Notorious ‘playboy rapist’ who boasted of friendship with Mariah Carey to return to jail

Convicted rapist and former actor Simon Monteiro – who once boasted of relationships with Mariah Carey and Barbara Hershey – is back behind bars after breaching supervision orders.

Monteiro appeared via video link at Gosford District Court for sentencing on Wednesday after pleading guilty to breaching many supervision orders which restricted his online activity and use of aliases.

He had been arrested in August last year after he was found with mobile phones and laptops he was not allowed to own under the supervision order, and admitting to opening What’s App, Facebook and Gumtree accounts under false names and without notifying police. 

Playboy rapist Simon Monteiro (second from left) pictured with Mariah Carey (third from left)

Judge Tanya Bright sentenced him on Wednesday to two years and eight months in jail, but he immediately vowed to appeal, sacked his barrister on the spot, interrupted the judge and stormed out of the video appearance.

During sentencing the court was told of the extensive and violent criminal history of Monteiro, whose original name was Simon Lowe.

He previously spent over ten years in jail for aggravated sexual assault on his then girlfriend in 2008.  

Convicted rapist Simon Monteiro (right) formerly rubbed shoulders with Hollywood A-lister Barbara Hershey (left)

Just prior to his release last year, supervision orders were put in place which were designed to restrain his online activity and ownership of devices such as phones and computers.

The orders were based on psychological profiling which diagnosed Monteiro with narcissistic personality disorder and which found he was at a high risk of re-offending both violently and sexually toward an intimate partner. 

Mug shot of rapist Simon Monteiro 

The orders included the use of only one mobile phone and to provide Corrective Service officers with this number along with the serial number and IP address of any internet devices, email addresses, login details and passwords. 

However the court heard that despite Monteiro telling his supervising officer he got rid of all of his devices and was just using a cheap Nokia phone, arresting police discovered an iPhone, a Huawei phone, a Macbook computer, and a HP laptop along with a number of hard drives.  

Further release orders included Monteiro was not to use an alternative name or alias or use any form of social media or dating websites.

Simon Monteiro (pictured) is back behind bars until August 17, 2022 for breaching court conditions

Yet evidence presented showed Monteiro had four social media accounts on various apps, was using ten aliases including the name of Shaun White on Facebook, had six different email addresses and had searched the profile of a female Corrective Services officer up to 80 times. 

Monteiro did not wait until his matter was finalised by the judge on Wednesday before storming out of the video suite. 

Monteiro’s case has been in the headlines for many years not only thanks to his formerly glamorous lifestyle and supposed ties to Hollywood A-listers, but in his complaints about prison conditions which included demands for a cell by the coast, a soft-bristled toothbrush and an orthopedic mattress. 

Convicted rapist Simon Monteiro (pictured) in his glory days

Monteiro also reportedly threatened to rape a prison guard’s wife while behind bars.

In October of 2017 Monteiro told the New South Wales state parole board it was ‘in the public interest’ he be released from prison despite the creation of a Change.org petition with over 46,000 signatures urging he should never be released.

The husband of murdered Melbourne woman Jill Meagher had made an impassioned statement about Monteiro to Change.org.

‘My wife was murdered in Melbourne by a parolee just like this unrepentant creep. I spoke personally with the Adult Parole Board of Victoria at the time warning them of the egregious mistake of putting serial sex offenders like him back out to terrorise women.

‘Let this man back out on the street and you will almost certainly see another headline like this one,’ he wrote, citing a report that Ms Meagher’s death was preventable had the offender been properly supervised. 

Change.org petition launched by concerned community members with 46,262 signatures