Behind the Black Flag: The Recruitment of an ISIS Killer

Hassan Aboud’s practiced baritone belied the malevolence in his words.

“Oh Darraji!” he sang. “Our state provided us ammunition and sent us to assassinate you.”

That state is the self-proclaimed Islamic State, also known as ISIS or ISIL, the terrorist group that controls territory in Syria and Iraq and has recently projected violence to Ankara, Beirut, Paris and San Bernardino, Calif. A soft-spoken double-amputee sometimes carried to meetings by fellow gunmen, Mr. Aboud is an Islamic State commander who also directs a network of assassins, including those who killed Darraji, a former subordinate, with bullets and flame.

The recording of his singing circulated among past associates this year. A taunting dark requiem, it serves as evidence and confession. Mr. Aboud, who defected from Syria’s rebels to the terrorist group in 2014, was admitting to previously unsolved killings of former friends.

“We plucked Adeeb Abbas’s head,” he continued, naming another of his one-time deputies, blasted from a motorcycle by a roadside bomb. “We spilled his filthy blood.”

He then vowed to kill more, as a male chorus chanted to those marked to die: “We will liquidate every traitor.”

Since rising to prominence as an international menace, the Islamic State has tried to glorify its members, describing them as religious warriors who raised arms to protect fellow Sunni Muslims and serve their understanding of God. But the journey of Mr. Aboud, and his recruitment by ISIS, including with cash, departs from scripts emphasizing piety or civil defense.

It is the chronicle of an underground fighter maimed and darkened by his long fight, the biography — replete with rivalries and fratricide — of a proven and once popular Islamist commander whose actions turned more violent and vengeful as he moved into the Islamic State’s orbit.

Mr. Aboud, his former neighbors and associates say, abandoned the defense of his hometown for money, power and the license for viciousness that came with joining the Islamic State. His path resembled not the airbrushed arcs laid out in jihadist propaganda mills but a Middle Eastern mafia tale set against the corrupting effects of war.

The journey from jihadist rank-and-file to feared underground figure was shaped by multiple forces. These include the American invasion of Iraq in 2003 and the oppression of a border-straddling Sunni Muslim population by governments in Damascus and Baghdad. It was further stoked by the indiscriminate killing of civilians by Syrian security forces since 2011, then channeled by the patient plotting of a jihadist organization, once shattered, that revived itself to eclipse Al Qaeda.

 Ultimately, his courtship by ISIS offers an unusually detailed look at how the group has selected commanders from a region that has produced uncountable militants since 2003. These chosen men, seduced by gifts and the Islamic State’s gloomy prestige, hold the terrain it needs to support its claim of being a caliphate.

Journalists for The New York Times met Mr. Aboud in Syria in 2013, as he led sieges around isolated army positions that were shelling the civilian population nearby; it was a fight he and the several hundred rebels he led, known as the Dawood Brigade, eventually won.

Sarmin, the town in the lowlands of Idlib Province where he headquartered his brigade, was itself under frequent shelling, and he was moving and accepting meetings with much more caution than many rebel commanders.

The interview was arranged by the son-in-law of his boss, but Mr. Aboud’s supporters had everyone wait in the basement of a mosque for part of the afternoon before leading the group to an abandoned building in the partially evacuated, battle-scarred town.

Mr. Aboud was rushed in from the outside by those who carried him. He had lost fighters in battle the previous day and seemed weary and suspicious of guests. His gray pants had been folded to hide his lower-leg stumps, which he crossed in front of himself as he sat on a cushion. He opened the conversation in a quiet voice, and threatened to kill the journalists if he were misquoted.

Abu Ayman, a bomb-maker who helped carry him into the room, spoke more than Mr. Aboud, who chose his words with care, even when repeating Islamist boilerplate.

He complained about the activities of many secular rebels, describing them as opportunists and profiteers. “There are Free Syrian Army brigades,” Mr. Aboud said, that get weapons and “sell them in trade.” He asserted, again speaking softly, that Syria was being plunged into sectarian war by Iran and those it underwrites, including the Syrian government and Hezbollah. “Iran is seeking to re-establish the Persian empire, to get control over the whole Middle East,” he said.

