Former bouncy castle salesman Siddhartha Dhar told his family he was ready to die for ISIS and said that he was 'prepared for death.'
In a telephone conversation, Dhar, also known as Abu Rumaysah, tried to reassure to his sister back in October 2015 about his future, telling her: 'Focus on the hereafter and don't worry.'
Dhar's sister Konika describes how she has struggled to deal with the 'snake' that she feels her brother has become.
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Dhar's sister Konika remembers how her brother used to be a big Arsenal football fan and didn't like to leave the house without styling his hair with brylcream when he was a young child
It has been claimed that on several occasions, Siddhartha Dhar, also known as Abu Rumaysah, was approached by British intelligence officers and offered the chance to work as a double agent
'I would rather see him rehabilitated in prison in the UK than dead on the Syrian battlefield,' she told the Sunday Times.
Konika remembers how her brother used to be a big Arsenal football fan and didn't like to leave the house without styling his hair with brylcream when he was a young child.
She described her brother as being like a 'teddy bear', who enjoyed music, particularly bands Nirvana and Linkin Park. He loved caring for animals and even had his own turtle, rabbit and hamster at home.
However around three years after his father's death, Dhar's ambitions to become a vet had seemingly disappeared as he took several retail jobs at Argos and Boots.
Konika described her brother as being like a 'teddy bear', who enjoyed music, particularly bands Nirvana and Linkin Park. He loved caring for animals and even had his own turtle, rabbit and hamster at home.
MI5 tried to recruit the suspected new Jihadi John Siddhartha Dhar as a double agent just before skipped bail and fled to Syria
Dhar became closer to a Muslim friend who he had known since his childhood and became more distant from his other friends from his teenage years.
By 2006, Dhar had converted to Islam and his Muslim friend set him up for an 'arranged marriage.'
His friend, who cannot be named for legal reasons, also influenced him into joining al-Muhajiroun before it was designated a terrorist organisation in 2010.
Dhar regularly held media interviews, promoting a radical brand of Islam and defending the actions of ISIS in Syria and Iraq.
Police and the Home Office have come under growing pressure to answer questions about security lapses that allowed Dhar to slip through the net.
The jihadi was able to leave Britain for Syria in September 2014 despite being on police bail and having been arrested on six occasions.
Police wrote to him politely asking him to call them because he had not surrendered his passport - weeks after he had already left the country.
Fresh claims have emerged that MI5 tried to recruit the suspected new Jihadi John Siddhartha Dhar as a double agent just before skipped bail and fled to Syria.
Siddhartha Dhar (pictured, far right, at a rally) was one of nine men detained on suspicion of encouraging terrorism and supporting the banned group Al-Muhajiroun
ISIS also threatened David Cameron in the video in which it executes five suspected spies (pictured)
The video also featured a Isa Dare, (pictured) the son of notorious British jihadi bride Grace 'Khadijah' Dare
It has been claimed that on several occasions, Siddhartha Dhar, also known as Abu Rumaysah, was approached by British intelligence officers and offered the chance to work as a double agent.
The former bouncer castle salesman was told that he would most likely be imprisoned or die if he remained in the UK or attempted to go to Syria.
Dhar's response to the job offer in September remains unclear but shortly after he was arrested, Dhar skipped police bail and fled to Syria with his family.
The revelations come amid widespread speculation that Siddhartha Dhar is the masked executor, dubbed Jihadi Sid, who featured in a graphic new ISIS video last week.
The video footage showed five Syrian men being executed for alleged espionage. After being forced to make a video testimony, the prisoners were forced to kneel in the desert before their executors.
The leading ISIS fighter in the video appears to have a prominent British accent and gives a threatening message, claiming that ISIS will invade the UK.
The episode also raised questions about Britain's borders, with Rumaysah - born a Hindu called Siddhartha Dhar- departing on a coach from London with his family the day after he was released on bail.
Lord Carlile, the former independent reviewer of terrorism legislation, told the Press Association: 'As I commented at the time of Dhar's departure from the UK, the circumstances were a matter of real concern.
'Why had he been granted police bail? Was the CPS consulted? Is there sufficient scrutiny of buses leaving the UK through ferry ports?
'The Home Office should now either release all the relevant documentation so that an open analysis and judgment can be made of what occurred, or appoint an independent person to review the circumstances of Dhar's flight from the UK and report to the Home Secretary.'
Dhar was arrested in September 2014 - when he was 31 - along with eight other men as part of an investigation into alleged support of the banned extremist group al-Muhajiroun.
Police wrote to him politely asking him to call them because he had not surrendered his passport - weeks after he had already left the country
Police have come under fire with questions raised over how Dhar was able to evade security services and flee to Syria with his family
Dhar regularly assisted at 'Islamic Roadshows' promoting Islam as the one true religion
However, he left Britain with his family the day after being freed on bail, travelling to Paris and then Syria where he posted a picture of himself on social media, holding his baby son in one hand and an AK-47 assault rifle in the other.
He wrote on Twitter: 'What a shoddy security system Britain must have to allow me to breeze through Europe to (IS).'
Following his release on September 26 2014, Rumaysah was given a week to voluntarily surrender his travel documents, which was a condition of his bail.
A letter from police reminding him of the need to hand over the passport by October 3 was not sent until more than a month later on November 7.
Shadow home secretary Andy Burnham wrote to Home Secretary Theresa May accusing her of 'repeatedly' failing to answer his questions in the Commons and calling on her to outline what measures had been taken to prevent a repeat of the lapse.
He wrote: 'This is a high-profile individual who was well-known to the authorities, whose disappearance raises serious questions about the robustness of the system.'
He also rejected the Home Secretary's claim that figures were not available for cases where terror suspects have absconded.
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