He was born poor in India and orphaned as a teenager but rose to the top of the corporate and philanthropic elite, only to be jailed for 'insider trading'.
He makes it in this list as he exemplifies the great American dream turning into a nightmare amid the financial gloom that wiped out many businesses and businessmen. Rajat Gupta moved in elite business and philanthropic circles for decades and had several prominent personalities like Bill Gates and Kofi Annan pleading the judge to show leniency when sentencing the former Goldman Sachs Group Inc board member.
A jury convicted Gupta in June and sentenced him to two years in prison for tipping his friend and business associate, Galleon Group hedge fund founder Raj Rajaratnam, about Goldman's boardroom secrets during the financial crisis.
He was also ordered to pay a $5 million fine. He was convicted for leaking secrets to Raj Rajaratnam, who for long had been at the center of a US government crackdown on insider trading.
The jury which convicted Rajat Gupta, one of the most prominent Indian-Americans in the US, for securities fraud, said it wanted him to walk a free man after the trial, but the evidence against him and his "need for greed" was just too "overwhelming".
In 2008, Gupta told Rajaratnam that influential investor Warren Buffett was infusing $5 billion into the investment bank. Rajaratnam traded on the information as the market was closing.
This rags-to-riches story has been in summed up in short by Gupta's lawyer Gary Naftalis who said: "This was an iconic figure who had been a role model for countless people around the globe."
But added, "He is no more."