In the aftermath of the 2008 financial crisis, the most commonly heard complaint has been: “Why hasn’t anyone gone to jail?” This past May, Newsweek asked, “Why Can’t Obama Bring Wall Street to Justice?” and Forbes wondered, “Obama’s DOJ and Wall Street: Too Big for Jail?” Even Rupert Murdoch’s New York Post recently chided the president because “not a single Wall Street fat-cat has been charged with violations of securities laws in connection with the 2008 collapse.”

There are many explanations — and plenty of conspiracy theories — about why this is the case, but there’s a different, more important question that needs to be asked: Has sending people to jail fixed anything?

Think back to the post-Enron years. The government convicted roughly a dozen former Enron executives, including former CEOs Kenneth Lay, who died awaiting sentencing, and Jeffrey Skilling, who is serving a 24-year prison sentence, and took accounting firm Arthur Andersen to trial, resulting in its demise. During that era, former WorldCom CEO Bernie Ebbers, former Quest CEO Joe Nacchio and former Adelphia executives were also convicted for misdeeds.

The goal, of course, was to deter future wrongdoing by those who don’t want to play by the rules, and those whose
appetite for risk could destroy a company. After that string of prosecutions, pundits (including yours truly) said that the world — or at least the business world — would be a much safer and steadier place.

Hmmm. By 2007, just one year after Lay and Skilling were convicted, the financial crisis, which had been decades in the making, was about to come crashing down on our heads. Part of the problem is that in corporate America, the odds are still very much in favor of those who game the system because the government, even at its most aggressive, doesn’t have enough resources to go after everyone. In addition, the rules create loopholes that clever people exploit, violating the spirit while still remaining within the letter of the law. On top of that, a lot of what most of us would call wrongdoing doesn’t involve intent — a necessary ingredient for a criminal prosecution. Instead, you find the very human capacity for self-delusion — and, sometimes, sheer stupidity.