Between the ages of 16 to18 he claims to have been jailed eight times.
However, he behaved little better when inside, smashing up his cell and spending time in solitary.
But during one of these prison terms in Bridgend, he started to change.
"It was New Year's Eve. Outside I could hear fireworks going off and people laughing in the town centre, and I began thinking how I could do better,"
It was never going to be easy. Darren, now 19, has had little contact with his parents and most of his friends were in trouble too. So when he transferred to Ashfield prison, Sam Jones, a youth worker from Bridgend, started visiting him and other young offenders twice-weekly.
Mr Jones turned out to be a constant reassuring presence.
"It was important to have someone to talk to from home and he's been great," said Darren. "I'd rather speak to someone Welsh."
Gradually his behaviour improved and he got moved to a drugs-free wing. He and Mr Jones shared recreational time, working out in the gym, doing music technology and digital stories on Sam's laptop. The relationship continued after Darren came out, and at times Mr Jones has been a lifeline, helping keep him out of trouble.
It was then that Darren expressed an interest in education and training.
Following his disrupted schooling, Darren started a construction course.
But the real turning point came when he was chosen from 15 applicants for an apprenticeship in painting and decorating.
The former tearaway now spends three days a week at work and two at Bridgend college.
"I love doing it and I like the people I work with," he said.
"I'm going to give it my all. Now I've seen what I can achieve I don't want to go back to crime."