It is straight out of Homeland. A British-born Muslim of Pakistani origin joins an Islamic aid expedition in Bosnia at 19, drops out of the London School of Economics to join a militant training camp in Afghanistan, serves jail time in India and by 28 is sentenced to death in Pakistan for his role in the kidnapping and execution of an American journalist.

This is the seemingly improbable life of Ahmed Omar Saeed Sheikh, a British citizen who has been directly involved in several high-profile terrorist cases, including the kidnapping in 1994 of three Britons and an American in Delhi, the 1999 hijacking of Air India flight IC-814 and the execution in Pakistan of Wall Street Journal correspondent Daniel Pearl in 2002.

Sheikh has previously been depicted by British actor Alyy Khan in A Mighty Heart (2007). The terrorist is now set to get the Bollywood treatment in Hansal Mehta’s upcoming Omerta, starring Rajkummar Rao. An initial promotional photograph, with references to 9/11 and the kidnapping of an American, suggests that the biopic is likely to touch on Sheikh’s role in kidnapping Pearl.

During his brief yet eventful decade of activity, of which he spent five years in jail in India, Sheikh was prolific. He trained at the Khalid bin Walid militant camp in Afghanistan. He was a member of the Harkat-ul-Mujahideen, the terror group founded by Maulana Masood Azhar, who later went on to establish Jaish-e-Mohammed. Sheikh also had ties to the more globally-oriented Al Qaeda, and might even have had a hand in wiring money to terrorists in the United States of America who were preparing for the 9/11 terror attack that would alter the course of American history.

If links to so many notorious terror organisations were not enough, Sheikh has also been accused of being a triple agent – working as a spy for the United Kingdom, Pakistan and even the US.

As Shyam Bhatia wrote for Rediff in 2002, soon after Sheikh’s arrest, “No one is under any illusion about what Sheikh was capable of doing. In the words of senior officers of the Federal Bureau of Investigation who visited South Asia, it was always a question of whether Sheikh was caught before or after he committed another atrocity.”

Sheikh, now 43, has been arrested and has served time in a Pakistani jail for 15 years. A court is yet to hear his appeal against the death penalty for his role in Pearl’s murder. But how did Sheikh, brilliant private school student from London, become a feared and ruthless terrorist?

Omar Saeed Sheikh in a handout photo from the Lahore police.

Sheikh was born in London in 1973, the eldest of three children. His father Saeed Sheikh, a successful cloth merchant, had moved to London from Pakistan five years earlier. The young Omar attended Forest, an expensive private school in east London, where he claims to have experienced racist bullying.

In 1987, when Sheikh was 13, the family moved back to Lahore. Sheikh’s father enrolled him in the exclusive Aitchison College, often referred to as the Eton of Pakistan, but within three years, he was thrown out for bullying other students. The family then returned to London, where Sheikh completed his schooling.

Sheikh is thought to have been radicalised at 19, when he travelled to Bosnia to join an Islamic aid group that was working against the Serb Christians’ ill-treatment of Muslims. He was at this time a first-year undergraduate student at LSE, where he was studying mathematics and statistics.

When he returned, fellow students reported him to have changed greatly. Soon after, Sheikh dropped out and is believed to have gone to a militant training camp in Afghanistan in June 1993, where within a year, he became an instructor himself.

Omar Saeed Sheikh.

By all accounts, Sheikh is a charismatic and intelligent man. He certainly must have been so in his early twenties, when in 1994, soon after his stint in Afghanistan, he lured an American and three British backpackers from their hotels in Delhi to an apartment, from where his partners in the terrorist group Harkat-ul-Mujahideen whisked them away to a hideout in Uttar Pradesh.

The Harkat-ul-Mujahideen, which actively supported militancy in Kashmir in the early 1990s, demanded the release from an Indian jail of their arrested leader, Maulana Masood Azhar, among others. This attempt led to Sheikh’s first stint in jail, when the police shot at and captured him during a rescue operation. He was duly packed off to jail, first in Meerut and then Tihar in Delhi.

London Times reporter Jon Stock interviewed Peter Gee, a British musician who had served time with Sheikh in Tihar for a few months in 1998 and 1999, before Sheikh was shifted to solitary confinement. Gee and Sheikh became good friends, perhaps because of their shared British cultural heritage, even going as far as to teach prisoners geography together.

Gee, Stock wrote, “like many of those who have come into contact with Sheikh, fell utterly under his spell”.

Sheikh, it seems, was also immensely self-aware. While in jail with Gee, he described to him his experiences in a jail in Meerut. Stock quotes Gee as saying:

“According to Omar he lived practically like a mafia don. He was natural leadership material. His voice had a quiet, persuasive authority, and he had powerful eyes which could hold you in their gaze for as long as he thought necessary. He told me that he had to be wary of being seduced by the power and glamour that came with his position.”

By all rights, Sheikh should have remained in jail in India for far longer than he did. But in 1999, the Harkat-ul-Mujahideen plotted a devastating rescue operation: the hijacking of Air India flight IC-814 from Kathmandu to Kandahar.

The 1994 kidnapping in which Sheikh participated had been just one of several such attempts by the Harkat-ul-Mujahideen to have Azhar released. In 1995, while Sheikh was still in prison, the group kidnapped 10 foreign backpackers in the Himalayan foothills. These victims were less fortunate and were murdered.

