T.J. Kirkpatrick for The New York Times
Michael D. Cohen was at a breaking point. He told friends he was suicidal. He insisted to lawyers he would never go to jail. Most of all, he feared that President Trump, his longtime boss, had forsaken him.
“Basically he needs a little loving and respect booster,” one of Mr. Cohen’s legal advisers at the time, Robert J. Costello, wrote in a text message to Rudolph W. Giuliani, the president’s lead lawyer. “He is not thinking clearly because he feels abandoned.”
That was last June. The “booster” from Mr. Trump never arrived. And by August, Mr. Cohen’s relationship with him had gone from fraught to hostile, casting a shadow on the Trump presidency and helping drive multiple criminal investigations into the president’s inner circle, including some that continued after the special counsel’s work ended.
In the biggest blow to the president personally, federal prosecutors in Manhattan effectively characterized Mr. Trump as an unindicted co-conspirator in a criminal case against Mr. Cohen involving hush money payments to a pornographic film actress. Mr. Cohen, and evidence gathered by prosecutors, implicated the president.
Now, as Mr. Cohen prepares to head to prison in two weeks, dozens of previously unreported emails, text messages and other confidential documents reviewed by The New York Times suggest that his falling out with Mr. Trump may have been avoidable.
Missed cues, clashing egos, veiled threats and unaddressed money worries all contributed to Mr. Cohen’s halting decision to turn on a man he had long idolized and even once vowed to take a bullet for, according to the documents and interviews with people close to the events. Some of the documents have been turned over to the prosecutors in Manhattan, and a small number were mentioned in the special counsel’s report released on Thursday, which dealt extensively with Mr. Cohen and referred to him more than 800 times.
Mr. Cohen held out hope for a different outcome until the very end, when he pleaded guilty and confessed to paying the illegal hush money to avert a potential sex scandal during the presidential campaign. Just hours earlier, wracked with indecision, he was still seeking guidance, looking, as one informal adviser put it, “for another way out.”
Mr. Cohen’s anxiety, on display in the documents, played a role in the undoing of his relationship with Mr. Trump, as did Mr. Costello’s lack of success in serving as a bridge to the White House. But also looming large were Mr. Giuliani’s and Mr. Trump’s failures to understand the threat that Mr. Cohen posed, and their inability — or unwillingness — to put his financial and emotional insecurities to rest.
After the Federal Bureau of Investigation raided Mr. Cohen’s home, office and hotel room last April, two of Mr. Cohen’s advisers explored whether the president might be open to a pardon, but Mr. Giuliani offered no assurances.
In June, Mr. Costello proposed that he and Mr. Giuliani, who have been friends for decades, meet urgently with Mr. Cohen to address his grievances and ease his anxieties. “Are we going to meet Thursday or Friday?” Mr. Costello texted Mr. Giuliani on a Monday. “I would like to get back to Michael with a response.”
But Mr. Giuliani did not respond. And when Mr. Costello followed up, “Can I get a response on the possible meeting?” Mr. Giuliani hesitated, replying, “Not yet because haven’t talked to President,” who was out of the country.
The next day, Mr. Cohen’s private admission to friends that he was open to cooperating with prosecutors suddenly appeared in the news. And Mr. Cohen relayed his growing displeasure with the Trump camp to Mr. Costello, sending the lawyer an article that suggested the president and his allies intended “to discredit Michael Cohen” and commenting in the email that “they are again on a bad path.” He also complained to Mr. Costello that the president had stopped covering his legal expenses.
Mr. Costello, who spoke with The Times after Mr. Cohen waived attorney-client privilege in February, said that without Mr. Cohen’s team and the president’s lawyers in sync, it was impossible to navigate the tumultuous relationship.
“What we had here was a failure to communicate,” said Mr. Costello, who was never formally retained by Mr. Cohen. “My mission was to get everyone tuned in to the same channel. My thought was a face-to-face meeting among all the lawyers together with Cohen would put everyone on the same channel. The meeting never happened, and the rest is history.”
In an interview, Mr. Giuliani acknowledged that the Trump team had pulled back from Mr. Cohen, saying it did so because prosecutors might have viewed friendly overtures as witness tampering, and because Mr. Cohen’s legal problems extended beyond his relationship with the president.
“It seemed like an unfortunate but sensible decision,” he said of the Trump team’s reticence toward Mr. Cohen. “The more I look back at it, the more I wonder if it was inevitable that Michael was going to crack.”
Mr. Cohen declined to comment, but his spokesman, Lanny Davis, suggested that the Trump team had initially tried to keep Mr. Cohen in “the liar’s club” of people covering for the president.
After pleading guilty in August, and hoping to reduce his three-year prison sentence, Mr. Cohen told federal prosecutors about Mr. Trump’s role in the hush-money scheme, as well as other aspects of the president’s company, where he had worked for a decade. He also suggested Mr. Trump’s team had dangled a pardon to keep him loyal, according to Mr. Davis, who described the effort as more an attempt “to keep Cohen in the tent of those lying and protecting Trump than anything else.”
Mr. Giuliani denied that a pardon had been offered. Mr. Costello told prosecutors in a recent meeting that the pardon discussion had been initiated by Mr. Cohen and rejected by Mr. Giuliani.
Unencumbered by the restraints on the investigation by Robert S. Mueller III, the special counsel, the prosecutors are now scrutinizing a wider swath of the president’s associates. About a dozen investigations are underway, including an inquiry into the Trump inaugural committee, which Mr. Cohen had assisted. Mr. Cohen also delivered congressional testimony that accused Mr. Trump of being a racist and a “con man.”
‘Blowing This Whole Thing’
The relationship between Mr. Cohen and Mr. Trump was looking up, at least for a brief period, last April.
Just days after F.B.I. agents searched his hotel room on Park Avenue, Mr. Cohen received a phone call from the president. “Stay strong,” Mr. Trump told him, according to the Mueller report and a person with knowledge of the call.
Mr. Cohen thanked Mr. Trump repeatedly, and later told people the message was clear: The president, who had a history of treating Mr. Cohen poorly, wanted to keep him on his team.
As federal prosecutors in Manhattan built a criminal case against Mr. Cohen, he set out to find a lawyer who had experience with the Manhattan United States attorney’s office, known as the Southern District of New York. That’s when an acquaintance at a local law firm emailed him to pitch the services of his colleague Mr. Costello. The firm was eager to become associated with such a high-profile case, and quickly embraced Mr. Cohen.
“I am really sorry to read about your troubles,” the acquaintance, Jeffrey Citron, wrote. “My partner Bob Costello was formerly the deputy chief of the criminal division of the U.S. Attorney’s office for the Southern District.” He said that if Mr. Cohen wanted to connect with Mr. Costello and obtain “his insight into your situation, it would be my pleasure to arrange.”
Mr. Cohen jumped at the offer: “I do. Can you connect me to him?”
Mr. Cohen met that day with Mr. Citron and Mr. Costello in a conference room at the Loews Regency Hotel, where he had been staying while his home underwent renovations. After drawing the curtains, Mr. Cohen revealed the depths of his despair.
“I was up on the roof. I was thinking of jumping,” Mr. Cohen told the two men, according to Mr. Costello.
Over the course of the two-hour meeting, Mr. Cohen and Mr. Costello discussed options for digging out of the mess, including possibly seeking immunity from prosecution in exchange for cooperation. They also talked about whether state prosecutors…