Michael Cohen and Rosie O’Donnell: A Love Story

The text came through on Michael D. Cohen’s iPhone on Monday morning, shortly before he took the stand in a Manhattan courtroom as the star witness in the criminal case against his former boss, Donald J. Trump: “breathe – relax – tell the truth – u got this – i love u.”

An hour later, another text came in from the same person: “Ur doing great.”

“Thank you and truly love you,” Mr. Cohen wrote back to the sender, who was not his wife, either of his children or another family member, but the comedian and actress Rosie O’Donnell.

Politics, the cliché goes, makes strange bedfellows. But few relationships seem as unlikely as the intense bond that has developed between Mr. Cohen and Ms. O’Donnell, two Long Island natives of the same generation who were pulled into Mr. Trump’s force field in vastly different ways years ago, and who connected as they surveyed the damage afterward.

It is not lost on Ms. O’Donnell, 62, that Mr. Cohen, 57, once helped carry out Mr. Trump’s campaign of insults against her, tormenting her for her looks and her weight and calling her “wacko.”

The story of their friendship is one of New York celebrity and Long Island aspirations, blustery personalities and oversize egos. It involves a prison visit, Barbara Walters, Twitter insults, forgiveness and a kind of shared world-weariness.

“We talk and communicate on a regular basis,” Ms. O’Donnell said in a long phone conversation on Monday. “I know this has been a tumultuous time, so I check in. It’s a big thing to be in a position to be able to change the whole country in some way.”

An Unlikely Pairing

To understand this story, you must first understand Ms. O’Donnell’s distaste for Mr. Trump, which stretches back three decades. In 1991, she got her big break in “A League of Their Own,” the film about a female baseball team during World War II.

One of her co-stars was Madonna, whom she read during filming had been on a date with Mr. Trump. When Ms. O’Donnell made a joke about it to Madonna, the singer responded that nothing of the sort had taken place, that Mr. Trump had simply made up the story for publicity.

In 1993, Ms. O’Donnell was cast in a Broadway revival of “Grease.” When a member of the cast was invited to Mr. Trump’s wedding to Marla Maples at the Plaza Hotel, Ms. O’Donnell attended as a plus one. She was not impressed with the groom.

“He walked down the aisle and shook the celebrities’ hands,” Ms. O’Donnell said on Monday.

Things escalated in 2006, when Ms. O’Donnell joined ABC’s “The View,” the chat fest co-created by the anchorwoman Barbara Walters.

Shortly before Christmas that year, news broke that the recently crowned Miss USA, Tara Conner, was caught doing cocaine in a New York nightclub.

Mr. Trump, who owned the Miss USA pageant, announced that Ms. Conner would be forgiven if she went to rehab. The media coverage he received for this was largely positive.

On “The View,” Ms. O’Donnell, who felt Mr. Trump was capitalizing on a young woman’s drug problem, veered from conventional wisdom. She flipped her hair over her face and did a withering impersonation of Mr. Trump, and she questioned his role as moral arbiter and successful businessman.

“He inherited a lot of money and he’s been bankrupt so many times,’’ she exclaimed, adding that “the people beneath him, who he owed money to, got shorted out of the money.” (Mr. Trump had never personally declared bankruptcy, though his businesses had.)

Mr. Trump threatened to sue “The View” and Ms. Walters personally. Ms. Walters got on the phone with him to smooth things over. Soon enough, Mr. Trump was appearing all over cable news calling Ms. O’Donnell “wacko” and “fat,” and he said Ms. Walters personally told him that she regretted hiring Ms. O’Donnell.

The year after, despite soaring ratings, Ms. O’Donnell left the show. But her feud with Mr. Trump never ended. She became a fixture and a punchline in the supermarket tabloids, which she always suspected, without being able to prove, was the work of Mr. Trump and of the man who was always at his side, Mr. Cohen.

The Letter to an Inmate

Ms. O’Donnell has long had what her friends sometimes call a rescuer complex. On her own talk show, she occasionally hired the most down-and-out stand-ups to work in the writers’ room. And despite what Ms. Walters reportedly said about her, Ms. O’Donnell accompanied her to the theater when, toward the end of her life, she was in failing health.

As a comic, Ms. O’Donnell is bighearted and pugnacious, with a desire both to lift people and to land a blow. So she was well suited, in a way, to become friends with a man who went from being the dedicated foot servant of her tormentor to his most dangerous defector.

On Dec. 18, 2019, she watched the House impeach Mr. Trump for the first time. She found herself thinking of his loyal fixer, Mr. Cohen, who had been sent upstate to prison that month, after pleading guilty to tax evasion and campaign finance violations. (The campaign finance charges are at the heart of the criminal case now being tried against Mr. Trump, who prosecutors say used Mr. Cohen to help cover up a story about his involvement with Stormy Daniels, a pornographic film actress. Mr. Trump has pleaded not guilty and denounced Mr. Cohen as a “rat” and a liar.)

