Douglas McAuthur McCain, tattooed and thin, never stayed in one place long. Born on Jan. 29, 1981, in Illinois, he would spend 33 years hopping from school to school, from business to business, continent to continent — until, finally, he landed in Syria, where he became the first American reported to die fighting for the Islamic State.

Much of the Douglas McAuthur McCain story remains unclear. It’s unclear how he died in a recent Islamic State battle, into which he carried his American passport and $800. It’s unexplained what led him down a path to Islamist radicalization and violence. And it’s unknown whether he traveled alone.

A review of court records, social media accounts and news clippings does little to answer any of those questions, but instead conveys the profound contrast between the McCain who violently died in Syria — and the Midwestern McCain who rapped, worked dead end jobs, picked up a few petty convictions and was “just a regular American kid,” as one friend told the San Diego Union-Tribune.

His early life was one slice of Americana after another: He followed the Chicago Bulls, was a fan of Michael Jordan, watched “The Simpsons” and developed an affinity for Pizza Hut. After moving to the Minneapolis area as a boy, he played basketball in high school, though classmates tell reporters he wasn’t any good. Between 1997 and 2000, he attended two different high schools in the Robbinsdale Area School District, though the New York Times says district records don’t show him graduating from either school.

“He was a goofball in high school,” one classmate told NBC News, which broke the story. “Doug was a fun guy to be around. Played basketball, joked a lot, had a small sense of humor. Got along with most…. Wasn’t the best athlete, but liked to play.”

It was around that time that McCain started getting in trouble. Over the next eight years, he amassed nine misdemeanor convictions, according to Minnesota state court records. Problems began with a 2000 conviction for disorderly conduct. Then, in 2001, he was busted for misdemeanor theft. Two years later came a misdemeanor conviction for marijuana possession — his first of two minor busts for that offense. His driver’s license was eventually revoked, but McCain kept driving and got caught for that, too.

According to the address listed on his Minnesota driver’s license, he lived on a suburban, tree-lined, road called Oregon Avenue in the town of New Hope just outside Minneapolis. It’s unclear when he left Minnesota — or why — but he eventually resettled in San Diego, where a search of court records reveals he had no further run-ins with the law. The move coincided with another tectonic shift in McCain’s life: mounting religious fervor. On May 14 of this year, he tweeted, “I reverted to Islam 10 years ago and I must say In sha Allah I will never look back the best thing that ever happen to me.

“Ya allah,” he wrote in another tweet, “when it’s my time to go have mercy on my soul have mercy on my bros.”

Though every Western foreign fighter leaves for Syria for different reasons, McCain’s early life carries themes found among other foreign militants. They often operate somewhere on the fringes of society and feel excluded, wrote expert Richard Barrett of the Soufan Group. “The French authorities categorize volunteers from France as disaffected, aimless and lacking a sense of identity or belonging,” Barrett wrote in his report. “This appears to be common across most nationalities and fits with the high number of converts, presumably people who are seeking a greater sense of purpose and meaning in their lives.”

Once settled in San Diego, McCain began working for a now-defunct Somali restaurant called African Spice in City Heights, the Union-Tribune reported. One woman interviewed by the paper recalled McCain was friends with the Somali owners. “They used to stand outside and smoke cigarettes,” she explained, requesting anonymity. “He wasn’t even very religious. He was just a regular American kid.”

But his social media soon suggested otherwise. His tenure on Twitter began innocuously with a late 2012 dispatch: “I’m not feelin this Twitter sh– … wallahi I wants fried chicken. … Watching the Help starting to make me hate white people. … Ok its official f— white people.” He spoke of smoking hookah, watching National Geographic, his Somali friends and his growing religious zeal.

But on Facebook, his imprint was substantially darker. In 2010, McCain, who later traveled to Sweden and Canada, uploaded several images of the black Islamist militant flag. His photo spread became a confounding mixture of family life beside militants clutching swords and images of gold-plated firearms. Then there was this message: The “soldiers of Allah” are “coming back.”

Sometime in the spring of this year, NBC News reported he traveled to Turkey under unknown circumstances. Several people told the news channel they met with McCain — who called himself “Duale” — at an Istanbul Burger King where “they talked about the NBA.” Afterward, on June 9, he sent a tweet to a purported member of the Islamic State: “I will be joining you guys soon.” Later, he wrote, “I’m with brothers now,” and retweeted a message saying, “It takes a warrior to understand a warrior. Pray for ISIS.”

It’s unclear how much his family knew of his travels. They told reporters on Tuesday they had thought he was in Turkey and hadn’t known he had begun fighting for the Islamic State. “I really don’t understand why and how and I have no words,” his sister said in a Facebook post. “I never thought this will be the way we say goodbye…. This is absolutely unreal to me I love you big brother.”