Nigel Milsom did not believe his painting of barrister Charles Waterstreet had any chance of winning the Archibald Prize.
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Milsom said he had forged a "weird kind of bond" with Waterstreet, a Fairfax Media columnist and the co-creator of the ABC television series Rake which is loosely based on his life.
"When you've got a barrister and your life feels like it's hinging on everything they say and do, you form a weird kind of bond," he said. "I was in a position where he was almost the closest person to me at the time. I was always speaking to him when I was in jail, I was speaking to him before it. I was always with him."
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