WASHINGTON — Like many teenage boys who grew up in the Midwest in the 1990s, Douglas McAuthur McCain was a fan of Michael Jordan’s Chicago Bulls and loved to play basketball.
But as he grew older, he lost interest in basketball as he shuttled between two suburban Minneapolis high schools. He never graduated, and in his late teens, he began to have run-ins with the law. In the decade that followed, he was arrested or cited nine times on charges including theft, marijuana possession and driving without a license.
McCain moved back and forth from Minneapolis to San Diego and then abroad. Officials now know he ended up in Syria, where three days ago, McCain became the first American to die while fighting for the Islamic State group. He was 33.
The rebels who killed him were fighting for the Free Syrian Army, a rival group backed by the United States, and they went on to behead six Islamic State fighters — but not McCain — and then posted the photographs on Facebook.
McCain’s death provides new insight for the authorities as they try to learn more about Islamic State and identify the Americans who have joined a group that has vowed to remake the Middle East and establish an Islamic caliphate. And it is a sign that Islamic State, at least in this case, is willing to use Americans on the battlefield in the Middle East rather than sending them back to the United States to launch attacks, as Western officials have feared.
“His death is further evidence that Americans are going there to fight for ISIS rather than to train as terrorists to attack at home,’’ said Richard Barrett, a former British intelligence officer who is now a vice president at the Soufan Group, security consultants in New York.
“Nor does it appear that ISIS regards Americans as assets that are too valuable to risk on the front line rather than to keep in reserve for terrorist attacks or propaganda purposes,’’ he said, using an acronym of another name for the group.
“This incident,’’ Barrett added, “also confirms that American and presumably other foreign fighters are prepared to attack where directed by ISIS.’’ Some of those attacks, he said, will be aimed at the forces of President Bashar Assad of Syria, but not all of them.
“They are going to join ISIS, not the fight for the future of Syria,’’ Barrett said.
In recent weeks, Islamic State has become one of the top national security preoccupations of the Obama administration. And the news of McCain’s death comes amid public anger over the beheading of U.S. journalist James Foley, an act that added urgency to the Obama administration’s deliberations to expand its air campaign against Islamic State into Syria.
Senior administration officials and lawmakers have described Islamic State as one of the most serious threats the United States has faced since the Sept. 11, 2001, attacks by al-Qaida, and some believe the group is determined to attack in the U.S.
U.S. officials said Tuesday that McCain’s case highlighted the difficulty of identifying Americans who want to travel to Syria to fight alongside rebels. When the United States faced a similar problem with Somalis several years ago, it was far easier for the authorities to identify those who wanted to travel there to fight because that conflict mostly attracted Somalis. And Somalis live in just a few cities in the United States.
But the Syrian conflict has attracted people from all different ages and parts of the United States — including many with no connection to Syria.
In May, Moner Mohammad Abusalha, a 22-year-old Florida man who had traveled to Syria to join the Nusra Front, died in a suicide bomb attack. He had an American mother and a Palestinian father. A year earlier, Nicole Lynn Mansfield, 33, of Flint, Michigan, was killed with Syrian rebels in Idlib Province.
The federal authorities learned only after he arrived in the country that McCain had traveled to Syria, according to senior American officials. In response, U.S. authorities included him on a watch list of potential terrorism suspects maintained by the federal government. Had McCain tried to re-enter the country, he would have almost certainly faced an extra level of scrutiny before boarding any commercial airliner bound for the United States, the officials said.
It is not clear how McCain was recruited by Islamic State and traveled to Syria. According to his Facebook page, he went to Canada and Sweden last year. Many Americans and Europeans who have ended up in Syria have tried to disguise their travels by passing through other countries before heading to Turkey and crossing over its porous border with Syria.
His posts on Twitter, where he went by the name Duale Khalid, give clues to his mindset. In one message from December 2012, he said that the movie “The Help,’’ which is about black maids in the South, made him “hate white people.’’ Other posts disparaged Somalis and gays.
It was on Twitter that he also discussed religion. He said that he was a convert to Islam and that it was the “best thing’’ that had ever happened to him. “It’s funny to me how all these so call Muslim claim that they love Allah but always curse the one who try to implement his laws,’’ he said in one post.
According to SITE, an intelligence group that monitors jihadist websites, McCain also appeared to grow more comfortable with the idea of losing his life in battle. “Ya Allah when it’s my time to go have mercy on my soul have mercy on my bros,’’ he said on Twitter.
The Obama administration released a statement on Tuesday evening confirming his death.
The fight in which McCain was killed occurred in the northern city of Marea, where Islamic State and the rebels had been fighting for control in recent weeks, according to members of the Free Syrian Army.
McCain and two other Islamic State fighters — a Tunisian and an Egyptian — sneaked up on a group of Free Syrian Army rebels, killing two of them. The other militants responded, killing McCain and dozens of Islamic State fighters. When the rebels went through McCain’s clothes, they found his U.S. passport and several hundred dollars in cash. His death was first reported by NBC News.
Much of McCain’s childhood was spent in New Hope, Minnesota, a Minneapolis suburb where he lived in a three-bedroom apartment with his parents and two siblings, according to Isaac Chase, a longtime friend and neighbor.
McCain was the middle child, and his mother worked as a cashier at a nearby supermarket, Chase said. She attended church every week, he said.
As McCain grew older, he lost interest in basketball, got several tattoos and lost a tooth. “He stuck around here,’’ Chase said. “I don’t think he knew what he wanted to do.’’
It was around that time that McCain’s father died. “He lost his anchor,’’ he said.
When Chase last saw McCain in 2008, he said that it was not clear that McCain was working, and he appeared as though he was using drugs. That was a far different person, he said, from the boy who had strong convictions about what was right and wrong.
When they were children, McCain reprimanded Chase after he stole from a gas station. “He told me who to hang out with,’’ he said. “He had a big heart.’’