The worst of times has resulted in the best of times for artist Nigel Milsom, the newly crowned winner of the Archibald prize.
Milsom's $100,000 portrait prize is potentially his most meaningful as he painted Charles Waterstreet, the barrister who helped him reduce his six-year sentencing for armed robbery.
Waterstreet argued that Milsom had been mentally ill at the time of his arrest, and held up a 7-Eleven store in the inner Sydney suburb of Glebe while high on a cocktail of drugs in 2012.
Milsom was sentenced to six years in prison, however he was released in the middle of last year.
Even he was surprised that something so positive could have come from such a difficult time in his life.
"I was shocked because it's not often you can bounce back from something that seemed to have ruined what could have been my career or even my life, so it was pretty extraordinary," Milsom said, just after he was announced as the winner at the Art Gallery of NSW on Friday.
The black and white oil painting on Belgian linen, titled Judo house pt 6 (the white bird), was representative of the faith Milsom placed in Waterstreet.
"I've wanted to try and capture the way he became, over time, like a sort of mythical kind of saviour in my mind. So much hinged on what he had to say and do, and it's a painting that's really sort of showing him as a giant in my life at the time," he said.
"It's not just about my relationship but I guess anyone's relationship with someone that they place a lot of trust in to pull them out of a tight situation. So it's a picture that to me represents a kind of dependence... a need."
Milsom wanted to express all facets of the man who serves as the inspiration for TV show Rake, who he describes as "complex".
The artist saw Waterstreet as being almost like a scarecrow or an insect and didn't set out to paint a beautiful or pretty picture. At first, Waterstreet wasn't quite sure of the depiction.
"He said `I really love it when I can bear to look at it'. I think he thought it was a bit spooky or eerie, but he's come around and he just thinks it's great," Milsom said.
Today's Archibald victory is Milsom's third major art prize win - he was also the recipient of the Doug Moran National Portrait Prize in 2014 ($150,000) and the Sulman Prize in 2012 ($30,000).
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