Last January, six months after Fox News ousted its chairman amid a sexual harassment scandal, the network’s top-rated host at the time, Bill O’Reilly, struck a $32 million agreement with a longtime network analyst to settle new sexual harassment allegations, according to two people briefed on the matter — an extraordinarily large amount for such cases.
Although the deal has not been previously made public, the network’s parent company, 21st Century Fox, acknowledges that it was aware of the woman’s complaints about Mr. O’Reilly. They included allegations of repeated harassment, a nonconsensual sexual relationship and the sending of gay pornography and other sexually explicit material to her, according to the people briefed on the matter.
It was at least the sixth agreement — and by far the largest — made by either Mr. O’Reilly or the company to settle harassment allegations against him. Despite that record, 21st Century Fox began contract negotiations with Mr. O’Reilly, and in February granted him a four-year extension that paid $25 million a year.
Interviews with people familiar with the settlement, and documents obtained by The New York Times, show how the company tried and ultimately failed to contain the second wave of a sexual harassment crisis that initially burst into public view the previous summer and cost the Fox News chairman, Roger Ailes, and eventually Mr. O’Reilly, their jobs.
In January, the reporting shows, Rupert Murdoch and his sons, Lachlan and James, the top executives at 21st Century Fox, made a business calculation to stand by Mr. O’Reilly despite his most recent, and potentially most explosive, harassment dispute.
But by April, the Murdochs decided to jettison Mr. O’Reilly as some of the settlements became public and posed a significant threat to their business empire.
Early that month, The Times reported on five settlements involving Mr. O’Reilly, leading advertisers to boycott his show and spawning protests calling for his ouster. About the same time, the O’Reilly settlements arose as an issue in 21st Century Fox’s attempt to buy the European satellite company Sky.
In addition, federal prosecutors who had been investigating the network’s handling of sexual harassment complaints against Mr. Ailes had asked for material related to allegations involving Mr. O’Reilly, according to an internal Fox email obtained by The Times.
“Their legal theory has been that we hid the fact that we had a problem with Roger,” Gerson Zweifach, Fox’s general counsel, wrote in the email, referring to the prosecutors and Mr. Ailes, “and now it will be applied to O’Reilly, and they will insist on full knowledge of all complaints about O’Reilly’s behavior in the workplace, regardless of who settled them.”
He warned the Murdochs that they should expect details from the January settlement to become public. Six days later, Mr. O’Reilly was fired.
In a statement, 21st Century Fox said it was not privy to the amount of the settlement and regarded Mr. O’Reilly’s January settlement, which was reached with a 15-year Fox News analyst named Lis Wiehl, as a personal issue between the two of them.
Regarding Mr. O’Reilly’s contract extension, the company said Fox News “surely would have wanted to renew’’ Mr. O’Reilly’s contract, noting that “he was the biggest star in cable TV.’’
It emphasized that provisions were added to the new contract that allowed for his dismissal if new allegations or other relevant information arose. “The company subsequently acted based on the terms of this contract,’’ the statement said.
In an interview on Wednesday, Mr. O’Reilly, at times combative and defiant, said there was no merit to any of the allegations against him. “I never mistreated anyone,” he said, adding that he had resolved matters privately because he wanted to protect his children from the publicity.
“It’s politically and financially motivated,” he said of the public outcry over the allegations against him, “and we can prove it with shocking information, but I’m not going to sit here in a courtroom for a year and a half and let my kids get beaten up every single day of their lives by a tabloid press that would sit there, and you know it.”
He declined to specifically address questions about the settlement with Ms. Wiehl or any others.
Mr. O’Reilly’s lawyer, Fredric S. Newman, described his client’s relationship with Ms Wiehl as an 18-year friendship in which she at times gave him legal advice.
Asked about the allegation of nonconsensual sexual relationship, a representative for Mr. O’Reilly, Mark Fabiani, said that 21st Century Fox was “well aware” Ms. Wiehl had signed a sworn affidavit “renouncing all allegations against him,” adding that after receiving the document Fox News offered Mr. O’Reilly “a record breaking contract.”