Immediately after the conversation, he was picked up, carried swiftly outside and set on the front passenger seat of a muddy S.U.V., which sped away.

The Times returned to the Turkish-Syrian border after his defection and vendetta killings to interview those who worked with him closely.

Today Mr. Aboud, in his mid-30s, is an exile from Sarmin, where he had lived most of his adult life. Past associates refer to him as either an ISIS wali or emir, titles conveying authority or military power that the Islamic State bestows on governors and its middle rank.

They note that he did not simply drift to ISIS; he has had a relationship with the original underground Sunni insurgents in Iraq’s Anbar Province, part of the crucible where ISIS formed, reaching back more than a decade.

Mr. Aboud and one of his brothers fought American forces there in 2004 and 2005, several townspeople said. Some suggested that the pair returned to Syria as a sleeper cell tied to Al Qaeda in Iraq, which was founded by Abu Musab al-Zarqawi and after his death in 2006 eventually became ISIS.

In the nearly year and a half since Mr. Aboud publicly joined the Islamic State, taking with him most of his fighters and many powerful weapons, he has been credited with, or blamed for, a sprawling mix of battlefield action and crime. Those who know him contend he led the capture of Palmyra, the town and ancient heritage site that ISIS defiled.

For all of Mr. Aboud’s activity, however, his story suggests limits to advancement within the group, which analysts say to a large degree remains led by Iraqis, including many connected to the dismantled Baathist regime of Saddam Hussein.

 Hassan al-Dugheim, a rebel cleric who said he had observed Mr. Aboud since 2011, said his tactical skill and ruthlessness were beyond question. He bluntly added, however, that he considered Mr. Aboud stupid, and that the Islamic State had found in him a man who could be flattered, bought, then used.

“Syrians are for fighting,” he said, and those who had joined ISIS recently faced a glass ceiling inside. “They are like animals to be ridden, like a horse or a mule.”

Crucible of Sunni Militancy

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Hassan Aboud was among the earliest of his townspeople to experience war on what would become the Islamic State’s turf.

In 2004, he and a brother, known as Abu Shadi, traveled to Iraq to join the fight against the American military around Falluja and Ramadi, according to residents of Sarmin. Mr. Aboud, a stoneworker, was in his 20s, entering freshly colonized turf in a militant underworld.

Accounts of his Iraq time vary. Some confusion, his townspeople say, is because Mr. Aboud was circumspect about his activities — an unsurprising behavior considering concerns in Syria’s Alawite-led government that those aligned with Sunni militants in Iraq could rekindle unrest in the Sunni population at home.

Mr. Aboud’s associates said he returned in 2005. A relative, who asked for anonymity so as not to draw his wrath, said that while away Mr. Aboud swore allegiance, or bayat, to his militant leaders. “It was known Hassan Aboud was Al Qaeda,” he said.

Another man, an activist from Sarmin who worked with the Dawood Brigade, said he had seen a video from 2005 of Mr. Aboud with Mr. Zarqawi.

A proponent of terrorism, deliberate savagery and management by fear, Mr. Zarqawi helped push Iraq into sectarian war, inspired a generation of jihadists and became one of the world’s most wanted men before American bombs killed him in 2006. His group later rebuffed top Qaeda leaders to form ISIS.

Mr. Dugheim, the cleric, said he doubted Mr. Aboud was a Qaeda member, noting that he concerned himself solely with local battles and was opposed to the Nusra Front, Syria’s official Qaeda franchise, as it gathered strength. “I exclude the possibility that he really gave bayat,” he said.

Others noted, however, that the Nusra Front and the Islamic State were competitors who became foes, and Mr. Aboud’s connections were not with the central Qaeda leadership that gave the Nusra Front its jihadist authority but with the Iraq wing. Opposition to the Nusra Front, by this view, did not exclude allegiance to the faction that became ISIS.

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Whatever the inner loyalties, Mr. Aboud’s life as a fighter once appeared to end. His return home was noteworthy. The activist who worked with him said he knew five men from Sarmin who fought in Iraq. Two died as suicide bombers.

