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.

In a series of detailed interviews, Caramadre said the companies designed the rules; all he did was exploit them. Their hunger for profits in a period of dizzying growth and competition, he contends, left them vulnerable to someone with his unusual acumen. The companies have argued in court that Caramadre is a fraud artist who should return every last dime he made. In his rulings to date, the federal judge hearing the civil cases has agreed with Caramadre’s contention that he was doing what the fine print allowed.

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

by Jake Bernstein
ProPublica, Aug. 24, 2012

Well written and well researched, this article is worth reading.  An article from the Wall Street Journal in 2010 also makes for good reading and that link is below.

Investors Recruit Terminally Ill to Outwit Insurers on Annuities – WSJ.com.