In the days leading up to the New York Times story about his secret $32 million settlement, Bill O'Reilly had high hopes about a deal with Sinclair.
He saw a path back to a nightly television broadcast -- a perch he lost in April when Fox ousted him amid a sexual harassment scandal.
Now, however, there are fresh doubts about his future. The revelation about O'Reilly's $32 million payment to Lis Wiehl, to stop her from suing him, has caused newfound embarrassment. "Nobody pays $32 million to anybody for false accusations. Nobody," former Fox anchor Gretchen Carlson said.
Many others share her skeptical view. In the wake of the Times story, O'Reilly lost the agents who had represented him for decades. The board of United Talent Agency, UTA for short, decided to drop him on Monday. The move will take effect at the end of the year, according to The Hollywood Reporter, which was first to report on UTA's decision.
Still, some right-wing media executives are not ruling anything out. "America is a very forgiving nation," Newsmax CEO Chris Ruddy told CNN.
O'Reilly's spokesman Mark Fabiani said Tuesday that "he has lined up new representation already." Fabiani said he could not identify who because "the firm isn't ready to announce formally yet."
When the Times story came out on Saturday, Fabiani decried the "leaks coming out of Fox," raising the prospect of competitive back-stabbing. O'Reilly didn't blame Fox explicitly, but he said he thought someone was trying to kill his chances at a new TV career.
His public posture hinted at his private hopes for a comeback. O'Reilly was feeling newly confident about the Sinclair possibility, according to people who spoke with him and others familiar with the negotiations.
There was talk about a new O'Reilly-branded 8 p.m. show on a cable channel that Sinclair is trying to acquire, according to two sources, both of whom insisted on anonymity to discuss private deliberations.
The sources disagreed on whether a deal was actively in the works. While one of the people said yes, others said this was wishful thinking on O'Reilly's part. There was agreement on one thing: O'Reilly was itching to get back in the arena through a tie-up with Sinclair.
In response to this story, a spokeswoman for the company said "Sinclair is not in discussions with Mr. O'Reilly."
For O'Reilly's allies, that doesn't rule out potential discussions in the future.
Some of his supporters are predisposed to dismiss the settlement stories as a product of anti-O'Reilly media outlets — an echo of the "fake news" charges promoted by President Trump's core supporters.
But advertisers are less inclined to look past the allegations of wrongdoing by O'Reilly. Dozens of companies yanked ads from his Fox show in April, and there's little reason to think they would line up to sponsor a new version of his show.
O'Reilly has touted the success of his nightly podcast and subscription-based web site, but his profile has been severely diminished by his exit from Fox.
His return to Fox's studio, in a late September visit to Sean Hannity's show, scored high ratings, but a second visit is exceedingly unlikely, in light of the $32 million settlement news. O'Reilly has adamantly denied the allegations, claiming that he agreed to the settlements to protect his family.
So that leaves companies like Sinclair -- ones that are looking to rival Fox in some respects.
The conservative-leaning Sinclair Broadcasting owns local TV stations across the company. It is in the process of buying another broadcaster, Tribune Media, although the deal faces some opposition.
Through Tribune, Sinclair could take over WGN America, a relatively small cable channel. There has been rampant speculation that Sinclair could seek to convert WGN into a Fox News challenger.
This is a lot easier said than done, given onerous cable contracts and the sheer amount of money that would be required to create a national news channel. Still, O'Reilly has been eying Sinclair, several sources said.
There are several cable channels with a conservative bent where O'Reilly would fit in, but they would have a hard time affording his salary -- even if he accepted a dramatic pay cut. He was reportedly paid $25 million a year in his last Fox contract.
One of the channels, One America News, also known as OANN, publicly yanked its job offer back in June.
OANN executives did not respond to requests for comment this week.
Ruddy has been building up Newsmax TV as a Fox alternative, but he has focused more on distribution deals than on talent deals.
He declined to comment directly on the possibility of hiring O'Reilly, but he didn't rule it out either.
"There's no question Bill O'Reilly has been damaged by some of this, but the bottom line is the recent accuser fully retracted all of her allegations," Ruddy said. "America is a very forgiving nation and people love a comeback story. If anybody can do it, Bill is the guy."
O'Reilly sometimes uses Newsmax's studio space in New York to record his podcast. Ruddy said it is not a business relationship, it's just a courtesy to a friend.
Glenn Beck is also a friend of O'Reilly's, but Beck's network The Blaze is facing financial problems. Beck laid off about 20 percent of his staff over the summer.
"Can O'Reilly make a comeback? Possibly," said Nicole Hemmer, author of "Messengers of the Right," a book about conservative media. "What will limit his opportunities isn't his tarnished reputation — it's whether smaller companies think they have deep enough pockets to cover future settlements."
Hemmer pointed out that disgraced former Fox News CEO Roger Ailes was reportedly working on a new conservative media venture in the days before his death in May.
"We've seen in the past few years that sexual harassment scandals are not deal breakers for conservative media," Hemmer said. The election of Donald Trump, who had broad support within right-wing media during the general election, is the prime example."