Mr. Aboud dodged that fate, and resumed an unassuming life: He owned a Kia truck and earned wages delivering cement and rebar.

By 2007 he and his brothers owned a workshop, made cinder blocks, sold decorative and patio stone and hired out for contracts. “I used to see him at a lot of houses under construction, and he had laborers working for him, five or six at a time,” the activist said.

Roughly two years before the uprising, Syrian security forces raided Sarmin, cracking down on Sunni networks. One of Mr. Aboud’s brothers was caught.

“Abu Shadi was detained in the street, and taken to Sednaya prison,” the activist said, referring to the infamous jail near Damascus where the government warehoused those it considered Sunni extremists.

In the interview with The Times in 2013, Mr. Aboud confirmed the arrest, but gave a minimal explanation, suggesting his brother had been punished for his faith. “My brother was sent to jail because of his beard,” he said.

He described Syria’s government as an oppressive weight. “They can fight you for an idea you carry in your mind, because of your beard, the way you pray or you dress,” he said. “It is like a siege on your emotions and your beliefs.”

Mr. Aboud seemed to elude the attention of intelligence services. Neighbors said he was conservative and religious, but not overtly so. He wore a beard, but kept it trimmed. Sometimes he smoked, although descriptions of him tend to center on his clean living.

He and his wife were raising a family. His night life consisted of staying up late, drinking tea. “He had a good reputation, nothing bad,” said a doctor in Sarmin who said he often met Mr. Aboud, but asked not to be named for his safety.

Return to War

In early 2011, after popular uprisings in Tunisia, Egypt and Libya, protests erupted in Syria against President Bashar al-Assad. Mr. Aboud went underground, beginning his long campaign.

“When it started in Tunisia, we were optimistic,” he told The Times. “We started to arrange and coordinate with people we trusted.”

The government fired on protesters in Dara’a that March, killing at least three. Mr. Aboud said bloodshed triggered action. “A day later we joined the revolution, beginning with demonstrations out of the mosques,” he said.

Syria was on a path to war. Mr. Aboud’s former allies recall his clear sense of the steps to take at each stage — skills they suspect he learned in Iraq.

Protest organizers left their homes to sleep in fields and among the trees, dodging security forces. Sarmin’s quiet stoneworker, they learned, was more ready than most. “Hassan Aboud would bring us bread and canned food,” said Ahmed al-Aasi, an activist with Ahrar al-Sham, a large Islamist fighting group.

He was quick to violence. As Syria deployed its army, Mr. Aboud was among the first armed rebels in a landscape that would eventually be awash in them.

In June 2011, while Syrian protesters appealed for international support, Mr. Aboud participated in the ambush of an army convoy near Jisr al-Shoughour, four associates said. The little band in which he fought with a friend, Dawood al-Sheikh, had only seven or eight rifles.

It was a quixotic clash. Mr. Sheikh was killed. The road remained open. Crackdowns continued apace. It also provided a glimpse of the future: Mr. Aboud soon formed a fighting group, named it the Dawood Brigade and left protests behind.

His brigade started small. But it set up a guerrilla base among olive groves and caves, where it trained, manufactured weapons and extended its fight. By late 2011, it joined Suqour al-Sham, or Sham Falcons brigade, an Islamist group founded by Ahmed Abu Issa, a former prisoner in Sednaya.

Many early rebel groups lacked experience, money, training and cohesion. The Dawood Brigade was different, Mr. Aboud’s townspeople said. It tended to details necessary to become a fighting force.

Mr. Aboud’s brother, released from Sednaya, organized logistics, including medical care and convalescence in Turkey for wounded fighters. Mr. Aboud established training regimens that even his critics say produced results.

“Hassan Aboud has a mean heart, and he is fierce, and he tells his fighters to be hard and fierce in battle,” said the activist who used to work with him. “No other group in Idlib had this ferocity, and he made them like this because of his training.”

“They had constant and continuous training,” the doctor said, in tactics, weapons and sports.

