How Nigel Milsom, who just won the $100,000 Archibald Prize, wound up in prison for robbery

Nigel Milsom. Photo: Supplied

The winner of the 2015 Archibald Prize was just announced at the Art Gallery of NSW and Nigel Mislom took home the $100,000 for his portrait of Sydney barrister Charles Waterstreet. This 2013 profile of Milsom by Ben Collins reveals the remarkable relationship the to two men share and Milsom’s fraught journey to become one of Australia’s greatest portrait painters.

Award-winning painter Nigel Milsom doesn’t draw in jail. He’s afraid other inmates will notice his ability and force him to do tattoos.

Milsom was in the maximum security wing at Cessnock prison last month when his girlfriend, Aimee Crouch, accepted Australia’s most lucrative art award, the Moran Prize, on his behalf.

He’s in prison because on a Wednesday night in April 2012, Milsom, high on heroin, ice, and prescription medication, robbed a 7-11 in the inner Sydney suburb of Glebe along with his drug dealer, James Simon.

Milsom was first through the door, carrying a sculpting tomahawk and wearing a red baseball cap.

He took the axe from his jacket pocket. The pair demanded the keys to the safe from shopkeeper Gurmit Singh.

Singh was hit in the head several times. Milsom and Simon made off with cash, cigarettes and more than $900 worth of mobile phone credit.

When confronted by police Milsom ran at the officers. He was Tasered and subdued.

He would later say he wanted to be shot.

Still delirious from the drugs, he was taken into custody. He later tried to kill himself with a seatbelt in the back of a prisoner transport van.

He’s serving a minimum of two and a half years for the robbery. It was the nadir in a life already in disarray – upended by depression, drug use and the deaths of several friends.

‘Uncle Paddy’. Image supplied

Milsom won the Moran and its accompanying $150,000 cash for his work ‘Uncle Paddy’. It is a portrait of a man his grandfather used to drink with at the NSW Leagues Club.

It’s a bleak work, a face against darkness, cut by shadows that make a tortured maw. Its subject is worn but alive.

The man, according to a statement with the entry, was one of the few people who went to the funeral when Milsom’s grandfather died.

“I knew Paddy’s Saturday nights would never be the same,” the artist wrote.

“There is a quiet sadness which stems from the realisation death will be visiting him soon too.”

“When I painted his portrait I got a sense he had learnt to sit with his feelings of sadness.”

Like many artists Milsom, described in his hearing as timid and withdrawn, has learned to sit with his own dark emotions, embracing them to paint. His work is melancholy, of figures disturbed, in stark colours on black canvasses.

On 18 April 2012 when he robbed the store, it was only weeks since he had won the Sulman prize, another prestigious award. He had taken a lot of drugs that day, before he and Simon – also known as “Jim Boy” – went to the 7-11 where Milsom regularly bought his cigarettes. They brought an axe, a toy gun, and a knife.

Milsom was so high that he later told the court he thought he was going to buy doughnuts.

He had no criminal record before the robbery. But he had a drug habit, mostly heroin, which he smoked rather than injected. He also took ice, which he was introduced to on the night he won the Sulman. Someone slipped him some as they were celebrating.

Milsom began to tailor his drug taking and developed a process which allowed him to work. It was detailed at his sentencing.

“I was just taking ice, smoking ice. And then when I wanted to stop and [do] some work, or slow down, I’d smoke the heroin,” he told the court, according to the transcript.

“Then I’d smoke the ice again, and I’d do some work, and then I’d smoke the heroin.

“[T]he Xanax and the Rivotril, all these other things, they didn’t seem to have any effect on me anyway.

“Then I’d be drinking at the same time.”

In court it was suggested Milsom – who at one point was earning many thousands each month from selling paintings – may have needed money for drugs. Before the robbery there was a time when he was spending $1000 a day buying from Jim Boy.

But with the Sulman he won $30,000. And he had cash in his account at the time of the robbery. He couldn’t explain why he found himself at the 7-11, wide-eyed and livid, screaming and hitting the shopkeeper, demanding money with an axe in his hand.


The creatively brilliant but socially dysfunctional artist isn’t a baseless stereotype. Professor Philip Mitchell, the head of the University Of New South Wales School Of Psychiatry, said tortured personalities were often inhibited rather than inspired.

Nigel MilsomPhoto: Supplied

But in rare cases, severe depression can bring a certain focus, leading the sufferer to a new distillation of truth.

