Tahawwur Rana was thought to be a mild-mannered north side travel agent and immigration specialist who hailed from Pakistan, until the November 2008 Mumbai Massacre.
The Mumbai Massacre is known as India's 9/11: a several-day siege of metropolitan Mumbai by terrorists from Pakistan.
The commando-style attacks took 175 lives, including six Americans.
Less than a year after the terror strike, the FBI in Chicago arrested Rana, and he was charged with providing material support to the Pakistani terror group that carried out the attack.
Rana and his boyhood friend from Pakistan, David Headley, were both charged with aiding the plot.
Headley cooperated with investigators, while Rana fought it and lost.
After serving a 14-year prison sentence, Rana was about to be freed from a U.S. prison when India requested his extradition.
As the I-Team has previously reported, Rana has been fighting that extradition request for the past year.
In court records, Rana's attorneys argued, "In the real world, Rana has little chance of making it to trial in India given that country's well-documented history of extrajudicial violence directed against Muslims in police custody."
On Wednesday, according to the court docket, Rana's attorney will have 20 minutes to argue why he shouldn't be sent to India and face their justice for the Mumbai Massacre.
Rana's defense has alleged double jeopardy or being tried twice for the same crime, which is barred by the U.S. Constitution, as well as the near certainty of Rana's death while in foreign custody.
ABC7 Chief Legal Analyst Gil Soffer told the I-Team it may be Rana's only legal strategy.
"It's a defense strategy. His lawyers are making the best arguments they can for why he shouldn't be extradited," Soffer said, while acknowledging, "There may be issues with the prison system in India as there are elsewhere, but that won't be grounds to prevent extradition."
Rana remains in custody, assigned to a federal prison in Los Angeles not far from where he did most of his main prison sentence.
His short plea for mercy is scheduled at the 9th Circuit U.S. Appeals Court in Pasadena.
Prosecutors will also be granted 20 minutes to argue why Rana should be sent to India.