Their last and only successful ransom attempt was the high profile hijacking of IC-814. Hijackers diverted the plane from Kathmandu first to Amritsar, then Lahore, Dubai and finally Kandahar, where the plane was given cover against any possible retaliation by the Taliban. The government was forced to yield and release three prisoners: Sheikh, then 27, Azhar, 32, and Mushtaq Ahmed Zargar, 33.

An archival Associated Press video of the IC-814 hijacking.

The consequences of the release were severe. Azhar would go on to plan and execute an attack on the Indian parliament in December 2001. Zargar is alleged to have trained militants for operations in Kashmir. And Sheikh, apart from accusations of being involved in transferring funds for 9/11 and being an Al Qaeda financier, played a direct role in the execution of Daniel Pearl.

Once taken to Kandahar, Sheikh travelled to Pakistan and is even rumoured to have visited his family in London with impunity in 2000, despite his having been involved in the kidnapping of British citizens.

At some point, he fell out with Azhar after Azhar founded Jaish-e-Mohammed. Robert Anson, in a profile of Sheikh in Vanity Fair, reports rumours that Azhar sidelined Sheikh “after getting fed up with his bragging about Indian exploits”.

Even so, some of his early charm must have remained intact when Sheikh set his sights on his next target: Daniel Pearl, a journalist at the Wall Street Journal, who had travelled to Pakistan to investigate a story on terror groups after 9/11.

Daniel Pearl.

On January 23, 2002, Sheikh, working under an alias, lured Pearl into travelling from Lahore to Karachi, where Pearl believed he would meet Sheikh Mubarak Ali Shah Gilani, leader of a terrorist group. Instead, the taxi that picked up Pearl led him to his kidnappers. Pearl was held hostage for a week before being executed on camera. The execution video was released a month after Pearl was kidnapped, but his body was discovered only in May.

Michael Winterbottom’s A Mighty Heart (2007), based on the memoir of the same name by Daniel Pearl’s wife Mariane Pearl, recreates the kidnapping and the murder. Alyy Khan plays Omar Sheikh, while Irrfan is the Karachi police chief who tries to save Pearl.

A Mighty Heart (2007).

Sheikh has always claimed that he had no hand in the execution. He claims that he sent a message to the group asking them to release Pearl, only to be told that it was too late. This argument did not hold in court. In June 2002, Sheikh was sentenced to death. Sheikh is reported to have issued a statement from prison soon after, threatening the court: “I will see whether who wants to kill me, will kill me first, or get himself killed.”

There are somewhat strong suggestions that Sheikh was associated with Pakistan’s intelligence agency Inter-Services Intelligence. In February 2002, at the height of the search for Daniel Pearl, the Pakistani police in an attempt to flush Sheikh out rounded up his relatives, including his 90-year-old grandfather. The tactic worked and Sheikh surrendered himself – to Brigadier Ijaz Shah, an ISI operative, who turned him over to the police only a week later. Sheikh has resolutely kept his silence on what he did during that period of time, and the link has never been proved.

Osama bin Laden is said to have regarded Sheikh as a son, according to a 2002 report in London Times, which also added that experts believed Sheikh to be brilliant enough to perhaps take over Al Qaeda after bin Laden.

No less than Pervez Musharraf, former president of Pakistan, wrote in his memoir In the Line of Fire of Sheikh’s links with MI6, Britain’s intelligence:

“It is believed in some quarters that while Omar Sheikh was at LSE, he was recruited by the British intelligence agency MI-6,” Musharraf wrote. It was believed that Sheikh went to Bosnia on the orders of that agency. However, this did not work out for them. “At some point,” Musharraf continued, “he probably became a rogue or double agent.”

It takes a twisted sort of charmer to be able to impress America’s most wanted terrorist at the same time as three competing espionage outfits.

Jail does not seem to have deterred Sheikh’s activities either. In 2008, soon after the 26/11 terror attacks on Mumbai, Sheikh attempted to start a war between India and Pakistan with a hoax call to Pakistani president Asif Ali Zardari and Ashfaq Parvez Kayani, the chief of army staff. Sheikh, with some measure of bravado, is reported to have pretended on those calls to be Pranab Mukherjee, who was the Indian home minister at the time.

The last time Sheikh was in the news was in 2014. Reportedly sick of being in jail, Sheikh had unsuccessfully attempted suicide.

Omerta director Hansal Mehta has previously featured Sheikh in his biopic Shahid (2013), in which Rajkummar Rao plays the slain human rights lawyer Shahid Azmi. Arrested on trumped-up charges and jailed at Tihar, Shahid meets Omar Sheikh. The terrorist, played by Prabal Panjabi, reveals the IC-814 hijacking plan to Shahid and tries to recruit him. Shahid is saved by a Kashmiri prisoner (Kay Kay Menon) who warns him against Omar’s gameplan and advises him that “If you want to change the system, be a part of it.”

The roles are reversed in Omerta, where Rajkummar Rao will play the sinister terrorist with a long trail of crimes to his name.

Prabal Panjabi as Omar Sheikh in Hansal Mehta’s Shahid (2013).