Free Republic

A dying mechanic wanted a few thousand dollars to leave to his wife, two sons and infant daughter. A politically connected millionaire, now running for Virginia governor, wanted to make some money. And a Rhode Island estate planner wanted to become ambassador to the Vatican. All three came together on paper in late 2006 in a deal struck just two months before the 44-year-old mechanic died of cancer. The mechanic got $5,000. The millionaire, Democrat Terry McAuliffe, made at least $47,000. But the estate planning lawyer, Joseph Caramadre, went to prison instead of Rome. Caramadre helped McAuliffe place a bet...

McAuliffe’s connection to Caramadre came to light about two weeks ago, as his race entered the homestretch against Attorney General Ken Cuccinelli, a Republican. According to court records made public then, McAuliffe’s investment paired him directly with the ailing mechanic, with forms identifying them as acquaintances. McAuliffe’s campaign said the candidate did not know the mechanic and doesn’t know why they were listed as acquaintances. But the episode still opened a wider window into how McAuliffe came to invest with Caramadre in 2006 — and provides yet another example of how the former chairman of the Democratic National Committee has...