Former male model dubbed the ‘Playboy Rapist’ is granted BAIL after being accused of yet another sickening crime

A notorious Sydney sex offender dubbed the 'playboy rapist' has been granted conditional bail after he allegedly stalked and intimidated an ex-partner. 

Simon Monteiro, 58, was charged last month with stalking and intimidating a woman at Hornsby Local Court on August 12 and breaching an extended supervision order.

It is only the latest in a string of charges against the former male model and aspiring actor, who has also gone by the names Simon Lowe and Bonito Monteiro - a name he told women was Portuguese for 'beautiful hunter'. 

He developed his 'playboy' nickname after boasting about his lavish lifestyle and relationships with US pop star Mariah Carey and Oscar nominee Barbara Hershey. 

In 2009, he was sentenced to 12 years' imprisonment after he was convicted of raping and assaulting his ex-girlfriend at her apartment in Bellevue Hill, in Sydney's east. 

He served nearly ten years before being granted parole. He was put on a five-year supervision order in July 2020, subject to a range of conditions.

On Wednesday, he appeared via camera from jail for a bail hearing on recent charges at King Street Supreme Court in Sydney, where he pleaded to get his 'life back'.

Police allege Monteiro approached a woman known to him at Hornsby Local Court on August 12 and stared in her direction, intending to cause her to fear for her safety. 

Simon Monteiro was granted bail over allegations he intentionally intimidated a former romantic partner. He is pictured leaving the Supreme Court in Sydney in December last year

Simon Monteiro was granted bail over allegations he intentionally intimidated a former romantic partner. He is pictured leaving the Supreme Court in Sydney in December last year

Monteiro was sentenced to 12 years behind bars in 2009 for the sexual assault of his ex-girlfriend. He was released on parole in 2020

Monteiro was sentenced to 12 years behind bars in 2009 for the sexual assault of his ex-girlfriend. He was released on parole in 2020

The woman, whom the Daily Mail has chosen not to identify, had attended the court for an unrelated matter and reported her discomfort to gathered police. 

She had an intimate relationship with Monteiro for several months earlier this year, before things soured and the pair took out mutual apprehended violence orders. 

Within days of the run-in at Hornsby Local Court, Monteiro turned himself in to Gosford Police Station. 

There, he was charged with breaching a supervision order, stalking/intimidating with intent to cause fear and attempting to stalk/intimidate with intent to cause fear. 

He was remanded in custody last month, where he remained until his bail was approved subject to strict conditions on Wednesday. 

Dressed in prison greens, the worse-for-wear former model represented himself from jail after parting ways with his lawyer John Stratton SC last week. 

He argued his bail was necessary for a range of reasons, including to prepare for an upcoming separate legal challenge, to attend university and to undergo surgery. 

The 58-year-old grew visibly emotional when claiming he was the only person able to provide assistance to his elderly father. 'He has no one', he said through tears. 

The 'playboy rapist' is accused of intimidating a woman at Hornsby Local Court last month

The 'playboy rapist' is accused of intimidating a woman at Hornsby Local Court last month

He also argued his notoriety meant his custodial conditions were particularly onerous, as he is kept apart from the general population. 

'I've done nothing wrong, I want my life back,' he told the court. 

Lawyer for the prosecution Saeed Saadie opposed the application for bail for a range of reasons, including Monteiro's past breaches of a supervision order. 

But the prosecution's case about the potential risks of Monteiro's release was confined by Mr Saadie to written submissions tendered ahead of the court date.

In reaching her decision, Justice McNaughton accepted whatever risk Monteiro posed to the community or victims could be ameliorated by imposing conditions. 

'I am of the view it is appropriate to grant the applicant conditional bail,' she said. 

Justice McNaughton did not consider the merits of the charges in any depth, beyond accepting the question of whether Monteiro attended Hornsby Local Court intending to intimidate the complainant was 'arguable'.

'That case cannot be said to be a strong Crown case,' Justice McNaughton said, adding the case was 'not necessarily weak' but not 'strong'. 

Justice McNaughton considered that Monteiro had not been charged with any violent or sexual offences in recent years.

Monteiro will be allowed to live among the community after being granted bail

Monteiro will be allowed to live among the community after being granted bail

She also held that any risks posed to the complainant could be mitigated by an existing AVO and bail conditions. 

He was released on bail subject to a several conditions including good behaviour, a curfew, and that he not approach within 500 metres of the complainant except where necessary for attending court. 

He will also be required to report to police three times a week and adhere to the conditions of any supervision or apprehended violence orders against him. 

Monteiro spent nine-and-a-half years in jail after being sentenced to 12 years for raping his ex-girlfriend in 2009. 

A jury was satisfied the former Sydney playboy had broken into her Bellevue Hill home in Sydney's east and threatened to suffocate her before the sexual assault.

Despite threatening her with iron bars and warning her he would 'gut her father like a fish' if she reported him to police, she proceeded to press charges.

He was released on a five-year supervision order in July 2020 subject to strict conditions, some of which were eased in December last year. 

He landed himself back behind bars by July 2021 after he was convicted of breaching his supervision order and was released in February 2022. 

Monteiro is due to appear at Hornsby Local Court on September 17. 

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