Bernie Madoff's Gullible Investors and Guileless Regulators

After all that transpired in 2008, investors still talk about risk-free investments. Isn't that just a tad retro?

Joyce Greenberg, a retired financial adviser in Houston, tells that she never questioned the steady returns Bernie Madoff produced over twenty years because at least in the early years his strategy was "riskless." The returns funded college tuition and helped build nest eggs for Greenberg's extended family, which invested heavily with Madoff and lost millions.

Actually, make that 100s of millions. Her step-mother's first cousin was a charter member of the Madoff Investment Club in the 1960s. His name? Carl Shapiro, former owner of Kay Windsor clothing business and a Madoff mentor. The Wall Street Journal reports that Shapiro had handed over $250 million just before Madoff ‘fessed up. That's apparently gone down the rabbit hole of risk-free investing as well.

Greenberg says she herself had maintained confidence in Madoff  because he used a straight-forward strategy known as "convertible arbitrage."  It was simple -- buy a basket of convertible bonds and short the underlying securities. "It's a riskless, a riskless technique," Greenberg says without a hint of irony.

Can a professional investor ever really refer to any investment as riskless? The word does not even appear in the Microsoft Word dictionary -- nor for that matter does subprime. Both, of course, were essential terms for the purveyors of Wall Street investment concoctions: "We've sliced and diced the risk away!"

Risk can be a matter of perspective: Treasury securities are commonly referred to as "safe havens" or as virtually risk-free -- also misleading given how rapidly the Treasury and Federal Reserve are pumping out greenback govvies. The risk of inflation in the next few years could make Treasury investments seem ... imprudent. I digress.