Lawyers for Ms. Wiehl, Jonathan S. Abady and O. Andrew F. Wilson of the firm Emery Celli Brinckerhoff & Abady, declined to comment.
Details of the settlement and how the company handled the O’Reilly situation emerged from interviews with two people briefed on the agreement and several others familiar with the dispute; all of them spoke on the condition of anonymity to discuss sensitive private negotiations. The Times also viewed a copy of a document partly outlining the agreement and other documents related to the dispute, and received answers to written questions from 21st Century Fox.
The disclosure of Ms. Wiehl’s settlement follows a wave of public accusations against the Hollywood studio mogul Harvey Weinstein, which has increased scrutiny of sexual harassment in the workplace. The Times reported this month that Mr. Weinstein had reached at least eight settlements with women, most of whom received between $80,000 to $150,000.
Ms. Wiehl’s $32 million deal dwarfs other previously known sexual harassment settlements at Fox News. The largest of those was the $20 million payout the former host Gretchen Carlson received after she sued Mr. Ailes in July 2016.
The settlement with Ms. Wiehl was more than three times the amount of any of Mr. O’Reilly’s previously known deals; in 2004, he had settled a lawsuit with a producer, Andrea Mackris, for about $9 million. Publicly known harassment settlements involving Mr. O’Reilly have totaled about $45 million.
Claims Covering 15 Years
A graduate of Harvard Law School, Ms. Wiehl started making regular appearances on Mr. O’Reilly’s show in 2001, when she joined Fox News as a legal analyst. During a segment in September of that year, Mr. O’Reilly announced that Ms. Wiehl had landed a job at the network and said she owed him.
“Hey, you know, Lis, I got you this job,” he said. “You know that?”
“I know you did, I know,” she replied.
“So you owe me,” Mr. O’Reilly said. “You owe me big.”
“No, no, no,” Ms. Wiehl said.
Mr. O’Reilly also made suggestive remarks to Ms. Wiehl on the air. During one segment on his radio show in 2005 about a strip club, he suggested that she learn how to dance for a $10,000 tip.
Ms. Wiehl last appeared on Mr. O’Reilly’s show on Dec. 20, 2016. On Jan. 2, Mr. O’Reilly received a draft of a lawsuit Ms. Wiehl was threatening to file outlining her allegations of sexual harassment, and 21st Century Fox received a copy of the complaint soon afterward.
Both Mr. O’Reilly and 21st Century Fox were at critical junctures. If the allegations became public, they would not only embarrass Mr. O’Reilly and harm his career, but could jeopardize his yearslong custody battle with his ex-wife. A hearing was set for later that month, when Mr. O’Reilly’s lawyers planned to argue that he should be given more time with his son, according to two people familiar with the dispute.
At Fox News, Ms. Kelly had just announced that she was leaving the network for NBC. Her departure made Mr. O’Reilly’s presence in the prime-time lineup even more crucial, with his show pulling in top ratings and generating hundreds of millions of dollars in revenue.
Mr. Newman told 21st Century Fox that Mr. O’Reilly considered it a personal matter and that he would resolve it on his own. Mr. Newman handled the negotiations with lawyers for Ms. Wiehl.
After a few days of negotiation, Mr. O’Reilly and Ms. Wiehl reached a deal, according to a copy of the term sheet for the agreement that was sent anonymously to The Times and confirmed by the people briefed on the settlement. Dated Jan. 7, it called for Ms. Wiehl to be paid over a period of time to ensure her silence. In return, she agreed not to sue Mr. O’Reilly, Fox News or 21st Century Fox. And all photos, text messages and other communications between the two would be destroyed.
Ms. Wiehl signed an affidavit, dated Jan. 17 and obtained by The Times, stating that the two sides had resolved their dispute and that she had “no claims against Bill O’Reilly concerning any of those emails or any of the allegations in the draft complaint.” In the affidavit, she said she had worked as a lawyer for Mr. O’Reilly and was serving in that capacity when he sent her “explicit emails that were sent to him.”
