With a career graph that could make the best burn with envy, Gupta, who boasts of posts like head of consultancy giant McKinsey, board seats at Goldman Sachs and Procter and Gamble and special adviser to the United Nations, among other things, has done what not many could have done in his 63 years of life.
A US court held Gupta guilty of providing insider information to Galleon hedge fund founder and friend Raj Rajaratnam, in one of America's biggest insider trading cases.
Born in Maniktala in Kolkata, son of a freedom fighter-turned-journalist father and a school teacher mother, Gupta was orphaned at the age of 18.
Ranking 15 in the IIT entrance exam of 1966, Gupta was admitted to IIT Delhi on a scholarship from where he did his B-Tech in Mechanical Engineering.
He then came to the United States for a graduate degree and finished top of his class at the prestigious Harvard Business School where he studied on a scholarship.
He landed a job at consulting giant McKinsey and quickly rose through the ranks.
In 1994, he was made the global head of the firm, the first non-American to hold that position.
Gupta's enviable resume boasted of job profiles as board members of some of the biggest US companies. After 10 years at McKinsey, Gupta joined the boards of many corporations and nonprofit organisations.
In addition to Procter & Gamble and Goldman, he was a director of the AMR Corporation, the parent company of American Airlines.
The Rockefeller Foundation appointed him a trustee; he was named an adviser to the former US President Bill Clinton and Bill Gates, Co-founder and Chairman of Microsoft, on their global health initiatives. He is also the co-founder of the Indian School of Business in Hyderabad.
Gupta was also appointed as special advisor on management reform to then UN Secretary-General Kofi Annan.
He additionally served on the UN Commission on the Private Sector and Development and was co-chairman of the United Nations Association of America.
While there are quite a few persons of Indian origin who have successfully handled leadership positions at one or another large global company, Gupta figures among the very few who have occupied corner offices of various such entities.
He is hailed as a poster-boy of Indians scaling great heights in corporate echelons abroad and his friends describe him as a God-fearing, "first-class guy".
But then the climate changed and Gupta found himself in the thick of an insider trading case.
Gupta's undoing began when his billionaire friend Raj Rajaratnam, a Sri Lankan, was charged by federal prosecutors of running of one of the biggest insider trading scams in US history.
Gupta met Galleon hedge fund founder Rajaratnam through another Indian-American McKinsey partner Anil Kumar.
Rajaratnam had made an anonymous contribution of a million dollars to the Indian School of Business, Hyderabad, which Gupta had co-founded with Kumar.
Together, they helped start New Silk Route Partners, a private equity firm focused on investments in India.
The two became friends and occasionally had lunch together, eating Indian takeout in Rajaratnam's office in Manhattan.
Rajaratnam is currently serving an 11-year prison sentence for making millions of dollars in profits and avoiding large scale losses thanks to confidential information he received.
The US Securities and Exchange Commission filed an administrative civil complaint against Gupta in March last year for insider trading.
Gupta "vigorously denied the SEC accusations" and instead filed a suit against the SEC saying that by bringing administrative charges him, the regulator is denying him the right to have a jury trial.
SEC later dropped the complaint. However, the day federal prosecutors formally brought charges against him in October, the SEC filed fresh insider trading charges against him.
Gupta was convicted on three counts of securities fraud and one count of conspiracy for passing along confidential boardroom information about Goldman and Proctor & Gamble companies to the hedge fund that earned millions of dollars trading on his tips.
He was acquitted of two counts of securities fraud. He was found guilty for information about the USD 5 billion investment by Warren Buffett's Berkshire Hathaway Inc,and of proving information to Rajaratnam on October 24, 2008 about Goldman stock.
Leading the government's charge against Gupta was fellow Indian-American, Manhattan US Attorney Preet Bharara, who has led a widespread crackdown on insider trading on Wall Street and had other successes in prosecuting several international terrorists, including Times Square bomber Faisal Shazad.
Gupta's wife and four daughters have regularly attended the trial, sitting right behind him in the spectators' benches in judge Jed Rakoff's courtroom.