Whether or not the claims against O'Reilly have merit, it does sound like extortion to me. The claims are titillating, but not substantial. For example, the former employee threatens to reveal that O'Reilly wife has a vibrator.) The main purpose was an exorbitant confidential settlement. Conventional wisdom says that extortion is legal if it is done by a lawyer, but the law doesn't actually read that way.
People think that Bill O'Reilly is a conservative, and he is on some issues, but he also suffers from the liberal delusion that courts, lawyers, government social workers, teachers, and other do-gooders can be relied upon to look out for the interests of children. On Oct. 3, 2002, he said:
That's one thing that Hillary Clinton got right -- everybody's gotta be looking out for the kids because sometimes the parents are not.It will be interesting to see how this lawsuit changes his worldview.
At one point in my wife's divorce lawsuit, her lawyer offered to keep the charges against me confidential. She was very careful not to make the offer in writing. She hinted about how I could be embarrassed by publicity from the case, and from the accusations that my wife was going to be making. She promised to file a motion to ask the court to seal the court records, but then refused to do so.
In retrospect, I was foolish to take her position at face value. She was using standard code words for an extortion attempt. Had I been represented by a lawyer, he would have advised me to respond with a confidential settlement offer. Her lawyer figured that I would be willing to pay a lot of money in order to keep her accusations secret.
But lawyers are almost never punished for extortion. (An isolated exception is cited on Volokh's legal blog.) The lawyers who were trying to extort Bill O'Reilly will just say that they were just trying to get a remedy for their client's grievances, and that they were even ethically bound to advance their client's interests in any way possible. My wife's lawyer would say something similar.