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.
Mr. 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, Mr. McCain became the first American to die while fighting for the Islamic State in Iraq and Syria. He was 33.