Ms. O’Donnell felt Mr. Cohen was paying the price for Mr. Trump’s sins. And Mr. Cohen, with his heavy Nassau County accent, reminded her of the boys she knew growing up in Commack, on Long Island. “He was every guy I went to high school with,” she said. (Mr. Cohen grew up in Lawrence, about 30 minutes from Commack.)

Mr. Cohen was sent to Otisville, 86 miles north of New York City, as part of a three-year sentence. Ms. O’Donnell found him. “I got his inmate number and I sent him a letter,” she said. It was six pages long.

In the letter, Ms. O’Donnell said she believed that Mr. Cohen had helped Mr. Trump wage his campaign to discredit her. Nevertheless, she said, she was grateful to him, and viewed his decision to turn on his boss as an act of heroism. She believed in redemption and wanted Mr. Cohen to know that she forgave him for everything that had transpired between her and Mr. Trump.

“When someone is in a relationship that unhealthy and breaks free, it’s a very lonely time,” she said on Monday, adding that she did not necessarily expect to hear back from Mr. Cohen. She also realized he might not be seeking her forgiveness.

But Inmate No. 86067-054 soon wrote back.

“He asked me to come visit him,” Ms. O’Donnell said. The last person she visited in prison, in 2004, was her friend Martha Stewart, who was serving five months in a federal penitentiary on charges related to insider trading.

To visit Ms. Stewart, Ms. O’Donnell had to fly to Alderson, W. Va. To see Mr. Cohen, Ms. O’Donnell simply got in a car and had her driver take her to Otisville.

She thought she would be with Mr. Cohen for an hour. Instead, they spent more than six hours talking. He apologized to her for the role he played in Mr. Trump’s attacks, Ms. O’Donnell said.

They discussed the state of the republic, they discussed Mr. Trump, and they discussed being parents and growing up on Long Island. At one point, they held hands, she said. Over the course of the afternoon, Mr. Cohen showed some of his old traits — a grandiosity and a boost in his self-esteem from being close to celebrity.

“Michael was sort of proudly introducing me to people, the friends he had met there,” Ms. O’Donnell said. Yet he also displayed signs of being “quiet,” inquisitive and self-reflective, she said.

Mr. Cohen’s character is a focus of Mr. Trump’s trial. Even as prosecutors present Mr. Cohen as the key witness against his former boss, they describe him as a liar and a jerk and suggest he can be trusted only sparingly.

Ms. O’Donnell, however, believes Mr. Cohen has been trying to sort out how his need for attention and the proximity of a celebrity led him to get “caught in the swirl and undertow” of a toxic relationship, as she put it in the interview on Monday.

Staying in Touch

After 13 months in Otisville, Mr. Cohen was released in May 2020 and permitted to serve the rest of his sentence from his Park Avenue apartment.

That September, Simon & Schuster published “Disloyal: A Memoir,” Mr. Cohen’s account of his life with Mr. Trump.

In it, Mr. Cohen described his own involvement in the smearing of Ms. O’Donnell, and how he had winced when Mr. Trump’s comments about her came up during a presidential debate moderated by Megyn Kelly in 2015. Ms. Kelly asked Mr. Trump about his verbal tirades against women, whom he called “fat pigs,” “dogs,” “slobs” and “disgusting animals.”

“Only Rosie O’Donnell,” Mr. Trump replied.

“The O’Donnell feud had indeed been one of the lowest of his many Twitter lows,” Mr. Cohen wrote in the memoir. “My knowledge was firsthand, because I had access to Trump’s Twitter account and permission to post on his behalf, one of only two people with that privilege. I’d been part of the brain trust coming up with juvenile taunts to O’Donnell and so I was acutely aware of the childish impulse behind the insults.”

With the book’s rollout came a podcast hosted by Mr. Cohen, “Mea Culpa,” whose first guest was Ms. O’Donnell. “I can’t say enough about her as a person, other than that the woman is truly a mensch,” he said to introduce her.

Mr. Cohen said the letter she sent him about his work for Mr. Trump was a “kick to the gut” that helped him realize “how much I had helped him to hurt people, yourself included.”

“Here was a woman I helped attack and vilify on behalf of Donald J. Trump and she reached out to me out of kindness and empathy,” he added. “I saw a better way forward.”

Since then, they have stayed in touch. In December, they had dinner at a restaurant in New York, the name of which eludes her.

“Some very fancy place on Park Avenue that’s popular with bankers,” she said by phone on Monday afternoon from her home in Los Angeles, as she packed for a trip to New York, where she will be filming scenes on “And Just Like That,” the “Sex and the City” revival.

“We had a steak,” she said.

Ms. O’Donnell said on Monday that it had not always been easy helping Mr. Cohen navigate his public profile. “He has a hard time taking suggestions.”

Last week, the judge overseeing the Trump trial made it clear to prosecutors that Mr. Cohen’s conduct, including his TikTok appearances taunting and disparaging Mr. Trump, was causing problems.

But Ms. O’Donnell’s assessment of what he did in court on Monday was unambiguous.

“A home run,” she texted him. “Day one done and u killed it.”

His response? “I’m beyond tired.”