David Letterman reveals extortion attempt and affairs

On October 1, 2009, David Letterman announced on his show that he had been the victim of a blackmail attempt by a person threatening to reveal his sexual relationships with several of his female employees—a fact Letterman immediately thereafter confirmed. The extortionist demanded $2 million, but Letterman contacted the Manhattan District Attorney's office and partook in a sting operation that involved the handover of a fake check. Joe Halderman, a producer of the CBS news magazine television series 48 Hours, was arrested after trying to deposit the check. He was indicted by a Manhattan grand jury following testimony from Letterman and pleaded not guilty to a charge of attempted grand larceny on October 2, 2009. Halderman pleaded guilty in March 2010 and was sentenced to six months in prison, followed by probation and community service. One of the women involved was Stephanie Birkitt, Letterman's longtime personal assistant who often appeared on the show. She had shared a residence with Halderman until a month before the revelations. The case raised questions about whether Letterman's affairs with subordinates created an unfair working environment. On October 3, 2009, TMZ reported that a former CBS employee, Holly Hester, had had a yearlong secret affair with Letterman in the early 1990s while she was his intern and a student at New York University. On October 5, 2009, Letterman publicly apologized to his wife and staff on his show. Three days later, Worldwide Pants announced that Birkitt had been placed on a 'paid leave of absence' from the Late Show.