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WASHINGTON — Like many teenage boys who grew up in the Midwest in the 1990s, Douglas McAuthur McCain was a fan of Michael Jordan and the Chicago Bulls and played basketball himself as he shuttled between two high schools in suburban Minneapolis.

It was a rootless existence, and in the next 10 years, he was arrested or received citations eight times on charges including theft, marijuana possession and driving without a license.

McCain moved back and forth from Minneapolis to San Diego, then abroad, where records of his movements ran cold. Officials now know he ended up in Syria, where three days ago, McCain, 33, became the first American to die while fighting for the Islamic State group.

McCain’s death is one of the first clues U.S. officials have as they try to identify the Americans who have joined a group that has vowed to remake the Middle East. And his death is evidence Islamic State 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.

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“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 office who is now a vice president at the Soufan Group, a security consultancy 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,” Barrett said, using an acronym for one of the militant group’s names.

“This incident,” he 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.

Islamic State has suddenly become one of the top national security preoccupations of the Obama administration. News of McCain’s death comes amid public anger over the beheading of U.S. journalist James Foley, which added urgency to deliberations over expanding the U.S. air campaign against Islamic State into Syria.

Senior administration officials and lawmakers have described Islamic State as the greatest threat the United States has faced since the Sept. 11, 2001, attacks by al-Qaida and have said the group is determined to attack in the U.S.

Six fighters beheaded

The federal authorities learned that McCain had traveled to Syria only after he arrived there, according to senior U.S. officials. In response, U.S. authorities put him on a watch list of potential terrorism suspects, ensuring an extra level of scrutiny if he tried to board any airliner bound for the United States, the officials said.

McCain was killed over the weekend by anti-Assad rebels backed by the United States and known as the Free Syrian Army. In that battle, the rebels went on to behead six Islamic State fighters — but not McCain — then posted the photographs on Facebook.

It is not clear how McCain was recruited by Islamic State and traveled to Syria. According to his Facebook page, he traveled to Canada and Sweden last year.

Many Americans and Europeans who have ended up in Syria have attempted to disguise their travel by passing through other countries before heading to Turkey and crossing over its porous border with Syria.

McCain lived most recently in Minnesota, according to public documents, and between 2000 and 2008 he was arrested several times. Among the charges he faced were theft and obstructing the legal process.

A State Department spokeswoman said that an American who grew up in Minnesota and attended college in San Diego was killed overseas but declined to confirm a report he died in Syria while fighting for ISIS.

San Diego City College officials confirmed McCain’s attendance but declined to provide additional details.

On the Facebook page identified as belonging to McCain, he referred to himself as Duke ThaslavfeofAllah. The Facebook page has since been taken down.

On a Twitter account identified as McCain’s, he used the name Duale Khalid and wrote, “It’s Islam over everything.”

The person using the name Khalid said he converted to Islam a decade ago: “I will never look back the best thing that ever happen to me,” reads one Twitter message.

The Twitter messages display hostility toward gays, white people and Somali immigrants in San Diego. The messages praise Allah and smoking hookah.

One tweet reads: “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.”

The Twitter account includes a translation of a speech by Islamic State spokesman Abu Muhammad Al-Adnani.

While in San Diego, McCain worked at an African restaurant but employees there declined to comment.

In a Twitter posting June 9, McCain said to someone who appeared to be a member of Islamic State that he would soon join them. Shortly thereafter, he posted he was “with the brothers now.”

Fatal firefight

The fight in which McCain was killed occurred in the northern city of Marea, where Islamic State and the rebels had been battling 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.

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.

The Syrian conflict has attracted people from all 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, a Sunni extremist group linked to al-Qaida, killed himself in a suicide bombing. He had an American mother and a Palestinian father.

A year earlier, Nicole Lynn Mansfield, 33, of Flint, Mich., was killed with Syrian rebels in Idlib province.

A former U.S. Army soldier from Phoenix, Eric G. Harroun, was indicted in Virginia by a federal grand jury last year related to allegations he fought alongside the Nusra FrontHe died in April at 31.

Also, a family representative said Tuesday that the Islamic State militant group is holding hostage a young American who was doing humanitarian aid work in Syria. The 26-year-old woman is the third American known to have been kidnapped by the militants.

The Islamic State group recently threatened to kill American hostages to avenge the crushing airstrikes in Iraq against militants advancing on Mount Sinjar and the Kurdish capital of Irbil.

The 26-year-old woman was captured last year while working with three humanitarian groups in Syria. A representative for the family and U.S. officials asked that she not be identified out of fear for her safety.

Other American hostages have been held by other militant groups, including Peter Curtis, who was recently released by Nusra Front, and reunited Tuesday with his mother in Boston.

Another U.S. freelance journalist, Austin Tice, of Houston, disappeared in Syria in August 2012 and is believed to be held by the Syrian government. Tice was working for The Washington Post, McClatchy Newspapers and other media outlets.

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