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An aerial view Sunday of the mass shooting scene at the Pulse nightclub in Orlando, Fla., where a gunman opened fire dying in a gunfight with SWAT officers, police said.

Red Huber/The Associated Press

Self-declared jihadi Omar Mateen, 29, trumpeted his allegiance to Islamic State in a 911 call a few minutes before the deadly massacre began shortly past 2 a.m. in an Orlando gay nightclub.

After exchanging shots with an off-duty policeman hired to provide security at Pulse, Mr. Mateen herded scores of terrified gay men into the washroom and then called 911 to voice personal fealty to Abu Bakr al-Baghdadi, the seldom-seen, black-clad Islamic State leader. Then, the shooting and hostage-taking unfolded bloodily into a massacre.

Mr. Mateen was twice investigated for extremist Islamist sympathies – and twice cleared – by the Federal Bureau of Investigation, which concluded the New York City-born security guard posed no real threat. Mr. Mateen first triggered alerts when, in 2013, co-workers reported him to the FBI for making extremist statements. He was investigated, interviewed twice and cleared, said FBI Special Agent Ronald Hopper at an afternoon briefing after the worst terrorist attack on U.S. soil since the Sept 11, 2001, al-Qaeda hijackings of four jetliners used to destroy New York's twin towers and set the Pentagon ablaze, killing nearly 3,000.

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Then, in 2014, Mr. Mateen contacted Moner Mohammed Abu-Salha, another U.S. citizen and Florida resident who was part of a four-person suicide attack for Jabhat al-Nusra, an al-Qaeda-linked Sunni extremist group. That triggered another FBI probe. "The contact was minimal," Mr. Hopper said, adding that Mr. Mateen was interviewed a third time by federal counterterrorism agents. However, he was "thoroughly investigated" and cleared again.

After twice triggering suspicions that he was a terrorist – or at least an Islamic State sympathizer – and twice being investigated and cleared by federal counterterrorism agents, the failure to deter or detain Mr. Mateen will again raise doubts about the performance of the FBI. The storied agency also failed, despite warnings and evidence, to correctly assess the danger posed by Islamic terrorists who attacked Fort Hood and the Boston Marathon.

Mr. Mateen, who worked as a security guard since 2007 and was recently assigned to a juvenile-detention facility, currently "wasn't under investigation and wasn't under surveillance," Mr. Hopper said.

Like Syed Rizwan Farook and Tashfeen Malik, the married couple inspired by but unknown to Islamic State, who killed 14 people and injured 22 others at an office party in San Bernardino six months ago, Mr. Mateen, may have self-radicalized, inspired by but not in direct contact with IS.

Amaq, an Islamic State news agency claimed "the armed attack that targeted a gay night club … which left over 100 people dead or injured was carried out by an Islamic State fighter." But it didn't suggest the operation was planned or directed by the extremist group that has carved out a nascent state in parts of Syria and Iraq. Brutally killing gays, often by tossing them from rooftops, has been a feature in IS videos.

Mr. Mateen swore allegiance to IS in his call to 911, the first time a terrorist has self-declared in the midst of an attack in the United States. "So far as we know at this time, his first direct contact was a pledge of bayat [loyalty] he made during the massacre," a U.S. counterterrorism official told Reuters. In the call, Mr. Mateen also praised Tamerlan and Dzhokhar Tsarnaev, another pair of homegrown jihadis who planted bombs at the 2013 Boston Marathon, killing three and wounding more than 250 others.

Russia warned the FBI about the Tsarnaev brothers' radical views but the top U.S. federal police agency investigated – and cleared them – in 2011. It also investigated and cleared Major Nidal Hasan, a U.S. military psychiatrist who had been e-mailing al-Qaeda cleric Anwar al-Awlaki. Major Nidal attacked soldiers at Fort Hood in 2009, killing 13 and injuring more than 30 others in the first major domestic terrorism attack on President Barack Obama's watch.

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After twice being cleared by FBI agents, Mr. Mateen apparently disappeared from the vast anti-terrorism net of U.S. government surveillance.

Less than 10 days ago, he walked into a Florida gun dealership and – lawfully – purchased a handgun and a military-style assault rifle.

His father, an Afghan immigrant, who was interviewed hours after the massacre, said his son had been infuriated when he saw two men kissing in public recently. But whether the self-recruited jihadi was motivated by IS ideology or vicious homophobia, or a mixture of both, remains unclear.

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