The legal facts of the Letterman blackmail story seem clear. A man says he has damaging information about David Letterman. The man threatens to release said information unless he is paid 2 million dollars. David Letterman goes to the district attorney's office. Police arrest the blackmailer. Simple, right?

Actually, says Joe Weisenthal, it's pretty confusing.

After all, it's ok to go to the press with an embarrassing story. And it's ok to be paid to keep a story quiet. And it's ok to sue over something embarrassing, but then drop the suit after a multi-million settlement from the accused.
So why isn't it okay to blackmail? There are a couple problems with a blackmail free market, Weisenthal acknowledges. With no guarantee of compliance on the part of the person paid off, the system wouldn't really work. But the question remains: is there something inconsistent in the current laws surrounding the crime?