First off, he's covered in his contract against civil suits, so it won't cost him anything. Seems as though BOR had a sexual harassment charge a few years back that they settled on.
The ladies are piling on to be part of the settlement, but look at his lawyers. I've disliked Kelly Megyn since the Trump thing. I don't watch her, don't know how anyone does. Trump would be dumb to go on her show ever again. Ailes, is crusty old guy, who gets his kicks flirting with young women. Probably harmless... but stupid.
He will be ruined by a charge easily made and hard to defend against. A person's reputation interest is as important as the fact he may have insurance or an indemnity clause in his contract. By the way intentional torts are not covered by insurance. Sexual harassment is probably an intentional tort. Kelly is a lawyer and knows that. Interesting in that they are all old charges and Carlson was fired hence has a motive to "get even.' Kelly is in the middle of negotiations over salary and perks hence has a motive to play "hardball." Carlson even praised Ailes in writing.