SYDNEY, Australia — The gunman who seized hostages in a downtown Sydney cafe and was killed in a police raid early Tuesday was known to both the police and leaders of Muslim organizations as a deeply troubled man with a long history of run-ins with the law, including a pending case involving the killing of his former wife.
“This guy was on the fringe of the fringe,” said Manny Conditsis, a lawyer who had represented the gunman, Man Haron Monis, in previous criminal cases. “He wasn’t accepted by anybody.”
Mr. Conditsis described the 16-hour seizure of the cafe, which also left two hostages dead, as “the ultimate cry for attention.”
The violence in Sydney occurred two months after a gunman killed a soldier and stormed Parliament in Ottawa, an episode that was a similar mix of personal disaffection and jihadist zealotry.
The Canadian gunman, Michael Zehaf-Bibeau, had criminal convictions in cases that included robbery and drug-related offenses and was a convert to Islam. He shot dead a young corporal guarding the tomb of the unknown soldier at the country’s National War Memorial. Two days before that, a 25-year-old man who had recently adopted radical Islam ran over two Canadian soldiers near Montreal, killing one.
Mr. Monis successfully sought political asylum in Australia two decades ago, the authorities said. According to Mr. Conditsis, the lawyer, Mr. Monis had been a Shiite cleric in Iran. The lawyer said he also believed that Mr. Monis later converted to the Sunni branch of Islam.
The attacks in Canada and the one in Sydney raise questions about the ability of governments to monitor radicalized, would-be killers and prevent them from doing harm.
The similarities among those attacks and one in New York in October, when a man with a hatchet set upon police officers, were the radicalization of people and their isolation from their communities, according to Greg Barton, the director of the Global Terrorism Research Center at Monash University in Melbourne.
The gunman, Man Haron Monis, had been involved in a number of cases, including one over the murder of his former wife. “This guy was on the fringe of the fringe,” said a lawyer who had represented him. Mr. Monis, originally from Iran, successfully sought political asylum in Australia two decades ago.
“There is no easy answer to how you deal with that,” Mr. Barton said. “It is just not possible to put people under 24-hour surveillance unless they are prime suspects.”
The Australian security and counterterrorism authorities do a good job monitoring large-scale operations and individuals within radicalized groups, he said, but “lone wolf operators present a different challenge.”
Mr. Monis entered the Lindt Chocolate Cafe on Martin Place in central Sydney about 9:45 a.m. on Monday and took 17 hostages, five of whom escaped. He had a black flag with white Arabic script, similar to those used by Islamic militants on other continents, which was later displayed in a window of the cafe.
Andrew Scipione, the New South Wales police commissioner, said Mr. Monis was fatally shot during the police raid, which took place shortly after 2 a.m. Tuesday. The police moved to storm the restaurant after gunshots were heard inside, Mr. Scipione said.
“They made the call because they believed that at that time, that if they didn’t enter, there would have been many more lives lost,” the commissioner said. Before the raid began, the police said they believed that no one in the cafe had been hurt.
A police statement released later did not make clear how the two hostages were killed, saying only that “shots were fired during the confrontation.”
Australian news media identified the two dead hostages as Katrina Dawson, 38, a lawyer, and the cafe’s manager, Tori Johnson, 34.
Alarmed by the prospect of Australians traveling to Syria and being radicalized by the civil war there, the government of Tony Abbott this year pushed through Parliament a raft of laws to prevent terrorism at home. The laws bar Australians from joining civil wars in foreign countries, make it easier for the government to confiscate passports, and make it an offense to incite terrorism through social media. Another measure steps up intelligence sharing between the military and the Australian Secret Intelligence Service.
Experts say the new laws were not helpful in the case of the Sydney siege because Mr. Monis did not travel overseas and apparently was not part of a gang or terrorist network. “The new laws don’t add anything to what can be done in advance in a situation like the siege,” said Bret Walker, a barrister who was Australia’s first independent monitor for national security laws.
Keysar Trad, a spokesman for the Islamic Friendship Association of Australia, based in Sydney, said that Mr. Monis had been acting alone and that that had made it difficult for the authorities to track him.
“If he had been part of a bigger group, he would have come up on the police radar” and been under constant surveillance, Mr. Trad said. “He didn’t.”
And yet Mr. Monis had repeatedly come to the attention of community leaders and the authorities.
Mr. Trad said he met with Mr. Monis several times, the first meeting prompted by sharply critical letters that Mr. Monis had sent to the families of Australian service members killed in Afghanistan. He was convicted and sentenced to community service for sending the letters, with the authorities using a rarely invoked law covering postal communications.
Mr. Monis was charged in November 2013 with being an accessory to the murder of his former wife, Noleen Hayson Pal, who had been stabbed and burned to death. A woman, Amirzh Droudis, 34, has been charged with her murder. Mr. Monis was granted bail and was awaiting trial.
“He had nothing to lose,” said Mr. Conditsis, the lawyer. “He may have been motivated by what he saw as the inevitability of going to prison.”
In April, Mr. Monis was also charged with the sexual assault of a woman in western Sydney in 2002. Forty more counts of sexual assault relating to six other women were later added to that case. Mr. Monis also seemed rattled by his inability to reunite with his family in Iran and by what he described as torture by prison guards during a stint in prison, Mr. Conditsis said.
Mr. Monis emigrated to Australia from Iran around 1996 and was previously known as Manteghi Boroujerdi or Mohammad Hassan Manteghi. In a broadcast interview in 2001, he claimed to have worked for Iranian intelligence.
According to Iranwire, a news website run by Iranian expatriates, Mr. Monis had published a book of poetry in Iran.
The state-run Iranian news agency, Fars, quoted a Foreign Ministry spokeswoman, Marziyeh Afkham, as saying that it had warned the Australian authorities about Mr. Monis.
“The history and mental-psychological conditions of this individual, who sought political asylum in Australia more than two decades ago, had been discussed with Australian authorities many times,” Ms. Afkham was quoted as saying.
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