NEW YORK -- Rajat Gupta, the former McKinsey & Co. chief and pal of imprisoned inside trader Raj Rajaratnam, has one goal after being convicted last month of securities fraud: to convince federal Judge Jed Rakoff that he deserves minimal jail time.
There is a compelling public interest, after all, in keeping white-collar criminals on the street. The financial markets need liquidity, as any summer intern at a Washington lobbying firm can tell you, and we would be facing dark days if we lost our best talent at leaking confidential information. What good is a tipster in a place where high-frequency trading means swapping cigarettes for a batch of washed and folded laundry?
I don't mean to suggest that his lawyers and throng of big-name business friends aren't already doing a serviceable job of portraying Mr. Gupta as an honorable man who doesn't belong in jail. Mr. Gupta's lawyer, Gary P. Naftalis, pushed so hard to be allowed to tell the jurors about Mr. Gupta's philanthropy that Judge Rakoff had to offer a reminder: Even Mother Teresa would be judged on the evidence -- but presumably not her saintliness -- if charged with robbing a bank.
The effort to tout his charity and good heart is a respectable start for the former Goldman Sachs director. But it doesn't go far enough.
With the sentencing slated for Oct. 18, there's no harm in maxing out on every possible pitch as to why the man found guilty of leaking confidential information to Rajaratnam should get a break. The community-service alternatives alone are boundless. A not-for-profit to wage war on bullying of school-bus monitors comes to mind. Or maybe a faux-feminist foundation that cranks out op-ed articles on why it's bad for women to receive equal pay to men.
Speaking of op-eds, it wouldn't be the worst idea for him to get his worker bees cracking on a competition among news media outlets for first dibs on a Gupta byline. If Mr. Gupta's lawyers balk, at least the public-relations people could ghostwrite a sermon on Mr. Gupta's finer points and hunt down a big name in business willing to put his name on it.
White-collar defendants with bottomless checkbooks have been known to make colossal efforts to paint themselves as philanthropic pillars of the community. Sometimes that charity begins right around the time investigators deliver their first subpoena. Other times, as in the case of Mr. Gupta, magnanimity is a long-established practice.
You might wonder who would care if a rich person found guilty of a crime has sprinkled a few crumbs among the little people -- and juries often wonder the same thing. Experts in selecting and analyzing juries say that jurors in mock trials and focus groups get turned off when there's too much talk about a defendant's good works. Philip K. Anthony, the director of jury consulting at DecisionQuest Inc. in Los Angeles, says jurors often mention that wealthy defendants derive benefits from their largess, including tax write-offs and goodwill from business associates and the community.
Paul Neale, the chief executive officer of Doar Litigation Consulting -- the Lynbrook, N.Y.-based firm that worked on the Gupta case -- declined to comment on the trial. But he did say he has never seen philanthropy as a "definitive factor" in 23 years of mock trials that his firm has conducted.
Reality, though, can play out differently. Richard M. Scrushy, the former CEO of HealthSouth Corp., was acquitted by a jury in 2005 on charges he directed an accounting fraud. The Birmingham, Ala., community got a heavy dose of his pious side even during the trial. Mr. Scrushy delivered a lecture and donated $5,000 to a church attended by one of the jurors. He and his wife hosted a Bible show that aired five days a week on local TV during the months before the trial began.
Even Rajaratnam benefited from hundreds of supportive letters to the court. Federal Judge Richard Holwell acknowledged Rajaratnam's "very significant dedication to others" at sentencing, giving him 11 years even though sentencing guidelines called for as much as 241/2 years.
Perhaps Mr. Gupta could catch a break if he winds up filing an appeal and selects a new legal team with the magic touch.
In one of the most famous insider-trading cases of the late 1980s, Martin Siegel faced as much as 10 years in prison and a $260,000 fine. He had sold inside information in return for suitcases full of cash. Despite his crime, he spent only two months in prison, five years of probation, and received no fine.
It's a pity that Mr. Gupta won't have a shot at hiring the lawyer who shepherded Mr. Siegel to his propitious outcome. Mr. Siegel used Jed Rakoff, the guy who will decide what sentence suits Mr. Gupta's crimes.
Susan Antilla, who has written about Wall Street and business for three decades and is the author of "Tales From the Boom-Boom Room," a book about sexual harassment at financial companies. She is a Bloomberg View columnist.