In a look at how the insurance industry has transformed from its traditional bread and butter of selling life insurance to selling complex financial products, ProPublica's Jake Bernstein and This American Life's Alex Blumberg explore how one man used variable annuities to make a fortune at the expense of other people dying. The story is told through the lens of Joseph Caramadre - a Rhode Island lawyer who is adept at exploiting fine print. Caramadre would offer $2,000 to $10,000 dollars to people who were close to death in exchange for their personal information so that he could buy an annuity on their life and then pocket any profit when that person died. Some involved with Caramadre's plot viewed him as a modern-day Robin Hood, offering sorely-needed financial support during their last days, while others cast him as a criminal taking advantage of people in a vulnerable state. While the ethics of his scheme are debatable, insurance companies and the government don't think there's much to dispute as criminal charges were brought against Caramadre for engaging in identity theft, conspiracy, and two different kinds of fraud for preying on the sick and deceiving the terminally ill to make millions for himself and his clients.