Rajat Gupta faces up to ten years in prison for his conviction on insider trading charges.
But if an outpouring of support from well-known friends and colleagues holds any sway with U.S. District Judge Jed Rakoff, the former Goldman Sachs director and chief of McKinsey & Company could receive a shorter sentence when he appears in court this afternoon.
"I know most personally, that the poor of the world have a profoundly capable and articulate advocate in Rajat Gupta," wrote Microsoft founder Bill Gates on Gupta's behalf, praising the former executive's work with the Global Fund to Fight AIDS, Tuberculosis and Malaria.
"He is a person who had conducted his life with an admirable sense of purpose," wrote Kofi Annan, the former UN Secretary General, who tapped Gupta to help him reform the management of the world body. "I came to respect his judgment, and we became good friends."
Close friends Ajit Jain, the chief of Berkshire Hathaway's Reinsurance Division, author Deepok Chopra, and Continental Grain Chairman and CEO Paul Fribourg also wrote in support of Gupta, attesting to his commitment to helping and mentoring others, amounting to a stack of letters that stands a foot high.
The missives form part of the defense's appeal to Judge Rakoff to sentence Gupta to "a significant period of probation", with a condition of what it calls rigorous community service in either Rwanda or in New York; an unlikely proposition says one former judge.
"I'd be very surprised if Rakoff were to go there, just because of the visibility of the crime and the need to send a message to the business community," said attorney Richard Holwell, who retired from the district bench after sentencing convicted Galleon Fund chief
(Read More: Goldman Stuck With a Defense Tab, Awaiting a Payback.)
Prosecutors are asking Rakoff to adhere to federal guidelines of an 8-to-10 year sentence, writing in the government's sentencing brief, "A significant term of imprisonment is necessary to reflect the seriousness of Gupta's crimes and to deter other corporate insiders." But attorneys and other legal analysts says Rakoff has been critical of strict sentencing guidelines, most notably in a securities fraud case in 2006, in which he wrote the calculations were "patently absurd" because they did not take in the particular circumstances of the case.
It's hard to imagine he will impose what the government is asking for, according to former federal prosecutor Steven Kobre, who believes Rakoff will likely sentence Gupta to a shorter time period. "I am thinking about 2 to 4 years."
Former judge Richard Holwell also believes Gupta will receive prison time, but "judging from Rakoff's past, it can be a steep discount from the guidelines." Gupta did not testify at trial, and his attorneys have not indicated whether he will speak on his own behalf during the sentencing hearing. (Read More: Best Places to Go to Prison.)
Even after his conviction, Gupta's wife Anita says he has never spoken ill of those who betrayed his trust.
In her petition to the judge for leniency she writes, "I know that in his heart he has long forgiven them," though she herself cannot.
— By CNBC's Bertha Coombs