Mr. Aboud gained access to funders from the Persian Gulf, and more support from Abu Issa. “Sham Falcons gave them a big share of the money and resources because they had results,” said Abu Ameen, another activist who worked with rebel commanders.

In 2012, the brigade had drawn in hundreds of local men, amassed weapons and paid salaries of $140 a month. “This was at a time when other rebel groups could not offer their fighters lunch,” said another activist, Mohyeddin Abdulrazzaq, who otherwise spoke harshly of Mr. Aboud.

The brigade also mastered a staple of militant war: the use of improvised bombs, with which it punished Syrian forces and controlled roads. “They had sophisticated bombing operations in the beginning, when no one else did it,” Abu Ameen said.

Other rebel units caught up to this tactic, and together shifted the nature of the war, forcing the Syrian Army to withdraw to outposts and bases.

One result was the creation of marginally governed territory into which foreign fighters flowed, and where ISIS would eventually assert a place. In the short term, Mr. Aboud achieved a degree of local popularity. “Hassan Aboud was sacred among his fighters,” Mr. Abdulrazzaq said. “When you mouthed bad words among his fighters, it was as if you mouthed bad words against God.”

As Mr. Aboud gained power his activities sometimes turned sinister. Mr. Aasi said he became involved in the abductions of Alawites, and sought ransoms for their release. Other rebel leaders once intervened to stop the Dawood Brigade from executing civilians near Fuoa, a government-controlled town, Mr. Aasi said; among the detainees were women and a child. “He had a criminal tendency,” he said. “He became a dictator even before we had an ISIS.”

His affinity for irregular war almost led to his death.

From its bases, the army increased the shelling of Sunni towns, setting in motion waves of refugees. The brigade’s arms-makers started producing rockets, which they fired at the soldiers concentrated at government positions. “We targeted their camps with lots of rockets,” Mr. Aboud told The Times in 2013. “It was good, accepted.”

In late 2012, the brigade was filming a video for a Qatari funder, an activist said, when a rocket exploded prematurely, gravely wounding several rebels, including Mr. Aboud, whose lower legs were mangled.

Mr. Aboud survived the ride to a clinic, where both his feet were amputated. The doctor recalled being surprised by his demeanor. “For someone who had just had his feet removed, he had high morale,” he said. “He was joking.”

When Mr. Aboud was interviewed months later by The Times, he mentioned the mishap only when asked. “One time we were launching a rocket and it exploded and that’s how I lost my legs,” he said, and changed the subject. “Now we have improved rockets,” he added. “More safe. More effective. Bigger.”

Frustration and Recruitment

By 2013 the Dawood Brigade had established more bases, expanded training, participated in prominent battles and captured many more weapons. By some counts Mr. Aboud possessed nine tanks, four B.M.P. fighting vehicles and a fleet of trucks carrying 14.5-millimeter machine guns.

A tactical powerhouse, he was in demand on Arabic-language news stations. With rebel prestige came rivalries, the office politics of war. Mr. Aboud, those who know him said, believed his successes had not been adequately rewarded or gained him autonomy.

“Dawood Brigade is the one who participated in the battles and made the gains, but all the support and money went to Abu Issa and the Sham Falcons,” his relative said.

Mr. Dugheim said that in 2013, as Islamist rebel groups discussed merging into a united front, Mr. Aboud wanted equal billing with the Falcons. Abu Issa rejected the proposal. Mr. Aboud seethed.

Distance from rebel leadership grew. “His funds went down with the loss of support, and he was in trouble,” Mr. Dugheim said.

It was then that ISIS made its move. A shadowy presence compared to now, it sought to lure him into its ranks.

People who know Mr. Aboud describe a series of meetings with Islamic State leaders from Iraq, including with Abu Ali al-Anbari, a former Iraqi military officer who moved outside the city of Aleppo with a security contingent and a mission to recruit local commanders.

Abu Ameen described a “secret operational phase” by ISIS in 2013 that targeted rebel and activist networks. Its timing aligned with Mr. Aboud’s disputes, he said, “and Dawood Brigade is one of the groups that was infiltrated.”

