David Coleman Headley, 49, admitted to using a friend's immigration company as a cover for surveillance activities in India and Denmark on behalf of two different Pakistan-based terrorist groups.
The Washington-born son of a former Pakistani diplomat and American woman, Headley reportedly befriended Bollywood stars and even dated an actress during his lengthy surveillance trips.
In a plot that reads like a movie thriller, Headley spent two years casing out Mumbai, including taking boat tours around the city's harbor to scope out landing sites for the attackers who killed 166 people, including six Americans.
Charging documents also indicated Headley was so eager to kill a Danish cartoonist who sparked outrage with cartoons depicting the Prophet Mohammed that he began working seriously on that plot two months before the bloody 60-hour Mumbai siege which began on November 26, 2008.
India and Washington blamed the deadly rampage on Pakistan's banned militant group Lashkar-e-Taiba (LeT). The attacks stalled a fragile four-year peace process between the two nuclear-armed south Asian rivals.
Headley - who said he began working with LeT in 2002 - also had Bollywood and one of India's most sacred Hindu temples in his sights as he began plotting a second India attack during a March 2009 surveillance trip.
Prosecutors said the potential targets also included the National Defense College, Chabad Houses in “several cities” in India Prosecutors and Shiv Sena, a political party in India with roots in Hindu nationalism.
Headley told prosecutors after his October arrest that he changed his name from Daood Gilani in 2006 so he could “present himself in India as an American who was neither Muslim nor Pakistani,” charging documents said.
Indian media have reported that Headley befriended Bollywood stars and developed a reputation as a fitness fanatic while staying in an expatriate enclave in south Mumbai near the US consulate during five lengthy surveillance trips.
He reportedly lived a more devout Muslim life in Chicago with his wife and children and prosecutors said he attending LeT terror training camps in Pakistan in 2002 and 2003.
Headley began working with an Al-Qaeda-linked group in Pakistan called Harakat-ul-Jihad-Islami on the Danish plot after LeT became distracted with the final planning for the Mumbai attack, charging documents said.
He was arrested at Chicago's O'Hare airport in October as he was on his way to deliver 13 surveillance videos he obtained after pretending to be interested in buying ads in Jyllands-Posten, Denmark's highest circulation daily.
Headley was later charged in the Mumbai attacks, as was his old friend from military school in Pakistan, Tahawwur Hussain Rana.
Rana, who owns the Chicago-based First World Immigration Services that Headley allegedly used as a cover, insists he is a pacifist who was “duped” by his friend. He has pleaded not guilty to the charges. - AFP