One of the recurring issues in the law of lawyering is deciding when a lawyer's demand letter is simply lawyering in the lawful sense and when it's extortion in the criminal sense. In California, we had the Flatley case, in which a lawyer demanded money from a famous dancer/choreographer but ended up getting sued for civil damages and, if I recall correctly, losing $11 million.
Now we are seeing news accounts about the extortion trial of Karen Sypher, who had claimed that she had been raped by Rick Pitino, a well-known college basketball coach. Sypher's lawyer had had his own intimate relationship with Sypher and he wrote a $10 million demand letter to Pitino. The prosecution theory, though, is that the lawyer had been manipulated by Sypher. Overlawyered, the ABA Journal, and USA Today are covering the trial.