Gupta, 65, convicted in 2012 of passing confidential board room information to his friend and business associate Raj Rajaratnam, is scheduled to begin his two-year prison term on June 17.
In a lengthy-118 page submission to Supreme Court Justice Ruth Bader Ginsburg, Gupta requested to remain free on bail, saying he is not a flight risk and if an appeals court rules in his favour, he will "likely" be entitled to a new trial.
Gupta "requests continuation of his release on bail pending the disposition of his petition for rehearing and rehearing en banc to the Second Circuit...and, if necessary, this Court?s disposition of his petition for a writ of certiorari," his lawyers said in the submission made public yesterday.Gupta had filed his petition for rehearing his case before the Second Circuit appeals court in April and the court is yet to act on that petition.
Ginsburg oversees emergency applications from New York, Connecticut and Vermont.
While she may herself rule on Gupta's request, she could also refer it to a full, nine-member Supreme Court panel. There is no deadline for Ginsburg to rule on the submission.
Gupta's team of lawyers, which includes former US solicitor general Seth Waxman, said if his bail is not continued, he would be required to report to prison next week despite satisfying the standards for bail pending appeal.
"If Gupta is forced to surrender before his certiorari proceedings are resolved, there is a high likelihood that, were this Court to grant certiorari, Gupta will have served at least half of his two-year sentence before the Court issues its decision," the submission said.
The Harvard-educated Gupta is one of the most high- profile Wall Street executives to be convicted of insider trading, charges that were brought against him by Manhattan's India-born top federal prosecutor Preet Bharara.
Apart from the two-year prison term, Gupta has been ordered to pay USD five million in fine and a separate USD six million in restitution to Goldman Sachs.
In his submission to the apex court, Gupta said the wiretaps of Rajaratnam's telephone used by the prosecution as the most powerful evidence against him in his trial were improperly admitted.
He said if any of the wiretaps should have been suppressed, the court is likely to reverse his conviction.
He further argues that evidence of his good character was "critically important" in this case but the character evidence presented at trial was only reluctantly admitted by the district court, which then refused to instruct the jury that they could take into account the character evidence to decide whether he was innocent or guilty.
Gupta said the contentions in his petition are "likely to result" in reversal of his conviction and a new trial on all counts.
The former Mckinsey head, who has so far remained free on bail, said he presents no risk of flight or danger to the community, and he has abided by all conditions of release set by the district court.
He had last month filed a motion in the court of appeals to stay his surrender date and for bail pending the disposition of his rehearing petition but the court of appeals had denied that motion.
His petition for certiorari, which his counsel said is prepared to file on an expedited basis should the court of appeals deny rehearing, is not for the purpose of delaying the case proceedings.
Gupta sought to make a strong case before the apex court that he has lead an exemplary life and has been involved in philanthropic causes and that the charges against him are only "deviations" from a life lived with integrity.
"For nearly four decades, Rajat Gupta enjoyed a sterling reputation in management consulting... The esteem in which Gupta was held led some of the nation?s leading corporations to elect him to their boards of directors.
He also pursued a life of extraordinary philanthropy, dedicating his wealth and time to causes great and small.
"Yet, at the pinnacle of his career, Gupta was indicted on one count of conspiracy and five counts of insider trading in violation of federal securities laws. The prosecution charged Gupta with acts that would have been gross deviations from the integrity and uprightness for which he was so well known," he said in the application.
Gupta has argued that there was no evidence that he received any direct financial benefit from any of Rajaratnam?s trades.
His lawyers add that the government did not have any witness who could testify to a tip or any recording of Gupta providing Rajaratnam the tips for his trades.
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