But when it comes to who is the most-hated man behind bars, all of my jail sources give the same answer: Simon Monteiro.
Known as the 'playboy rapist', Monteiro is a notorious sex offender and compulsive liar who is loathed by prisoners and officers alike. A Corrective Services psychologist once told a court he believed Monteiro was a psychopath.
Monteiro's case has been in the headlines for many years, not only thanks to his formerly glamorous lifestyle and supposed ties to Hollywood and high society, but in his complaints about prison conditions which included demands for a cell by the coast, a soft-bristled toothbrush and an orthopedic mattress.
He is also known to hold grudges and is apparently obsessed with revenge, correctional sources tell me.
After being convicted and jailed for 12 years in 2009 over the brutal rape of his ex-girlfriend, Monteiro has made it his mission to cause problems wherever he goes.
'Monteiro is easily the worst. He is one of the only inmates that everyone is terrified of and that's the truth,' a jail insider says.
'His entire wing at Long Bay put in a "Non-Association" application against him so if - or when - he gets chucked back in jail he can't be housed there.'
An aspiring actor and self-proclaimed one-time model, Monteiro once partied with Sydney's rich and famous, flaunting his lavish lifestyle, and even boasted about having a relationship with Mariah Carey.
But behind the 'playboy' persona was a sadistic and violent man who had seduced and manipulated a string of women across Sydney.
In the late '90s, he was charged with assault, stalking and intimidation.
After walking free, he went on to reoffend in 2009 when he broke into the home of his ex-girlfriend, holding scissors to her throat as he carried out a prolonged and violent sexual assault.
Monteiro threatened her with iron bars and told her he would 'gut her dad like a fish' if she ever went to the police.
Despite these threats, she was brave enough to press charges and Monteiro was sentenced to 12 years in prison.
But behind bars Monteiro became angry that he'd lost access to the luxuries to which he felt entitled.
'He honestly just thinks he is above every single person,' a prison source tells me.
'He is forever getting his legal team to get him things. He wanted a heater in his room, special meals of raw vegetables, and even tried for a laptop in his cell.
'He tries to divide everyone, too. Prison officers and inmates mostly have a good relationship, but he'd just cause drama and twist situations so people would fall out.'
Another insider tells me Monteiro would keep 'pages and pages of case notes' because he 'tries to sue everyone all the time'.
During his parole hearing in 2018, one of his alleged victims, Kay Schubach, was interviewed on Channel Nine's A Current Affair and begged authorities to keep him behind bars.
'I know the way that he behaves and I know that he will need to find another victim really quickly because he doesn't know anything else,' Ms Schubach told host Leila McKinnon.
'I think he is a parasite and he needs to find a new host. He goes for high-achieving, successful woman with means, and he is going to do that again. He is not reformed.'
According our sources, Monteiro has never forgotten that interview - and in particular holds a grudge against the journalist who spoke to Schubach.
'He absolutely hates Leila McKinnon,' we are told.
'He doesn't see [interviewing Schubach] as her job. He sees it as a personal attack and he is just furious with her. He got out of jail, got thrown back in again, and still hates Leila seven years on.
'He was the same with a prison officer he didn't like as well. The last time he got out he was caught trying to look her up online.'
When his rape sentence expired in 2020, Monteiro was given a five-year extended supervision order, with 26 conditions put in place to keep the community safe.
Two doctors also assessed Monteiro, with the first noting: 'He falls squarely in the highest category of risk of re-offending.'
Another doctor said, 'He is a highly selfish and entitled individual with no insight and no respect for authority,' and that 'prospects of being successfully rehabilitated are so poor as to be classified as dismal'.
He was back behind bars by June 2021 after he was convicted of breaching his supervision order.
He was released again in February 2022 then jailed for further breaches in June 2024 after police took out an AVO against him to protect a local woman in Umina, on the NSW Central Coast.
Monteiro is currently out of jail and appealing his strict release conditions that include wearing an ankle bracelet and informing his supervising officer if he starts a sexual relationship.
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