There’s an old saying among professional swindlers that “you can’t con an honest man.” The “mark” was looking for something for nothing, or even running their own con, and just got taken in by a better one. A rationalization? Yes, but don’t be too quick to dismiss it. What type of person does fall for the too-good-to-be-true scenarios that con men concoct, and who enables them?

So what are we to make of Wall Street’s Bernie Madoff and his accomplices, and his victims? Sure, the crime was straightforward, no mystery really—rather the biggest pyramid fraud of all time, involving tens of billions of dollars of investors’ money going into illicit pockets. The grandfather of all Ponzi schemes was roundly sentenced to prison until the year 2159, when he would be 221 years old. But Madoff was merely the hub of a huge wheel of feeder funds, accountants, and regulators who all fiddled while lifetimes of savings burned. The public, and the courts, have asked the obvious question: what did these people know, and when did they know it? Over time, a few individuals who handled funds, or false documents, have followed Madoff to the Big House.images-17

Yet the deepest mysteries of all still haunt the shadows of the disappearing billions-mysteries of greed, and the human psyche. One talented financial analyst, Harry Markopolis, did everything short of run the streets naked with his hair on fire for years to call attention to the obvious fraud. He let regulators know, repeatedly, that the numbers simply didn’t add up. Why was he ignored by the Securities and Exchange Commission for so long? Why were individuals with enough business acumen to assemble large chunks of investment money naive enough to believe Madoff’s rosy investment reports? It’s easy to cast Bernie as the Devil Incarnate and give him 150 years in prison. We feel righteous, having decisively struck back at evil, in contrast to our honesty and innocence.

But the question should give us pause: was Madoff, contrary to the legend, conning a bunch of honest men and women? What will the money trail and the backstory tell us? Join us as we explore the question: how could Madoff have stolen so much from so many? We open the Madoff file.

Former Madoff associates found guilty of fraud | Reuters YORK Five former aides to investment manager Bernard Madoff were convicted on Monday of charges that they helped their boss conceal his multibillion-dollar Ponzi scheme for…