At one point, activists said, Abu Ali called a meeting of rebel leaders in Idlib Province to discuss relationships with ISIS. He also sent ISIS agents to Sarmin to woo Mr. Aboud, who had begun to noticeably fall under the Islamic State’s sway.

Mr. Dugheim said he mediated between Abu Issa and Mr. Aboud at the time. ISIS, he said, was flattering the brigade with attention and gifts.

“ISIS offered Hassan Aboud a big amount of money — $2 million — when Hassan Aboud actually had nothing in hand,” Mr. Dugheim said. “They gave him weapons and money and food.”

This sum could not be independently confirmed.

 Abu Ameen said Abu Ali’s calculated strategy won over many fighters. “Some joined ISIS publicly, but some joined ISIS but remained within the same group they were part of,” he said. “With money and promises, ISIS got control of hearts and minds.”

Even before the public defection, hints of extremist influence appeared in his brigade.

Through 2013, associates said, the brigade had not been linked to suicide bombings. Mr. Aboud, they said, did not use his fighters, mostly local men, that way.

But a video of brigade training, posted online in October 2013, shows recruits being lectured in suicide tactics by a middle-aged man with closely cropped hair and a long beard. The Dawood logo is superimposed on the scene.

An American military official who analyzes ISIS said the recruitment and changes fit a pattern. “It was a successful intelligence operation,” she said. “They were able to go in, find people who were vulnerable and could be flipped, flip them, and turn it into what they perceive as a state.”

Mr. Dugheim said by then Mr. Aboud parroted the Islamic State’s style, sometimes behaving like a takfiri, one who labels other Muslims as insufficiently religious, and thus impure.

The change in persona, Mr. Dugheim said, indicated a man out of his depth. “One of the problems in human nature is when you have a hero who is stupid,” he said. “And Hassan Aboud is a hero who is stupid.”

“He misread the situation,” he added.

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Defection and Fratricide

The killings began before the Dawood Brigade drove out of Sarmin. Mr. Aboud was turning on his own.

Among the first victims were Darraji and Bassim Abdulrazzaq, brothers who had joined the brigade in 2012.

The pair had formed a smaller rebel group that occasionally collaborated with its old boss. In December 2013, they joined the brigade in a battle against a Syrian checkpoint, according to Mohyeddin Abdulrazzaq, a second cousin of the men.

The checkpoint fell. But one brother was wounded, several fighters were killed and a heavy machine gun they relied on was destroyed. Shaken, they asked Mr. Aboud for a 14.5-millimeter machine gun to cover their loss. He refused.

In January 2014, Mohyeddin Abdulrazzaq said, the brothers asked again. They visited Mr. Aboud, were cheered when he consented and drove off with their new weapon. They did not make it far.

“A few hours later came news to the town of a vehicle burned on the road,” he said. “It held Darraji and his brother. Aboud gave them the machine gun, and then had them killed.”

It was not just that Mr. Aboud did not like being asked twice. Darraji had publicly spoken against ISIS in the fall, when it had kidnapped workers from the International Committee of the Red Cross near Sarmin.

Mr. Aboud appeared for the funeral and paid respects.

Not long after, Mr. Aboud announced he was joining a new group, Jaish al-Sham. Throughout early 2014 the group seemed a symbol of infighting and dysfunction, repeatedly clashing with other rebels. Mr. Aboud’s associates said that sometimes he expressed allegiance to the Islamic State, and that other times he renounced it.

Abu Ameen said, in hindsight, that Mr. Aboud was following new masters. “Getting instructions from ISIS,” he said.

Residents said they suspected Mr. Aboud of organizing hits, including on a Dawood commander, nicknamed Hyena, and Abu Abbas, the brigade’s Shariah instructor. But there was no clear proof, and the brigade’s brooding presence created disincentives to inquiry.

Mr. Aboud’s affiliation finally became explicit in July, when he formed his brigade into a convoy, ostensibly bound for Aleppo and yet another fight. “Only those close to him knew the real plan,” his relative said.

