Hours into Monday’s lengthy standoff in downtown Sydney that left two hostages dead, the gunmen issued a list of demands. One: Man Haron Monis wanted to speak with Australian Prime Minister Tony Abbott. And two: He wanted a new black Islamic flag. Monis realized the flag he was using inside the chocolate shop didn’t reflect his new allegiance to the Islamic State. He had been using the wrong one.

This was just one of many peculiarities of the self-proclaimed Iranian “sheik,” who started a siege in the heart of Sydney after taking hostages at a popular cafe and was ultimately fatally shot by Australian riot police after a long standoff.

Rejected by Australia’s Muslim communities, he was a man reportedly beset by personal crises when he entered the chocolate shop clutching a shotgun. Despite his professed religious devotion, experts say he was often confused about Islam and conflated separate veins of Islamic ideology. Experts also say his ties to the Islamic State now seem tenuous at best, though he proclaimed allegiance to the group weeks ago.

“This is a person in personal crisis, at the end of his tether,” terrorism analyst Adam Dolnik of the University of Wollongong told the Sydney Morning Herald. “The references to the Islamic State were overtones on top of an action that was very personal.” The scholar added Monis’s request to speak directly to Abbott suggested “motivations [that] were selfish” rather than reflections of religious fanaticism.

But there was nonetheless something unhinged about his Web site, which showed a bloody image of murdered children and Islamic rantings. “Islamic extremism has become fertile ground for many malcontents to protest against their societies,” wrote Ali Mamouri of the Australian Catholic University in the Conversation. “This is even the case for people who aren’t religious hardliners or who aren’t even Muslims.”

It’s not unusual for recruits of organizations like the Islamic State — often disaffected, young, male and unemployed — to be more concerned with mayhem than religion. British investigators discovered that two Britons who had gone to Syria for an eight-month tour had purchased books like “Islam For Dummies,” “The Koran For Dummies” and “Arabic For Dummies.”

By those designations, however, Monis was something of an outlier. He was 50, chased by numerous criminal investigations and a lifelong Muslim — though not the Islamic State’s kind. Until weeks ago, Monis was in fact Shia, a sect of Islam the Sunni-dominated Islamic State branded blasphemous and seeks to obliterate.

“A quick browsing of Monis’ website, which has now been taken down, shows  that he was not aware of basic Islamic theology, including the differences between doctrines and ideologies,” Mamouri wrote. “That is why he mixed up Sunni, Shiite, Salafist, Sufist and other religious expressions in his statements and speeches.”

Previously known as Muhammad Hassan Manteghi, he was born in the Iranian city of Borujerd. In 1996, he published a book of Persian poems called “Daroon and Boroon.” He later claimed he was booted out of Iran for assuming a liberal stance on Islam.

But he reportedly had little success finding a religious footing in Australia, which granted him asylum. He didn’t belong to any mosque or Islamic organization, reported Mamouri in the Conversation, though he came to call himself a “spiritual healer.”

Then 2009 arrived, and things went downhill. That was when Monis was convicted for dispatching taunting letters to families of Australian soldiers who died fighting in Afghanistan. His battle to overturn the conviction consumed him, reports show, and he became convinced of governmental plots to “victimize” him. “Something [had] happened to cause him to become unhinged,” his former lawyer told the BBC, though it wasn’t certain that it involved radical Islam.

He allegedly spiraled further out of control following a bloody night in April of 2013 when his wife, 30-year-old Noleen Hayson Pal, was stabbed to death and set alight in apartment stairwell. Monis was charged as an accessory to the murder in the vicious killing. “This man is damaged goods,” according to Keysar Trad, founder of the Islamic Friendship Association of Australia. “This guy pushed himself to the fringe by his actions and did not seem to be welcomed by any part of the [Muslim] community.”

Monis’s life became a series of court appearances and unhinged rants. Around the time he proclaimed adherence to the Islamic State, he appeared before another Australian court, where he faced 40 charges involving allegations of sexual assault from his time as a “spiritual healer.” One 27-year-old woman, the Guardian reported, had visited him at his business in 2002 after spotting one of his “spiritual consultation” advertisements in a local newspaper.

And so, condemned by many Muslim groups, hounded by sexual assault and murder conspiracy charges, Monis apparently sank deeper into religious fanaticism. He turned to the Islamic State, which isn’t known to discriminate against recruits with shady backgrounds. On his Web site, Monis began calling himself an ex “rafidi,” employing a derogatory Arabic term Sunnis use to belittle Shias. “I used to be a Rafidi, but not anymore,” he wrote. “Now I am a Muslim.”

In the last weeks of Monis’s life, it’s possible what attracted him to the Islamic State was the the idea of personal redemption. The Islamic State advocates finding absolution through violence. “The lesson of Islamic State’s call for random attacks is they are not fussy about who carries them out,” terrorism expert Greg Barton told the Sydney Morning Herald. “If people have made a mess of their lives, the [Islamic State] is offering a glorious way out.”

And few had made more a mess of their lives than Man Haron Monis.