The change of plea comes five months after Headley, an American-Islamic fundamentalist, was arrested at his Chicago home by the FBI. He has been cooperating with federal authorities ever since being arrested.
Raised by his father in Pakistan as a devout Muslim, Headley arrived in Philadelphia at age 17 to live with his American mother, a former socialite who ran a bar called the Khyber Pass. Depending on the setting, he alternates between the name he adopted in the United States, David Headley, and the Urdu one he was given at birth, Daood Gilani. Even his eyes - one brown, the other green - hint at roots in two places.
Headley is accused of being the lead operative in a loose-knit group of Pakistani militants plotting revenge against a Danish newspaper that published cartoons of Prophet Muhammad. The indictment against him, that charges he had a key supporting role in the Nov. 2008 massacre in Mumbai, India, portrays a man who moved easily between different worlds.
The guilty plea comes as a blow to the defense of accused co-conspirator Tahawwur Hussain Rana. The Chicago businessman, who was born in Pakistan and is a citizen of Canada, was arrested and charged a few weeks after Headley. The men are boyhood friends from their days at a Pakistani military academy. At first they were charged with plotting an attack on the Danish newspaper that published cartoons perceived as anti-Muslim.
The investigation broadened quickly to include a partnership between Al Qaeda and Lashkar-e-Taiba and eventually the charged plot against numerous targets in Mumbai.
A trained medical doctor, Rana immigrated to Canada in 1997 and became a citizen a few years later. Moving to Chicago with his wife and three children, he started a travel agency that also provided immigration services on Devon Avenue. Rana also owns a goat slaughterhouse in rural, downstate Illinois that was subjected to a raid by federal counter-terrorism agents last fall.
Their alleged partnership is odd and was born out of Muslim extremism, according to U.S. prosecutors. In 1998, Headley, then 38, was convicted of conspiring to smuggle heroin into the U.S. from Pakistan. Court records reported by the ABC7 I-Team show that after his arrest, he provided so much information about his own involvement with drug trafficking, and about his Pakistani suppliers, that he was sentenced to less than two years in jail. It was shortly thereafter that Headley later went to Pakistan to conduct undercover surveillance operations for the Drug Enforcement Administration.
Headley's Chicago lawyer John Theis confirmed the change-of-plea hearing for Thursday afternoon and said that he would probably comment publicly about the matter after court. A message left for Rana's attorney, Patrick Blegen, was not immediately answered.