It has been noted that a text came through on Michael D. Cohen’s iPhone on Monday morning ahead of taking 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.
A few relationships seem as unlikely as the intense bond that has developed between Cohen and 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.
O’Donnell noted that Cohen 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 oversized 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.”
The relationship blossomed with O’Donnell’s distaste for 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 Trump. Ms. O’Donnell made a joke about it to Madonna, the singer responded that nothing of the sort had taken place, and that Trump had simply made up the story for publicity.
In 1993, 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 O’Donnell joined ABC’s “The View,” the chat fest co-created by the anchorwoman Barbara Walters. Shortly ahead of Christmas that year, news broke that the recently crowned Miss USA, Tara Conner, was caught doing cocaine in a New York nightclub.
Trump, who owned the Miss USA pageant, announced that Conner would be forgiven if she went to rehab. The media coverage he received for this was largely positive. On “The View,” O’Donnell, who felt Trump was capitalizing on a young woman’s drug problem, veered from conventional wisdom. She went on to flip 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.)
It has been noted that Trump threatened to sue “The View” and Walters personally. Walters got on the phone with him to smooth things over. Soon, 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.