In response to questions about why he sent sexually explicit material to Ms. Wiehl, Mr. O’Reilly said that during his time at the network, he had been sent threatening messages almost every day, including some that had obscene material. To deal with this problem, Mr. O’Reilly said, he set up a system in which the material would be forwarded to his lawyers so they could evaluate whether he needed to take any legal action. Mr. O’Reilly said Ms. Wiehl was among those lawyers.
Although the matter had been settled confidentially, Mr. O’Reilly’s lawyers were concerned about keeping the dollar figure secret. Mr. Newman provided the company with a document that informed them of the deal but did not include the dollar figure.
The company said Mr. Newman made clear that it would not be told the financial terms because Mr. O’Reilly thought the company “leaked sensitive information.’’
In February, Mr. O’Reilly received his new contract, with a salary increase to $25 million, from about $18 million. It’s not clear who initiated negotiations for the extension. Mr. Newman says Fox News pushed to renew the contract; the company says the negotiations were bilateral.
“It was Fox News that wanted to renew Bill O’Reilly because of the Megyn Kelly defection,” Mr. Newman said, adding that Mr. O’Reilly was a wealthy man who had no need for extra money. The company said it would have renewed his contract whether Ms. Kelly stayed or left.
Mr. Fabiani, Mr. O’Reilly’s representative, said that he was concerned that 21st Century Fox’s statements about Mr. O’Reilly were designed to hurt his brand.
“Up to this point, Fox News and Mr. O’Reilly have had a constructive business relationship — with Fox News even running ads for his new book on their air,” Mr. Newman said. “We hope that all the leaks coming out of Fox are not designed to hurt Bill O’Reilly in the marketplace.”
‘A Critical Development’
In mid-April, after The Times revealed five of Mr. O’Reilly’s settlements, the public scrutiny was creating more problems for Fox, and the company started an investigation into his behavior. On April 13, Mr. Zweifach, the company’s general counsel, notified the Murdochs about a new document request from federal prosecutors investigating the network.
“We have had a critical development in the O’Reilly matter,” Mr. Zweifach wrote in an email, which was delivered anonymously to The Times. (The company declined to comment on the email.)
In the email, Mr. Zweifach explained to the Murdochs that the government request for all documents related to sexual harassment allegations against Mr. O’Reilly would “clearly call for the production of the Wiehl materials.”
Mr. Zweifach said 21st Century Fox could try to challenge the request by telling prosecutors that the case had not been settled by the company, so shareholder money was not involved. But he added that there was “virtually no chance that they will back off.”
“The fact that it seems like a bogus theory of federal securities law disclosure will not stop them from exploring it,” Mr. Zweifach added.
The public outcry, advertising boycott and federal inquiry were not the only issues weighing on the Murdochs. The bid for the Sky satellite company was a high priority for the elder Mr. Murdoch, an acquisition he considered important to his legacy.
Mr. O’Reilly’s settlements arose as an issue at an April 18 meeting between 21st Century Fox executives and the British regulators who were reviewing the company’s bid, according to a government report on the meeting. The report said regulators were “concerned that board members regarded Mr. O’Reilly’s settling cases personally as somehow a point in his favor.”
A day after the meeting with regulators, while Mr. O’Reilly was on vacation in Italy, he was dismissed. He left the network with a $25 million payout.
In a statement provided this past week, the company said: “21st Century Fox has taken concerted action to transform Fox News including installing new leaders, overhauling management and on-air talent, expanding training, and increasing the channels through which employees can report harassment or discrimination.’’ It added that “these changes come from the top.’’
The company’s bid for Sky remains under regulatory scrutiny.
In response to questions from The Times, the company said that it had “complied fully” with document requests from the United States attorney’s office and that “it would be inappropriate to comment on a pending investigation other than to reiterate that we are cooperating fully.”
In recent weeks Mr. O’Reilly has made several public appearances to promote a new book. He said on the “Today’’ show that he never sent a lewd text or email to a Fox News employee, that his conscience is clear and that “a political and financial hit job” brought him down.
“This is horrible, it’s horrible what I went through, horrible what my family went through,” Mr. O’Reilly said in a raised voice at the end of the interview with The Times. “This is crap, and you know it.”