Having spent more than half his life behind bars, he is desperately trying to stay out of jail, where he has lived most of his adult life.

This time on the outside, he has gone for two-and-a-half years without falling foul of the law. He’s been to rehab to break addictions to ice and booze. He’s held the demons of anxiety, depression and post traumatic stress disorder at bay.

“I’ve reached the point where I don’t want to go back to jail. I know if I go back, I’ll die in jail,” he says, tears welling. 

“I want to break the cycle but I’ve found myself living back among the people I need to get away from. I just want a place of my own to make a start.”

Bobby is like many others. They do their time. They get off the drugs. They cut the booze. Then, they find themselves living back among the peers who led them into crime in the first place. That’s the last thing Bobby wants. He has ambitions to mentor young Indigenous kids – to steer them away from the life of crime he knows.

He desperately wants a one-bedroom home of his own, one that’s not located in a neighbourhood where drug addiction and alcohol abuse is rife.

“I can’t live with the same group of people I left years ago,” he says.

Finding a place is proving extremely difficult. Just navigating the paperwork, locating a birth certificate, getting a proof of age card, getting bank statements seem like mountainous tasks for a person who’s lived their adult life in jail, where every decision is made for you, every minute of every day programmed for you.

“I lack the tools everyone else has to deal with these things,” he says. “I really need someone to help me adjust to life on the outside.”

Bobby fell into crime as a 14-year-old in Mt Druitt, jailed for burglary and stealing cars. It began a cycle that only ended two-and-a-half years ago. 

On our second meeting, he’s accompanied by his brother Andrew, who works at Oolong House in Nowra treating drug addiction.

Andrew is a member of the acclaimed Doonooch dance company. He’s travelled widely overseas. The contrast in outcomes for two siblings are stark.

Bobby puts his rocky path down to undiagnosed ADHD. This led to trouble at school and anger issues. Falling in with a bad crowd put him on the road to prison. “I was lost,” he says.

Inside, he studied and learned to write. 

“Education became a form of escape for me in prison,” he says.

At 40, he is desperate to remain free. “This is my last chance,” he says.