Joshua Crawley, 31, has spent over 10 of the last 11 years in prison, being sent back six times since 2010, with his longest period of freedom being two months.

"He does not know how to live a normal life in the community," Judge Andrew Haesler said when jailing him for at least two years in the NSW District Court at Wollongong on Tuesday.

"In the community, he takes what he wants and does what he wants. It is the only life he knows."

After hearing Crawley give evidence acknowledging how many times he had failed before and how he has to prove to himself he can stay on track, the judge commented as he grows older he may learn.

"He may learn enough to know the life he has led is no life at all," he said.

Crawley pleaded guilty to seven offences including possessing an unregistered unauthorised pistol - a gel capsule pistol - in public; and break, enter and steal involving taking a householder's bag containing a laptop, two phones and his daughter's bag containing her schoolwork.

He also unlawfully delivered a shiv to an inmate who then assaulted a fellow prisoner and knowingly drove a stolen car, stealing property inside the vehicle worth about $3000.

"Crawley's crimes hurt or harmed a large number of people in our community," the judge said.

"It is not just that they lost property or had it trashed and damaged.

"There is also a loss of trust that harms us all. If we lose trust in others we lose part of what makes us a community."

The judge said Crawley expressed appropriate remorse in his evidence, and said he was ready to engage in programs and not run away from responsibility, as he had done so many times before.

One of two reports before the judge indicated that at long last Crawley was showing some insight into his offending and its impact on individuals and the community.

"Unlike some leaders in our community he is capable of saying 'sorry'," the judge said.

"Both reports highlight a background blighted by his parent's drug use, violence and crime."

Crawley had never had a stable home life or responsible role models, had been traumatised by his experience at home and in juvenile detention and his only associates are other criminals.'

"He has used and abused illicit drugs since well before he was old enough to make rational choices.

"Many of his crimes appear impulsive and occur without thought of consequence."

In setting a maximum term of three years and three months, the judge noted he had never lived a normal life in the community and will need help whenever he is released.

Australian Associated Press