A Sydney man long known to authorities as the "Playboy Rapist" was granted conditional bail on Wednesday after being charged with stalking and intimidating a former partner and breaching an extended supervision order.
Simon Monteiro, 58, appeared via video link from custody at the King Street Supreme Court in Sydney and was released on strict conditions including a curfew, good behaviour, a requirement to report to police three times a week, and an order to stay at least 500 metres clear of the complainant except when attending court.
Police allege Monteiro approached a woman he previously had an intimate relationship with at Hornsby Local Court on August 12 and stared in her direction with the intention of causing her to fear for her safety. The woman had attended court on an unrelated matter and later reported feeling uncomfortable to police, according to court documents. Within days of the incident, Monteiro surrendered to Gosford police and was charged with breaching a supervision order, stalking and intimidating with intent to cause fear, and attempting to stalk or intimidate with intent to cause fear. He was remanded in custody until Wednesday's bail decision.
Justice Jennifer McNaughton said the risk Monteiro posed could be mitigated by the conditions attached to bail and by existing apprehended violence orders. She described the Crown's case as "arguable" but not a strong one, and noted Monteiro had not been charged with violent or sexual offences in recent years. The prosecution, led by Saeed Saadie, opposed bail partly on the basis of past breaches of supervision orders, but confined those submissions to written material rather than oral argument at the hearing.
Monteiro, who has also used the names Simon Lowe and Bonito Monteiro, represented himself at the hearing after parting ways last week with counsel John Stratton SC. Dressed in prison issue clothing, he told the court he wanted to "get his life back," saying his notoriety made custodial conditions particularly onerous and that he was the only person able to care for his elderly father. He also said bail was necessary to prepare for an unrelated legal challenge, to attend university and to undergo surgery.
Monteiro's criminal history includes a high-profile conviction in 2009 after a jury found he broke into the Bellevue Hill apartment of an ex-girlfriend, threatened her and sexually assaulted her. He was sentenced to 12 years' imprisonment, served nearly 10 years and was released on parole in 2020. A five-year supervision order was imposed in July 2020 with a range of conditions, some of which were eased in December of last year. He returned to custody in July 2021 after being convicted of breaching that supervision order and was released again in February 2022.
The nickname "playboy" has been used in media reports to describe Monteiro's past public persona; he has previously claimed relationships with high-profile figures and marketed himself as a former model and aspiring actor.
Monteiro is due to appear at Hornsby Local Court on September 17. The bail conditions require him to comply with any current supervision or apprehended violence orders and to report regularly to police while the new charges proceed through the court system.