“The pain of a depressive existence can sometimes take the blinkers off,” Mitchell said. “They can see life as it is, without any pretence or denial.”

“It can make you less likely to pretend, or deny the realities in the world around you.”

Studies have shown artists to have a higher rate of depression and bi-polar disorder than the general population, Mitchell said. With those afflictions come higher rates of drug and alcohol abuse.

“Sometimes the depression is so painful people use alcohol or substances to self-medicate.

“That’s their way of coping.”

The court heard about Milsom’s battle with depression. It was backed by testimony from an expert witness, and from those close to him.

Well-known Sydney barrister Charles Waterstreet represented Milsom in his sentencing. He called as witnesses a close friend of the artist, and the psychiatrist who had treated him since he was released from remand on bail. All, and Crouch, described him as a gentle, shy man, a reclusive painter who liked to watch birds. He was not prone to violence.

The judge, Justice Peter Maiden, heard that after Milsom’s arrest he returned to the police station to apologise to the officer who had Tasered him, upset the cop had had to resort to his stun-gun.

“Nigel just felt really bad about putting him through that kind of situation,” Crouch said in court.

“And the officer said to him ‘I should have shot you because you were running towards me.’

“That scared Nigel when he said that.”

Photo: Supplied

Milsom also asked if he could apologise to Singh, but police warned him against it. Instead he wrote the shopkeeper a letter, which was passed on by one of the officers.

Throughout the sentencing hearing Waterstreet argued his client should not be sent to jail. He had no prior offences, and a history of community service. While he agreed Milsom was suffering from a mental illness at the time of the crime, Justice Maiden said its violence left him with little option but to send him to prison.

What made it worse, according to the judge, was that in the days before the robbery he had stopped taking his medication, the anti-depressant Zoloft.

“It was one moment of madness,” Waterstreet told Business Insider. “It wasn’t a robbery interceded to gain anything.”

After hearing the evidence and considering Milsom’s circumstances, Maiden gave him a six-and-a-half-year jail term, with a minimum of two and a half years before release. Simon, despite a lengthy rap sheet, received the same sentence with a longer non-parole period.


Photo: Supplied

Milsom completed a bachelor of visual arts at The University of Newcastle, and then a bachelor of fine arts from The University of New South Wales, then his honours and master’s degree, which he was awarded in 2002.

On top of the awards he has won – most recently The Moran – he has also exhibited widely. Ben Quilty, another well-known Australian painter, was one of the judges who awarded Milsom the Moran. He told Business Insider the quality of Milsom’s entry was standout.

“The painting was literally best in show,” he said. “Nigel is a ‘painter’s painter’. The work is sophisticated in its simplicity and quiet power and was the only work that both Daniel Thomas and I could agree on.

“It was a very easy choice in that sense.”

His work conjures the morbidity and the mask of human faces, explained his art dealer, and the director of the Yuill|Crowley gallery in Sydney’s Surry Hills, Kerry Crowley.

“What Milsom does is make painted surfaces that beguile and dazzle.

“He takes his subject matter as he finds it: a potted orchid, dog races, home town Newcastle street-scapes or photographs of long-dead children.”

Crowley, who supported him at his hearing, also said his work is influenced by the nineteenth-century Japanese master Hokusai, Edward Hopper, white-on-white abstractionist Robert Ryman, Gerhard Richter, and Pop figurative painter Alex Katz.

“In this age of image saturation and immersive video installations, he asks himself ‘can painting be continually stretched further into the future?’”

There has been no shortage of inspiration for his darker works.

His sentencing heard a history of suicides and deaths which have affected his outlook. In 2009 his younger sister Leigh died from a drug overdose. Before that, in 2000, he found the body of his cousin Richard – who he was living with, also dead from the same cause.

“That greatly affected him,” Crouch said. “To the point where he could not return to the house.”

Waterstreet said, besides his cousin and sister, several of his friends had also taken their lives.

Milsom was also mentored by the late art curator Nick Waterlow, who was stabbed to death in his Eastern Suburbs home by his mentally-ill son in 2009. The incident, the court heard, had a severe effect on Milsom.

While he was on bail for the robbery, his contemporary and friend Adam Cullen, died. Cullen was another painter driven by his darker moods, described by friends as cheery, though with a morbid fascination with death that he often expressed in interviews. Before he died, Cullen – also represented by Waterstreet – had been given a 10-month suspended sentence. Police had pulled him over and found him drunk, with his car full of guns.


