Tracing the Trail of Hush-Money Deals That Led to Trump’s Prosecution

Donald J. Trump and two confidants hatched a plan in August 2015 to boost his upstart presidential campaign, prosecutors say. They carried it out, and Mr. Trump won the election.

Nearly nine years later, Mr. Trump will face the same men, Michael Cohen and David Pecker. But unlike at that long-ago meeting, he won’t be seated at the desk in his 26th-floor Trump Tower office: He will be at the defendant’s table in a Lower Manhattan courtroom.

With his criminal trial set to begin in earnest on Monday, Mr. Trump’s former allies are each expected to take a turn on the witness stand, giving testimony that could help make him the first president convicted of a felony.

Mr. Trump is charged in a 34-count indictment with falsifying business records to cover up a $130,000 hush-money payment to a former porn star in order to influence the 2016 election. Mr. Cohen paid the woman, Stormy Daniels, less than two weeks before the election to keep silent about her claim that she had sex with Mr. Trump a decade before.

Lawyers defending Mr. Trump, who denies he had sex with her, will likely argue that his employees were responsible for the paper trail that falsely described the reimbursement of the hush money as legal fees for Mr. Cohen.

But prosecutors for Alvin L. Bragg, the Manhattan district attorney, will try to show that the payment was part of a larger effort to suppress negative news about Mr. Trump to sway the election. That scheme, they will contend, resulted in not just the hush-money payment at the center of the trial, but two others.

Though the other episodes are not part of the formal indictment in the case, prosecutors will use them to argue that the true purpose of the Daniels payment was related to the election, making it a federal campaign finance violation, and that his company’s records were falsified to cover it up. The accusation that Mr. Trump concealed another crime elevates charges that would normally be misdemeanors into felonies.

The August 2015 meeting at Trump Tower is the beginning of a story that prosecutors have foreshadowed in filings and arguments in court. The details in this article are drawn from court documents, interviews with people involved in the events or familiar with them, private communications and other records.

Mr. Cohen had been a lawyer and dogged fixer for Mr. Trump. Mr. Pecker was the publisher of The National Enquirer, and had traded favors with Mr. Trump since the 1990s.

Mr. Trump had announced his presidential campaign in June 2015. The plan the men laid out two months later was simple: Mr. Pecker would use The Enquirer to publish positive stories about Mr. Trump’s campaign and negative stories about his rivals. He would alert Mr. Trump, through Mr. Cohen, when The Enquirer learned of stories that might threaten Mr. Trump. The Enquirer could buy the rights to those stories in order to suppress them, a practice known in the tabloid world as “catch and kill.”

“The entire point of the Trump Tower meeting was to control the flow of information that reached the electorate, to accentuate the positive, hide the negative and exaggerate information,” Joshua Steinglass, a prosecutor, told Justice Juan M. Merchan, the judge in the hush-money case, in court.

Todd Blanche, one of Mr. Trump’s lawyers, asked Justice Merchan to bar evidence about the meeting and other hush-money deals, saying a “side trial” would prejudice the jury.

“This is just to embarrass President Trump,” he complained, but the judge disagreed.

Mr. Trump’s associates paid a price for helping him. Mr. Cohen pleaded guilty to federal campaign finance crimes in 2018. The Enquirer’s parent company, American Media Inc., made a deal that year to avoid federal prosecution, acknowledging that it had illegally tried to influence the election. On the witness stand, they are expected to testify that the payment to Ms. Daniels was intended to get Mr. Trump elected.

After Mr. Cohen and Mr. Pecker met Mr. Trump in his office, it took only a few months for the first situation that needed their attention to arise.

The Doorman

The information was potentially explosive. Dino Sajudin, a former doorman at a Manhattan building managed by the Trump Organization, called The Enquirer’s tip line in late 2015. He said he had overheard other employees saying that Mr. Trump fathered a child out of wedlock with a woman who had worked for him.

In November 2015, American Media guaranteed Mr. Sajudin $30,000 if it published a story based on his tip, and its reporters began to investigate.

They did not immediately alert Mr. Cohen or Mr. Trump; first, The Enquirer’s editor, Dylan Howard, set out to determine whether the information was accurate. The tabloid arranged for Mr. Sajudin to take a lie-detector test, according to a memo that Mr. Howard wrote.

Though the test indicated that Mr. Sajudin had been truthful about what he had heard, Enquirer reporters doubted the child was actually Mr. Trump’s: She strongly resembled the man she knew as her father, a Trump Organization driver.

Mr. Cohen, then special counsel to Mr. Trump, learned of the doorman’s claims after a reporter contacted the company. He called Mr. Howard, irate, insisting the story was false.

American Media nonetheless amended Mr. Sajudin’s deal to pay him regardless of whether The Enquirer published anything. The amendment also included a confidentiality provision requiring him to pay the company $1 million if he disclosed the tip elsewhere.

