Allen Stanford
© ReutersConvicted financier Allen Stanford arrives at Federal Court in Houston for sentencing
Two white-collar criminals received justice last week - Allen Stanford of Stanford International Bank and Rajat Gupta of McKinsey & Co and Goldman Sachs. One's actions are easy to understand, the other's extremely hard.

Stanford, a Ponzi schemer who stole $2 billion of his eager depositors' money, is easy: if he is not a psychopath, he certainly behaved like one for two decades. Gupta, convicted of fraud and conspiracy for leaking price-sensitive titbits about Goldman to Raj Rajaratnam, the criminally corrupt hedge fund manager who was his confidant and friend, is the puzzle.

Gary Naftalis, Gupta's lawyer, told the jury shortly before his conviction: "Rajat Gupta was in the seventh decade of an accomplished and praiseworthy life. It strains common sense that [he] would ...throw away everything he had done for 40 years, and wilfully and knowingly commit crimes. That just doesn't make sense."

Maybe not, but he leaked inside information and was caught on tape gossiping to Rajaratnam about the discussions at Goldman board meetings, in clear breach of his fiduciary and ethical duty. "The way he behaved was professionally disgraceful," says one former McKinsey partner.

Was Gupta always bad, or did he turn bad?

Either he fooled McKinsey into electing - and twice re-electing - a fraud as its managing partner or he only later turned into a corporate Narcissus who did not regard himself as needing to obey the usual rules as a board member of Goldman and Procter & Gamble. If he had a moral compass, he lost it.

Psychopathy is "a disorder rooted in lying, manipulation, deceit, egocentricity, callousness and other destructive traits," write Paul Babiak and Robert Hare in the book Snakes in Suits. Psychopaths are often charismatic and grandiose, with no compunction about manipulating and exploiting others. "I was the puppet master pulling the strings," one happily reminisced.

Stanford had these characteristics in abundance - he was clever, deceitful, egotistical and manipulative, he bribed regulators and took billions from depositors who were swayed by Madoff-like promises of consistently high returns. Instead, he lived high on their cash - flying in private jets, running his own cricket tournament, and gambling away $500,000 at the Bellagio in Las Vegas.

He is not in the least remorseful about it, despite being sentenced to 110 years in prison. Instead, in his ridiculous final plea to the judge, he claimed that it was everyone else's fault - the depositors he fleeced had loaned him money with no recourse and he had "created a synergy whereby Stanford companies supported, complemented and enhanced one another."

Gupta is no psychopath - his crime was far smaller and he lacks Stanford's blind egotism. His sage advice was valued both as a board director and a consultant. Alan Lafley, the former chief executive of Procter & Gamble, once compared him to Thomas Aquinas, the philosopher-saint.

So was it a pretence? Opinions vary among McKinsey's partners and alumni. Most of them say he showed no signs of a dark side while he was there and his head must have been turned by falling in with the Davos set after leaving. He was wealthy - with $130 million in assets - but traded secrets for status.

The minority view is that he always had suspect traits, although he kept them well hidden. "His main objective was to make the senior partners wealthy and he didn't care about the juniors," says one former partner. This school dismisses his professed respect for the work of Vivekananda, the 19th-century Hindu Bengali monk, as a pose calculated to charm naive executives.

Gupta clearly has charisma, of the quiet rather than bombastic variety, and used it to ascend smoothly throughout his career. Like politicians, executives who reach the top are not saints - they must build alliances, defeat rivals and be highly ambitious. They may behave with nobility once in the job but that is not how they got there.

Studies have found that many executives share qualities with psychopaths. One study of British managers identified similar traits in both - superficial charm, grandiosity, lack of empathy, manipulativeness. These flaws, far from holding them back, had helped them rise.

Of course, sharing traits does not mean that all managers actually are psychopaths. If that were so, many of us would fall into the spectrum. Few chief executives are as coldly heartless as Stanford.

But I am struck by Babiak and Hare's description of sociopathy, which is not a mental illness: "Sociopaths may have a well-developed sense of conscience and a normal capacity for empathy, guilt and loyalty, but their sense of right and wrong is based on the norms and expectations of their subculture or group. Many criminals might be described as sociopaths."

That sounds distinctly like Gupta, who became part of Rajaratnam's circle and, as one prosecutor put it, "launches right into a detailed discussion of what happened at a Goldman board meeting in St Petersberg as if he's talking about what happened at a Yankees game."

He was also taped calmly talking about the fact that Rajaratnam was paying Anil Kumar, a McKinsey partner, $1 million a year for information. Did it slip his mind that he once ran the place, or did he always approve of partners taking bribes?

The nastiest conclusion is that the "norms and expectations" of the corporate elite are corrupt - that at such heights, illegal information-sharing is no big deal. I hope that is not the puzzle's answer.