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What not to say to a big insurance company during a policy dispute

"No judge in the world is going to rule for a 200 billion dollar company," Anthony Digati is alleged to have told the New York Life Insurance Company. He was wrong about that.

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Anthony Digati wasn’t just another disgruntled client of the New York Life Insurance Company. He was a former agent and manager at the firm who had become ensnared in a $49,500 policy dispute.

Like many customers of large insurance companies, Mr. Digati, 52, of Chino, Calif., felt he was being cheated and treated unfairly.

The company disagreed.

Rather than walk away, Digati decided to take the dispute to another level. He created a website dedicated to New York Life’s products and hired an email spam service.

Then he did something that would get him into a lot of trouble. He sent a letter and several emails advising New York Life officials that it would be in the company’s best interests to pay him his money… or else.

This week a federal grand jury in New York indicted Digati for allegedly attempting to extort up to $3 million from the company in exchange for not unleashing a massive Internet spam attack on New York Life’s business reputation.

Extortion or just hyperbole?

The case is interesting because it is not entirely clear from court documents whether Digati was – as the government claims – intent on extortion – or whether he was merely an extraordinarily frustrated and dissatisfied customer who engaged in hyperbole and exaggerated threats.

“I’m sorry it had to come to this, but I guess you won’t listen to what the customers [sic] concerns are,” he wrote New York Life in an email in February. “You enjoy ripping policy holders off with obscure products bought because of the trust you have established over 160+ years. You enjoy misleading the public and I will make it my purpose in life to educate them.”

Digati’s website NewYorkLifeproducts.com is no longer in service. Prosecutors have not disclosed the content of the site in court documents. Instead, the indictment focuses on a series of threatening emails Digati sent to more than a dozen New York Life employees, executives, and one board member.

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