Short of Aleppo, Mr. Aboud stopped and announced that he was a servant of Abu Bakr al-Baghdadi, the Islamic State’s leader, and was heading to Raqqa, its operational hub, to join the caliphate.

“Hassan told them that he had given bayat to Abu Bakr, and those who wanted to stay with him could stay and those who wanted to go were free,” the activist who worked with him said.

How many members were present is a matter of dispute. Several former associates said a few hundred. (News reports claimed as many as 1,000; an exaggeration, residents of Sarmin say.)

About 100 fighters declined, and returned home with the news.

The brigade’s departure deepened the troubles of an already beleaguered town. Its defenses were weakened, residents said, because Mr. Aboud took a large fraction of the area’s weapons, forsaking those he had vowed to protect.

Behind the Black Banner

Since Mr. Aboud arrived in Raqqa, his associates said, they have had only occasional insight into his militant life. ISIS, they note, is a such a closed system that little is known even of Mr. Baghdadi and the nature of his power. Mr. Aboud and his brigade, once he defected, dialed back their social media presence and interviews. His activities, they said, have been assembled piecemeal.

Mr. Dugheim was among the last to speak with him before his defection. ISIS had just swept across part of Iraq, capturing Mosul and Tikrit. Mr. Aboud appeared smitten, as if it were 2004 again.

“I said to him, ‘Why do you like ISIS?’” Mr. Dugheim said. The reply had little to do with Syria’s revolution: “Because ISIS is being fought by the U.S.A.”

The American military analyst said that today Mr. Aboud appeared to be “of midlevel stature,” and that “ISIL-core will exploit his quote-unquote ‘talents’” while seeing him as “disposable, expendable.”

This matched what his townspeople described — the Dawood Brigade’s movement across the Islamic State’s Syrian territory on a range of shifting missions. Based on where his fighters have been killed, they said, Mr. Aboud has fought in Kobani, Aleppo, near Raqqa, near Homs and for the Shaer gas field and the capture of Palmyra.

The brigade has also been accused, without public evidence, of assassinating the leadership of Ahrar al-Sham, and of holding the abducted journalist James Foley before turning him over to ISIS. (ISIS beheaded Mr. Foley in 2014. Claims of a Dawood Brigade role in his detention, made in news reports and echoed on social media, do not align with facts known of his case.)

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One sighting of Mr. Aboud occurred in June in Palmyra. Khaled al-Homsi, an activist, said he was briefly imprisoned there, and Mr. Aboud toured the jail on crutches. “He met me privately in a room,” he said, “to convince me to pledge allegiance.”

After the Islamic State consolidated control in Palmyra, he added, some of the staff in the courts were from the Dawood Brigade, suggesting Mr. Aboud was trying to govern.

Efforts to reach Mr. Aboud this fall were unsuccessful. But former associates said they expected he would fail at such aspirations.

Mr. Aasi said Mr. Aboud’s role was obvious — as an enforcer, an instrument of purposeful violence to help ISIS gain territory and rule by fear. “With ISIS there are no limits, and you can abduct and kill whomever you like,” he said. “Hassan Aboud does not have a problem with killing. He likes it.”

The rebels’ former ally, he said, “is sick in his mind.”

Mr. Dugheim, the cleric, said Mr. Aboud left Sham Falcons for an even more complicated game, and had peaked. “Regardless of his title, he cannot make a decision,” he said, because ISIS limits the authority of its Syrian commanders.

Another American military official who analyzes ISIS said that under the pressure of airstrikes and internal strife, members with titles like emir and wali now gain rank through attrition, not design. “We watch the deck shuffle constantly, as they attempt to determine who will fit a role that has been vacated,” he said, “vacated” being a euphemism for “killed.”

Whatever Mr. Aboud’s eventual fate, his relative said, much of the legacy was already known. The recording of Mr. Aboud singing — coolly in tune as he described killing old friends — was a marker of a man lost to crime, a revolution soured and a people betrayed.

 “His violence, his assassinations, his killing people — he is really behind this,” he said. “It is a mess now. Everything we have is a mess.”