Damien is from Northern Idaho in the United States, born and raised. His dad went to prison when he was only four years old, so he's never really knew him. His mom raised him by herself for the majority of his life. She was pretty much his only family. He never had a real role model in his life, so he started to grow some bad habits, namely smoking, drinking and theft. It didn't help that he attracted the wrong kind of crowd. Damien always struggled in school, but he managed to get by and finally graduate. The reason was because he became really good at cheating. He cheated so much, it became natural to him. Since graduating, he's never had a steady job. He kept getting fired for either failing drug tests or because he simply slept often and didn't show up to work. He got in quite a few fights because he drank too much at the bar, and little things set him off. He's been arrested a few times because of this, too.
After being arrested one too many times for getting into fights, drinking and driving and theft, he finally decided that something was wrong with his life. He needed to change, but not necessarily in the most righteous way. He wanted more control of his life, and he felt that drinking was the reason that he couldn't progress himself. He decided to stop being lazy, and everything he does, he should put in 120%. He decided to quit drinking (at least excessively), and train himself to have a sharper mind. He wanted to be smarter about his crimes. He had no intention of quitting being a thief, he actually enjoyed that. He doesn't think about what's right and what's wrong anymore, unless it pertains to close friends of his.
Ever since he decided to turn his life around, he's gotten out of a lot of trouble. He didn't necessarily stop stealing, but he did it better and smarter. At age 31, he took a month to plan a heist, and when the time came, he executed it almost perfectly, except when he went to the place to meet with his getaway ride, he found no one. He heard police sirens coming towards his location, but there should have been no way that they would have found him there. Damien got betrayed. The man he was supposed to meet ratted him out. He decided to run before the cops actually got to the location. He made it back to his car, but found that it was also surrounded by police cars. He ran to the nearest city, stole a car and headed home. When he got home, he also found cop cars there. He wasn't safe anywhere. He had to leave the United States.
Unfortunately, he couldn't say goodbye to his mom. He faked an identity, which he got really good at doing, and left the country. He got away with most of the money from that last heist, and used a good amount of it to bribe a man to let him on his private plane. He was from Chernarus and was heading home. Damien didn't care where he was headed, as long as it was out of the United States. It was about May of 2016 when he fled and started his new life in Chernarus. Damien caused a lot of trouble in Chernarus, too, but he never got caught. He kind of missed the attention he had back in the United States, so he started leaving hints every time he stole from someone, letting them know that he was The Barefoot Bandit. The real Barefoot Bandit was thief from the United States that he looked up to, so he started going by that name. And that's how he ended up in Chernarus.