onetime finance chief under oath in a deposition soon after his release from jail.

Mr. Weisselberg’s criminal lawyers expressed concern about his testifying. Doing so could expose Mr. Weisselberg to perjury charges.

Mr. Trump’s lawyers were adamant that he testify, noting that if he invoked his Fifth Amendment right against self-incrimination, the judge deciding the case could hold it against the defense and doom their case. The Trump lawyers argued that prosecutors could charge Mr. Weisselberg whether or not he testified at the deposition.

It was Mr. Weisselberg’s decision to make, and he chose to testify. But as his criminal lawyers had feared, the district attorney’s office concluded that he had lied, and Mr. Weisselberg pleaded guilty to perjury on March 4.

He will soon return to Rikers.

The property manager and the vice president

Mr. Trump’s divergent approaches to Mr. Cohen and Mr. Weisselberg have been replicated in his approach to witnesses in the two federal cases against him.

The cases, brought by a special counsel, Jack Smith, include one in Florida, where Mr. Trump is accused of mishandling classified documents, and one in Washington, where the former president has been charged with plotting to overturn the results of the 2020 election.

As Mr. Smith was investigating, Mr. Trump used part of his political fund-raising operation to pay the legal bills for several former aides and allies who had been called before grand juries to testify about him. Mr. Trump also paid for lawyers for his two co-defendants in the classified documents case: Walt Nauta, a personal aide who works for the former president at his Mar-a-Lago estate, and Carlos De Oliveira, the property manager there.

Like Mr. Weisselberg, Mr. Nauta and Mr. De Oliveira remained loyal, and they are now paying the price: Mr. Smith charged both men not only with obstruction of justice, but also with lying to investigators.

And like Mr. Cohen, the former Trump aides who were possible witnesses against him have felt his wrath on his social media site, Truth Social.

Mr. Trump has attacked his vice president, Mike Pence, claiming that Mr. Pence has gone to the “Dark Side.” He has taken aim at his onetime chief of staff, Mark Meadows, whom Mr. Trump likened to “weaklings and cowards” after fearing that he might be cooperating with federal prosecutors. And after Alyssa Farah, a former White House communications aide who talked to investigators about Mr. Trump’s actions following the 2020 election, criticized him publicly, he called her a “loser.”

Late last year, Mr. Smith, tiring of the outbursts, told a federal appeals court that the hostility “was part of a pattern, stretching back years, in which people publicly targeted by” Mr. Trump were “subject to harassment, threats, and intimidation” as a result.

Mr. Smith cited many of the attacks to obtain a gag order against Mr. Trump in the election-interference case in Washington.

“Mr. Trump’s documented pattern of speech and its demonstrated real-time, real-world consequences pose a significant and imminent threat,” an appeals court in Washington wrote in affirming the order.

More recently, prosecutors have also sought to protect witnesses in the Florida case. Mr. Smith’s team has even opened a separate criminal investigation into threats made on social media against a witness.

When the former president’s lawyers tried to put the witnesses’ names in public court filings, prosecutors complained to the judge overseeing the case. Releasing the names, they said, would risk “exposing them to significant and immediate risks of threats, intimidation, and harassment.”

And when aides become witnesses, Mr. Trump sometimes seeks to clarify their allegiances.

During the documents investigation, his team questioned whether Mr. De Oliveira was loyal. One of Mr. De Oliveira’s friends, Brian Butler, responded affirmatively: He would not do anything to jeopardize his relationship with Mr. Trump.

Within 15 minutes, Mr. Butler said, Mr. Trump called Mr. De Oliveira and offered to get him a lawyer.