Death Takes a Policy: How a Lawyer Exploited the Fine Print and Found Himself Facing Federal Charges

Joseph Caramadre has spent a lifetime scouring the fine print. He's hardwired to seek the angle, an overlooked clause in a contract that allows him to transform a company's carelessness into a personal windfall. He calls these insights his "creations," and he numbers them. There have been about 19 in his lifetime, he says. For example, there was number four, which involved an office superstore coupon he parlayed into enough nearly free office furniture to fill a three-car garage. Number three consisted of a sure-fire but short-lived system for winning money at the local dog track. But the one that landed him on the evening news as a suspect in a criminal conspiracy was number 18, which promised investors a unique arrangement: You can keep your winnings and have someone else cover your losses.

Caramadre portrays himself as a modern-day Robin Hood. He's an Italian kid from Providence, R.I., who grew up modestly, became a certified public accountant and then put himself through night school to get a law degree. He has given millions to charities and the Catholic Church. As he tells his life story, his native ability helps him outsmart a phalanx of high-priced lawyers, actuaries and corporate suits. Number 18 came to fruition, he says, when a sizeable segment of the life insurance industry ignored centuries of experience and commonsense in a heated competition for market share.

Federal prosecutors in Rhode Island and insurance companies paint a very different picture of Caramadre: They say he's an unscrupulous con artist who engaged in identity theft, conspiracy and two different kinds of fraud. Prosecutors contend he deceived the terminally ill to make millions for himself and his clients. For them, Caramadre's can't-miss investment strategy was an illusion in which he preyed on the sick and vulnerable.

ProPublica has taken a close look at the Caramadre case because it offers a window into a larger issue: The transformation of the life insurance industry away from its traditional business of insuring lives to peddling complex financial products. This shift has not been a smooth one. Particularly during the lead up to the financial crisis, companies wrote billions worth of contracts that now imperil their financial health.


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Death Takes a Policy: How a Lawyer Exploited the Fine Print and Found Himself Facing Federal Charges