Newly published emails suggest the man who became known as "Jihadi John" had suicidal thoughts before leaving Britain for Syria.
In an email exchange with the Mail on Sunday five years ago, he talked of taking too many sleeping pills and sleeping forever as a way to get away from British security service scrutiny.
Mohammed Emwazi told a journalist at the newspaper in an email that he felt like a "dead man walking".
Emwazi was revealed this week to be the Islamic State militant known as "Jihadi John," who appears in beheading videos brandishing a large knife.
He was a computer science graduate who lived in west London before leaving for Syria in 2013. He was interrogated by security services while in Britain but was never arrested or charged.
In Sunday's edition of the Mail on Sunday, journalist Robert Verkaik described meeting Emwazi in 2010 when he was using the name Mohammed al-Zuhary.
"He seemed to have a persecution complex and desperately wanted his story to be told," Verkaik wrote of his encounter with the young man.
At the time, Emwazi was pursuing a complaint against police for alleged mistreatment.
"His concerns seemed to border on paranoia," Verkaik wrote. He described Emwazi as someone who was polite and understood how journalists worked.
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