Images from Eric Harroun’s iPhone, which he took with him into Syria. In a video, he warned, “Assad, your days are numbered.” Images courtesy Ann Harroun and via Facebook

In December, 2012, an itinerant American named Eric Harroun checked into a youth hostel in Istanbul. A thirty-year-old U.S. Army veteran with sandy-blond hair, Harroun had left the service in 2003, and since then he had travelled everywhere from Lebanon to Thailand. He was living out of a green duffelbag and a tan camouflage backpack, navigating the world one Lonely Planet guidebook at a time.

At the hostel, Harroun, who made friends easily, met a liberal Syrian activist from Aleppo. “We were hanging out every night, drinking until morning, and talking about the revolution in Syria,” the activist said. The revolt against Bashar al-Assad was approaching its third year, and the activist lamented that Assad was bombarding his people with tanks, jets, and poison gas. Human-rights organizations had accused Syrian soldiers of war crimes, including raping prisoners and massacring children. “The atrocities that were being committed by that totalitarian regime, it made me mad,” Harroun later recalled. “It made me very angry to where I wanted to pick up arms and actually fight against people who would do that.”

On December 5th, Harroun called his mother, Ann, who lived in Phoenix, and informed her that he was going to war. Through the activist, he had met a commander from the Free Syrian Army, which opposed Assad; Harroun had immediately joined the cause. In a message over Skype, he wrote to Ann that, because he was a “qualified expert with an M-16,” he had been placed in “a squad that has scopes, aka sniper rifles.” Harroun assured Ann that he would be fighting alongside honorable men, because “the USA is secretly supplying the FSA.”

Ann urged him to reconsider. She admired his desire to express solidarity with the Syrian opposition but didn’t want him to risk his life. “Can’t you help these people more from the outside, trying to get food and water to them?” she wrote. But Harroun had made up his mind. When his ex-girlfriend Teresa Richard, a Spanish yoga instructor he’d met in Beirut, told him that he would be “crazy” to fight in Syria, Harroun replied, “You have to break an egg to make an omelette.”

The U.S. director of national intelligence, James Clapper, has called Syria “an apocalyptic disaster.” The U.N. estimates that nearly two hundred thousand Syrians have died since 2011. The mayhem has forced virtually all foreign diplomats and intelligence officers to flee; very few journalists continue to report inside Syria, and those who dare to enter become kidnapping targets. (Eighty reporters have been killed.) Joel Simon, the executive director of the Committee to Protect Journalists, told me that Syria has become a “black hole.”

And yet, to a certain kind of person, the extreme danger made Syria only more enticing. Harroun spent the next few weeks preparing for battle. “I am bringing multivitamins and medicine, and I am bringing a rucksack of canned food and bread,” he told Ann.

Harroun and the activist planned to fly to the southern Turkish city of Gaziantep and then cross the border into Syria, where the activist would arrange to leave Harroun with another Free Syrian Army commander. (The activist, whose family remains in Syria, asked for his name to be withheld.) On January 4, 2013, Harroun told his mother, “I will be in Syria for 1 month, then take a break for a couple weeks.” He was bringing his iPhone but doubted that he would find a reliable Internet connection. He warned her that it might be a while before she heard from him.

“Stay safe,” she wrote. “i do not want to lose any of my children before me!!!”

Harroun had caused his mother worry long before he set off to fight in a foreign land. Growing up, he was rarely cowed by authority, and in his teen-age years she was the only one at home to challenge him: Ann had divorced Harroun’s father, Darryl, a truck driver, when Eric was nine.

In the ninth grade, Harroun was arrested for robbery, and found with knives in his sock. When Ann reprimanded him, he tried to choke her. She called the police. Not long afterward, Ann found Harroun asleep on the dining-room floor, near a pistol. She tiptoed across the room, hid the weapon, and contacted the authorities again.

That summer, Ann moved Harroun and his younger sister, Sarah, to Oakes, North Dakota, a small town southwest of Fargo. Ann had a sister who lived there, and she hoped that family support and a tight community would temper her son. But he was picked on as an outsider, and acted up at school. Harroun had multiple piercings, and he shaved his hair on the sides, combing back the rest with gel. Kids called him Slick 50, and, to press the insult, someone poured motor oil on Ann’s car in the middle of the night. Harroun’s grades suffered, and Ann eventually enrolled him in a Christian vocational center for troubled youth. Darryl, who lived in Phoenix and spoke to Eric on the phone several times a week, told me, “He was just lost.”

Eventually, Harroun earned his G.E.D. and enlisted in the Army. In 2000, he went to boot camp at Fort Leonard Wood, Missouri. “That was the best place for him,” Darryl said. He attended Harroun’s graduation ceremony and recalls the day as “probably the proudest I ever was of him.” Harroun had an uneventful soldiering career, never deploying overseas. He wanted to become an infantryman but trained instead as a mechanic. A fellow-recruit, Jason Craig, served with Harroun at Fort Riley, Kansas, and said that the two of them were “inseparable.” Though Harroun enjoyed the camaraderie of the Army, Craig said, he lacked discipline. “We got punished quite often,” Craig added. “Lots of pushups.”

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Harroun suffered from depression and mood swings, and his military records indicate that he had a “personality disorder.” According to Craig, Harroun was “about a week away from receiving a full-blown dishonorable discharge” when, one Saturday in April, 2003, they left the base to hang out with friends at a waterfall near Manhattan, Kansas. After hours of drinking, Harroun rode back to Fort Riley in a truck with a woman who was, as Craig put it, “tanked.” She crashed into a tree and Harroun’s head hit the dashboard, fracturing his skull. He was medevaced to a nearby hospital, where a surgeon inserted a steel plate in his head.

A few weeks later, Harroun was given a medical waiver with an honorable discharge, entitling him to full benefits. He also began receiving a monthly disability check of about twenty-five hundred dollars. Doctors prescribed antidepressants, and narcotics to manage residual pain from the accident.

Harroun moved back to Arizona. He cycled through jobs: brokering mortgages, waiting tables, selling cars. He dated a student at Arizona State University named Melissa Hutton. After they split up, she told me, he turned “borderline stalkerish” and begged her to take him back; when she refused, he shot himself in the abdomen. On another occasion, Harroun tried to punch a friend of Hutton’s, and he was arrested for disorderly conduct. Subsequently, he was arrested twice for driving under the influence.

While Harroun awaited various court hearings, he began following the news, and developed a fascination with the Middle East. He wondered how his old Army friends were faring in Iraq, and wanted to make a contribution. In 2005, he boarded a commercial flight to Kuwait. He assumed that, with his background, a military contractor would hire him upon arrival. He even brought a gun, stashed in a checked bag. But, when he landed, authorities in Kuwait questioned him and put him on the next flight home. The experience left him feeling dejected but undeterred: if he couldn’t tap into someone else’s adventure, he would create his own.