When he entered the prison population, Milsom became just one of the many inmates with depression, a condition far more prevalent amongst prisoners than in the general community.

Over a third of people sent to Australian jails report having a mental illness, said Tim Beard, a spokesperson for the Australian Institute of Health and Welfare.

“We estimate that the rate is approximately two and a half times higher than that of the general population.”

Milsom was receiving treatment before he was jailed, and his psychiatrist told the court that, in his opinion, aided by his support network and ongoing medical assistance the artist would recover if spared a custodial sentence.


Photo: Supplied

It was through Cullen that Waterstreet met Milsom and his girlfriend Aimee. She regularly visits him in jail and says some of the things keeping him going inside are the photocopied books and letters that she and others send in to him. After his arrest, Waterstreet – on whom the ABC TV program Rake is based – arranged his bail, and organised for him to be admitted to The Sydney Clinic, an intense rehabilitation facility.

“His girlfriend rang me and I got him out on bail, got him into rehab.”

When Crouch went to see Milsom, after he had tried to kill himself in the back of a police car, he had no memory of the attempt. But it wasn’t the first time he had tried it.

At his sentencing, the court heard extracts from a police interview which followed his arrest, in which he told officers he’d nearly hung himself on a previous occasion.

“I tried to kill myself the other night by putting noose around my neck,” Waterstreet said in court, reading Milsom’s words from the document.

“I took 18 Valium, I also took a few cups of red wine. I stood on a ladder, wait for it to kick in, I thought this was bullshit, I came back down off the ladder.”

Milsom got to know Simon – who he had met four years before the robbery – after allowing him to do odd jobs at his Glebe studio. Crouch had met Simon previously, but told Business Insider she didn’t know he was her boyfriend’s drug dealer until after the robbery.

“Jim Boy (Simon) said to me at the opening to the Archibald: ‘I will let you know if I ever find out Nigel is taking drugs,’” she said.

When he came to the studio, Simon would smoke heroin, and eventually, about two years into the friendship, Milsom decided he would try it.

“He would smoke it and I wouldn’t touch it but it slowly kind of crept into our relationship,” he explained in court.

He would buy drugs from Jim Boy and they would smoke it together. Milsom told the court he thought Simon was stealing from him, by giving him less heroin than he was paying for.

At the Friend in Hand pub in Glebe, a short walk from his studio, Milsom would use the ATM to withdraw cash, and then buy drugs off Simon, who would follow him home later.

“He could give me an hour[‘s] peace to do my own thing and then he would arrive at my door.”

Milsom told the court that on other occasions Simon would be waiting when he went to buy beer, or a bottle of wine.

“I couldn’t go to the corner shop without Jim Boy waiting for me.”

Milsom made efforts to avoid him once he realised he was developing an addiction but it proved difficult. He was not good at extricating himself from damaging relationships.

At the sentencing hearing, Samson Roberts – his psychiatrist – told the court Milsom was the type of person who could be easily led. “It would appear that Nigel exhibits a personality vulnerability characterised by being overly trusting of people, overly generous to people.

“He’s consistently recounted the fact he was unable to deflect the attentions of his co-accused.”

When Maiden suggested Milsom may have gone with Simon to rob the 7-11 as he owed the dealer money, the artist said it was actually the other way around.

“He used my money to buy drugs for himself and he was always promising to pay me back, back in money.”


The case has rankled Waterstreet, a man who has described his own battle with depression in his published writing. He thinks Milsom’s clean record and mental health problems should have saved him from jail. From his interactions with the judge, Waterstreet believed his client was not going to be imprisoned. The sentence came as a shock.

In fact, while Milsom was on bail awaiting his sentence, he had moved home to Newcastle and his 16-year-old son had come to live with him. Before he was sentenced, the two of them had stretched six canvasses out, with Milsom intending to work on them after the case.

Waterstreet thinks the jail term handed down did not take into account Milsom’s time at the rehab clinic and sessions with a psychiatrist.

“Milsom is a man who got no credit for rehabilitating himself,” Waterstreet said.

He intends to lodge an appeal.

* Editor’s note: Milsom’s appeal was successful in June 2014 and he was re-sentenced to two years and four months’ imprisonment, with a non-parole period of 341 days, and was paroled in April. He is on parole until August 25, 2016.

ORIGINALLY PUBLISHED AS: How One Of Australia’s Most Successful Working Artists Wound Up In Prison For Armed Robbery

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