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Mark Dunn described Maddren (25) as a hard worker with a troubled background, including spending time in foster care ''that set him up for running from government institutions''.
Maddren knew he would be sent back to prison again and told Mr Dunn and other friends he could escape from Otago Corrections Facility, as ''he doesn't believe he fits in with that crowd''.
On Tuesday afternoon, a barefoot Maddren became the first person to escape from the Milburn prison, and remains at large.
''He believed he could do it,'' Mr Dunn said.
''Because in society he is considered a nobody, I guess this is a way of becoming somebody.''
Mr Dunn said if he was asked by police, ''I could get him to come in''.
''I expected him to turn up at my place ... he left the last stuff he owned at my house.''
He was sure if police called off the search Maddren, who he described as ''fearless'', would return to Dunedin.
If the search continued, Maddren - who had lived rough at times - would continue to be elusive.
''The more pressure they put on him, the worse the outcome,'' he said.
''Our family hasn't given up on him. We want to see him rehabilitated back to the community but just how that happens we aren't sure.''
Mr Dunn said he first met Maddren several years ago when he approached Mr Dunn's father for some work.
He was very shy and would cover his mouth due to his lack of teeth.
He had recently sought help to get new teeth.
The Dunn family helped organise employment so he could raise the required $2000 but Maddren ended up giving some of his money away to friends who were also struggling financially.
''That is typical of him - he liked to make people happy and go out of his way to help someone with a greater need than him.''
Mr Dunn has not given up hope Maddren will turn his life around, ''but someone needs to listen to his whole story''.