Headley, 49, was arrested on October 3 by the Federal Bureau of Investigation and has been charged for being involved in the 26/11 Mumbai terror attacks, in which 166 people, including six US nationals, were killed.
Given the strong case against him, Headley is unlikely to come out of the jail and faces death penalty. "But by talking this time, Headley might escape the death penalty," Philadelphia Inquirer said.
However, Headley, with the experience of having been informant to federal prosecutors at least twice as a result of which his sentence was reduced, has again turned out an informant this time so as to avoid death penalty.
The FBI chargesheet filed against Headley gives an indication of it, in which the federal prosecutors say that he is cooperating in the investigation. He has pleaded not guilty.
Court records indicate that Headley, earlier known as Dawood Gilani, was arrested twice on drug charges and on both the occasions, his sentence was reduced and was able to leave the jail early as he turned out to be a good informant to the drug enforcement agencies and helped them in unearthing of some of the major drug cartels.
"He wasn't tough to crack: Before the day was out, Daood 'David' Gilani decided to save his own skin, agreeing to betray his drug-dealing partners by helping US drug agents set up a sting," the paper reported referring to his arrest in 1988 on charges of possessing two kilos of heroine.
"It was the beginning of a complicated, off-and-on relationship as a confidential informant with the Drug Enforcement Administration -- one that lasted more than a decade," it said.
In fact, Gilani was so helpful as a DEA informant in the late 1990s on heroin imported from Pakistan, according to records and Inquirer interviews, that prosecutors made a rare move: They ended his probation years early, allowing him to travel freely. Within weeks, investigators say, he began training with terrorists in Pakistan," the newspaper said.
Headley was again arrested in New York in 1997, smuggling drugs into the country. This time he again got off with a lighter sentence by testifying against his partners.
"Once again (after his recent arrest), Headley immediately switched sides. Prosecutors say he admitted taking trips to the jihadist camps and performing surveillance and photo reconnaissance for terrorist plots in Denmark and India, including preparations for the deadly 2008 Mumbai attacks," the newspaper said.
Headley has been charged by the FBI in a 12-count criminal information with six counts of conspiracy to bomb places in India and Denmark and for providing material support to terrorist plots. The next hearing of his case will be held on January 12, 2010.