Even if untrue, the story still endangered Mr. Trump’s chances in the 2016 election. Now the threat had been neutralized. Enquirer staff members were told not to pursue the story further.

Mr. Bragg’s prosecutors said in a court filing last year that even though Mr. Pecker concluded that Mr. Sajudin’s story wasn’t true, he did not release Mr. Sajudin from his confidentiality agreement until after Mr. Trump won the election. They say that shows the deal’s true objective.

The Playboy Model

By the middle of 2016, Mr. Trump had driven every other Republican rival from the race. As the general election campaign against Hillary Clinton began, a woman from Mr. Trump’s past began exploring the sale of her story.

That woman, Karen McDougal, had been Playboy’s Playmate of the Year for 1998. Ms. McDougal said she met Mr. Trump at the Playboy Mansion in June 2006, and they began a 10-month affair, spending time at his bungalow at the Beverly Hills Hotel in Los Angeles, his golf course in New Jersey and in his Trump Tower apartment.

Ms. McDougal, living in Arizona, saw a chance to revive a flagging modeling career. In June 2016, she hired a Beverly Hills lawyer, Keith Davidson, to represent her in the sale of her story. Mr. Davidson contacted Mr. Howard, the Enquirer editor.

At a meeting in Los Angeles, Mr. Howard debriefed Ms. McDougal, who now expressed reservations about coming forward.

Afterward, Mr. Howard jumped on a three-way call with Mr. Pecker and Mr. Cohen. Mr. Howard relayed Ms. McDougal’s hesitation, and told them that she had shown no hard documentation of the affair. The Enquirer decided not to purchase her story — for the moment.

That changed. In late June, Mr. Trump called Mr. Pecker personally, asking him to keep Ms. McDougal from talking, the tabloid executive has told prosecutors.

After conversations she had started with ABC News about telling her story on air grew serious, American Media swooped in with an offer.

The company agreed in early August to pay Ms. McDougal $150,000 for the rights to her story, one that The Enquirer would never publish. To camouflage the purpose of the deal, the contract guaranteed that American Media would put her on two magazine covers and have the right to publish fitness columns by her.

Mr. Davidson, who also represented Ms. Daniels in her hush-money deal, is likely to testify about both agreements. Prosecutors also referred in court documents to another piece of evidence they might use: a recording of Mr. Trump that Mr. Cohen secretly made on his phone as the men discussed a deal, which never went through, to buy the rights to Ms. McDougal’s story back from Mr. Pecker.

“So what do we got to pay for this? One-fifty?” Mr. Trump asked on the recording.

The Porn Star

Ms. Daniels also tried to benefit from Mr. Trump’s momentum in early 2016.

Her agent reached out to Mr. Howard and editors at other publications, seeking about $200,000 to tell her story of having sex with Mr. Trump in 2006 when he was at a golf tournament in Lake Tahoe, Nev.

Ms. Daniels had no takers. Mr. Howard thought her story had little value because it had already been written about on a gossip site in 2011. At the time, she had publicly denied the encounter.

But a month before the general election, her story’s value suddenly increased. On Oct. 7, 2016, The Washington Post published a recording of Mr. Trump on the set of “Access Hollywood” talking about groping women. The ensuing uproar revived Ms. Daniels’s negotiations with The Enquirer. Her agent negotiated a price of $120,000 with Mr. Howard, but Mr. Pecker nixed the deal, unwilling to spend more after paying Ms. McDougal.

“We can’t pay 120k,” Mr. Pecker texted. They agreed that Mr. Cohen would have to handle the problem.

“Spoke to MC. All sorted,” Mr. Howard later texted Mr. Pecker. “No fingerprints.”

Mr. Cohen had been in London visiting his daughter, who was studying abroad, when the “Access Hollywood” recording hit. He had gotten on a three-way call with Mr. Trump and Hope Hicks, the campaign’s press secretary, and then spoke to Ms. Hicks alone to discuss damage control. Ms. Hicks is also expected to testify.

Mr. Steinglass, the prosecutor, said in court that after the recording emerged, Mr. Trump was desperate to “lock down the Stormy Daniels story” and prevent more damage.

On Oct. 10, Mr. Cohen began to negotiate a price with Mr. Davidson, the lawyer representing Ms. Daniels, settling on $130,000. A nondisclosure agreement identified Ms. Daniels by the pseudonym Peggy Peterson, or “PP,” and Mr. Trump as David Dennison, or “DD.”

But Mr. Cohen delayed paying for weeks, and Ms. Daniels began contacting news outlets again.

With the election rapidly approaching, Mr. Cohen drew the money from his own home equity line of credit and wired it to Ms. Daniels’s lawyer through a shell company on Oct. 27.

Her silence was assured.