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Legal experts around the country are in disagreement as to how comedian David Letterman should have handled threats of extortion against him. Some think it was wise to contact the authorities right from the start while others think it could have been handled in a more private manner.

Details of the bizarre story emerged last week when Letterman divulged some of the details on his late night show. He told the audience that someone had given him a package that contained information that showed that Letterman had engaged in sexual activity with some of the females that work for him on the show. It was later revealed that the person in question was a producer for the television show 48 Hours by the name of Robert “Joe” Halderman. In exchange for keeping quiet, Halderman demanded $2 million from Letterman.

Letterman immediately contacted his attorney who met with Halderman at the Essex House hotel. After three meetings with Letterman’s lawyer, Halderman was arrested on September 30 when he tried to cash the $2 million check. Halderman is said to have learned of Letterman’s affairs through his former girlfriend, Stephanie Birkitt, who was Letterman’s former assistant.

When Letterman revealed this information to his audience last week they thought he was kidding and some people even laughed. The staff was not told ahead of time what was happening so they were unprepared as well. From the moment Letterman dropped the bombshell that is all people have been talking about.

Criminal defense attorney Mark Geragos believes that Letterman could have handled things a lot more discreetly. He has handled several cases for celebrities and high profile people and claims that he has never had to shell out any money for extortion cases once you let the blackmailer know that he or she is committing a crime.

Besides the legal ramifications, Geragos feels that Letterman has left himself wide open to being the butt of jokes, criticism for his behavior and backlash from people who believe that he is guilty of sexual harassment, something that is taken very seriously in today’s society.

On the other side of the fence is professional crisis manager Eric Dezenhall who feels that sometimes it is best to go right to the authorities, especially if you are dealing with an amateur. He claims that there are ways to legally demand money from celebrities without really breaking the law. He has had his share of clients whom he has had to protect but he wouldn’t name any names.

Extortion demands against high profile personalities are certainly nothing new. Bill Cosby had to admit to an extramarital affair years ago and most recently John Travolta and his wife Kelly Preston were victims of a cruel request for money in exchange for keeping details of their son’s death quiet.

The fate of Letterman’s career and marriage are on the line and it is anyone’s guess as to how they will play out. He apologized on his show to the women on his staff and especially his wife of five years, Regina.

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