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New details emerge on Minnesota native turned ISIS fighter

Douglas McCain, a Minnesota native, was killed in Syria while fighting for extremist group ISIS.2 / 2

San Diego, CA (CNN) - There are new details on Douglas McCain, the American citizen turned ISIS fighter. We are learning when he first caught the attention of US intelligence, and the path he took to extremist jihad.

American jihadi fighter Douglas McAuthur McCain first crossed investigators' radar in the early 2000s. What attracted their attention? His association with other people with radical beliefs.

One was a high school classmate and friend of McCain’s in Minnesota who died in Somalia fighting alongside al-Shabaab militants in 2009. The FBI in Minnesota, McCain’s home state, says jihadi recruiters have taken a vested interest in their troubled youth.

Kyle Loven - FBI Spokesperson: "Unfortunately the recruiters and those who would lure youth overseas are very aware that they have a pool of potential travelers here in Minneapolis."

Still, there was no indication then that McCain, who studied Arabic at San Diego City College, was involved in anything nefarious. According to law enforcement, he seemed to radicalize gradually in the years since converting from Christianity to Islam.

Kenyata McCain - Cousin of Douglas McCain: "He grew to have really strong Muslim beliefs. I know his religion was very important to him. But those people, the ISIS people, they don't represent what my cousin's beliefs are."

Despite being on a terror watch list, US authorities did not discover McCain was headed to the Middle East until after he arrived. Exactly how and why he became radicalized bewilders those who knew the 33-year-old. While living in San Diego, McCain worked for a program assisting people with disabilities.

Justin Filley - Friend of Douglas McCain: "Yeah that's him."

Justin Filley was one of McCain’s friends at the program. He says that for two years McCain helped him with day-to-day activities and spent time with him.

Justin Filley: "He was just a genuine fun guy. We would do fun things together, hang out."

Filley says they became close, but lost touch after McCain told him that he was going back to Minnesota. Eventually he was unable to reach him.

Justin Filley: "It's just a scary picture to imagine. I miss him a lot and it's kind of sad right now."

Now he and others are deeply puzzled about what would cause a one-time care provider to fight for a terrorist group.