David Boies, a lawyer who represented Mr. Weinstein when his contract was up for renewal in 2015, said in an interview that the board and the company were made aware at the time of three or four confidential settlements with women.
And in the waning hours of last week, as he struggled to retain control of the business in the wake of allegations first reported by The New York Times, Harvey Weinstein fired off an email to his brother and other board members asserting that they knew about the payouts, according to people who spoke on the condition of anonymity about the confidential communication.
Lance Maerov, the board member who handled the contract negotiations, acknowledged in an interview that he had been told of settlements, but said that he had assumed they were used to cover up consensual affairs. Mr. Maerov said that his chief concern had been whether Mr. Weinstein’s behavior posed a legal liability for the business, and that after receiving assurances that no company money was used and that no complaints against Mr. Weinstein were pending, he had approved the contract.
Mr. Glasser declined to comment, as did Bob Weinstein. The board members Tarak Ben Ammar and Richard Koenigsberg did not respond to messages.
The contract came up for renewal just as Ambra Battilana, an Italian model, reported to the police that Harvey Weinstein had groped her during a work meeting at his Manhattan office. (Working with the police, she captured Mr. Weinstein speaking about the encounter in audio that was published along with an article in The New Yorker on Tuesday.)
The district attorney’s office declined to press charges, and Mr. Weinstein insisted that it was a setup, but some board members and top executives worried that Mr. Weinstein had engaged in a pattern of behavior that could jeopardize the company.
After the episode, Mr. Maerov said, Mr. Weinstein refused to let the board review his personnel file directly. Instead, it was examined by an outside lawyer, H. Rodgin Cohen, who assured the board in a September 2015 letter that it was legally safe to retain Mr. Weinstein because there were no unresolved complaints or threats of litigation against him, according to two people who saw the letter and spoke on the condition of anonymity.
In the file, Mr. Cohen came across a single sexual harassment allegation, from 2014, involving a former temporary employee, Emily Nestor, according to a person familiar with his review.
Ms. Nestor was new to the job at the company’s Los Angeles office when Mr. Weinstein invited her to breakfast at the Peninsula Beverly Hills and made her an offer: If she accepted his sexual advances, he would boost her career, according to accounts, viewed by The Times, that she provided to colleagues who passed them along to executives. She declined the offer and never intended to complain to human resources personnel, internal records show.
It is unclear whether the board was told of her allegation — by the executives or by Mr. Cohen, who declined to comment for this article. Mr. Maerov said, “Her name came up in 2015, but I don’t remember who brought it up.”
Mr. Cohen’s letter to the board did not describe the contents of Mr. Weinstein’s file, nor did it address whether Mr. Weinstein had entered into private settlements with women who complained of misconduct.
Mr. Boies said that at the time of the contract negotiations, he was aware of three or four settlements with women. He would not specify which ones, and would not say who within the company or the board was told of them or how the information was communicated.
His law firm, Boies, Schiller & Flexner, has represented the Weinstein Company and its predecessor, Miramax, in a variety of legal matters. He has also worked directly for Mr. Weinstein, as was the case during the contract negotiations. Mr. Boies said there was one settlement to which he “gave advice at or about the time it was being entered into” but declined to say which one.
The Times reported last week that Mr. Weinstein had entered into private settlements with at least eight women who complained of misconduct while he was at the Weinstein Company or Miramax. The Times was able to identify five of them. In the 1990s, payments were made to two female Miramax employees and the actress Rose McGowan. In 2015, settlements were struck with Ms. Battilana and Lauren O’Connor, an employee of the Weinstein Company who submitted a searing memo in November that year alleging persistent sexual harassment by Mr. Weinstein.
Mr. Maerov said that he had been prepared to investigate Ms. O’Connor’s allegations but that Mr. Weinstein’s lawyers told him she had withdrawn her complaint as part of a settlement. He said they also told him that Ms. O’Connor had submitted a letter of appreciation to the company and continued to work there for a period of time. He said he did not see a need to press for more details or follow through with an investigation.
He recalled being told of the existence of other settlements, but never their details. He said he assumed they involved consensual affairs because Mr. Weinstein had insinuated that he was a philanderer. He said he was never told of a settlement with Ms. Battilana or any other payments made to women who alleged misconduct.
To address any lingering concern about Mr. Weinstein’s behavior, Mr. Maerov said he successfully pushed a new code of conduct at the company that included a detailed description of sexual harassment. The contracts for Mr. Weinstein and other top executives also came with a new clause: They would face costly fines if the company ever had to pay a settlement for their misconduct.
“I don’t know what else I could have done,” Mr. Maerov said.
Over the last week, four members seen as friendly with Mr. Weinstein have left the board. Last Friday, the four who remained — Bob Weinstein, Mr. Ben Ammar, Mr. Koenigsberg and Mr. Maerov — announced that Harvey Weinstein would take a leave of absence while an outside lawyer investigated the complaints. Two days later, they fired him, and began discussing changing the company’s name and removing him from the credits of upcoming projects.
The effort to separate him from the company is complicated by the fact that he and his brother own 42 percent of the business, its largest share.
In their statement on Tuesday, the four board members said they would assist with any investigations “while pursuing justice for the victims and a full and independent investigation of our own.”